Open AccessDesign, Synthesis and in vitro Cytotoxicity Evaluation of New Fluorinated Ionic Salt (S)-(+)-2,3-Dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione as Strategies for Improving Anticonvulsant Activity
Author(s) -
V. Natchimuthu,
Satyam Ravi,
Murugan Ramalingam,
V. Renuga
Publication year - 2020
Publication title -
asian journal of chemistry/asian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.145
H-Index - 34
eISSN - 0975-427X
pISSN - 0970-7077
DOI - 10.14233/ajchem.2020.22510
Subject(s) - chemistry , moiety , cytotoxicity , benzoic acid , proton nmr , carbon 13 nmr , trifluoromethyl , stereochemistry , medicinal chemistry , nuclear chemistry , in vitro , organic chemistry , biochemistry , alkyl
The reaction of (S)-(+)-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione (1) with 4-(trifluoromethyl)benzoic acid (2, C8H5F3O2) in dimethylformamide leads to the formation of C8H5F3O2 (1) as a classical ionic salt 3. The structure of new compound has been characterized by FTIR, 1H NMR, 13C NMR, HRMS spectroscopy. The new compound was tested for in vitro cytotoxicity evaluation by MTT assay against breast adenocarcinoma cell line of MCF-7 cells. A new compound 3 (IC50:199 μM) emerged as minimal toxic when compared to clinical drugs carbamazepine, topiramate and benzodiazepine. A preliminary study of structure activity relationship revealed that the incorporation of fluoro or trifluoromethyl moiety into the compound, even through ionic bond formation, had a great effect on the biological activity and with less toxicity or side effects.