ZnO Nanocatalyst Mediated Convergent Synthesis of Highly Substituted Imidazole and Imidazole-derived Bi-heterocyclic Scaffolds as Potential Antibacterial Agents

A. Jayashree, B. Narayana, Gauthama B. Uppine, Vivek M. Ghate, Shaila A. Lewis, Bharathi Prakash, Sarojini B. Kunhanna, Madan S. Kumar

Research output: Contribution to journalArticle

Abstract

A new series of novel highly substituted imidazole and imidazole bi-heterocycles have been synthesized via atom economic, one-pot condensation reaction using benzil, substituted benzaldehydes, various amine scaffolds, and ammonium acetate using ZnO nanoparticles as effective catalyst. Simple operation, cheap catalyst, good to excellent yield, etc, are some of the advantages of this protocol. The characterization of the synthesized imidazole analogues was performed by Fourier transform infrared, nuclear magnetic resonance (1H and 13C), mass analysis, and elemental analysis. The structures were unequivocally confirmed by single-crystal X-ray diffraction analysis. Synthesized compounds were tested for antibacterial activities by resazurin reduction assay. All compounds tested showed significant activity against bacteria. Among the 24 compounds tested, compounds 1c, 1i, 2c, 2g, and 3a proved to be more active against the bacterial strain tested.

Original languageEnglish
Pages (from-to)2398-2410
Number of pages13
JournalJournal of Heterocyclic Chemistry
Volume56
Issue number9
DOIs
Publication statusPublished - 01-09-2019

Fingerprint

Scaffolds
Anti-Bacterial Agents
Benzaldehydes
Catalysts
Condensation reactions
X ray diffraction analysis
Amines
Assays
Bacteria
Fourier transforms
Nuclear magnetic resonance
Single crystals
Nanoparticles
Infrared radiation
Atoms
Economics
Chemical analysis
imidazole
benzil
resazurin

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Jayashree, A. ; Narayana, B. ; Uppine, Gauthama B. ; Ghate, Vivek M. ; Lewis, Shaila A. ; Prakash, Bharathi ; Kunhanna, Sarojini B. ; Kumar, Madan S. / ZnO Nanocatalyst Mediated Convergent Synthesis of Highly Substituted Imidazole and Imidazole-derived Bi-heterocyclic Scaffolds as Potential Antibacterial Agents. In: Journal of Heterocyclic Chemistry. 2019 ; Vol. 56, No. 9. pp. 2398-2410.
@article{de2b7845c9b14417a8076ed0b490bd4b,
title = "ZnO Nanocatalyst Mediated Convergent Synthesis of Highly Substituted Imidazole and Imidazole-derived Bi-heterocyclic Scaffolds as Potential Antibacterial Agents",
abstract = "A new series of novel highly substituted imidazole and imidazole bi-heterocycles have been synthesized via atom economic, one-pot condensation reaction using benzil, substituted benzaldehydes, various amine scaffolds, and ammonium acetate using ZnO nanoparticles as effective catalyst. Simple operation, cheap catalyst, good to excellent yield, etc, are some of the advantages of this protocol. The characterization of the synthesized imidazole analogues was performed by Fourier transform infrared, nuclear magnetic resonance (1H and 13C), mass analysis, and elemental analysis. The structures were unequivocally confirmed by single-crystal X-ray diffraction analysis. Synthesized compounds were tested for antibacterial activities by resazurin reduction assay. All compounds tested showed significant activity against bacteria. Among the 24 compounds tested, compounds 1c, 1i, 2c, 2g, and 3a proved to be more active against the bacterial strain tested.",
author = "A. Jayashree and B. Narayana and Uppine, {Gauthama B.} and Ghate, {Vivek M.} and Lewis, {Shaila A.} and Bharathi Prakash and Kunhanna, {Sarojini B.} and Kumar, {Madan S.}",
year = "2019",
month = "9",
day = "1",
doi = "10.1002/jhet.3627",
language = "English",
volume = "56",
pages = "2398--2410",
journal = "Journal of Heterocyclic Chemistry",
issn = "0022-152X",
publisher = "Heterocorporation",
number = "9",

}

ZnO Nanocatalyst Mediated Convergent Synthesis of Highly Substituted Imidazole and Imidazole-derived Bi-heterocyclic Scaffolds as Potential Antibacterial Agents. / Jayashree, A.; Narayana, B.; Uppine, Gauthama B.; Ghate, Vivek M.; Lewis, Shaila A.; Prakash, Bharathi; Kunhanna, Sarojini B.; Kumar, Madan S.

In: Journal of Heterocyclic Chemistry, Vol. 56, No. 9, 01.09.2019, p. 2398-2410.

Research output: Contribution to journalArticle

TY - JOUR

T1 - ZnO Nanocatalyst Mediated Convergent Synthesis of Highly Substituted Imidazole and Imidazole-derived Bi-heterocyclic Scaffolds as Potential Antibacterial Agents

AU - Jayashree, A.

AU - Narayana, B.

AU - Uppine, Gauthama B.

AU - Ghate, Vivek M.

AU - Lewis, Shaila A.

AU - Prakash, Bharathi

AU - Kunhanna, Sarojini B.

AU - Kumar, Madan S.

PY - 2019/9/1

Y1 - 2019/9/1

N2 - A new series of novel highly substituted imidazole and imidazole bi-heterocycles have been synthesized via atom economic, one-pot condensation reaction using benzil, substituted benzaldehydes, various amine scaffolds, and ammonium acetate using ZnO nanoparticles as effective catalyst. Simple operation, cheap catalyst, good to excellent yield, etc, are some of the advantages of this protocol. The characterization of the synthesized imidazole analogues was performed by Fourier transform infrared, nuclear magnetic resonance (1H and 13C), mass analysis, and elemental analysis. The structures were unequivocally confirmed by single-crystal X-ray diffraction analysis. Synthesized compounds were tested for antibacterial activities by resazurin reduction assay. All compounds tested showed significant activity against bacteria. Among the 24 compounds tested, compounds 1c, 1i, 2c, 2g, and 3a proved to be more active against the bacterial strain tested.

AB - A new series of novel highly substituted imidazole and imidazole bi-heterocycles have been synthesized via atom economic, one-pot condensation reaction using benzil, substituted benzaldehydes, various amine scaffolds, and ammonium acetate using ZnO nanoparticles as effective catalyst. Simple operation, cheap catalyst, good to excellent yield, etc, are some of the advantages of this protocol. The characterization of the synthesized imidazole analogues was performed by Fourier transform infrared, nuclear magnetic resonance (1H and 13C), mass analysis, and elemental analysis. The structures were unequivocally confirmed by single-crystal X-ray diffraction analysis. Synthesized compounds were tested for antibacterial activities by resazurin reduction assay. All compounds tested showed significant activity against bacteria. Among the 24 compounds tested, compounds 1c, 1i, 2c, 2g, and 3a proved to be more active against the bacterial strain tested.

UR - http://www.scopus.com/inward/record.url?scp=85070075010&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85070075010&partnerID=8YFLogxK

U2 - 10.1002/jhet.3627

DO - 10.1002/jhet.3627

M3 - Article

AN - SCOPUS:85070075010

VL - 56

SP - 2398

EP - 2410

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

SN - 0022-152X

IS - 9

ER -