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Synthesis of Novel Thiazole-Based Heterocycles as New Anti-bacterial and Anti-fungal Agents.

Article

Last updated: 01 Jan 2025

Subjects

-

Tags

Organic chemistry

Abstract

Due to the potential biological and medicinal effects of heterocyclic moieties, they have attracted attention, so the objective of the current work is to create some newly generated heterocyclic compounds with anticipated biological activity. This can be accomplished by reacting 5-methylthiazol-2-amine (1) and ethyl cyanoacetate (2) to yield 2-cyano-N-(5-methylthiazol-2-yl)acetamide (3). Compouund 3 reacts with aromatic aldehydes, aromatic diazonium salts 5a-c, hydrozonoyl halide derivatives 7a-c, active methylene reagents 2,11,14 , hydrazines and ethyl 2-cyanoacrylate derivatives 19a,b to form the corresponding acrylamide derivatives 4a,b, hydrazones 6a-c, aminopyrazoles 9a-c, pyridine-3-carbonitrile derivatives 13a,b,16, aminopyrazoles 18a,b and oxopyridine-3-carboxylate derivatives 21a,b, respectively. The sensitivity of acrylamide 4a to several chemical substances was investigated through its reaction with ethyl cyanoacetate (2), hydrazines, 3-amino-(2H)-1,2,4-triazole (28) and 5-methylthiazol-2-amine (1) to form phenylpyridine-3-carboxylate derivative 24, aminopyrazole derivatives 27a,b, triazolo[1,5-a]pyrimidine derivative 30 and thiazolo[3,2-a]pyrimidine derivative 32, respectively. All synthesized compounds' structures were verified using infrared radiation, 1H-NMR, and 13C-NMR. In addition, mass spectroscopy and elemental assessment were done. The antibacterial and antifungal properties of some of the created substances were also examined. From all the investigated substances, only 3, 9a, 9c, 4a, and 6c demonstrated good antibacterial activity, while compounds 16, 21a, 21b, and 24 demonstrated effective antifungal and antibacterial activities towards bacterial strains that were either Gram-positive or Gram-negative.

DOI

10.21608/ejchem.2023.180589.7326

Keywords

acrylamide, Aminopyrazole, Carbonitrile, Cyanoa acetamide, Hydrazines, Hydrozonoyl halide

Authors

First Name

Marwa M.

Last Name

Fouad

MiddleName

-

Affiliation

Basic Sciences Department, Modern Academy for Engineering & Technology, Cairo, Egypt

Email

mar.mfouad@gmail.com

City

-

Orcid

0000-0002-1586-6910

First Name

Ahmad M.

Last Name

Farag

MiddleName

-

Affiliation

Chemistry department, Faculty of Science, Cairo University, Giza, Egypt

Email

afarag49@yahoo.com

City

-

Orcid

0000-0003-4796-1266

First Name

Galal H.

Last Name

Elgemeie

MiddleName

-

Affiliation

Chemistry department, Faculty of Science, Helwan University, Cairo, Egypt

Email

elgemeie@yahoo.com

City

-

Orcid

0000-0003-3268-5975

First Name

N. O.

Last Name

Shaker

MiddleName

-

Affiliation

Chemistry department, Faculty of Science (Girls), Al-Azhar University, Cairo, Egypt

Email

nihal_shaker@hotmail.com

City

-

Orcid

-

First Name

N. A.

Last Name

Alian

MiddleName

-

Affiliation

Chemistry department, Faculty of Science (Girls), Al-Azhar University, Cairo, Egypt

Email

nohaalian90@gmail.com

City

-

Orcid

-

Volume

66

Article Issue

13

Related Issue

43707

Issue Date

2023-12-01

Receive Date

2022-12-13

Publish Date

2023-12-01

Page Start

733

Page End

743

Print ISSN

0449-2285

Online ISSN

2357-0245

Link

https://ejchem.journals.ekb.eg/article_297912.html

Detail API

https://ejchem.journals.ekb.eg/service?article_code=297912

Order

297,912

Type

Original Article

Type Code

297

Publication Type

Journal

Publication Title

Egyptian Journal of Chemistry

Publication Link

https://ejchem.journals.ekb.eg/

MainTitle

Synthesis of Novel Thiazole-Based Heterocycles as New Anti-bacterial and Anti-fungal Agents.

Details

Type

Article

Created At

30 Dec 2024