A new class of nonhormonal pregnancy-terminating agents. Synthesis and contragestational activity of 3,5-diaryl-s-triazoles

Abstract

A series of 3,5-diaryl-s-triazoles were synthesized and evaluated as postimplantation contragestational agents. The introduction of various substituents (e.g., an o-alkyl chain on one phenyl and a m-alkoxy group on the other) was found to increase the potency. Several compounds with very high pregnancy-terminating activity in both hamsters and rats were obtained. One of these, 3-(2-ethylphenyl)-5-(3-methoxyphenyl)-s-triazole, DL 111 (36), was selected for detailed evaluation in various animal species. A synthetic scheme for the preparation of these compounds and preliminary structure-activity relationships are presented.

Synthesis of Some N, N′‐Diacylhydrazine Derivatives with Radical‐Scavenging and Antifungal Activity

“…All the intermediate‐substituted acylhydrazines were synthesized according references, and the m.p. of these intermediates accorded with references (27–37).…”

Effect of S–Se Bioisosteric Exchange on Affinity and Intrinsic Efficacy of Novel N-acylhydrazone Derivatives at the Adenosine A2A Receptor

“…The synthesis of the new NAH compounds ( 3 – 5 ) was performed in three steps [ 4 ]. First, the esters ( 10a and 10b ) [ 26 , 27 ] were prepared by Yamada oxidation in methanol of the corresponding commercial aldehydes ( 9a and 9b ) [ 28 ], and then submitted to hydrazinolysis reaction in ethanol to produce the key hydrazide intermediates 11a and 11b ( Scheme 1 ) [ 29 , 30 ]. Finally, the desired NAH derivatives ( 3 – 5 ) were obtained in high overall yields by an acid-catalyzed condensation reaction with the corresponding aldehydes (2-formylthiophene or 2-formylselenophene, Scheme 1 ).…”

Synthesis of Polysubstituted‐1,2,4‐Triazoles

“…The preparation of compounds 1 , 1a , 1b , 1c , 2 , 2a , 2b , 2c , 2d , 2e , 3 , 3a , 3b , 3c , 3d , 3e , 4 , 4a , 4b , 4c , 4d , 4e , 4f , 4g , 5 , 5a , 5b is shown in Scheme . Compounds 1a and 1b were prepared according to a literature method [17]. Compounds 1c [18], 2a , 2b , 2c , 2d , 2e [19], and 3a , 3b , 3c , 3d , 3e [19] were synthesized and purified according to procedures in the literature.…”

“…Compounds 1a and 1b were prepared according to a literature method [16]. Compounds 1c [17], 2a , 2b , 2c , 2d , 2e [18], and 3a , 3b , 3c , 3d , 3e [18] were synthesized and purified according to other procedures in the literature. The starting material 4‐nitrobenzoylhydrazine and 4‐pyridinecarbonylhydrazine were also prepared according to a literature method [19].…”