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Synthesis, Docking, and Bioavailability of 2′‐Oxo‐3‐phenylspiro[cyclopropane‐1,3′‐indoline]‐2,2‐dicarbonitriles as Antibacterial Agents In Silico
Author(s) -
Avula Vijay Kumar Reddy,
Chintha Venkata Ramaiah,
Vallela Swetha,
Anireddy Jaya Shree,
Chamarthi Naga Raju,
Wudayagiri Rajendra
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3396
Subject(s) - chemistry , indoline , cyclopropane , in silico , bioavailability , dna gyrase , combinatorial chemistry , docking (animal) , antibacterial activity , stereochemistry , organic chemistry , biochemistry , escherichia coli , bacteria , pharmacology , ring (chemistry) , medicine , nursing , gene , genetics , biology
An efficient method has been developed for the synthesis of N ‐alkylated 2′‐oxo‐3‐phenylspiro[cyclopropane‐1,3′‐indoline]‐2,2‐dicarbonitrile from 3‐chloroindolin‐2‐one and 2‐benzylidenemalononitrile by using triethylamine as a base at room temperature and obtained the products in moderate to good yields. In extension, the scope of the reaction has been investigated by stepwise and one‐pot methods. Furthermore, in silico antibacterial activity was carried out in order to understand possible binding modes of novel derivatives with the active site of DNA gyrase A enzyme, and the results were well complemented. Additionally, absorption, distribution, metabolism, and excretion properties of compounds have shown drug likeness with good oral absorption and moderate blood–brain barrier permeability.