Synthesis, biological evaluation and QSAR studies of a novel series of annelated triazolo[4,3-c]quinazolines

A series of novel annelated triazolo[4,3-c]quinazolines 6a-m have been synthesized and characterized by physicochemical as well as spectral means. The bioactivity assay for the newly synthesized compounds against Gram-positive and Gram-negative bacteria, and fungi indicates that most new compounds e...

Full description

Saved in:
Bibliographic Details
Published inIndian journal of chemistry. Sect. B. Organic chemistry, including medicinal chemistry Vol. 55; no. 7; pp. 898 - 911
Main Authors Reddy, Cherkupally Sanjeeva, Sunitha, Bommineni, Raviteja, Padma, Kumar, Gaddam Rajesh, Manjari, Padma Sunitha
Format Journal Article
LanguageEnglish
Published NEW DELHI Natl Inst Science Communication & Information Resources-Niscair 01.07.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
synthesis
molecular descriptors
Annelated triazoloquinazolines
ANTIBACTERIAL
QSAR studies
antimicrobial activity
COUMARINS
Online AccessGet full text

Cover

More Information
Summary:A series of novel annelated triazolo[4,3-c]quinazolines 6a-m have been synthesized and characterized by physicochemical as well as spectral means. The bioactivity assay for the newly synthesized compounds against Gram-positive and Gram-negative bacteria, and fungi indicates that most new compounds exhibit good antibacterial and antifungal activities in comparison with standard drugs. 2-[(4-Methoxyanilino)methy1]-5-phenyl-2,3-dihydro[1,2,4] triazolo[4,3-c]quinazoline-3-thione 6f, and 2-[(4-aminoanilino)methy1]-5-pheny1-2,3-dihydro[1,2,4]triazolo [4,3-c] quinazoline-3-thione 6m have emerged as the most potent antimicrobial agents with activity (pMIC(am), = 2.26 and 2.38 mu M/mL respectively) almost equal to the reference drugs streptomycin, penicillin and amphotericin B. The results of QSAR studies demonstrate that antibacterial, antifungal and over all antimicrobial activities of synthesized quinazoline derivatives are governed by electronic parameter, hydrophobicity (log P) and chemical potential (mu). The validity of Hammett's linear free energy relationship for the first time has been verified, from the linear plot of log activity against substituent constant (sigma). The observed low residual activity and high cross validated q(2) values indicate the predictive ability of the developed models, which further simplify the design and synthesis of new biologically potent molecules.
ISSN:0376-4699
0019-5103