Carlos Corral

Synthesis and preliminary pharmacological evaluation of thiophene analogues of viloxazine as potentialantidepressant drugs

A series of eight thienyloxymethylmorpholines, thiophene analogues of viloxazine, have been synthesized by three different routes. The preliminary pharmacological evaluation of this series shows antidepressant properties on the mice models used with a light sedative action. The structure-activity relationship is established in a first approximation.

Synthesis and properties of 1H-1,2,4-benzotriazepines☆

Abstract The synthesis of some N,N-disubstituted benzhydrazidoyl chlorides and their reaction with cyano compounds in the presence of a Lewis acid are described. Whereas N-methyl-N-phenylbenzhydrazidoyl chloride (1a) gave 1H-1,2,4-triazoles, N,N-diphenylbenzhydrazidoyl chloride (1b) afforded 1H-1,2,4-benzotriazepines (3b) and N,N-(2,2′-biphenylen)benzhydrazidoyl chloride (10) yielded the corresponding 1H-1,2,4-benzotriazepine (12) or a hydrolysis product (13). Properties of compounds 3b, specially their near-quantative acid hydrolysis to 1-phenylindazoles, are reported.

Synthesis and central relaxant activity of thiophene analogs of mephenesin and methocarbamol

Abstract The thiophene analogs of mephenesin, mephenesin carbamate and methocarbamol have been synthesized and subjected to pharmacological evaluation. Two of these compounds showed interesting muscle relaxant activity and seem worthy of further study.

Reactions with methyl 3-hydroxythiophene-2-carboxylate. Part 2. A new route to mono- and di-alkyl ethers of thiotetronic and α-halogenothiotetronic acids

Methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylates (2), obtained from methyl 3-hydroxythiophene-2-carboxylate by straightforward halogenation, added alcohols and then lost hydrogen chloride at room temperature to yield thiophene-2,4-diols (4). Successive O-alkylation and alkaline hydrolysis of these compounds gave 3,5-dialkoxythiophene-2-carboxylic acids (6) in nearly quantitative yield. The latter could either be thermally decarboxylated or decarboxylated and partially dealkylated at room temperature by aqueous acid to the ethers of thiotetronic and α-halogenothiotetronic acids in high yield.

Conformational analysis of thiophene analogs of propranolol

Abstract Conformation of 3-tert-butylamino-1-thienyloxy-2-propanol, a thiophene analogue of propanolol, have been theoretically investigated by molecular mechanics and semiempirical calculations. The conformational minima obtained have been compared with those reported for propranolol using molecular graphics. The good “fit” obtained can account for the similar biological activity of these compounds.