Potent ACE inhibitors from 5-hydroxy indanone derivatives |
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Institution: | 1. Department of Chemistry, University of Science and Technology of China, Hefei 230026, PR China;2. The USTC-Anhui Tobacco Joint Laboratory of Chemistry and Combustion, Hefei 230066, PR China |
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Abstract: | A novel triazole derivatives(±)-2-(hydroxymethyl)-7,8-dihydro-1H-indeno5,4-b]furan-6(2H)-one (12a–j) were designed and synthesized by the reaction between racemic azide and terminal acetylenes under click chemistry reaction conditions followed by biological evaluation as angiotensin converting enzyme (ACE) inhibitors. β-Amino alcohol derivatives of 1-indanone (15a–l) were synthesized from 5-hydroxy indanone, it was reacted with epichlorohydrin and followed by oxirane ring opening with various piperazine derivatives. Among the newly synthesized compounds 12b (IC50: 1.388024 µM), 12g (IC50: 1.220696 µM), 12j (IC50: 1.312428 µM) and 15k (IC50: 1.349671 µM) and 15l (IC50: 1.330764 µM) emerged as most active non-carboxylic acid ACE inhibitors with minimal toxicity comparable to clinical drug Lisinopril. |
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Keywords: | Triazoles Epi-chlorohydrin Click chemistry Piperazines ACE inhibitors Hypertension |
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