Synthesis and acylation of 1,2,3,4-tetrahydroisoquinoline derivatives

1,2,3,4-Tetrahydroisoquinolines were synthesized, and their acylation was studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 780–783, June, 1993.     

Reactions of 1-(3,4-diethoxybenzylidene)-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline with polyfluorocarbonyl compounds

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1689, December, 1990.     

Synthesis and pharmacological evaluation of 1-isopropyl-1,2,3,4-tetrahydroisoquinoline derivatives as novel antihypertensive agents

A series of 1-isopropyl-1,2,3,4-tetrahydroisoquinoline derivatives were synthesized and their bradycardic activities were evaluated in isolated guinea pig right atria. Structure-activity relationship studies revealed that the introduction of an appropriate substituent and its position on the 1,2,3,4-tetrahydroisoquinoline ring are essential for potent in vitro activity. Furthermore, the tether between the piperidyl moiety and the terminal aromatic ring is important for potent antihypertensive activity. Oral administration of 6-fluoro-1-isopropyl-2-{[1-(2-phenylethyl)piperidin-4-yl]carbonyl}-1,2,3,4-tetrahydroisoquinoline (3b) to spontaneously hypertensive rats (SHR) elicited antihypertensive effects without inducing reflex tachycardia, which is often caused by traditional L-type Ca2? channel blockers.     

Cyclodehydration of N-(2-nitroaryl)-1,2,3,4-tetrahydroisoquinoline derivatives

Compounds 1a-1g gave the corresponding N-oxide derivatives 3a-3g when heated with acetic or propionic acid.     

Synthesis and acylation of tertiary enamines: 1,2,3,4-tetrahydroisoquinoline derivatives

N-methyl-3,3-R¹R²-1-(R³-methylene)-1,2,3,4-tetrahydroisoquinolines were obtained; they react with acylating agents forming enaminocarbonyl derivatives.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 939–942, July, 1988.     

Synthesis, Crystalline Structure, and Spectra of 3,3-Dimethyl-1-(3-methyl-1-phenylpyrazol-5-onylidene-4)-1,2,3,4-tetrahydroisoquinoline

3,3-Dimethyl-1-(3-methyl-1-phenylpyrazol-5-onylidene-4)-1,2,3,4-tetrahydroisoquinoline has been synthesized and its crystalline and molecular structures determined. It was found by IR and electronic absorption spectroscopic methods that the structure of this compound is not changed in solutions.     

Synthesis of (-) or (+) -threo-3-(3,4-dihydroxyphenyl) serine and (-) or (+) -erythro-3-(3,4-dihydroxyphenyl)-serine]

The known synthesis of DL -3-(3,4-dihydroxyphenyl)-serine (DOPS) has been modified so that the diastereomeric threo and erythro forms could be separated. These were resolved into their antipodes, whose chemical, physical, and spectrochemical properties are discussed.     

Synthesis and pharmacological evaluation of 2-(3-piperidyl)-1,2,3,4-tetrahydroisoquinoline derivatives as specific bradycardic agents

Novel 1,2,3,4-tetrahydroisoquinoline derivatives bearing directly a cyclic amine at the 2-position were prepared and examined for their bradycardic activities in isolated right atria and in anesthetized rats. The structure-activity relationships (SAR) study revealed that the 2-(3-piperidyl)-1,2,3,4-tetrahydroisoquinoline skeleton is essential for the appearance of potent in vitro activity, and that the presence of at least one methoxy group at the 6- or 7-position of the 1,2,3,4-tetrahydroisoquinoline ring is important to exert potent in vitro activity. In vivo tests of selected compounds demonstrated that 2-(1-benzyl-3-piperidyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (6c) exhibited potent bradycardic activity with negligible influence on mean blood pressure in rats, although its potency is a half of that of Zatebradine.     

Synthesis and Structure of Metal Complexes of 1-(1-R-3-Methylpyrazole-5-onilidene-4)-1,2,3,4-tetrahydroisoquinoline Derivatives

Twenty new complexes were synthesized by reacting Co(II), Cu(II), Zn, Cr(III), Fe(III), Cd and Ag salts with 3,3-dimethyl-1-(3-methylpyrazole-5-onilidene-4)-1,2,3,4-tetrahydroisoquinoline (L¹), spiro{cyclohexane-1,3"-[1-(1-phenyl-3-methylpyrazole-5-onilidene-4)-1,2,3,4-tetrahydroisoquinoline]} (L²), and 3,3-dimethyl-1-(1-phenyl-3-methylpyrazole-5-onilidene-4)-1,2,3,4-tetrahydroisoquinoline (L³). These compounds were studied by IR and electronic absorption spectroscopy. The type of coordination of their ligands was discussed on the basis of the results obtained and X-ray diffraction data for L³ and [CuL₂ ² Cl₂] · 2L² obtained previously.     

Synthesis and Structure of the Copper(II) Nitrate Complex with 1-(3-Methyl-1-phenylpyrazol-5-onylidene-4)-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline

The complex [CuL(NO₃)₂] ? CH₃CN(I), where L is 1-(3-methyl-1-phenylpyrazol-5-onylidene-4)-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline, is synthesized and studied by X-ray diffraction and IR and electronic absorption spectroscopies. Complex I is prepared by the reaction of copper(II) nitrate crystal hydrate with L in acetonitrile. The coordination polyhedron of the Cu atom in I is a distorted (4 + 1) five-vertex polyhedron, and ligand L in the structure acts as N,O-bidentate bridge. The nitrate groups in I perform different structural functions: monodentate-terminal and anisobidentate. Structure I is composed of polymeric chains -L-Cu(NO₃)₂-L- and solvate acetonitrile molecules arranged between the chains.     

Synthesis,Configuration Judgment and Potentiation Activity of (2S,3S,E)-4-(3,4-Dihydroxybenzylidene)-3-(3,4-dihydroxyphenyl)-5-oxotetrahydrofuran-2-carboxylic Acid

The title compound(2S,3S,E)-4-(3,4-dihydroxybenzylidene)-3-(3,4-dihydroxyphenyl)-5-oxotetrahydrofuran-2-carboxylic acid was synthesized and the 2D structure was characterized by ~1H-NMR ~(13)C-NMR and LCMS. The absolute configuration was determined by single-crystal X-ray diffraction of the key intermediate(2S,3S,E)-ethyl 4-(3,4-dimethoxybenzylidene)-3-(3,4-dimethoxyphenyl)-5-oxotetrahydrofuran-2-carboxylate. The crystal belongs to tetragonal system, space group P4_1 with a = 13.0665(2), b = 13.0665(2), c = 13.4735(2) ?, V = 2300.4(6) ?~3, Z = 4, D_c = 1.278 g/cm~3, μ(CuKα) = 0.801 mm~(-1), F(000) = 936, S = 1.050, R = 0.0364 and wR(I 2σ(I)) = 0.1071. X-ray diffraction results showed that the molecular structure is stabilized totally by Van der Waals force. The antibacterial activity tests showed that the title compound possesses slight synergistic effect against MRSA and Acinetobacter baumanii.     

R 和 s-1-(3'-溴-4'-甲氧基)苄基-2-甲基-6-甲氧基-7-羟基-1, 2,3,4-四氢异喹啉的合成

本文报道了R和S-1-(3'-溴-4'-甲氧基)苄基-2-甲基-6-甲氧基-7-羟基-1,2,3,4-四氢异喹啉的合成。     

Synthesis of new 3,4-di-and 1,2,3,4-tetrahydroquinazolin-4-one derivatives and X-ray diffraction study of crystal solvates of 3-methylsulfonylamino-2-(2-methylsulfonylaminophenyl)-1,2,3,4-tetrahydroquinazolin-4-one

The reactions of hydrazide, mesyl hydrazide, succinyl hydrazide, and maleyl hydrazide of anthranilic acid with carbonyl compounds were studied, and new di-and tetrahydroquinazolin-4-one derivatives were prepared. The structure of one reaction product, viz., 3-methylsulfonylamino-2-(2-methylsulfonylaminophenyl)-1,2,3,4-tetrahydroquinazolin-4-one, was established by X-ray diffraction study of two crystal solvates of this compound. The characteristic features of the crystal packings of these solvates are discussed. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1183–1191, July, 2006.