The Knoevenagel reaction of cyanoacetylhydrazine with pregnenolone: Synthesis of thiophene, thieno[2,3-d]pyrimidine, 1,2,4-triazole, pyran and pyridine derivatives with anti-inflammatory and anti-ulcer activities

Steroids
Nahed N E El-SayedRafat M Mohareb

Abstract

The reaction of pregnenolone with cyanoacetylhydrazine and ammonium acetate at 120°C gave the Knoevenagel condensation product 3. The latter reacted with different reagents to give thiophene, thieno[2,3-d]pyrimidine, 1,2,4-triazole and pyran derivatives. The anti-inflammatory and anti-ulcer evaluations of the newly synthesized products were evaluated and the results showed that compounds 4, 8c, 10, 11, 13c, 15a, 15c, 17a, 17b, 17e, 18a and 18f possessed higher activity compared to the rest of the compounds. In addition to this, the toxicity of these active compounds was studied against shrimp larvae where compounds 15a, 15c and 18a showed non-toxicity against the tested organisms.

References

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Feb 24, 2015·Steroids·Malika Ibrahim-Ouali

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Citations

Dec 6, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nahed N E El-SayedAbir Ben Bacha
May 2, 2017·Chemical & Pharmaceutical Bulletin·Amira Elsayed Mahmoud AbdallahMenna Alla Mohamed Abd Elaleem Elshamy
Dec 20, 2017·Anti-cancer Drugs·Flaviana Alves Dos SantosMaira Galdino da Rocha Pitta
Jan 29, 2021·Journal of Enzyme Inhibition and Medicinal Chemistry·Reham R KhattabNasser A Hassan
Apr 2, 2021·Steroids·Arfeen Iqbal, Tabassum Siddiqui

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