Synthesis and Evaluation of The Antiviral Activity of Novel 2-Thiopyrimidine-5-Carbonitrile Derivatives

Mohamed, Mosaad Sayed; Awad, Samir Mohamed; Abd El-tawab, Neama Abdallah; Ahmed, Naglaa Mohamed

doi:10.21608/ejchem.2022.152932.6624

	Synthesis and Evaluation of The Antiviral Activity of Novel 2-Thiopyrimidine-5-Carbonitrile Derivatives
Egyptian Journal of Chemistry
Article 37, Volume 66, Issue 6, June 2023, Page 371-382 PDF (761.49 K)
Document Type: Original Article
DOI: 10.21608/ejchem.2022.152932.6624
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Authors
Mosaad Sayed Mohamed¹; Samir Mohamed Awad ²; Neama Abdallah Abd El-tawab ²; Naglaa Mohamed Ahmed³
¹pharmaceutical organic chemistry department-faculty of pharmacy-helwan university. Ain Helwan. Helwan. Egypt
²Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Helwan University, Ain Helwan, Helwan, Egypt
³Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Helwan University, Ain Helwan, Helwan, Egypt.
Abstract
2-Thiouracil-5-carbonitriles are promising compounds that have been prepared in the last twenty years and have proven to have a diversity of biological activity. In line with this approach, our new compounds were prepared starting from Biginilli condensation of thiourea, ethyl cyanoacetate and 2,4-dichlorobenzaldehyde in basic medium to give a thiouracil derivative (1) which was subjected to chlorination at4th position by POCl3/PCl5 mixture producing chloropyrimidine (2) which in turns was reacted with m-aminoacetophenone in pyridine yielding acetyl derivative (3) which was condensed with a series of four aromatic aldehydes in alcoholic sodium hydroxide producing chalcones (4a-d) which were used as starting materials for the preparation of many heterocyclic nuclei by their reaction with hydrazine, phenyl hydrazine, hydroxylamine HCl, thiourea, ethyl cyanoacetate /ammonium acetate, malononitrile, ethyl cyanoacetate/acetic acid/sodium acetate to give pyrazoline, phenyl pyrazoline, isoxazoline, thiopyrimidine, pyridinone, aminopyridine and aminopyran derivatives (5a-d) to (11a-d) respectively . Some of the newly synthesized compounds were investigated as antiviral agents. Compounds (2), (7a), and (7c) show promising antiviral activity against Bovine Viral Diarrhea Virus (BVDV). The structures of the newly synthesized compounds were confirmed by elemental analysis in addition to spectral data and physical methods.
Keywords
Antiviral; 2-Thiouracil-5- carbonitriles; synthesis; and evaluation


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