Synthesis, antileishmanial activity and structure–activity relationship of 1-N-X-phenyl-3-N′-Y-phenyl-benzamidines
Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treat...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Rodrigues-Santos, Cláudio Eduardo [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2013transfer abstract |
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| Schlagwörter: |
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| Umfang: |
9 |
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| Übergeordnetes Werk: |
Enthalten in: Electrochemical synthesis, photodegradation and antibacterial properties of PEG capped zinc oxide nanoparticles - Jose, Ajay ELSEVIER, 2018, Amsterdam [u.a.] |
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| Übergeordnetes Werk: |
volume:67 ; year:2013 ; pages:166-174 ; extent:9 |
| Links: |
|---|
| DOI / URN: |
10.1016/j.ejmech.2013.06.040 |
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| 245 | 1 | 0 | |a Synthesis, antileishmanial activity and structure–activity relationship of 1-N-X-phenyl-3-N′-Y-phenyl-benzamidines |
| 264 | 1 | |c 2013transfer abstract | |
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| 520 | |a Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series. | ||
| 520 | |a Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series. | ||
| 650 | 7 | |a Leishmania chagasi |2 Elsevier | |
| 650 | 7 | |a Leishmania braziliensis |2 Elsevier | |
| 650 | 7 | |a QSAR |2 Elsevier | |
| 650 | 7 | |a N,N′-Diphenyl-benzamidines |2 Elsevier | |
| 650 | 7 | |a Leishmania amazonensis |2 Elsevier | |
| 650 | 7 | |a Hansch model |2 Elsevier | |
| 700 | 1 | |a Leon, Leonor L. |4 oth | |
| 700 | 1 | |a Bortoluzzi, Adailton J. |4 oth | |
| 700 | 1 | |a Canto-Cavalheiro, Marilene Marcuzzo |4 oth | |
| 700 | 1 | |a Machado, Gérzia C. |4 oth | |
| 700 | 1 | |a Echevarria, Aurea |4 oth | |
| 773 | 0 | 8 | |i Enthalten in |n Elsevier Science |a Jose, Ajay ELSEVIER |t Electrochemical synthesis, photodegradation and antibacterial properties of PEG capped zinc oxide nanoparticles |d 2018 |g Amsterdam [u.a.] |w (DE-627)ELV000457477 |
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10.1016/j.ejmech.2013.06.040 doi GBVA2013007000026.pica (DE-627)ELV016734866 (ELSEVIER)S0223-5234(13)00408-X DE-627 ger DE-627 rakwb eng 610 610 DE-600 570 540 VZ BIODIV DE-30 fid 42.00 bkl Rodrigues-Santos, Cláudio Eduardo verfasserin aut Synthesis, antileishmanial activity and structure–activity relationship of 1-N-X-phenyl-3-N′-Y-phenyl-benzamidines 2013transfer abstract 9 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series. Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series. Leishmania chagasi Elsevier Leishmania braziliensis Elsevier QSAR Elsevier N,N′-Diphenyl-benzamidines Elsevier Leishmania amazonensis Elsevier Hansch model Elsevier Leon, Leonor L. oth Bortoluzzi, Adailton J. oth Canto-Cavalheiro, Marilene Marcuzzo oth Machado, Gérzia C. oth Echevarria, Aurea oth Enthalten in Elsevier Science Jose, Ajay ELSEVIER Electrochemical synthesis, photodegradation and antibacterial properties of PEG capped zinc oxide nanoparticles 2018 Amsterdam [u.a.] (DE-627)ELV000457477 volume:67 year:2013 pages:166-174 extent:9 https://doi.org/10.1016/j.ejmech.2013.06.040 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U FID-BIODIV SSG-OLC-PHA 42.00 Biologie: Allgemeines VZ AR 67 2013 166-174 9 045F 610 |
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10.1016/j.ejmech.2013.06.040 doi GBVA2013007000026.pica (DE-627)ELV016734866 (ELSEVIER)S0223-5234(13)00408-X DE-627 ger DE-627 rakwb eng 610 610 DE-600 570 540 VZ BIODIV DE-30 fid 42.00 bkl Rodrigues-Santos, Cláudio Eduardo verfasserin aut Synthesis, antileishmanial activity and structure–activity relationship of 1-N-X-phenyl-3-N′-Y-phenyl-benzamidines 2013transfer abstract 9 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series. Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series. Leishmania chagasi Elsevier Leishmania braziliensis Elsevier QSAR Elsevier N,N′-Diphenyl-benzamidines Elsevier Leishmania amazonensis Elsevier Hansch model Elsevier Leon, Leonor L. oth Bortoluzzi, Adailton J. oth Canto-Cavalheiro, Marilene Marcuzzo oth Machado, Gérzia C. oth Echevarria, Aurea oth Enthalten in Elsevier Science Jose, Ajay ELSEVIER Electrochemical synthesis, photodegradation and antibacterial properties of PEG capped zinc oxide nanoparticles 2018 Amsterdam [u.a.] (DE-627)ELV000457477 volume:67 year:2013 pages:166-174 extent:9 https://doi.org/10.1016/j.ejmech.2013.06.040 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U FID-BIODIV SSG-OLC-PHA 42.00 Biologie: Allgemeines VZ AR 67 2013 166-174 9 045F 610 |
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10.1016/j.ejmech.2013.06.040 doi GBVA2013007000026.pica (DE-627)ELV016734866 (ELSEVIER)S0223-5234(13)00408-X DE-627 ger DE-627 rakwb eng 610 610 DE-600 570 540 VZ BIODIV DE-30 fid 42.00 bkl Rodrigues-Santos, Cláudio Eduardo verfasserin aut Synthesis, antileishmanial activity and structure–activity relationship of 1-N-X-phenyl-3-N′-Y-phenyl-benzamidines 2013transfer abstract 9 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series. Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series. Leishmania chagasi Elsevier Leishmania braziliensis Elsevier QSAR Elsevier N,N′-Diphenyl-benzamidines Elsevier Leishmania amazonensis Elsevier Hansch model Elsevier Leon, Leonor L. oth Bortoluzzi, Adailton J. oth Canto-Cavalheiro, Marilene Marcuzzo oth Machado, Gérzia C. oth Echevarria, Aurea oth Enthalten in Elsevier Science Jose, Ajay ELSEVIER Electrochemical synthesis, photodegradation and antibacterial properties of PEG capped zinc oxide nanoparticles 2018 Amsterdam [u.a.] (DE-627)ELV000457477 volume:67 year:2013 pages:166-174 extent:9 https://doi.org/10.1016/j.ejmech.2013.06.040 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U FID-BIODIV SSG-OLC-PHA 42.00 Biologie: Allgemeines VZ AR 67 2013 166-174 9 045F 610 |
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10.1016/j.ejmech.2013.06.040 doi GBVA2013007000026.pica (DE-627)ELV016734866 (ELSEVIER)S0223-5234(13)00408-X DE-627 ger DE-627 rakwb eng 610 610 DE-600 570 540 VZ BIODIV DE-30 fid 42.00 bkl Rodrigues-Santos, Cláudio Eduardo verfasserin aut Synthesis, antileishmanial activity and structure–activity relationship of 1-N-X-phenyl-3-N′-Y-phenyl-benzamidines 2013transfer abstract 9 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series. Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series. Leishmania chagasi Elsevier Leishmania braziliensis Elsevier QSAR Elsevier N,N′-Diphenyl-benzamidines Elsevier Leishmania amazonensis Elsevier Hansch model Elsevier Leon, Leonor L. oth Bortoluzzi, Adailton J. oth Canto-Cavalheiro, Marilene Marcuzzo oth Machado, Gérzia C. oth Echevarria, Aurea oth Enthalten in Elsevier Science Jose, Ajay ELSEVIER Electrochemical synthesis, photodegradation and antibacterial properties of PEG capped zinc oxide nanoparticles 2018 Amsterdam [u.a.] (DE-627)ELV000457477 volume:67 year:2013 pages:166-174 extent:9 https://doi.org/10.1016/j.ejmech.2013.06.040 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U FID-BIODIV SSG-OLC-PHA 42.00 Biologie: Allgemeines VZ AR 67 2013 166-174 9 045F 610 |
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10.1016/j.ejmech.2013.06.040 doi GBVA2013007000026.pica (DE-627)ELV016734866 (ELSEVIER)S0223-5234(13)00408-X DE-627 ger DE-627 rakwb eng 610 610 DE-600 570 540 VZ BIODIV DE-30 fid 42.00 bkl Rodrigues-Santos, Cláudio Eduardo verfasserin aut Synthesis, antileishmanial activity and structure–activity relationship of 1-N-X-phenyl-3-N′-Y-phenyl-benzamidines 2013transfer abstract 9 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series. Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series. Leishmania chagasi Elsevier Leishmania braziliensis Elsevier QSAR Elsevier N,N′-Diphenyl-benzamidines Elsevier Leishmania amazonensis Elsevier Hansch model Elsevier Leon, Leonor L. oth Bortoluzzi, Adailton J. oth Canto-Cavalheiro, Marilene Marcuzzo oth Machado, Gérzia C. oth Echevarria, Aurea oth Enthalten in Elsevier Science Jose, Ajay ELSEVIER Electrochemical synthesis, photodegradation and antibacterial properties of PEG capped zinc oxide nanoparticles 2018 Amsterdam [u.a.] (DE-627)ELV000457477 volume:67 year:2013 pages:166-174 extent:9 https://doi.org/10.1016/j.ejmech.2013.06.040 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U FID-BIODIV SSG-OLC-PHA 42.00 Biologie: Allgemeines VZ AR 67 2013 166-174 9 045F 610 |
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Enthalten in Electrochemical synthesis, photodegradation and antibacterial properties of PEG capped zinc oxide nanoparticles Amsterdam [u.a.] volume:67 year:2013 pages:166-174 extent:9 |
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Synthesis, antileishmanial activity and structure–activity relationship of 1-N-X-phenyl-3-N′-Y-phenyl-benzamidines |
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Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series. |
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Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series. |
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Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series. |
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Synthesis, antileishmanial activity and structure–activity relationship of 1-N-X-phenyl-3-N′-Y-phenyl-benzamidines |
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Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series.</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">Two series of N,N′-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series.</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Leishmania chagasi</subfield><subfield code="2">Elsevier</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Leishmania braziliensis</subfield><subfield code="2">Elsevier</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">QSAR</subfield><subfield code="2">Elsevier</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">N,N′-Diphenyl-benzamidines</subfield><subfield code="2">Elsevier</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Leishmania amazonensis</subfield><subfield code="2">Elsevier</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Hansch model</subfield><subfield code="2">Elsevier</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Leon, Leonor L.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Bortoluzzi, Adailton J.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Canto-Cavalheiro, Marilene Marcuzzo</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Machado, Gérzia C.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Echevarria, Aurea</subfield><subfield code="4">oth</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">Enthalten in</subfield><subfield code="n">Elsevier Science</subfield><subfield code="a">Jose, Ajay ELSEVIER</subfield><subfield code="t">Electrochemical synthesis, photodegradation and antibacterial properties of PEG capped zinc oxide nanoparticles</subfield><subfield code="d">2018</subfield><subfield code="g">Amsterdam [u.a.]</subfield><subfield code="w">(DE-627)ELV000457477</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:67</subfield><subfield code="g">year:2013</subfield><subfield code="g">pages:166-174</subfield><subfield code="g">extent:9</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">https://doi.org/10.1016/j.ejmech.2013.06.040</subfield><subfield code="3">Volltext</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_U</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ELV</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SYSFLAG_U</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">FID-BIODIV</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SSG-OLC-PHA</subfield></datafield><datafield tag="936" ind1="b" ind2="k"><subfield code="a">42.00</subfield><subfield code="j">Biologie: Allgemeines</subfield><subfield code="q">VZ</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">67</subfield><subfield code="j">2013</subfield><subfield code="h">166-174</subfield><subfield code="g">9</subfield></datafield><datafield tag="953" ind1=" " ind2=" "><subfield code="2">045F</subfield><subfield code="a">610</subfield></datafield></record></collection>
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