Design, Synthesis and Molecular Docking Studies of Novel Thiadiazole Analogues with Potential Antimicrobial and Antiinflammatory Activities.

Mehta, DK; Taya, P; Das, R; Dua, K

Design, Synthesis and Molecular Docking Studies of Novel Thiadiazole Analogues with Potential Antimicrobial and Antiinflammatory Activities.

Mehta, DK Taya, P Das, R Dua, K

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Publisher:: Bentham Science Publishers Ltd.
Publication Type:: Journal Article
Citation:: Anti-inflammatory & anti-allergy agents in medicinal chemistry, 2019, 18, (2), pp. 91-109
Issue Date:: 2019-01

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Field	Value	Language
dc.contributor.author	Mehta, DK
dc.contributor.author	Taya, P
dc.contributor.author	Das, R
dc.contributor.author	Dua, K https://orcid.org/0000-0002-7507-1159
dc.date.accessioned	2020-06-11T00:49:27Z
dc.date.available	2019-02-27
dc.date.available	2020-06-11T00:49:27Z
dc.date.issued	2019-01
dc.identifier.citation	Anti-inflammatory & anti-allergy agents in medicinal chemistry, 2019, 18, (2), pp. 91-109
dc.identifier.issn	1871-5230
dc.identifier.issn	1875-614X
dc.identifier.uri	http://hdl.handle.net/10453/141234
dc.description.abstract	BACKGROUND:Chemical modification of thiadiazole may lead to a potent therapeutic agent. In this study, biological properties of thiadiazole derivatives were evaluated by assessing their antimicrobial and anti-inflammatory activities. METHODS:A series of novel derivatives of N-(5-(1-methyl-indol-3-yl)-1,3,4-thiadiazol-2- yl)-2-(5-substitutedphenyl)-3-(phenylamino)-4,5-dihydropyrazol-1-yl) acetamide have been synthesized and evaluated for their antimicrobial activity. Anti-inflammatory activity was done using carrageenan-induced inflammation in rat paw edema model. In-silico molecular docking studies of the synthesized compounds were performed on crystal structures of Aspergillus niger, Bacillus subtilis, Candida albicans, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Cyclooxygenase-2 (obtained from www.rcsb.org) using GRIP batch docking method of V-life MDS 3.0 software. The structures of the newly synthesized compounds were confirmed by FT-IR, 1H-NMR, 13C-NMR and Mass spectroscopy. RESULTS:Antimicrobial and Anti-inflammatory activity study of the novel synthesized compounds were screened. Synthesized compounds having methoxy substitution on the 3rd and 4th positions of aromatic ring are utmost active amongst all the derivatives. Compounds 6d, 6i, 6j and 6l were found to possess good anti-inflammatory activity having percentage of inhibition to the extent of 46.8%, 48.1%, 49.4%, and 48.5% as compared with Diclofenac. CONCLUSION:The experimental results were further supported by molecular docking analysis describing the better interaction patterns.
dc.format	Print
dc.language	eng
dc.publisher	Bentham Science Publishers Ltd.
dc.relation.ispartof	Anti-inflammatory & anti-allergy agents in medicinal chemistry
dc.relation.isbasedon	10.2174/1871520619666190307162442
dc.rights	info:eu-repo/semantics/restrictedAccess
dc.subject	0304 Medicinal and Biomolecular Chemistry, 1107 Immunology
dc.subject.classification	Medicinal & Biomolecular Chemistry
dc.subject.mesh	Animals
dc.subject.mesh	Humans
dc.subject.mesh	Rats
dc.subject.mesh	Rats, Wistar
dc.subject.mesh	Pseudomonas aeruginosa
dc.subject.mesh	Escherichia coli
dc.subject.mesh	Staphylococcus aureus
dc.subject.mesh	Candida albicans
dc.subject.mesh	Disease Models, Animal
dc.subject.mesh	Inflammation
dc.subject.mesh	Edema
dc.subject.mesh	Thiadiazoles
dc.subject.mesh	Carrageenan
dc.subject.mesh	Anti-Inflammatory Agents
dc.subject.mesh	Anti-Infective Agents
dc.subject.mesh	Molecular Structure
dc.subject.mesh	Structure-Activity Relationship
dc.subject.mesh	Female
dc.subject.mesh	Male
dc.subject.mesh	Molecular Docking Simulation
dc.subject.mesh	Animals
dc.subject.mesh	Humans
dc.subject.mesh	Rats
dc.subject.mesh	Rats, Wistar
dc.subject.mesh	Pseudomonas aeruginosa
dc.subject.mesh	Escherichia coli
dc.subject.mesh	Staphylococcus aureus
dc.subject.mesh	Candida albicans
dc.subject.mesh	Disease Models, Animal
dc.subject.mesh	Inflammation
dc.subject.mesh	Edema
dc.subject.mesh	Thiadiazoles
dc.subject.mesh	Carrageenan
dc.subject.mesh	Anti-Inflammatory Agents
dc.subject.mesh	Anti-Infective Agents
dc.subject.mesh	Molecular Structure
dc.subject.mesh	Structure-Activity Relationship
dc.subject.mesh	Female
dc.subject.mesh	Male
dc.subject.mesh	Molecular Docking Simulation
dc.subject.mesh	Animals
dc.subject.mesh	Anti-Infective Agents
dc.subject.mesh	Anti-Inflammatory Agents
dc.subject.mesh	Candida albicans
dc.subject.mesh	Carrageenan
dc.subject.mesh	Disease Models, Animal
dc.subject.mesh	Edema
dc.subject.mesh	Escherichia coli
dc.subject.mesh	Female
dc.subject.mesh	Humans
dc.subject.mesh	Inflammation
dc.subject.mesh	Male
dc.subject.mesh	Molecular Docking Simulation
dc.subject.mesh	Molecular Structure
dc.subject.mesh	Pseudomonas aeruginosa
dc.subject.mesh	Rats
dc.subject.mesh	Rats, Wistar
dc.subject.mesh	Staphylococcus aureus
dc.subject.mesh	Structure-Activity Relationship
dc.subject.mesh	Thiadiazoles
dc.title	Design, Synthesis and Molecular Docking Studies of Novel Thiadiazole Analogues with Potential Antimicrobial and Antiinflammatory Activities.
dc.type	Journal Article
utslib.citation.volume	18
utslib.location.activity	United Arab Emirates
utslib.for	0304 Medicinal and Biomolecular Chemistry
utslib.for	1107 Immunology
pubs.organisational-group	/University of Technology Sydney/Graduate School of Health
pubs.organisational-group	/University of Technology Sydney
utslib.copyright.status	closed_access	*
pubs.consider-herdc	false
dc.date.updated	2020-06-11T00:49:22Z
pubs.issue	2
pubs.publication-status	Published
pubs.volume	18
utslib.citation.issue	2

Abstract:

BACKGROUND:Chemical modification of thiadiazole may lead to a potent therapeutic agent. In this study, biological properties of thiadiazole derivatives were evaluated by assessing their antimicrobial and anti-inflammatory activities. METHODS:A series of novel derivatives of N-(5-(1-methyl-indol-3-yl)-1,3,4-thiadiazol-2- yl)-2-(5-substitutedphenyl)-3-(phenylamino)-4,5-dihydropyrazol-1-yl) acetamide have been synthesized and evaluated for their antimicrobial activity. Anti-inflammatory activity was done using carrageenan-induced inflammation in rat paw edema model. In-silico molecular docking studies of the synthesized compounds were performed on crystal structures of Aspergillus niger, Bacillus subtilis, Candida albicans, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Cyclooxygenase-2 (obtained from www.rcsb.org) using GRIP batch docking method of V-life MDS 3.0 software. The structures of the newly synthesized compounds were confirmed by FT-IR, 1H-NMR, 13C-NMR and Mass spectroscopy. RESULTS:Antimicrobial and Anti-inflammatory activity study of the novel synthesized compounds were screened. Synthesized compounds having methoxy substitution on the 3rd and 4th positions of aromatic ring are utmost active amongst all the derivatives. Compounds 6d, 6i, 6j and 6l were found to possess good anti-inflammatory activity having percentage of inhibition to the extent of 46.8%, 48.1%, 49.4%, and 48.5% as compared with Diclofenac. CONCLUSION:The experimental results were further supported by molecular docking analysis describing the better interaction patterns.

Please use this identifier to cite or link to this item:

http://hdl.handle.net/10453/141234