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3D‐quantitative structure activity analysis and quantum chemical analysis of pyrido‐di‐indoles
Author(s) -
Pasha Farhan A.,
Chung Hwan W.,
Kang Soon B.,
Cho Seung J.
Publication year - 2007
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.21474
Subject(s) - chemistry , quantitative structure–activity relationship , ring (chemistry) , computational chemistry , electrophile , quantum chemical , density functional theory , fukui function , stereochemistry , molecule , organic chemistry , catalysis
The computational analyses of pyrido‐di‐indoles have been performed with various methods such as quantum mechanical studies (AM1, PM3, and DFT) and 3D‐QSAR analyses (CoMFA and CoMSIA). The electrophilicity index along with some other properties has been related with biological activities. Electrostatic field has been identified as an important descriptor from the 3D‐QSAR analyses. The AM1 geometry and Gasteiger–Marsili charged base CoMFA (r predictive 2= 0.75) and CoMSIA (r predictive 2= 0.62) give strong correlation and indicate that a substitution at sites 2 and 3 of Ring A might affect the activity. In addition, a plausible statistical model has been found with DFT‐based local philicity and negative Fukui function with a value of r 2 = 0.82 and r cv 2 = 0.60. The DFT analysis indicates that electron density of nitrogen atom of Ring B significantly contributes to activity. © 2007 Wiley Periodicals, Inc. Int J Quantum Chem, 2008