Novel 5-Nitrofuran-Tagged Imidazo-Fused Azines and Azoles Amenable by the Groebke-Blackburn-Bienayme Multicomponent Reaction: Activity Profile against ESKAPE Pathogens and Mycobacteria

被引：1

作者：

Sapegin, Alexander ^{[1
]}

Rogacheva, Elizaveta ^{[2
]}

Kraeva, Lyudmila ^{[2
]}

Gureev, Maxim ^{[3
]}

Dogonadze, Marine ^{[4
]}

Vinogradova, Tatiana ^{[4
]}

Yablonsky, Petr ^{[4
]}

Balalaie, Saeed ^{[5
,6
]}

Baykov, Sergey, V ^{[1
]}

Krasavin, Mikhail ^{[1
,7
]}

机构：

[1] St Petersburg State Univ, Inst Chem, St Petersburg 199034, Russia

[2] Pasteur Inst Epidemiol & Microbiol, 14 Mira St, St Petersburg 197101, Russia

[3] Sechenov First Moscow State Med Univ, Lab Chemoinformat & Bioinformat, Moscow 119435, Russia

[4] St Petersburg Res Inst Phthisiopulmonol, 2-4 Ligovsky Prospekt, St Petersburg 191036, Russia

[5] KN Toosi Univ Technol, Peptide Chem Res Ctr, Tehran 19697, Iran

[6] Kermanshah Univ Med Sci Kermanshah, Med Biol Res Ctr, Kermanshah 67155, Iran

[7] Immanuel Kant Baltic Fed Univ, Sch Living Syst, Kaliningrad 236041, Russia

来源：

BIOMEDICINES | 2022年 / 10卷 / 09期

基金：

美国国家科学基金会;

关键词：

Groebke-Blackburn-Bienayme multicomponent reaction; imidazo-fused azines and azoles; 5-nitrofurancarboxaldehyde; ESKAPE pathogens; antibacterial testing; antimycobacterial activity; flexible docking; strained ligand-protein interactions; EFFICACIOUS IN-VITRO; DRUG DISCOVERY; ANTIMICROBIAL ACTIVITY; NOSOCOMIAL PATHOGENS; NONTOXIC NITROFURANS; PYRIMIDINES; CHEMISTRY; PYRAZINES; PROTEIN; MOIETY;

D O I：

10.3390/biomedicines10092203

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A chemically diverse set of 13 5-nitrofuran-tagged heterocyclic compounds has been prepared via the Groebke-Blackburn-Bienayme multicomponent reaction. The testing of these compounds against the so-called ESKAPE panel of pathogens identified an apparent lead compound-N-cyclohexyl-2-(5-nitrofuran-2-yl)imidazo[1,2-a]pyridine-3-amine (4a)-which showed an excellent profile against Enterobacter cloacae, Staphylococcus aureus, Klebsiella pneumoniae, and Enterococcus faecalis (MIC 0.25, 0.06, 0.25 and 0.25 mu g/mL, respectively). Its antibacterial profile and practically convenient synthesis warrant further pre-clinical development. Certain structure-activity relationships were established in the course of this study which were rationalized by the flexible docking experiments in silico. The assessment of antitubercular potential of the compounds synthesized against drug sensitive H37v strain of Mycobacterium tuberculosis revealed little potential of the imidazo-fused products of the Groebke-Blackburn-Bienayme multicomponent reaction as chemotherapeutic agents against this pathogen.

引用

页数：17

共 1 条

[1] Synthesis of novel imidazo[1,2-a]pyridine-4-hydroxy-2H-coumarins by Groebke-Blackburn-Bienayme multicomponent reaction as potential NS5B inhibitors
Manvar, Parth
Shaikh, Faraz
Kakadiya, Rajesh
Mehariya, Krunal
Khunt, Ranjan
Pandey, Bipin
Shah, Anamik
[J]. TETRAHEDRON, 2016, 72 (10) : 1293 - 1300

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