title: Synthesis and anti-inflammatory activity evaluation of novel triazolyl-isatin hybrids.
abstract: New isatin-triazole based hybrids have been synthesized and evaluated for their inhibitory activity of TNF-α induced expression of Intercellular Adhesion Molecule-1 (ICAM-1) on the surface of human endothelial cells. Structure-activity relationship (SAR) studies revealed that the presence of the electron-attracting bromo substituent at position-5 of the isatin moiety played an important role in enhancing the anti-inflammatory potential of the synthesized compounds. Z-1-[3-(1H-1,2,4-Triazol-1-yl)propyl]-5-bromo-3-[2-(4-methoxyphenyl)hydrazono]indolin-2-one (19) with an IC50 = 20 μM and 89% ICAM-1 inhibition with MTD at 200 μM was found to be the most potent of all the synthesized derivatives. Introduction of 1,2,4-triazole ring and electron-donating methoxy group on the phenylhydrazone moiety resulted in four-fold increase of the anti-inflammatory activity.
authors.affiliation: a Department of Chemistry , Bioorganic Laboratory, University of Delhi , Delhi , India .|b Chemical Research Laboratory, Wockhardt Research Centre , Aurangabad , Maharashtra , India .
authors.forename: Pramod K
authors.initials: PK
authors.lastname: Sharma
authors.affiliation: c Immunogenetics Laboratory, CSIR-Institute of Genomics and Integrative Biology , Delhi , India .
authors.forename: Sakshi
authors.initials: S
authors.lastname: Balwani
authors.affiliation: a Department of Chemistry , Bioorganic Laboratory, University of Delhi , Delhi , India .|d Department of Chemistry , Daulat Ram College, University of Delhi , Delhi , India .
authors.forename: Divya
authors.initials: D
authors.lastname: Mathur
authors.affiliation: a Department of Chemistry , Bioorganic Laboratory, University of Delhi , Delhi , India .
authors.forename: Shashwat
authors.initials: S
authors.lastname: Malhotra
authors.affiliation: a Department of Chemistry , Bioorganic Laboratory, University of Delhi , Delhi , India .
authors.forename: Brajendra K
authors.initials: BK
authors.lastname: Singh
authors.affiliation: a Department of Chemistry , Bioorganic Laboratory, University of Delhi , Delhi , India .
authors.forename: Ashok K
authors.initials: AK
authors.lastname: Prasad
authors.affiliation: e Sorbonne Universités, Université de Technologie de Compiègne (UTC), Ecole Supérieure de Chimie Organique et Minérale (ESCOM) , Compiègne Cedex , France .|f Department of Chemistry , University of Hull , Hull , UK .
authors.forename: Christophe
authors.initials: C
authors.lastname: Len
authors.affiliation: g Department of Chemistry , Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), University of Leuven (KU Leuven) , Leuven , Belgium .
authors.forename: Erik V
authors.initials: EV
authors.lastname: Van der Eycken
authors.affiliation: c Immunogenetics Laboratory, CSIR-Institute of Genomics and Integrative Biology , Delhi , India .
authors.forename: Balaram
authors.initials: B
authors.lastname: Ghosh
authors.affiliation: h Department of Chemistry and Chemical Biology , Indiana University-Purdue University (IUPUI) , Indianapolis , IN , USA , and.|i School of Chemistry, College of Physical Sciences & Engineering, Cardiff University , Cardiff , UK.
authors.forename: Nigel G J
authors.initials: NG
authors.lastname: Richards
authors.affiliation: a Department of Chemistry , Bioorganic Laboratory, University of Delhi , Delhi , India .|e Sorbonne Universités, Université de Technologie de Compiègne (UTC), Ecole Supérieure de Chimie Organique et Minérale (ESCOM) , Compiègne Cedex , France .|h Department of Chemistry and Chemical Biology , Indiana University-Purdue University (IUPUI) , Indianapolis , IN , USA , and.
authors.forename: Virinder S
authors.initials: VS
authors.lastname: Parmar
mesh_terms: D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002478:Cells, Cultured; D004730:Endothelium, Vascular / Q000166:cytology / Q000187:drug effects; D004797:Enzyme-Linked Immunosorbent Assay; D006801:Humans; D007510:Isatin / Q000494:pharmacology*; D066244:Proton Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000893:Anti-Inflammatory Agents; D014230:Triazoles; D007510:Isatin
keywords: 1,2,4-Triazole; ICAM-1; anti-inflammatory activity; isatin; triazolylisatins