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Synthesis of new heterocyclic compounds containing nitrogen, sulphur and study their biological activity

Basma Saad Baaiu, Mansour Abdelsalam, Fateh Eltaboni, Wafiyah Amhalhil

Abstract


Several substituted pyridines with brominated coumarin and with other substituents were achieved by condensing brominated coumarin IV with 4-methoxybenzaldehyde in basic solution forming α,β-unsaturated ketone II. Hantzsch reaction of this ketone with β-ketoester to provide precursor substituted pyridines. The Hantzsch reaction product was subjected to different reactions. The other targeted heterocyclic compound was obtained by reaction of α,β-unsaturated ketone II with hydrazine carbothioamide to give substituted pyrazole with brominated coumarin, also converted to different substituents. Structure analysis of the prepared heterocyclic compounds was confirmed by spectral data, elemental analysis. Antibacterial activity was screened towards some microorganism thus low and intermediate activity against Gram positive and negative bacteria were noted.


Keywords


3-acetyl-7-bromo-2H-chromen-2-one, pyridines, pyrazolines, hiazolines and chalcone

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References


R. Kenchappa, Yadav D. Bodke, A. Chandrashekar, Sandeep Telkar, K. S. Manjunatha, M. ArunaSindhe. Synthesis of some 2,6-bis(1-coumarin-2-yl)-4-(4-substitutedphenyl) pyridine derivatives as potent biological agents. Arabian Journal of Chemistry. 2013; 1-9p.

Rafat M. Mohareb, Nadia Y. Megally Abdo. Uses of 3-(2-Bromoacetyl)-2H-chromen-2-one in the Synthesis of Heterocyclic Compounds Incorporating Coumarin: Synthesis, Characterization and Cytotoxicity. Molecules. 2015; 20: 11535-11553.

Pravin O. Patil, Sanjay B. Bari, Sandip D. Firke, Prashant K. Deshmukh, Shailesh T. Donda, Dilip A. Patil. A comprehensive review on synthesis and designing aspects of coumarin derivatives as monoamine oxidase inhibitors for depression and Alzheimer’s disease. Bioorganic & Medicinal Chemistry. 2013; 21: 2434-2450.

Mohammad Asif. Overview of Diverse Pharmacological Activities of Substituted Coumarins: Compounds with Therapeutic Potentials. American Journal of Current Organic Chemistry. 2014; 1: 1-16.

Marwa Sayed El‐Gendy, Anhar Abdel‐Aziem, Abdou Osman Abdelhamid. Reactions and Antimicrobial activity of (3-(3-(4-Methoxyphenyl)acryloyl)-2H-Chromen-2-one. International Journal of Advanced Research. 2013; 1: 557-567.

Nada Elsharif, Mohamed Alnaily, Amnnah Loujanqi. Synthesis and Evaluation of Chalcone Derivatives and Schiff bases Derivatives as Antibacterial. Journal of Modern Chemistry & Chemical Technology. 2018; 9: 1-7.

Mirela Filipan-Litvić, Mladen Litvić, Ivica Cepanec, Vladimir Vinković. Hantzsch Synthesis of 2,6-Dimethyl-3,5-dimethoxycarbonyl-4-(o-methoxyphenyl)-1,4-dihydropyridine; a Novel Cyclisation Leading to an Unusual Formation of 1-Amino-2-methoxycarbonyl-3,5-bis(o-methoxyphenyl)-4-oxa-cyclohexan-1-ene. Molecules. 2007; 12: 2546-2558.

Anhar Abdel-Aziem, Basma Saad Baaiu, Eslam R. El-Sawy. Reactions and Antibacterial Activity of 6-Bromo-3-(2-Bromoacetyl)-2H-Chromen-2-One. Polycyclic Aromatic Compounds. 2021; 1-9.

A. F. Zahoor1, S. Naheed, M. Irfan, S. Ahmad, M. N. Anjum, M. Yousaf. Advances in the synthesis and reactivity of acyl azides (2005-2015). AFINIDAD. 2018; 75: 228-238.

Anhar Abdel-Aziem, Basma S. Baaiu, Abdou O. Abdelhamid. Synthesis and Evaluation of Antimicrobial Activity of Some Novel Heterocyclic Compounds from 5-Bromosalicylaldehyde. J. Heterocyclic Chem. 2107; 54: 3471-3480.




DOI: https://doi.org/10.37591/etce.v8i3.6034

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