SYNTHESIS AND EVALUATION OF 5-(6-METHOXYNAPHTHALEN-2-YL)-1-ARYL-1-(4-(TRIFLUOROMETHYL)PHENYLAMINO)PENTAN-3-ONE AS POTENTIAL ANTIDIABETIC AGENTS
We wish to report a set of seventeen ketones bearing nabumetone and trifluoro- methylaniline(TFMA) moieties. Synthesized via direct Mannich reaction in a solution of ethanol- chloroform catalyzed by concentrated hydrochloric acid, the chemical structures of these compounds were characterized by IR,...
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Sociedad Chilena de Química
2011
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oai:scielo:S0717-970720110004000232012-03-06SYNTHESIS AND EVALUATION OF 5-(6-METHOXYNAPHTHALEN-2-YL)-1-ARYL-1-(4-(TRIFLUOROMETHYL)PHENYLAMINO)PENTAN-3-ONE AS POTENTIAL ANTIDIABETIC AGENTSYAN,HAN HAIFANG,YAN JUJIN,XUFei,YELI,FANGUANG-MING,ZHOUDA-CHENG,YANG Diabetes Mellitus PPRE α-Glucosidase PTP 1B ketones Mannich base We wish to report a set of seventeen ketones bearing nabumetone and trifluoro- methylaniline(TFMA) moieties. Synthesized via direct Mannich reaction in a solution of ethanol- chloroform catalyzed by concentrated hydrochloric acid, the chemical structures of these compounds were characterized by IR, ¹H NMR, 13C NMR, ESI MS and HR MS. Studies on their antidiabetic activities revealed that all title compounds possessed moderate α-glucosidase inhibitory activities and protein tyrosine phosphatase 1B (PTP 1B) inhibitory activities. Among them, a few compounds also exhibit considerable peroxisome proliferator-activated receptor response element (PPRE) agonist activity, in particular the relative PPRE agonist activity of compounds 1r and 1l reached 54.02% and 57.60%, respectively. These results represent significant examples of new molecular type for antidiabetic agents that merit further evaluation.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.56 n.4 20112011-12-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072011000400023en10.4067/S0717-97072011000400023 |
institution |
Scielo Chile |
collection |
Scielo Chile |
language |
English |
topic |
Diabetes Mellitus PPRE α-Glucosidase PTP 1B ketones Mannich base |
spellingShingle |
Diabetes Mellitus PPRE α-Glucosidase PTP 1B ketones Mannich base YAN,HAN HAI FANG,YAN JU JIN,XU Fei,YE LI,FAN GUANG-MING,ZHOU DA-CHENG,YANG SYNTHESIS AND EVALUATION OF 5-(6-METHOXYNAPHTHALEN-2-YL)-1-ARYL-1-(4-(TRIFLUOROMETHYL)PHENYLAMINO)PENTAN-3-ONE AS POTENTIAL ANTIDIABETIC AGENTS |
description |
We wish to report a set of seventeen ketones bearing nabumetone and trifluoro- methylaniline(TFMA) moieties. Synthesized via direct Mannich reaction in a solution of ethanol- chloroform catalyzed by concentrated hydrochloric acid, the chemical structures of these compounds were characterized by IR, ¹H NMR, 13C NMR, ESI MS and HR MS. Studies on their antidiabetic activities revealed that all title compounds possessed moderate α-glucosidase inhibitory activities and protein tyrosine phosphatase 1B (PTP 1B) inhibitory activities. Among them, a few compounds also exhibit considerable peroxisome proliferator-activated receptor response element (PPRE) agonist activity, in particular the relative PPRE agonist activity of compounds 1r and 1l reached 54.02% and 57.60%, respectively. These results represent significant examples of new molecular type for antidiabetic agents that merit further evaluation. |
author |
YAN,HAN HAI FANG,YAN JU JIN,XU Fei,YE LI,FAN GUANG-MING,ZHOU DA-CHENG,YANG |
author_facet |
YAN,HAN HAI FANG,YAN JU JIN,XU Fei,YE LI,FAN GUANG-MING,ZHOU DA-CHENG,YANG |
author_sort |
YAN,HAN HAI |
title |
SYNTHESIS AND EVALUATION OF 5-(6-METHOXYNAPHTHALEN-2-YL)-1-ARYL-1-(4-(TRIFLUOROMETHYL)PHENYLAMINO)PENTAN-3-ONE AS POTENTIAL ANTIDIABETIC AGENTS |
title_short |
SYNTHESIS AND EVALUATION OF 5-(6-METHOXYNAPHTHALEN-2-YL)-1-ARYL-1-(4-(TRIFLUOROMETHYL)PHENYLAMINO)PENTAN-3-ONE AS POTENTIAL ANTIDIABETIC AGENTS |
title_full |
SYNTHESIS AND EVALUATION OF 5-(6-METHOXYNAPHTHALEN-2-YL)-1-ARYL-1-(4-(TRIFLUOROMETHYL)PHENYLAMINO)PENTAN-3-ONE AS POTENTIAL ANTIDIABETIC AGENTS |
title_fullStr |
SYNTHESIS AND EVALUATION OF 5-(6-METHOXYNAPHTHALEN-2-YL)-1-ARYL-1-(4-(TRIFLUOROMETHYL)PHENYLAMINO)PENTAN-3-ONE AS POTENTIAL ANTIDIABETIC AGENTS |
title_full_unstemmed |
SYNTHESIS AND EVALUATION OF 5-(6-METHOXYNAPHTHALEN-2-YL)-1-ARYL-1-(4-(TRIFLUOROMETHYL)PHENYLAMINO)PENTAN-3-ONE AS POTENTIAL ANTIDIABETIC AGENTS |
title_sort |
synthesis and evaluation of 5-(6-methoxynaphthalen-2-yl)-1-aryl-1-(4-(trifluoromethyl)phenylamino)pentan-3-one as potential antidiabetic agents |
publisher |
Sociedad Chilena de Química |
publishDate |
2011 |
url |
http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072011000400023 |
work_keys_str_mv |
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_version_ |
1718445457106010112 |