Synthesis of Some Novel (Z)-3-ethylidene-5,7-dimethylthiochroman- 4-one Derivatives and Study of its Monoamine Oxidases Inhibitory Activity

  • Somesh Kumar Saxena Department of Pharmaceutical Chemistry, Patel College of Pharmacy, Madhyanchal Professional University, Bhopal, Madhya Pradesh, INDIA.
  • Om Prakash Agrawal Department of Pharmaceutical Chemistry, Patel College of Pharmacy, Madhyanchal Professional University, Bhopal, Madhya Pradesh, INDIA.
  • Ashish Pathak Department of Pharmaceutical Chemistry, Ravishankar College of Pharmacy, Bhopal, Madhya Pradesh, INDIA
Keywords: Chromanone, Chalcones, Schiff base, hMAO inhibitory activity, dimethylthiochroman-4-one.

Abstract

Background: Chroman-4-one, also known as 2,3-dihydro-1-benzopyran- 4-one, is a heterocyclic compound with a benzene nucleus fused to a 2,3-dihydro-g-pyranone ring. The synthesis of chroman-4-one derivatives is a very appealing aspect in the field of natural and medicinal chemistry. Materials and Methods: The (Z)-3-ethylidene-5,7-dimethylthiochroman- 4-one derivatives were, synthesized and evaluated intended for their Monoamine oxidases (MAO)-A and MAO-B inhibitory activity using in vitro fluorometric technique. The majority of synthetic process to acquire(Z)-3-ethylidene-5,7-dimethylthiochroman-4-one derivatives engage condensation catalyzed by acid or base of a range of derivatives of 5,7-dimethylchroman-4-one and 4,6-dimethylbenzofuran-3(2H)-one with the benzaldehyde. The Z-isomers that resulted were usually obtained by photoisomerization of the synthesized E-isomers. Synthesized molecules structures (S-1 to S-18) were established by IR, NMR, mass and elemental analysis. Results: The in vitro activity of synthesized (Z)-3-ethylidene-5,7- dimethylthiochroman-4-one derivatives against MAO isoform displayed selectivity in the direction of MAO B isoform. The synthesized derivatives S11 of (Z)-3-ethylidene-5,7-dimethylthiochroman-4-one displayed 7.32 μM (IC50) against MAO-B. Conclusion: Weak to moderate electron pumping and withdrawing groups favor selectivity for hMAO-B, whereas strong deactivators render them non-selective for isoforms. Mono-substitution of methoxy groups at the o- and m-positions improves potency while bi-substitution improves potency and selectivity. The active compounds’ ADME predictions revealed that these synthesized compounds may possess drug likeliness confirmed by excellent pharmacokinetic profiles.

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Synthesis of Some Novel (Z)-3-ethylidene-5,7-dimethylthiochroman- 4-one Derivatives and Study of its Monoamine Oxidases Inhibitory Activity
Published
2022-10-06
How to Cite
1.
Saxena SK, Agrawal OP, Pathak A. Synthesis of Some Novel (Z)-3-ethylidene-5,7-dimethylthiochroman- 4-one Derivatives and Study of its Monoamine Oxidases Inhibitory Activity. ijpi [Internet]. 6Oct.2022 [cited 10Dec.2022];12(4):449-54. Available from: https://www.jpionline.org/index.php/ijpi/article/view/1412