Improved Synthesis of Asymmetric Curcuminoids and Their Assessment as Antioxidants

In this paper, the syntheses of twelve asymmetric curcumin analogs using Pabon’s method are reported. Generally, the previously reported yields of asymmetric curcuminoids, such as <b<9a</b< (53%), <b<9c</b< (38%), and <b<9k</b< (38%), have been moderate or low. He...
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Autor*in:	Yang-Je Cheng [verfasserIn] Cai-Wei Li [verfasserIn] Cing-Ling Kuo [verfasserIn] Tzenge-Lien Shih [verfasserIn] Jih-Jung Chen [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2022

Schlagwörter:	asymmetric curcuminoids curcuminoids Pabon’s method 2,4-pentanedione

Übergeordnetes Werk:	In: Molecules - MDPI AG, 2003, 27(2022), 8, p 2547
Übergeordnetes Werk:	volume:27 ; year:2022 ; number:8, p 2547

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/molecules27082547

Katalog-ID:	DOAJ038612372

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520			\|a In this paper, the syntheses of twelve asymmetric curcumin analogs using Pabon’s method are reported. Generally, the previously reported yields of asymmetric curcuminoids, such as <b<9a</b< (53%), <b<9c</b< (38%), and <b<9k</b< (38%), have been moderate or low. Herein, we propose that the low yields were due to the presence of water and <i<n</i<-BuNH<sub<2</sub< in the reaction media. To prove this formulated hypothesis, we have demonstrated that the yields can be improved by adding molecular sieves (MS) (4 Å) to the reaction mixture, thus reducing the interference of water. Therefore, improved yields (41–76%) were obtained, except for <b<9b</b< (36.7%), <b<9g</b< (34%), and <b<9l</b< (39.5%). Furthermore, compounds <b<9b</b<, <b<9d</b<, <b<9e</b<, <b<9f</b<, <b<9g</b<, <b<9h</b<, <b<9i</b<, <b<9j</b<, and <b<9l</b< are reported herein for the first time. The structures of these synthetic compounds were determined by spectroscopic and mass spectrometry analyses. The free radical scavenging ability of these synthetic asymmetric curcuminoids was evaluated and compared to that of the positive control butylated hydroxytoluene (BHT). Among the synthesized asymmetric curcuminoids, compounds <b<9a</b< (IC<sub<50</sub< = 37.57 ± 0.89 μM) and <b<9e</b< (IC<sub<50</sub< = 37.17 ± 1.76 μM) possessed effective 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging abilities, and compounds <b<9h</b< (IC<sub<50</sub< = 11.36 ± 0.65 μM) and <b<9i</b< (IC<sub<50</sub< = 10.91 ± 0.77 μM) displayed potent 2,2’-azinobis-(3-ethylbenzthiazoline-6-sulphonate) (ABTS) radical scavenging abilities comparable to that of curcumin (IC<sub<50</sub< = 10.14 ± 1.04 μM). Furthermore, all the synthetic asymmetric curcuminoids were more active than BHT.
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allfields	10.3390/molecules27082547 doi (DE-627)DOAJ038612372 (DE-599)DOAJ8d1215e11a334eb8ae350a5c8a02a4c2 DE-627 ger DE-627 rakwb eng QD241-441 Yang-Je Cheng verfasserin aut Improved Synthesis of Asymmetric Curcuminoids and Their Assessment as Antioxidants 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this paper, the syntheses of twelve asymmetric curcumin analogs using Pabon’s method are reported. Generally, the previously reported yields of asymmetric curcuminoids, such as <b<9a</b< (53%), <b<9c</b< (38%), and <b<9k</b< (38%), have been moderate or low. Herein, we propose that the low yields were due to the presence of water and <i<n</i<-BuNH<sub<2</sub< in the reaction media. To prove this formulated hypothesis, we have demonstrated that the yields can be improved by adding molecular sieves (MS) (4 Å) to the reaction mixture, thus reducing the interference of water. Therefore, improved yields (41–76%) were obtained, except for <b<9b</b< (36.7%), <b<9g</b< (34%), and <b<9l</b< (39.5%). Furthermore, compounds <b<9b</b<, <b<9d</b<, <b<9e</b<, <b<9f</b<, <b<9g</b<, <b<9h</b<, <b<9i</b<, <b<9j</b<, and <b<9l</b< are reported herein for the first time. The structures of these synthetic compounds were determined by spectroscopic and mass spectrometry analyses. The free radical scavenging ability of these synthetic asymmetric curcuminoids was evaluated and compared to that of the positive control butylated hydroxytoluene (BHT). Among the synthesized asymmetric curcuminoids, compounds <b<9a</b< (IC<sub<50</sub< = 37.57 ± 0.89 μM) and <b<9e</b< (IC<sub<50</sub< = 37.17 ± 1.76 μM) possessed effective 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging abilities, and compounds <b<9h</b< (IC<sub<50</sub< = 11.36 ± 0.65 μM) and <b<9i</b< (IC<sub<50</sub< = 10.91 ± 0.77 μM) displayed potent 2,2’-azinobis-(3-ethylbenzthiazoline-6-sulphonate) (ABTS) radical scavenging abilities comparable to that of curcumin (IC<sub<50</sub< = 10.14 ± 1.04 μM). Furthermore, all the synthetic asymmetric curcuminoids were more active than BHT. asymmetric curcuminoids curcuminoids Pabon’s method 2,4-pentanedione Organic chemistry Cai-Wei Li verfasserin aut Cing-Ling Kuo verfasserin aut Tzenge-Lien Shih verfasserin aut Jih-Jung Chen verfasserin aut In Molecules MDPI AG, 2003 27(2022), 8, p 2547 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:27 year:2022 number:8, p 2547 https://doi.org/10.3390/molecules27082547 kostenfrei https://doaj.org/article/8d1215e11a334eb8ae350a5c8a02a4c2 kostenfrei https://www.mdpi.com/1420-3049/27/8/2547 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 27 2022 8, p 2547
spelling	10.3390/molecules27082547 doi (DE-627)DOAJ038612372 (DE-599)DOAJ8d1215e11a334eb8ae350a5c8a02a4c2 DE-627 ger DE-627 rakwb eng QD241-441 Yang-Je Cheng verfasserin aut Improved Synthesis of Asymmetric Curcuminoids and Their Assessment as Antioxidants 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this paper, the syntheses of twelve asymmetric curcumin analogs using Pabon’s method are reported. Generally, the previously reported yields of asymmetric curcuminoids, such as <b<9a</b< (53%), <b<9c</b< (38%), and <b<9k</b< (38%), have been moderate or low. Herein, we propose that the low yields were due to the presence of water and <i<n</i<-BuNH<sub<2</sub< in the reaction media. To prove this formulated hypothesis, we have demonstrated that the yields can be improved by adding molecular sieves (MS) (4 Å) to the reaction mixture, thus reducing the interference of water. Therefore, improved yields (41–76%) were obtained, except for <b<9b</b< (36.7%), <b<9g</b< (34%), and <b<9l</b< (39.5%). Furthermore, compounds <b<9b</b<, <b<9d</b<, <b<9e</b<, <b<9f</b<, <b<9g</b<, <b<9h</b<, <b<9i</b<, <b<9j</b<, and <b<9l</b< are reported herein for the first time. The structures of these synthetic compounds were determined by spectroscopic and mass spectrometry analyses. The free radical scavenging ability of these synthetic asymmetric curcuminoids was evaluated and compared to that of the positive control butylated hydroxytoluene (BHT). Among the synthesized asymmetric curcuminoids, compounds <b<9a</b< (IC<sub<50</sub< = 37.57 ± 0.89 μM) and <b<9e</b< (IC<sub<50</sub< = 37.17 ± 1.76 μM) possessed effective 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging abilities, and compounds <b<9h</b< (IC<sub<50</sub< = 11.36 ± 0.65 μM) and <b<9i</b< (IC<sub<50</sub< = 10.91 ± 0.77 μM) displayed potent 2,2’-azinobis-(3-ethylbenzthiazoline-6-sulphonate) (ABTS) radical scavenging abilities comparable to that of curcumin (IC<sub<50</sub< = 10.14 ± 1.04 μM). Furthermore, all the synthetic asymmetric curcuminoids were more active than BHT. asymmetric curcuminoids curcuminoids Pabon’s method 2,4-pentanedione Organic chemistry Cai-Wei Li verfasserin aut Cing-Ling Kuo verfasserin aut Tzenge-Lien Shih verfasserin aut Jih-Jung Chen verfasserin aut In Molecules MDPI AG, 2003 27(2022), 8, p 2547 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:27 year:2022 number:8, p 2547 https://doi.org/10.3390/molecules27082547 kostenfrei https://doaj.org/article/8d1215e11a334eb8ae350a5c8a02a4c2 kostenfrei https://www.mdpi.com/1420-3049/27/8/2547 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 27 2022 8, p 2547
allfields_unstemmed	10.3390/molecules27082547 doi (DE-627)DOAJ038612372 (DE-599)DOAJ8d1215e11a334eb8ae350a5c8a02a4c2 DE-627 ger DE-627 rakwb eng QD241-441 Yang-Je Cheng verfasserin aut Improved Synthesis of Asymmetric Curcuminoids and Their Assessment as Antioxidants 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this paper, the syntheses of twelve asymmetric curcumin analogs using Pabon’s method are reported. Generally, the previously reported yields of asymmetric curcuminoids, such as <b<9a</b< (53%), <b<9c</b< (38%), and <b<9k</b< (38%), have been moderate or low. Herein, we propose that the low yields were due to the presence of water and <i<n</i<-BuNH<sub<2</sub< in the reaction media. To prove this formulated hypothesis, we have demonstrated that the yields can be improved by adding molecular sieves (MS) (4 Å) to the reaction mixture, thus reducing the interference of water. Therefore, improved yields (41–76%) were obtained, except for <b<9b</b< (36.7%), <b<9g</b< (34%), and <b<9l</b< (39.5%). Furthermore, compounds <b<9b</b<, <b<9d</b<, <b<9e</b<, <b<9f</b<, <b<9g</b<, <b<9h</b<, <b<9i</b<, <b<9j</b<, and <b<9l</b< are reported herein for the first time. The structures of these synthetic compounds were determined by spectroscopic and mass spectrometry analyses. The free radical scavenging ability of these synthetic asymmetric curcuminoids was evaluated and compared to that of the positive control butylated hydroxytoluene (BHT). Among the synthesized asymmetric curcuminoids, compounds <b<9a</b< (IC<sub<50</sub< = 37.57 ± 0.89 μM) and <b<9e</b< (IC<sub<50</sub< = 37.17 ± 1.76 μM) possessed effective 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging abilities, and compounds <b<9h</b< (IC<sub<50</sub< = 11.36 ± 0.65 μM) and <b<9i</b< (IC<sub<50</sub< = 10.91 ± 0.77 μM) displayed potent 2,2’-azinobis-(3-ethylbenzthiazoline-6-sulphonate) (ABTS) radical scavenging abilities comparable to that of curcumin (IC<sub<50</sub< = 10.14 ± 1.04 μM). Furthermore, all the synthetic asymmetric curcuminoids were more active than BHT. asymmetric curcuminoids curcuminoids Pabon’s method 2,4-pentanedione Organic chemistry Cai-Wei Li verfasserin aut Cing-Ling Kuo verfasserin aut Tzenge-Lien Shih verfasserin aut Jih-Jung Chen verfasserin aut In Molecules MDPI AG, 2003 27(2022), 8, p 2547 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:27 year:2022 number:8, p 2547 https://doi.org/10.3390/molecules27082547 kostenfrei https://doaj.org/article/8d1215e11a334eb8ae350a5c8a02a4c2 kostenfrei https://www.mdpi.com/1420-3049/27/8/2547 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 27 2022 8, p 2547
allfieldsGer	10.3390/molecules27082547 doi (DE-627)DOAJ038612372 (DE-599)DOAJ8d1215e11a334eb8ae350a5c8a02a4c2 DE-627 ger DE-627 rakwb eng QD241-441 Yang-Je Cheng verfasserin aut Improved Synthesis of Asymmetric Curcuminoids and Their Assessment as Antioxidants 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this paper, the syntheses of twelve asymmetric curcumin analogs using Pabon’s method are reported. Generally, the previously reported yields of asymmetric curcuminoids, such as <b<9a</b< (53%), <b<9c</b< (38%), and <b<9k</b< (38%), have been moderate or low. Herein, we propose that the low yields were due to the presence of water and <i<n</i<-BuNH<sub<2</sub< in the reaction media. To prove this formulated hypothesis, we have demonstrated that the yields can be improved by adding molecular sieves (MS) (4 Å) to the reaction mixture, thus reducing the interference of water. Therefore, improved yields (41–76%) were obtained, except for <b<9b</b< (36.7%), <b<9g</b< (34%), and <b<9l</b< (39.5%). Furthermore, compounds <b<9b</b<, <b<9d</b<, <b<9e</b<, <b<9f</b<, <b<9g</b<, <b<9h</b<, <b<9i</b<, <b<9j</b<, and <b<9l</b< are reported herein for the first time. The structures of these synthetic compounds were determined by spectroscopic and mass spectrometry analyses. The free radical scavenging ability of these synthetic asymmetric curcuminoids was evaluated and compared to that of the positive control butylated hydroxytoluene (BHT). Among the synthesized asymmetric curcuminoids, compounds <b<9a</b< (IC<sub<50</sub< = 37.57 ± 0.89 μM) and <b<9e</b< (IC<sub<50</sub< = 37.17 ± 1.76 μM) possessed effective 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging abilities, and compounds <b<9h</b< (IC<sub<50</sub< = 11.36 ± 0.65 μM) and <b<9i</b< (IC<sub<50</sub< = 10.91 ± 0.77 μM) displayed potent 2,2’-azinobis-(3-ethylbenzthiazoline-6-sulphonate) (ABTS) radical scavenging abilities comparable to that of curcumin (IC<sub<50</sub< = 10.14 ± 1.04 μM). Furthermore, all the synthetic asymmetric curcuminoids were more active than BHT. asymmetric curcuminoids curcuminoids Pabon’s method 2,4-pentanedione Organic chemistry Cai-Wei Li verfasserin aut Cing-Ling Kuo verfasserin aut Tzenge-Lien Shih verfasserin aut Jih-Jung Chen verfasserin aut In Molecules MDPI AG, 2003 27(2022), 8, p 2547 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:27 year:2022 number:8, p 2547 https://doi.org/10.3390/molecules27082547 kostenfrei https://doaj.org/article/8d1215e11a334eb8ae350a5c8a02a4c2 kostenfrei https://www.mdpi.com/1420-3049/27/8/2547 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 27 2022 8, p 2547
allfieldsSound	10.3390/molecules27082547 doi (DE-627)DOAJ038612372 (DE-599)DOAJ8d1215e11a334eb8ae350a5c8a02a4c2 DE-627 ger DE-627 rakwb eng QD241-441 Yang-Je Cheng verfasserin aut Improved Synthesis of Asymmetric Curcuminoids and Their Assessment as Antioxidants 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this paper, the syntheses of twelve asymmetric curcumin analogs using Pabon’s method are reported. Generally, the previously reported yields of asymmetric curcuminoids, such as <b<9a</b< (53%), <b<9c</b< (38%), and <b<9k</b< (38%), have been moderate or low. Herein, we propose that the low yields were due to the presence of water and <i<n</i<-BuNH<sub<2</sub< in the reaction media. To prove this formulated hypothesis, we have demonstrated that the yields can be improved by adding molecular sieves (MS) (4 Å) to the reaction mixture, thus reducing the interference of water. Therefore, improved yields (41–76%) were obtained, except for <b<9b</b< (36.7%), <b<9g</b< (34%), and <b<9l</b< (39.5%). Furthermore, compounds <b<9b</b<, <b<9d</b<, <b<9e</b<, <b<9f</b<, <b<9g</b<, <b<9h</b<, <b<9i</b<, <b<9j</b<, and <b<9l</b< are reported herein for the first time. The structures of these synthetic compounds were determined by spectroscopic and mass spectrometry analyses. The free radical scavenging ability of these synthetic asymmetric curcuminoids was evaluated and compared to that of the positive control butylated hydroxytoluene (BHT). Among the synthesized asymmetric curcuminoids, compounds <b<9a</b< (IC<sub<50</sub< = 37.57 ± 0.89 μM) and <b<9e</b< (IC<sub<50</sub< = 37.17 ± 1.76 μM) possessed effective 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging abilities, and compounds <b<9h</b< (IC<sub<50</sub< = 11.36 ± 0.65 μM) and <b<9i</b< (IC<sub<50</sub< = 10.91 ± 0.77 μM) displayed potent 2,2’-azinobis-(3-ethylbenzthiazoline-6-sulphonate) (ABTS) radical scavenging abilities comparable to that of curcumin (IC<sub<50</sub< = 10.14 ± 1.04 μM). Furthermore, all the synthetic asymmetric curcuminoids were more active than BHT. asymmetric curcuminoids curcuminoids Pabon’s method 2,4-pentanedione Organic chemistry Cai-Wei Li verfasserin aut Cing-Ling Kuo verfasserin aut Tzenge-Lien Shih verfasserin aut Jih-Jung Chen verfasserin aut In Molecules MDPI AG, 2003 27(2022), 8, p 2547 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:27 year:2022 number:8, p 2547 https://doi.org/10.3390/molecules27082547 kostenfrei https://doaj.org/article/8d1215e11a334eb8ae350a5c8a02a4c2 kostenfrei https://www.mdpi.com/1420-3049/27/8/2547 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 27 2022 8, p 2547
language	English
source	In Molecules 27(2022), 8, p 2547 volume:27 year:2022 number:8, p 2547
sourceStr	In Molecules 27(2022), 8, p 2547 volume:27 year:2022 number:8, p 2547
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	asymmetric curcuminoids curcuminoids Pabon’s method 2,4-pentanedione Organic chemistry
isfreeaccess_bool	true
container_title	Molecules
authorswithroles_txt_mv	Yang-Je Cheng @@aut@@ Cai-Wei Li @@aut@@ Cing-Ling Kuo @@aut@@ Tzenge-Lien Shih @@aut@@ Jih-Jung Chen @@aut@@
publishDateDaySort_date	2022-01-01T00:00:00Z
hierarchy_top_id	311313132
id	DOAJ038612372
language_de	englisch
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Generally, the previously reported yields of asymmetric curcuminoids, such as <b<9a</b< (53%), <b<9c</b< (38%), and <b<9k</b< (38%), have been moderate or low. Herein, we propose that the low yields were due to the presence of water and <i<n</i<-BuNH<sub<2</sub< in the reaction media. To prove this formulated hypothesis, we have demonstrated that the yields can be improved by adding molecular sieves (MS) (4 Å) to the reaction mixture, thus reducing the interference of water. Therefore, improved yields (41–76%) were obtained, except for <b<9b</b< (36.7%), <b<9g</b< (34%), and <b<9l</b< (39.5%). Furthermore, compounds <b<9b</b<, <b<9d</b<, <b<9e</b<, <b<9f</b<, <b<9g</b<, <b<9h</b<, <b<9i</b<, <b<9j</b<, and <b<9l</b< are reported herein for the first time. The structures of these synthetic compounds were determined by spectroscopic and mass spectrometry analyses. The free radical scavenging ability of these synthetic asymmetric curcuminoids was evaluated and compared to that of the positive control butylated hydroxytoluene (BHT). Among the synthesized asymmetric curcuminoids, compounds <b<9a</b< (IC<sub<50</sub< = 37.57 ± 0.89 μM) and <b<9e</b< (IC<sub<50</sub< = 37.17 ± 1.76 μM) possessed effective 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging abilities, and compounds <b<9h</b< (IC<sub<50</sub< = 11.36 ± 0.65 μM) and <b<9i</b< (IC<sub<50</sub< = 10.91 ± 0.77 μM) displayed potent 2,2’-azinobis-(3-ethylbenzthiazoline-6-sulphonate) (ABTS) radical scavenging abilities comparable to that of curcumin (IC<sub<50</sub< = 10.14 ± 1.04 μM). 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callnumber-first	Q - Science
author	Yang-Je Cheng
spellingShingle	Yang-Je Cheng misc QD241-441 misc asymmetric curcuminoids misc curcuminoids misc Pabon’s method misc 2,4-pentanedione misc Organic chemistry Improved Synthesis of Asymmetric Curcuminoids and Their Assessment as Antioxidants
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topic_title	QD241-441 Improved Synthesis of Asymmetric Curcuminoids and Their Assessment as Antioxidants asymmetric curcuminoids curcuminoids Pabon’s method 2,4-pentanedione
topic	misc QD241-441 misc asymmetric curcuminoids misc curcuminoids misc Pabon’s method misc 2,4-pentanedione misc Organic chemistry
topic_unstemmed	misc QD241-441 misc asymmetric curcuminoids misc curcuminoids misc Pabon’s method misc 2,4-pentanedione misc Organic chemistry
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title	Improved Synthesis of Asymmetric Curcuminoids and Their Assessment as Antioxidants
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title_full	Improved Synthesis of Asymmetric Curcuminoids and Their Assessment as Antioxidants
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title_sort	improved synthesis of asymmetric curcuminoids and their assessment as antioxidants
callnumber	QD241-441
title_auth	Improved Synthesis of Asymmetric Curcuminoids and Their Assessment as Antioxidants
abstract	In this paper, the syntheses of twelve asymmetric curcumin analogs using Pabon’s method are reported. Generally, the previously reported yields of asymmetric curcuminoids, such as <b<9a</b< (53%), <b<9c</b< (38%), and <b<9k</b< (38%), have been moderate or low. Herein, we propose that the low yields were due to the presence of water and <i<n</i<-BuNH<sub<2</sub< in the reaction media. To prove this formulated hypothesis, we have demonstrated that the yields can be improved by adding molecular sieves (MS) (4 Å) to the reaction mixture, thus reducing the interference of water. Therefore, improved yields (41–76%) were obtained, except for <b<9b</b< (36.7%), <b<9g</b< (34%), and <b<9l</b< (39.5%). Furthermore, compounds <b<9b</b<, <b<9d</b<, <b<9e</b<, <b<9f</b<, <b<9g</b<, <b<9h</b<, <b<9i</b<, <b<9j</b<, and <b<9l</b< are reported herein for the first time. The structures of these synthetic compounds were determined by spectroscopic and mass spectrometry analyses. The free radical scavenging ability of these synthetic asymmetric curcuminoids was evaluated and compared to that of the positive control butylated hydroxytoluene (BHT). Among the synthesized asymmetric curcuminoids, compounds <b<9a</b< (IC<sub<50</sub< = 37.57 ± 0.89 μM) and <b<9e</b< (IC<sub<50</sub< = 37.17 ± 1.76 μM) possessed effective 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging abilities, and compounds <b<9h</b< (IC<sub<50</sub< = 11.36 ± 0.65 μM) and <b<9i</b< (IC<sub<50</sub< = 10.91 ± 0.77 μM) displayed potent 2,2’-azinobis-(3-ethylbenzthiazoline-6-sulphonate) (ABTS) radical scavenging abilities comparable to that of curcumin (IC<sub<50</sub< = 10.14 ± 1.04 μM). Furthermore, all the synthetic asymmetric curcuminoids were more active than BHT.
abstractGer	In this paper, the syntheses of twelve asymmetric curcumin analogs using Pabon’s method are reported. Generally, the previously reported yields of asymmetric curcuminoids, such as <b<9a</b< (53%), <b<9c</b< (38%), and <b<9k</b< (38%), have been moderate or low. Herein, we propose that the low yields were due to the presence of water and <i<n</i<-BuNH<sub<2</sub< in the reaction media. To prove this formulated hypothesis, we have demonstrated that the yields can be improved by adding molecular sieves (MS) (4 Å) to the reaction mixture, thus reducing the interference of water. Therefore, improved yields (41–76%) were obtained, except for <b<9b</b< (36.7%), <b<9g</b< (34%), and <b<9l</b< (39.5%). Furthermore, compounds <b<9b</b<, <b<9d</b<, <b<9e</b<, <b<9f</b<, <b<9g</b<, <b<9h</b<, <b<9i</b<, <b<9j</b<, and <b<9l</b< are reported herein for the first time. The structures of these synthetic compounds were determined by spectroscopic and mass spectrometry analyses. The free radical scavenging ability of these synthetic asymmetric curcuminoids was evaluated and compared to that of the positive control butylated hydroxytoluene (BHT). Among the synthesized asymmetric curcuminoids, compounds <b<9a</b< (IC<sub<50</sub< = 37.57 ± 0.89 μM) and <b<9e</b< (IC<sub<50</sub< = 37.17 ± 1.76 μM) possessed effective 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging abilities, and compounds <b<9h</b< (IC<sub<50</sub< = 11.36 ± 0.65 μM) and <b<9i</b< (IC<sub<50</sub< = 10.91 ± 0.77 μM) displayed potent 2,2’-azinobis-(3-ethylbenzthiazoline-6-sulphonate) (ABTS) radical scavenging abilities comparable to that of curcumin (IC<sub<50</sub< = 10.14 ± 1.04 μM). Furthermore, all the synthetic asymmetric curcuminoids were more active than BHT.
abstract_unstemmed	In this paper, the syntheses of twelve asymmetric curcumin analogs using Pabon’s method are reported. Generally, the previously reported yields of asymmetric curcuminoids, such as <b<9a</b< (53%), <b<9c</b< (38%), and <b<9k</b< (38%), have been moderate or low. Herein, we propose that the low yields were due to the presence of water and <i<n</i<-BuNH<sub<2</sub< in the reaction media. To prove this formulated hypothesis, we have demonstrated that the yields can be improved by adding molecular sieves (MS) (4 Å) to the reaction mixture, thus reducing the interference of water. Therefore, improved yields (41–76%) were obtained, except for <b<9b</b< (36.7%), <b<9g</b< (34%), and <b<9l</b< (39.5%). Furthermore, compounds <b<9b</b<, <b<9d</b<, <b<9e</b<, <b<9f</b<, <b<9g</b<, <b<9h</b<, <b<9i</b<, <b<9j</b<, and <b<9l</b< are reported herein for the first time. The structures of these synthetic compounds were determined by spectroscopic and mass spectrometry analyses. The free radical scavenging ability of these synthetic asymmetric curcuminoids was evaluated and compared to that of the positive control butylated hydroxytoluene (BHT). Among the synthesized asymmetric curcuminoids, compounds <b<9a</b< (IC<sub<50</sub< = 37.57 ± 0.89 μM) and <b<9e</b< (IC<sub<50</sub< = 37.17 ± 1.76 μM) possessed effective 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging abilities, and compounds <b<9h</b< (IC<sub<50</sub< = 11.36 ± 0.65 μM) and <b<9i</b< (IC<sub<50</sub< = 10.91 ± 0.77 μM) displayed potent 2,2’-azinobis-(3-ethylbenzthiazoline-6-sulphonate) (ABTS) radical scavenging abilities comparable to that of curcumin (IC<sub<50</sub< = 10.14 ± 1.04 μM). Furthermore, all the synthetic asymmetric curcuminoids were more active than BHT.
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title_short	Improved Synthesis of Asymmetric Curcuminoids and Their Assessment as Antioxidants
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