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Synthesis, Antioxidant Evaluation, Density Functional Theory Study of Dihydropyrimidine Festooned Phenothiazines
Author(s) -
Padmavathy Krishnaraj,
Krishnan Kannan Gokula,
Kumar Chandran Udhaya,
Sutha Peramasivan,
Sivaramakarthikeyan Ramar,
Ramalingan Chennan
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201800748
Subject(s) - density functional theory , molecule , isopropyl , computational chemistry , chemistry , ascorbic acid , basis set , phenothiazine , nitro , antioxidant , combinatorial chemistry , organic chemistry , medicine , alkyl , food science , pharmacology
A series of dihydropyrimidine decorated phenothiazine and their derivatives 7 a‐7 i possessing a diverse range of functionalities such as isopropyl, methoxy, chloro, fluoro, nitro, naphthyl have been synthesized by adopting a multistep synthetic strategy and characterized using various physical and spectroscopic techniques. Preliminary antioxidant evaluation of all the molecules has been executed and exerted activity upto 69.34% (IC 50 148 μM) with respect to the standard ascorbic acid. Computational studies of a representative molecule 7 a have also been executed and appropriate results are compared with the experimental ones. The optimized structure with their bonding features and vibrational frequencies of 7 a have been determined by employing DFT−B3LYP method with 6–311++G(d,p) basis set. The theoretically calculated and experimentally resulted vibrational frequencies of 7 a are in good harmony with each other. Further, the 1 H and 13 C chemical shifts of 7 a have been calculated by the Gauge Independent Atomic Orbital (GIAO) technique and compared with the experimental ones.