Synthesis of (2S,3S)-[3-(2)H1]-4-methyleneglutamic acid and (2S,3R)-[2,3-(2)H2]-4-methyleneglutamic acid

(2S,3S)-[3-(2)H1]-4-Methyleneglutamic acid 1a and (2S,3R)-[2,3-(2)H2]-4-methyleneglutamic acid 1b have been synthesised for use in biosynthetic and metabolic studies.     

Preparation of 2(3)-O-[2-(hydroxyamino)-2-oxoethyl]- and 2(3)-O-[3-(hydroxyamino)-3-oxopropyl]dextran

Hydroxame derivatives of carboxymethyl- and carboxyethyldextrans have been prepared and characterized by elemental analysis as well as by IR and UV spectroscopy. The effect of reaction conditions on the products yield has been studied.     

Synthesis and base hydrolysis of chloro(N-(2-pyridinylmethylene)-N′-[3-[(2-pyridinylmethylene)amino]-propyl]-1,3-propanediamine)cobalt(III) perchlora

Synthesis of [Co(pyDPT)Cl](ClO₄)₂ from pentadentate ligand and cobalt(II) yields one cis isomer. Hydrolysis in base is extremely rapid (k_OH 1.8 × 10⁶ M^?1 s^?1 at 250°) in this complex, where the geometry and ligand character fix the single site for conjugate base formation as cis to the leaving group.     

Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols

Structural alteration of the N^b-substituents of psilocin (3-[2-dimethylamino)ethyl]indol-4-ol) ( 12a ) has led to a number of compounds containing known pharmacophoric groups. Further, it is hoped that the subtle changes in the nature of these substituents may lead to a clearer understanding of the structure-activity relationships of the 4-hydroxytryptamine hallucinogens.     

3-Alkyl-2-[3(4)-pyridyl]-5-(2-vinyloxyethoxymethyl)-oxazolidines

1-Alkylamino-3-(2-vinyloxyethoxy)-2-propanols react with 3-and 4-pyridinecarbaldehydes to give equimolar mixtures of cis- and trans-3-alkyl-5-(2-vinyloxyethoxymethyl)-2-[3(4)-pyridyl]oxazolidines.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 1, 2005, pp. 104–108.Original Russian Text Copyright © 2005 by Kukharev, Stankevich, Lobanova, Klimenko, Kukhareva.     

Synthesis and calcium antagonistic activity of (+)-(R)- and (-)-(S)-3-acetyl-2-[5-methoxy-2-[4-[N-methyl-N-(3,4,5- trimethoxyphenethyl)amino]butoxy]phenyl]benzothiazoline hydrochloride

SA2572 ((+)-1), 3-acetyl-2-[5-methoxy-2-[4-[N-methyl-N-(3,4,5-trimethoxyphenethyl) amino] butoxy]phenyl]-benzothiazoline hydrochloride is a newly synthesized Ca2+ antagonist having a inhibitory effect on the fast Na+ inward channel. In order to clarify the absolute configurations and the pharmacological properties of both enantiomers, compounds ((+)-1 and (-)-1) were synthesized. The configurations of these compounds were assigned on the basis of an X-ray crystallographic analysis of synthetic precursor (5). The in vitro Ca2+ channel blocking activities of (+)-1 and (-)-1 were evaluated in terms of the inhibitory activities on depolarization-induced contraction of guinea pig taenia cecum and rabbit aorta. The in vivo efficacy of the enantiomers was evaluated with their hypotensive effects in spontaneously hypertensive rats. Compound (-)-1 showed more potent Ca2+ antagonistic activities on guinea pig taenia cecum and rabbit aorta and the hypotensive effect than those activities of (+)-1. In the electrophysiological study of Langendorff perfused rabbit hearts, compound (+)-1 showed more potent inhibitory effect on the fast Na+ inward channel than that of compound (-)-1, and an approximately equal potent inhibitory effect on the slow Ca2+ inward channel as compared with compound (-)-1. Stereoselectivity of the pharmacological activity was found.     

COPPER(II) COMPLEXES OF 1-[O-ALLYLPHENOXY]-3-[ISOPROPYLAMINO]-2-PROPANOL (ALPRENOLOL)

Abstract

Complexation of Cu(II) with the antihypertension drug Alprenolol (HAlp) under different conditions (metal/ligand ratios and solvents) results in the formation of two complexes - a binuclear green one, Cu₂Alp₂Cl₂ (1), and a mononuclear violet species CuAlp₂·2H₂O (2). Single crystals of (1) were isolated and its structure determined by X-ray diffraction. In the complex Alprenolol molecules are bidentately coordinated and each Cu atom is bound with NH, and bridged by the deprotonated OH group of the ligand to the second Cu centre. The chloride ions are coordinated to copper as terminal ligands. The mononuclear complex (2) was characterized using electronic and IR spectra, EPR, magnetochemical, calorimetric, thermogravimetric methods and elemental analysis. Copper is coordinated through O^? and N of OH and NH groups of the ligands in a distorted tetrahedral structure. The structure includes also two solvent molecules per CuAlp₂ unit.     

3-[ω-(2-Benzimidazolyl)alkyl]benzoxazolones

A new method for the preparation of -(3-benzoxazolonyl) butyric acids from sodium salts of benzoxazolones and -butyrolactone was developed. 3-[-(2-benzimidazolyl)alkyl]benzoxazolones were synthesized by the reaction of these acids and also (3-benzoxazolonyl)acetic and -(3-benzoxazolonyl)propionic acids with o-phenylenediamine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 464–466, April, 1973.     

The synthesis and biological activity of new 7-[2-(cyanomethyl)piperazinyl]- and 7-[3-(cyanomethyl)piperazinyl]quinolone antibacterials

Some novel 7-[2- or 3-(cyanomethyl)piperazinyl]quinolones have been prepared. Most notable, 2-cyanomethyl-piperazine 5 and 1-methyl-2-cyanomethylpiperazine 8 at the quinolone C-7 position produce products with good in vitro antibacterial activity. The key step in the synthesis of these products involves the regioselective deprotection of the benzyl group in function of the time reaction.     

Synthesis of 2-[3′-(trifluoromethyl)anilino] -5-hydroxynicotinic acid

2-[3′-(Trifluoromethyl)anilino]-5-hydroxynicotinic acid (2) was synthesized by two routes: a) by direct hydroxylation of 2-[3′-(trifluoromethyl)anilino]nicotinie acid (1) ; and b) by the following sequence starting from 2-chloro-3-methyl-5-nitropyridine (3) via 5-amino-2-chloro-3-methylpyridine (4) , 2-ehloro-5-hydroxy-3-methylpyridine (6) , 5-acetoxy-2-chloro-3-methylpyridine (7) , 5-acetoxy-2-chloronicotinie acid (8) , and 2-chloro-5-hydroxynicotinic acid (9). The correlation of 2 with one of the metabolites of 1 has been accomplished, and the identities of both compounds have been proven.