Modification of biologically active amides and amines with fluorine-containing heterocycles

Russian Chemical Bulletin - A synthetic approach to the modification of the drug “riluzole” with pharmacologically active fragments such as carbazole, tetrahydrocarbazole,...     

Modification of biologically active amides and amines with fluorine-containing heterocycles 3*. Piracetam in the three-component reaction with methyl trifluoropyruvate and 1,3-binucleophiles

Three-component reaction of Piracetam, methyl trifluoropyruvate and 1,3-binucleophiles, such as 6-aminouracils, 6-aminothiouracils, 4-(4-tolylamino)pent-3-en-2-one and N-substituted ureas, has been studied. This reaction resulted in fluorinated heterocyclic derivatives of Piracetam.

     

Modification of biologically active amides and amines with fluorine-containing heterocycles 4. Trifluoromethyl-containing heterocyclic pyracetam derivatives

A one-pot method for the synthesis of trifluoromethyl-containing heterocyclic pyracetam derivatives has been suggested by the reaction of pyracetam, hexafluoroacetone, and 1,3-binucleophiles, viz., 3-aminocrotononitrile, 6-aminouracyls, 6-aminothiouracyl, N-benzyl-3-aminocyclohexenone, and 2-aminothiazoline.     

Modification of biologically active amides and amines with fluorine-containing heterocycles 1. Novel fluorine-containing heterocyclic derivatives of streptocide

Three-component reaction of Piracetam, methyl trifluoropyruvate and 1,3-binucleophiles, such as 6-aminouracils, 6-aminothiouracils, 4-(4-tolylamino)pent-3-en-2-one and N-substituted ureas, has been studied. This reaction resulted in fluorinated heterocyclic derivatives of Piracetam.     

Modification of biologically active amides and amines with fluorine-containing heterocycles 7. Fluorine-containing heterocyclic derivatives of the acetazolamide

An approach is proposed to modification of a medical product acetazolamide (N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide) by interaction of 2-(5-acetylamino-1,3,4-thiadiazole-2-yl)sulfonyl imine methyl trifluoropyruvate, which is in-situ generated from acetazolamide, with 1,3-binucleophiles: 6-aminouracils, 6-aminothiouracils, and N-substituted ureas, to yield heterocyclic compounds with the CF₃ substituent in the nitrogen-containing mono- or bicycle.     

Modification of biologically active amides and amines with fluorine-containing heterocycles 2*. N-(2-Thienyl)imines on the base of methyl trifluoropyruvate in cyclocondensation with 1,3-N,N-binucleophiles

An approach to the modification of the biologically active compounds, substituted 2-aminothiophenes, with fluorine-containing five-membered heterocycles is proposed. The reaction of 2-aminothiophenes with methyl trifluoropyruvate yields the corresponding N-(2-thienyl)imines, their subsequent cyclocondensation with 1,3-N,N-binucleophiles (2-aminothiazoline and benzamidines) furnished 5-oxo-6-trifluoromethyl-2,3,5,6-tetrahydroimidazothiazoles and 5-oxo-2-phenyl-4-trifluoromethyl-4,5-dihydro-1H-imidazoles.     

Synthesis,Molecular Structure,and Spectral Characteristics of Lead(II) Complexes with 1,5-Dimethyl-4-[2-(3-methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)hydrazinyl]-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

Russian Journal of General Chemistry - Pb(II) cations form complexes with...     

Modification of biologically active amides and amines with fluorine-containing heterocycles 12.* Endo- and exocyclic modifications of the drug riluzole with trifluoromethyl-containing heterocycles

New derivatives of the drug riluzole, 6-(trifluoromethoxy)benzothiazol-2-ylamine, modified at the endo- and exocyclic nitrogen atoms with trifluoromethyl-containing heterocycles were synthesized via transformations of methyltrifluoropyruvate and hexafluoroacetone N-6-(trifluoromethoxy)benzothiazol-2-ylimines by meams of cycloaddition and cyclocondensation reactions, respectively. The influence of the resulting compounds on neuronal NMDA receptors, as well as on the release and reuptake of the neurotransmitter glutamate was investigated.     

Modification of biologically active amides and amines with fluoro-containing heterocycles 5. Fluoro-containing heterocyclic derivatives of 2-amino-1,3,4-thiadiazoles

An approach to modification of biologically active 2-amino-1,3,4-thiadiazoles with fluoro-containing five-membered heterocycles was proposed. The approach involves reactions of imines (generated in situ from 2-amino-1,3,4-thiadiazoles and methyl trifluoropyruvate) with 1,3-binucleophiles such as 6-aminouracils, 6-aminothiouracils, N-substituted 3-aminocyclohexenones, N-substituted ureas, N-substituted benzamidines, and 3-aminocrotononitrile.     

Reactions of 4-chloro-6-oxo-2,3-dihydro-5-azabenzofurans with amines

The reaction of 7-nitro- and 7-unsubstituted 4-chloro-6-oxo-2,3-dihydro-5-azabenzofurans with primary and secondary amines proceeds with substitution of the chlorine atoms by amine residues and with recyclization of the compounds to 5- and 7-azaindoline derivatives.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No, 10, pp. 1311–1313, October, 1973.We thank Yu. N. Sheinker, E. M. Peresleni, L. M. Alekseeva, N. A. Zosimova, and Yu. I. Pomerantsev for their assistance in conducting the spectral investigations.     

A Recording Medium Based on Copolymer of 4-((1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)diazenyl)phenyl Methacrylate with Nonyl Methacrylate for Polarization Holography

A recording medium based on a novel copolymer of 4-((4-hydroxyphenyl)diazenyl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one with nonyl methacrylate is created, and the possibility of its use for polarization holography is investigated. It is shown that, for films based on this copolymer, holograms can be recorded without special heating due to a fairly low softening temperature. The recorded holograms are characterized by low noisiness.     

Modification of biologically active amides and amines with fluoro-containing heterocycles 13.* Carbazoles and tetrahydrocarbazoles modified with 2-substituted (imidazo[1,2-a]pyridine-3-yl)propionamidic fragments

Russian Chemical Bulletin - An approach to modify biologically active carbazoles and tetrahydrocarbazoles with 2-trifluoromethyl and 2-methoxycarbonyl(imidazo[1,2-a]pyridin-3-yl)propionylamidic...     

Solvent extraction of cobalt(II), zinc(II) and europium(III) with 4-thiobenzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one (SBMPP)

Solvent extraction of⁶⁵zinc,⁶⁰cobalt and^152+154europium from aqueous buffers into benzene containing 4-thiobenzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one (SBMPP) has been investigated in detail (μ=0.1, T=26±1°C). The species extracted and the values of log K_ex, where K_ex refers to the extraction equilibrium, are ZnL₂ (−2.68) CoL₂(−3.08) and EuL₃(−7.08), where L is the anion of the ligand. The sulfur analog appears to be more effective than the parent ligand 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one in the extraction of zinc(II) and cobalt(II), whereas the reverse is true with europium(III).