Synthesis, biological evaluation and molecular docking studies of novel 2-alkylthiopyrimidino-tacrines as anticholinesterase agents and their DFT calculations
To search for effective and selective inhibitors of cholinesterases (AChE and BuChE), a series of poly-functionalized Tacrine-derived compounds specifically 2-(alkylthio)-4-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-5-amines were designed an synthesized via Friedlander reaction. The structures o...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Derabli, Chamseddine [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2020transfer abstract |
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| Schlagwörter: |
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| Übergeordnetes Werk: |
Enthalten in: Artificial neural network modelling of amido black dye sorption on iron composite nano material: Kinetics and thermodynamics studies - Ali, Imran ELSEVIER, 2017, New York, NY [u.a.] |
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| Übergeordnetes Werk: |
volume:1209 ; year:2020 ; day:5 ; month:06 ; pages:0 |
| Links: |
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| DOI / URN: |
10.1016/j.molstruc.2020.127902 |
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| 245 | 1 | 0 | |a Synthesis, biological evaluation and molecular docking studies of novel 2-alkylthiopyrimidino-tacrines as anticholinesterase agents and their DFT calculations |
| 264 | 1 | |c 2020transfer abstract | |
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| 520 | |a To search for effective and selective inhibitors of cholinesterases (AChE and BuChE), a series of poly-functionalized Tacrine-derived compounds specifically 2-(alkylthio)-4-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-5-amines were designed an synthesized via Friedlander reaction. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data (1H NMR, 13C NMR) and elemental analyses (CHNS). Compounds 3a-h were evaluated for their abilities to inhibit AChE and BChE. The obtained biological results revealed that some synthesized compounds displayed higher anti-cholinesterase activity in comparison to Galantamine. Among them, compound 3d bearing S-ethyl and 4-chlorophenyl moieties showed the most potent activity against AChE/BuChE with IC50s values of 4,32 and 15,10 μM, respectively. The anti-AChE activity of 3d was 5-fold more than that of reference drug Galantamine. Moreover, molecular docking studies were performed for the most active derivatives, 3d and 3c, in which binding mode between these compounds and the receptors were determined. Density functional theory (DFT) method at B3LYP/6–311++G (d,p) level of theory was employed to gain insights into the molecular structure of the target compounds. Molecular electrostatic potential (MEP) mapping, reactivity indices such as electronegativity, electrophilic index, softness and hardness as well as frontier molecular orbitals HOMO-LUMO have been investigated for 3a-3c as representative compounds. In addition, their antiradical activity has been predicted by computing bond dissociation enthalpies (BDEs). | ||
| 520 | |a To search for effective and selective inhibitors of cholinesterases (AChE and BuChE), a series of poly-functionalized Tacrine-derived compounds specifically 2-(alkylthio)-4-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-5-amines were designed an synthesized via Friedlander reaction. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data (1H NMR, 13C NMR) and elemental analyses (CHNS). Compounds 3a-h were evaluated for their abilities to inhibit AChE and BChE. The obtained biological results revealed that some synthesized compounds displayed higher anti-cholinesterase activity in comparison to Galantamine. Among them, compound 3d bearing S-ethyl and 4-chlorophenyl moieties showed the most potent activity against AChE/BuChE with IC50s values of 4,32 and 15,10 μM, respectively. The anti-AChE activity of 3d was 5-fold more than that of reference drug Galantamine. Moreover, molecular docking studies were performed for the most active derivatives, 3d and 3c, in which binding mode between these compounds and the receptors were determined. Density functional theory (DFT) method at B3LYP/6–311++G (d,p) level of theory was employed to gain insights into the molecular structure of the target compounds. Molecular electrostatic potential (MEP) mapping, reactivity indices such as electronegativity, electrophilic index, softness and hardness as well as frontier molecular orbitals HOMO-LUMO have been investigated for 3a-3c as representative compounds. In addition, their antiradical activity has been predicted by computing bond dissociation enthalpies (BDEs). | ||
| 650 | 7 | |a Alzheimer’s disease |2 Elsevier | |
| 650 | 7 | |a Inhibitors of cholinesterases |2 Elsevier | |
| 650 | 7 | |a 2-Alkylthiopyrimidino-Tacrines |2 Elsevier | |
| 650 | 7 | |a Molecular docking |2 Elsevier | |
| 650 | 7 | |a DFT calculations |2 Elsevier | |
| 700 | 1 | |a Boulebd, Houssem |4 oth | |
| 700 | 1 | |a Abdelwahab, Ahmed B. |4 oth | |
| 700 | 1 | |a Boucheraine, Celia |4 oth | |
| 700 | 1 | |a Zerrouki, Sarah |4 oth | |
| 700 | 1 | |a Bensouici, Chawki |4 oth | |
| 700 | 1 | |a Kirsch, Gilbert |4 oth | |
| 700 | 1 | |a Boulcina, Raouf |4 oth | |
| 700 | 1 | |a Debache, Abdelmadjid |4 oth | |
| 773 | 0 | 8 | |i Enthalten in |n Elsevier |a Ali, Imran ELSEVIER |t Artificial neural network modelling of amido black dye sorption on iron composite nano material: Kinetics and thermodynamics studies |d 2017 |g New York, NY [u.a.] |w (DE-627)ELV005044758 |
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10.1016/j.molstruc.2020.127902 doi /cbs_pica/cbs_olc/import_discovery/elsevier/einzuspielen/GBV00000000000955.pica (DE-627)ELV049823728 (ELSEVIER)S0022-2860(20)30226-X DE-627 ger DE-627 rakwb eng 540 VZ 35.21 bkl Derabli, Chamseddine verfasserin aut Synthesis, biological evaluation and molecular docking studies of novel 2-alkylthiopyrimidino-tacrines as anticholinesterase agents and their DFT calculations 2020transfer abstract nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier To search for effective and selective inhibitors of cholinesterases (AChE and BuChE), a series of poly-functionalized Tacrine-derived compounds specifically 2-(alkylthio)-4-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-5-amines were designed an synthesized via Friedlander reaction. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data (1H NMR, 13C NMR) and elemental analyses (CHNS). Compounds 3a-h were evaluated for their abilities to inhibit AChE and BChE. The obtained biological results revealed that some synthesized compounds displayed higher anti-cholinesterase activity in comparison to Galantamine. Among them, compound 3d bearing S-ethyl and 4-chlorophenyl moieties showed the most potent activity against AChE/BuChE with IC50s values of 4,32 and 15,10 μM, respectively. The anti-AChE activity of 3d was 5-fold more than that of reference drug Galantamine. Moreover, molecular docking studies were performed for the most active derivatives, 3d and 3c, in which binding mode between these compounds and the receptors were determined. Density functional theory (DFT) method at B3LYP/6–311++G (d,p) level of theory was employed to gain insights into the molecular structure of the target compounds. Molecular electrostatic potential (MEP) mapping, reactivity indices such as electronegativity, electrophilic index, softness and hardness as well as frontier molecular orbitals HOMO-LUMO have been investigated for 3a-3c as representative compounds. In addition, their antiradical activity has been predicted by computing bond dissociation enthalpies (BDEs). To search for effective and selective inhibitors of cholinesterases (AChE and BuChE), a series of poly-functionalized Tacrine-derived compounds specifically 2-(alkylthio)-4-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-5-amines were designed an synthesized via Friedlander reaction. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data (1H NMR, 13C NMR) and elemental analyses (CHNS). Compounds 3a-h were evaluated for their abilities to inhibit AChE and BChE. The obtained biological results revealed that some synthesized compounds displayed higher anti-cholinesterase activity in comparison to Galantamine. Among them, compound 3d bearing S-ethyl and 4-chlorophenyl moieties showed the most potent activity against AChE/BuChE with IC50s values of 4,32 and 15,10 μM, respectively. The anti-AChE activity of 3d was 5-fold more than that of reference drug Galantamine. Moreover, molecular docking studies were performed for the most active derivatives, 3d and 3c, in which binding mode between these compounds and the receptors were determined. Density functional theory (DFT) method at B3LYP/6–311++G (d,p) level of theory was employed to gain insights into the molecular structure of the target compounds. Molecular electrostatic potential (MEP) mapping, reactivity indices such as electronegativity, electrophilic index, softness and hardness as well as frontier molecular orbitals HOMO-LUMO have been investigated for 3a-3c as representative compounds. In addition, their antiradical activity has been predicted by computing bond dissociation enthalpies (BDEs). Alzheimer’s disease Elsevier Inhibitors of cholinesterases Elsevier 2-Alkylthiopyrimidino-Tacrines Elsevier Molecular docking Elsevier DFT calculations Elsevier Boulebd, Houssem oth Abdelwahab, Ahmed B. oth Boucheraine, Celia oth Zerrouki, Sarah oth Bensouici, Chawki oth Kirsch, Gilbert oth Boulcina, Raouf oth Debache, Abdelmadjid oth Enthalten in Elsevier Ali, Imran ELSEVIER Artificial neural network modelling of amido black dye sorption on iron composite nano material: Kinetics and thermodynamics studies 2017 New York, NY [u.a.] (DE-627)ELV005044758 volume:1209 year:2020 day:5 month:06 pages:0 https://doi.org/10.1016/j.molstruc.2020.127902 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 35.21 Lösungen Flüssigkeiten Physikalische Chemie VZ AR 1209 2020 5 0605 0 |
| spelling |
10.1016/j.molstruc.2020.127902 doi /cbs_pica/cbs_olc/import_discovery/elsevier/einzuspielen/GBV00000000000955.pica (DE-627)ELV049823728 (ELSEVIER)S0022-2860(20)30226-X DE-627 ger DE-627 rakwb eng 540 VZ 35.21 bkl Derabli, Chamseddine verfasserin aut Synthesis, biological evaluation and molecular docking studies of novel 2-alkylthiopyrimidino-tacrines as anticholinesterase agents and their DFT calculations 2020transfer abstract nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier To search for effective and selective inhibitors of cholinesterases (AChE and BuChE), a series of poly-functionalized Tacrine-derived compounds specifically 2-(alkylthio)-4-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-5-amines were designed an synthesized via Friedlander reaction. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data (1H NMR, 13C NMR) and elemental analyses (CHNS). Compounds 3a-h were evaluated for their abilities to inhibit AChE and BChE. The obtained biological results revealed that some synthesized compounds displayed higher anti-cholinesterase activity in comparison to Galantamine. Among them, compound 3d bearing S-ethyl and 4-chlorophenyl moieties showed the most potent activity against AChE/BuChE with IC50s values of 4,32 and 15,10 μM, respectively. The anti-AChE activity of 3d was 5-fold more than that of reference drug Galantamine. Moreover, molecular docking studies were performed for the most active derivatives, 3d and 3c, in which binding mode between these compounds and the receptors were determined. Density functional theory (DFT) method at B3LYP/6–311++G (d,p) level of theory was employed to gain insights into the molecular structure of the target compounds. Molecular electrostatic potential (MEP) mapping, reactivity indices such as electronegativity, electrophilic index, softness and hardness as well as frontier molecular orbitals HOMO-LUMO have been investigated for 3a-3c as representative compounds. In addition, their antiradical activity has been predicted by computing bond dissociation enthalpies (BDEs). To search for effective and selective inhibitors of cholinesterases (AChE and BuChE), a series of poly-functionalized Tacrine-derived compounds specifically 2-(alkylthio)-4-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-5-amines were designed an synthesized via Friedlander reaction. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data (1H NMR, 13C NMR) and elemental analyses (CHNS). Compounds 3a-h were evaluated for their abilities to inhibit AChE and BChE. The obtained biological results revealed that some synthesized compounds displayed higher anti-cholinesterase activity in comparison to Galantamine. Among them, compound 3d bearing S-ethyl and 4-chlorophenyl moieties showed the most potent activity against AChE/BuChE with IC50s values of 4,32 and 15,10 μM, respectively. The anti-AChE activity of 3d was 5-fold more than that of reference drug Galantamine. Moreover, molecular docking studies were performed for the most active derivatives, 3d and 3c, in which binding mode between these compounds and the receptors were determined. Density functional theory (DFT) method at B3LYP/6–311++G (d,p) level of theory was employed to gain insights into the molecular structure of the target compounds. Molecular electrostatic potential (MEP) mapping, reactivity indices such as electronegativity, electrophilic index, softness and hardness as well as frontier molecular orbitals HOMO-LUMO have been investigated for 3a-3c as representative compounds. In addition, their antiradical activity has been predicted by computing bond dissociation enthalpies (BDEs). Alzheimer’s disease Elsevier Inhibitors of cholinesterases Elsevier 2-Alkylthiopyrimidino-Tacrines Elsevier Molecular docking Elsevier DFT calculations Elsevier Boulebd, Houssem oth Abdelwahab, Ahmed B. oth Boucheraine, Celia oth Zerrouki, Sarah oth Bensouici, Chawki oth Kirsch, Gilbert oth Boulcina, Raouf oth Debache, Abdelmadjid oth Enthalten in Elsevier Ali, Imran ELSEVIER Artificial neural network modelling of amido black dye sorption on iron composite nano material: Kinetics and thermodynamics studies 2017 New York, NY [u.a.] (DE-627)ELV005044758 volume:1209 year:2020 day:5 month:06 pages:0 https://doi.org/10.1016/j.molstruc.2020.127902 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 35.21 Lösungen Flüssigkeiten Physikalische Chemie VZ AR 1209 2020 5 0605 0 |
| allfields_unstemmed |
10.1016/j.molstruc.2020.127902 doi /cbs_pica/cbs_olc/import_discovery/elsevier/einzuspielen/GBV00000000000955.pica (DE-627)ELV049823728 (ELSEVIER)S0022-2860(20)30226-X DE-627 ger DE-627 rakwb eng 540 VZ 35.21 bkl Derabli, Chamseddine verfasserin aut Synthesis, biological evaluation and molecular docking studies of novel 2-alkylthiopyrimidino-tacrines as anticholinesterase agents and their DFT calculations 2020transfer abstract nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier To search for effective and selective inhibitors of cholinesterases (AChE and BuChE), a series of poly-functionalized Tacrine-derived compounds specifically 2-(alkylthio)-4-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-5-amines were designed an synthesized via Friedlander reaction. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data (1H NMR, 13C NMR) and elemental analyses (CHNS). Compounds 3a-h were evaluated for their abilities to inhibit AChE and BChE. The obtained biological results revealed that some synthesized compounds displayed higher anti-cholinesterase activity in comparison to Galantamine. Among them, compound 3d bearing S-ethyl and 4-chlorophenyl moieties showed the most potent activity against AChE/BuChE with IC50s values of 4,32 and 15,10 μM, respectively. The anti-AChE activity of 3d was 5-fold more than that of reference drug Galantamine. Moreover, molecular docking studies were performed for the most active derivatives, 3d and 3c, in which binding mode between these compounds and the receptors were determined. Density functional theory (DFT) method at B3LYP/6–311++G (d,p) level of theory was employed to gain insights into the molecular structure of the target compounds. Molecular electrostatic potential (MEP) mapping, reactivity indices such as electronegativity, electrophilic index, softness and hardness as well as frontier molecular orbitals HOMO-LUMO have been investigated for 3a-3c as representative compounds. In addition, their antiradical activity has been predicted by computing bond dissociation enthalpies (BDEs). To search for effective and selective inhibitors of cholinesterases (AChE and BuChE), a series of poly-functionalized Tacrine-derived compounds specifically 2-(alkylthio)-4-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-5-amines were designed an synthesized via Friedlander reaction. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data (1H NMR, 13C NMR) and elemental analyses (CHNS). Compounds 3a-h were evaluated for their abilities to inhibit AChE and BChE. The obtained biological results revealed that some synthesized compounds displayed higher anti-cholinesterase activity in comparison to Galantamine. Among them, compound 3d bearing S-ethyl and 4-chlorophenyl moieties showed the most potent activity against AChE/BuChE with IC50s values of 4,32 and 15,10 μM, respectively. The anti-AChE activity of 3d was 5-fold more than that of reference drug Galantamine. Moreover, molecular docking studies were performed for the most active derivatives, 3d and 3c, in which binding mode between these compounds and the receptors were determined. Density functional theory (DFT) method at B3LYP/6–311++G (d,p) level of theory was employed to gain insights into the molecular structure of the target compounds. Molecular electrostatic potential (MEP) mapping, reactivity indices such as electronegativity, electrophilic index, softness and hardness as well as frontier molecular orbitals HOMO-LUMO have been investigated for 3a-3c as representative compounds. In addition, their antiradical activity has been predicted by computing bond dissociation enthalpies (BDEs). Alzheimer’s disease Elsevier Inhibitors of cholinesterases Elsevier 2-Alkylthiopyrimidino-Tacrines Elsevier Molecular docking Elsevier DFT calculations Elsevier Boulebd, Houssem oth Abdelwahab, Ahmed B. oth Boucheraine, Celia oth Zerrouki, Sarah oth Bensouici, Chawki oth Kirsch, Gilbert oth Boulcina, Raouf oth Debache, Abdelmadjid oth Enthalten in Elsevier Ali, Imran ELSEVIER Artificial neural network modelling of amido black dye sorption on iron composite nano material: Kinetics and thermodynamics studies 2017 New York, NY [u.a.] (DE-627)ELV005044758 volume:1209 year:2020 day:5 month:06 pages:0 https://doi.org/10.1016/j.molstruc.2020.127902 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 35.21 Lösungen Flüssigkeiten Physikalische Chemie VZ AR 1209 2020 5 0605 0 |
| allfieldsGer |
10.1016/j.molstruc.2020.127902 doi /cbs_pica/cbs_olc/import_discovery/elsevier/einzuspielen/GBV00000000000955.pica (DE-627)ELV049823728 (ELSEVIER)S0022-2860(20)30226-X DE-627 ger DE-627 rakwb eng 540 VZ 35.21 bkl Derabli, Chamseddine verfasserin aut Synthesis, biological evaluation and molecular docking studies of novel 2-alkylthiopyrimidino-tacrines as anticholinesterase agents and their DFT calculations 2020transfer abstract nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier To search for effective and selective inhibitors of cholinesterases (AChE and BuChE), a series of poly-functionalized Tacrine-derived compounds specifically 2-(alkylthio)-4-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-5-amines were designed an synthesized via Friedlander reaction. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data (1H NMR, 13C NMR) and elemental analyses (CHNS). Compounds 3a-h were evaluated for their abilities to inhibit AChE and BChE. The obtained biological results revealed that some synthesized compounds displayed higher anti-cholinesterase activity in comparison to Galantamine. Among them, compound 3d bearing S-ethyl and 4-chlorophenyl moieties showed the most potent activity against AChE/BuChE with IC50s values of 4,32 and 15,10 μM, respectively. The anti-AChE activity of 3d was 5-fold more than that of reference drug Galantamine. Moreover, molecular docking studies were performed for the most active derivatives, 3d and 3c, in which binding mode between these compounds and the receptors were determined. Density functional theory (DFT) method at B3LYP/6–311++G (d,p) level of theory was employed to gain insights into the molecular structure of the target compounds. Molecular electrostatic potential (MEP) mapping, reactivity indices such as electronegativity, electrophilic index, softness and hardness as well as frontier molecular orbitals HOMO-LUMO have been investigated for 3a-3c as representative compounds. In addition, their antiradical activity has been predicted by computing bond dissociation enthalpies (BDEs). To search for effective and selective inhibitors of cholinesterases (AChE and BuChE), a series of poly-functionalized Tacrine-derived compounds specifically 2-(alkylthio)-4-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-5-amines were designed an synthesized via Friedlander reaction. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data (1H NMR, 13C NMR) and elemental analyses (CHNS). Compounds 3a-h were evaluated for their abilities to inhibit AChE and BChE. The obtained biological results revealed that some synthesized compounds displayed higher anti-cholinesterase activity in comparison to Galantamine. Among them, compound 3d bearing S-ethyl and 4-chlorophenyl moieties showed the most potent activity against AChE/BuChE with IC50s values of 4,32 and 15,10 μM, respectively. The anti-AChE activity of 3d was 5-fold more than that of reference drug Galantamine. Moreover, molecular docking studies were performed for the most active derivatives, 3d and 3c, in which binding mode between these compounds and the receptors were determined. Density functional theory (DFT) method at B3LYP/6–311++G (d,p) level of theory was employed to gain insights into the molecular structure of the target compounds. Molecular electrostatic potential (MEP) mapping, reactivity indices such as electronegativity, electrophilic index, softness and hardness as well as frontier molecular orbitals HOMO-LUMO have been investigated for 3a-3c as representative compounds. In addition, their antiradical activity has been predicted by computing bond dissociation enthalpies (BDEs). Alzheimer’s disease Elsevier Inhibitors of cholinesterases Elsevier 2-Alkylthiopyrimidino-Tacrines Elsevier Molecular docking Elsevier DFT calculations Elsevier Boulebd, Houssem oth Abdelwahab, Ahmed B. oth Boucheraine, Celia oth Zerrouki, Sarah oth Bensouici, Chawki oth Kirsch, Gilbert oth Boulcina, Raouf oth Debache, Abdelmadjid oth Enthalten in Elsevier Ali, Imran ELSEVIER Artificial neural network modelling of amido black dye sorption on iron composite nano material: Kinetics and thermodynamics studies 2017 New York, NY [u.a.] (DE-627)ELV005044758 volume:1209 year:2020 day:5 month:06 pages:0 https://doi.org/10.1016/j.molstruc.2020.127902 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 35.21 Lösungen Flüssigkeiten Physikalische Chemie VZ AR 1209 2020 5 0605 0 |
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10.1016/j.molstruc.2020.127902 doi /cbs_pica/cbs_olc/import_discovery/elsevier/einzuspielen/GBV00000000000955.pica (DE-627)ELV049823728 (ELSEVIER)S0022-2860(20)30226-X DE-627 ger DE-627 rakwb eng 540 VZ 35.21 bkl Derabli, Chamseddine verfasserin aut Synthesis, biological evaluation and molecular docking studies of novel 2-alkylthiopyrimidino-tacrines as anticholinesterase agents and their DFT calculations 2020transfer abstract nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier To search for effective and selective inhibitors of cholinesterases (AChE and BuChE), a series of poly-functionalized Tacrine-derived compounds specifically 2-(alkylthio)-4-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-5-amines were designed an synthesized via Friedlander reaction. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data (1H NMR, 13C NMR) and elemental analyses (CHNS). Compounds 3a-h were evaluated for their abilities to inhibit AChE and BChE. The obtained biological results revealed that some synthesized compounds displayed higher anti-cholinesterase activity in comparison to Galantamine. Among them, compound 3d bearing S-ethyl and 4-chlorophenyl moieties showed the most potent activity against AChE/BuChE with IC50s values of 4,32 and 15,10 μM, respectively. The anti-AChE activity of 3d was 5-fold more than that of reference drug Galantamine. Moreover, molecular docking studies were performed for the most active derivatives, 3d and 3c, in which binding mode between these compounds and the receptors were determined. Density functional theory (DFT) method at B3LYP/6–311++G (d,p) level of theory was employed to gain insights into the molecular structure of the target compounds. Molecular electrostatic potential (MEP) mapping, reactivity indices such as electronegativity, electrophilic index, softness and hardness as well as frontier molecular orbitals HOMO-LUMO have been investigated for 3a-3c as representative compounds. In addition, their antiradical activity has been predicted by computing bond dissociation enthalpies (BDEs). To search for effective and selective inhibitors of cholinesterases (AChE and BuChE), a series of poly-functionalized Tacrine-derived compounds specifically 2-(alkylthio)-4-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-5-amines were designed an synthesized via Friedlander reaction. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data (1H NMR, 13C NMR) and elemental analyses (CHNS). Compounds 3a-h were evaluated for their abilities to inhibit AChE and BChE. The obtained biological results revealed that some synthesized compounds displayed higher anti-cholinesterase activity in comparison to Galantamine. Among them, compound 3d bearing S-ethyl and 4-chlorophenyl moieties showed the most potent activity against AChE/BuChE with IC50s values of 4,32 and 15,10 μM, respectively. The anti-AChE activity of 3d was 5-fold more than that of reference drug Galantamine. Moreover, molecular docking studies were performed for the most active derivatives, 3d and 3c, in which binding mode between these compounds and the receptors were determined. Density functional theory (DFT) method at B3LYP/6–311++G (d,p) level of theory was employed to gain insights into the molecular structure of the target compounds. Molecular electrostatic potential (MEP) mapping, reactivity indices such as electronegativity, electrophilic index, softness and hardness as well as frontier molecular orbitals HOMO-LUMO have been investigated for 3a-3c as representative compounds. In addition, their antiradical activity has been predicted by computing bond dissociation enthalpies (BDEs). Alzheimer’s disease Elsevier Inhibitors of cholinesterases Elsevier 2-Alkylthiopyrimidino-Tacrines Elsevier Molecular docking Elsevier DFT calculations Elsevier Boulebd, Houssem oth Abdelwahab, Ahmed B. oth Boucheraine, Celia oth Zerrouki, Sarah oth Bensouici, Chawki oth Kirsch, Gilbert oth Boulcina, Raouf oth Debache, Abdelmadjid oth Enthalten in Elsevier Ali, Imran ELSEVIER Artificial neural network modelling of amido black dye sorption on iron composite nano material: Kinetics and thermodynamics studies 2017 New York, NY [u.a.] (DE-627)ELV005044758 volume:1209 year:2020 day:5 month:06 pages:0 https://doi.org/10.1016/j.molstruc.2020.127902 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 35.21 Lösungen Flüssigkeiten Physikalische Chemie VZ AR 1209 2020 5 0605 0 |
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Synthesis, biological evaluation and molecular docking studies of novel 2-alkylthiopyrimidino-tacrines as anticholinesterase agents and their DFT calculations |
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To search for effective and selective inhibitors of cholinesterases (AChE and BuChE), a series of poly-functionalized Tacrine-derived compounds specifically 2-(alkylthio)-4-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-5-amines were designed an synthesized via Friedlander reaction. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data (1H NMR, 13C NMR) and elemental analyses (CHNS). Compounds 3a-h were evaluated for their abilities to inhibit AChE and BChE. The obtained biological results revealed that some synthesized compounds displayed higher anti-cholinesterase activity in comparison to Galantamine. Among them, compound 3d bearing S-ethyl and 4-chlorophenyl moieties showed the most potent activity against AChE/BuChE with IC50s values of 4,32 and 15,10 μM, respectively. The anti-AChE activity of 3d was 5-fold more than that of reference drug Galantamine. Moreover, molecular docking studies were performed for the most active derivatives, 3d and 3c, in which binding mode between these compounds and the receptors were determined. Density functional theory (DFT) method at B3LYP/6–311++G (d,p) level of theory was employed to gain insights into the molecular structure of the target compounds. Molecular electrostatic potential (MEP) mapping, reactivity indices such as electronegativity, electrophilic index, softness and hardness as well as frontier molecular orbitals HOMO-LUMO have been investigated for 3a-3c as representative compounds. In addition, their antiradical activity has been predicted by computing bond dissociation enthalpies (BDEs). |
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To search for effective and selective inhibitors of cholinesterases (AChE and BuChE), a series of poly-functionalized Tacrine-derived compounds specifically 2-(alkylthio)-4-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-5-amines were designed an synthesized via Friedlander reaction. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data (1H NMR, 13C NMR) and elemental analyses (CHNS). Compounds 3a-h were evaluated for their abilities to inhibit AChE and BChE. The obtained biological results revealed that some synthesized compounds displayed higher anti-cholinesterase activity in comparison to Galantamine. Among them, compound 3d bearing S-ethyl and 4-chlorophenyl moieties showed the most potent activity against AChE/BuChE with IC50s values of 4,32 and 15,10 μM, respectively. The anti-AChE activity of 3d was 5-fold more than that of reference drug Galantamine. Moreover, molecular docking studies were performed for the most active derivatives, 3d and 3c, in which binding mode between these compounds and the receptors were determined. Density functional theory (DFT) method at B3LYP/6–311++G (d,p) level of theory was employed to gain insights into the molecular structure of the target compounds. Molecular electrostatic potential (MEP) mapping, reactivity indices such as electronegativity, electrophilic index, softness and hardness as well as frontier molecular orbitals HOMO-LUMO have been investigated for 3a-3c as representative compounds. In addition, their antiradical activity has been predicted by computing bond dissociation enthalpies (BDEs). |
| abstract_unstemmed |
To search for effective and selective inhibitors of cholinesterases (AChE and BuChE), a series of poly-functionalized Tacrine-derived compounds specifically 2-(alkylthio)-4-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-5-amines were designed an synthesized via Friedlander reaction. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data (1H NMR, 13C NMR) and elemental analyses (CHNS). Compounds 3a-h were evaluated for their abilities to inhibit AChE and BChE. The obtained biological results revealed that some synthesized compounds displayed higher anti-cholinesterase activity in comparison to Galantamine. Among them, compound 3d bearing S-ethyl and 4-chlorophenyl moieties showed the most potent activity against AChE/BuChE with IC50s values of 4,32 and 15,10 μM, respectively. The anti-AChE activity of 3d was 5-fold more than that of reference drug Galantamine. Moreover, molecular docking studies were performed for the most active derivatives, 3d and 3c, in which binding mode between these compounds and the receptors were determined. Density functional theory (DFT) method at B3LYP/6–311++G (d,p) level of theory was employed to gain insights into the molecular structure of the target compounds. Molecular electrostatic potential (MEP) mapping, reactivity indices such as electronegativity, electrophilic index, softness and hardness as well as frontier molecular orbitals HOMO-LUMO have been investigated for 3a-3c as representative compounds. In addition, their antiradical activity has been predicted by computing bond dissociation enthalpies (BDEs). |
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| title_short |
Synthesis, biological evaluation and molecular docking studies of novel 2-alkylthiopyrimidino-tacrines as anticholinesterase agents and their DFT calculations |
| url |
https://doi.org/10.1016/j.molstruc.2020.127902 |
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Boulebd, Houssem Abdelwahab, Ahmed B. Boucheraine, Celia Zerrouki, Sarah Bensouici, Chawki Kirsch, Gilbert Boulcina, Raouf Debache, Abdelmadjid |
| author2Str |
Boulebd, Houssem Abdelwahab, Ahmed B. Boucheraine, Celia Zerrouki, Sarah Bensouici, Chawki Kirsch, Gilbert Boulcina, Raouf Debache, Abdelmadjid |
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| doi_str |
10.1016/j.molstruc.2020.127902 |
| up_date |
2024-07-06T22:37:56.755Z |
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