title: Multi-component one-pot synthesis and antimicrobial activities of 3-methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydro-pyrazolo[5,4-b]pyrimidino[5,4-e]pyridine-5-one and related derivatives.
abstract: The synthesis of 3-methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydropyrazolo[5,4-b] pyrimidino[5,4-e]pyridine-5-one (6) was achieved by two different one-pot multi-component synthesis (one-pot three-component and one-pot four component synthesis). Mono and dialkylation of 6 under different conditions gave compounds 7-11. The hydrazine 12 produced from reaction of 9 with N₂H₄ was subjected to reactions with some aromatic aldehydes, ethyl acetoacetate, acetyl acetone, ethyl cyanoacetate and triethyl orthoformate to give 13-17, respectively. Compound 12 upon reaction with CS₂, nitrous acid, benzoin, chloroacetone and phenacyl bromide gave 18,20,21,22. Alkylation of 18 with ethyl iodide, ethyl chloroacetate and phenacyl bromide gave 19a-c. The antibacterial and antifungal activities of selected derivatives were evaluated.
authors.affiliation: Department of Chemistry, Faculty of Science, Assiut University, Assiut 71516, Egypt. emarytalaat@yahoo.com
authors.forename: Talaat I
authors.initials: TI
authors.lastname: El-Emary
authors.forename: Shawkat A Abd
authors.initials: SA
authors.lastname: El-Mohsen
mesh_terms: D000478:Alkylation; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D015394:Molecular Structure; D011720:Pyrazoles / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011728:Pyridones / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*
chemical_list: C581279:3-methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydro-pyrazolo(5,4-b)pyrimidino(5,4-e)pyridine-5-one; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D011720:Pyrazoles; D011725:Pyridines; D011728:Pyridones; D011743:Pyrimidines