Synthesis of substituted 1H-imidazol-1 …

T1 - Synthesis and antiviral evaluation of polyhalogenated imidazole nucleosides

Synthesis and SAR of 1-hydroxy-1 H -benzo[ d ]imidazol …

AB - A series of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones were synthesized and evaluated for their ability to inhibit human and porcine forms of d-amino acid oxidase (DAAO). The inhibitory potency is largely dependent on the size and position of substituents on the benzene ring with IC 50 values of the compounds ranging from 70 nM to greater than 100 μM. Structure-activity relationships of this new class of DAAO inhibitors will be presented in detail along with comparisons to previously published SAR data from other classes of DAAO inhibitors. Two of these compounds were given to mice orally together with d-serine to assess their effects on plasma d-serine pharmacokinetics.

PROCESS FOR THE SYNTHESIS OF 5- (METHYL-lH-IMIDAZOL …

Imidazole-2-thiones are an interesting class of compounds. The synthesis and evaluation of oxygen and nitrogen analogs of the soft thione group demonstrated that the S atom is necessary for optimal activity ().

N2 - A series of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones were synthesized and evaluated for their ability to inhibit human and porcine forms of d-amino acid oxidase (DAAO). The inhibitory potency is largely dependent on the size and position of substituents on the benzene ring with IC 50 values of the compounds ranging from 70 nM to greater than 100 μM. Structure-activity relationships of this new class of DAAO inhibitors will be presented in detail along with comparisons to previously published SAR data from other classes of DAAO inhibitors. Two of these compounds were given to mice orally together with d-serine to assess their effects on plasma d-serine pharmacokinetics.


Synthesis of N -Heterocycles - Organic Chemistry Portal

A series of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones were synthesized and evaluated for their ability to inhibit human and porcine forms of d-amino acid oxidase (DAAO). The inhibitory potency is largely dependent on the size and position of substituents on the benzene ring with IC 50 values of the compounds ranging from 70 nM to greater than 100 μM. Structure-activity relationships of this new class of DAAO inhibitors will be presented in detail along with comparisons to previously published SAR data from other classes of DAAO inhibitors. Two of these compounds were given to mice orally together with d-serine to assess their effects on plasma d-serine pharmacokinetics.

Synthesis of piperidines - Organic Chemistry Portal

US patent 7,115,748 describes a method of making an imidazole-2-thione which comprises the steps of reacting a vicinal diamine with a compound having a thiocarbonyl moiety and oxidizing the resulting reaction product to obtain the said imidazole-2-thione (29). The first step of the sequence, the Strecker synthesis with phenylacetaldehyde (23), yields amino nitrile (24). Reaction of various suitable aldehydes, also yields imidazole-2-thione with different R substituents. Dibal reduction of 2-amino-3-phenylpropanenitrile (24), gave 3-phenyl-1,2-diaminopropane (25) in 68% yield after distillation. Dibal (Diisobutylaluminium hydride) was the best of several reducing agents tried by for the reduction of 2-amino-3-phenylpropanenitrile (24). Treatment of 3-phenyl-1,2-diaminopropane with 1,1`-thiocarbonyldiimidazole rapidly produced 4-benzyl-2-imidazolidinethione (26). Before oxidation sulfur group was protected by reaction with aryl halide. Alkylation with benzyl chloride, p-methoxybenzyl chloride, p-acetoxybenzyl chloride or allyl chloride resulted in alkylated sulfur. Swern oxidation of the resulting isothiouronium salts (27) gave the protected imidazole derivatives (28). Deprotecting the p-methoxybenzyl derivative with acid, the p-acetoxybenzyl derivative with base and the allyl derivative with p-toluenesulfinic acid in the presence of a catalytic amount of tetrakis (triphenylphosphine) palladium (Pd(PPh3)4] afforded 4-benzylimidazolidine-2-thione (29) (Scheme 9) ().

Online Chemical Catalog - R&D Chemicals

US patent 2007/0197795 describes a method for the synthesis of 4-substituted imidazole-2-one and thiones. Substituted methylene urea (36a) or thiourea (36b) was synthesized by by the reaction of substituted primary amine (35) with potassium cyanate or potassium thiocyanate respectively for one hour at room temperature. The solution of substituted methylene urea (36a) or thiourea (36b) in dichloromethane was then cooled to -40°C and a solution of diisobutylaluminium hydride (Dibal) was added slowly with stirring. The reaction mixture was then acidified with mixture of conc. HCl and crushed ice resulting in the formation of 4-substituted imidazole-2-one(37a) or thione (37b) (Scheme 11) ().