Coupling of acceptor-substituted diazo compounds and tertiary thioamides: synthesis of enamino carbonyl compounds and their pharmacological evaluation

Jim Secka, Arpan Pal, Francis A. Acquah, Blaine H.M. Mooers, Anand B. Karki, Dania Mahjoub, Mohamed K. Fakhr, David R. Wallace, Takuya Okada, Naoki Toyooka, Adama Kuta, Naga Koduri, Deacon Herndon, Kenneth P. Roberts, Zhiguo Wang, Bethany Hileman, Nisha Rajagopal, Syed R. Hussaini

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2 Scopus citations

Abstract

This paper describes the synthesis of enamino carbonyl compounds by the copper(i)-catalyzed coupling of acceptor-substituted diazo compounds and tertiary thioamides. We plan to use this method to synthesize indolizidine (−)-237D analogs to find α6-selective antismoking agents. Therefore, we also performed in silico α6-nAchRs binding studies of selected products. Compounds with low root-mean-square deviation values showed more favorable binding free energies. We also report preliminary pharmacokinetic data on indolizidine (−)-237D and found it to have weak activity at CYP3A4. In addition, as enamino carbonyl compounds are also known for antimicrobial properties, we screened previously reported and new enamino carbonyl compounds for antibacterial, antimicrobial, and antifungal properties. Eleven compounds showed significant antimicrobial activities.

Original languageEnglish
Pages (from-to)19431-19444
Number of pages14
JournalRSC Advances
Volume12
Issue number30
DOIs
StatePublished - 5 Jul 2022

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