title: 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.
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.
authors.affiliation: Department of Chemistry, College of Science, King Saud University, Girls Section, P.O. Box 2457, Riyadh 11495, Saudi Arabia; National Organization for Drug Control and Research, Cairo, P.O. 29, Egypt.
authors.forename: Nahed N E
authors.initials: NN
authors.lastname: El-Sayed
authors.affiliation: Department of Chemistry, Faculty of Science, University of Tabuk, Tabuk 71491, P.O. Box 741, Saudi Arabia.
authors.forename: Mahmoud A
authors.initials: MA
authors.lastname: Abdelaziz
authors.affiliation: National Organization for Drug Control and Research, Cairo, P.O. 29, Egypt.
authors.forename: Wagnat W
authors.initials: WW
authors.lastname: Wardakhan
authors.affiliation: Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt. Electronic address: raafat_mohareb@yahoo.com.
authors.forename: Rafat M
authors.initials: RM
authors.lastname: Mohareb
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000897:Anti-Ulcer Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006834:Hydrazines / Q000737:chemistry*; D033542:Pandalidae; D011284:Pregnenolone / Q000737:chemistry*; D013876:Thiophenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000893:Anti-Inflammatory Agents; D000897:Anti-Ulcer Agents; D006834:Hydrazines; D013876:Thiophenes; D014230:Triazoles; D011284:Pregnenolone
keywords: 1,2,4-Triazole; Anti-inflammatory; Antiulcer activity; Pregnenolone; Pyran; Thiophene