Hydrazonoyl Halides as Precursors for New Fused Heterocycles of 5α‐Reductase Inhibitors

Abstract

A new series of benzo[6,7]cyclohepta[1,2-d]triazolo[4,3-a]pyrimidines 8a-l was synthesized via reaction of heterocyclic thione 4 or its methyl derivatives 10 with hydrazonoyl halides 5a-l. Also, reaction of compound 4 with a mixture of chloroacetic acid and aromatic aldehyde derivatives gave benzo[6,7]cyclohepta[1,2-d]thiazolo[3,2-a]pyrimidin-3-ones 12-14. The microanalyses and spectral data of the synthesized compounds are in full agreement with their molecular structure. All the newly synthesized products were screened against 5α-reductase and showed activities with good ED(50) for all compounds.

Synthesis and Antimicrobial Activity of Some New 1,3,4-Thiadiazole Derivatives

“…Recently, we published the antimicrobial activity results of a series of N -[3-aryl-5-(3-dimethylamino-acryloyl)-3 H -[1,3,4]-thiadiazol-2-ylidene]-benzamides, which showed promising activity [ 11 ]. Based on these findings, and in continuation of our interest in synthesis of bioactive compounds [ 12 , 13 , 14 , 15 , 16 ], we have now prepared a new series of 1,3,4-thiadiazoles via reaction of N -[3-aryl-5-(3-dimethylamino- acryloyl)-3 H -[1,3,4]-thiadiazol-2-ylidene]-benzamides with 1,3-dipoles and some nitrogen nucleophiles to investigate the antimicrobial activity of the products and study their structure activity relationship (SAR) towards some microorganisms.…”

Synthesis and antimicrobial evaluation of novel 1,3-thiazoles and unsymmetrical azines

“…We previously reported that when thiosemicarbazide derivative reacts with hydrazonoyl chlorides in dioxane in the presence of triethylamine, a cyclic product like 12 is formed [30]. However, when thiosemicarbazide derivatives 5a,b react with hydrazonoyl chlorides 9a-c, it affords compounds 13a-e rather than the expected analog of 12.…”

Terephthalaldehyde: An Effecient Key Precursor for Novel Synthesis of Some Interesting Bis‐thiazoles and Bis‐triazolopyrimidinones

“…Another active heterocyclic ring system is triazolopyrimidine derivatives, which are known by their activities as antimicrobial , antitumor and analgesic, and anti‐inflammatory . Encouraged by all these findings and in continuation of our program focusing on the synthesis of bis ‐heterocyclic compounds that expected to be biologically active , we reported in the present work an efficient and rapid method for the synthesis of a series of bis ‐thiazole and bis ‐triazolopyrimidine derivatives from the titled aldehyde. The synthesized bis‐ compounds will be attractive species for the medicinal researchers to investigate their biological activity.…”