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

被引：2

作者：

Secka, Jim ^{[1
,7
]}

Pal, Arpan ^{[1
,7
]}

Acquah, Francis A. ^{[2
,3
,4
]}

Mooers, Blaine H. M. ^{[2
,3
,4
]}

Karki, Anand B. ^{[5
]}

Mahjoub, Dania ^{[5
]}

Fakhr, Mohamed K. ^{[5
]}

Wallace, David R. ^{[6
]}

Okada, Takuya

Toyooka, Naoki

Kuta, Adama ^{[1
,7
]}

Koduri, Naga ^{[1
,7
]}

Herndon, Deacon ^{[1
,7
]}

Roberts, Kenneth P. ^{[1
,7
]}

Wang, Zhiguo ^{[7
]}

Hileman, Bethany ^{[1
,7
]}

Rajagopal, Nisha ^{[1
,7
]}

Hussaini, Syed R. ^{[1
,7
]}

机构：

[1] Univ Tulsa, Dept Chem & Biochem, 800 S Tucker Dr, Tulsa, OK 74104 USA

[2] Univ Oklahoma, Hlth Sci Ctr, Dept Biochem & Mol Biol, Oklahoma City, OK 73104 USA

[3] Univ Oklahoma Hlth Sci Ctr, Stephenson Canc Ctr, Oklahoma Hlth Sci Ctr, Oklahoma City, OK 73104 USA

[4] Univ Oklahoma Hlth Sci Ctr, Lab Biomol Struct & Funct, Oklahoma City, OK 73104 USA

[5] Univ Tulsa, Dept Biol Sci, 800 S Tucker Dr, Tulsa, OK 74104 USA

[6] Oklahoma State Univ Ctr Hlth Sci, Dept Pharmacol & Physiol, Tulsa, OK 74107 USA

[7] Toyama Univ, Fac Engn, 3190 Gofuku, Toyama 9308555, Japan

来源：

RSC ADVANCES | 2022年 / 12卷 / 30期

基金：

美国国家科学基金会;

关键词：

NICOTINIC CHOLINERGIC-RECEPTORS; RAT-BRAIN; ALPHA; CATALYST; AGONIST; BINDING; ESTERS; AMIDES;

D O I：

10.1039/d2ra02415b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 alpha 6-selective antismoking agents. Therefore, we also performed in silico alpha 6-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.

引用

页码：19431 / 19444

页数：14

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