Induction of intrinsic apoptosis pathway in colon cancer HCT-116 cells by novel 2-substituted-5,6,7,8-tetrahydronaphthalene derivatives.

2-Acetyl tetralin (1) reacted with N,N-dimethylformamide dimethylacetal (DMF-DMA) to afford the enaminone 3. The reaction of 3 with piperidine and morpholine afforded the trans enaminone 5a,b, respectively. Compound 3 was treated with primary aromatic amines to give secondary enaminones 6a-e.

Convenient synthesis, anti-inflammatory, analgesic and ulcerogenic activites of some new bis-hydrazones and pyrazole derivatives.

The reaction of acid hydrazides (1a-c) with 2-chloro-1-(4-chlorophenyl)ethanone (2a) or 2-bromo-1-(4-bromophenyl)ethanone (2b) afforded bis-hydrazones 6a-d, while the reaction of la-c with 2-oxo-N-arylpropanehydrazonoyl chlorides (3a,b) furnished N-(aryl)propanehydrazonoyl chlorides 8a-c. The reaction of the latter chlorides with sodium benzenesulfinate furnished sulfones 11a-c. On the other hand, treatment of benzothiazole-2-carbohydrazide (1c) with the appropriate ketones yielded the corresponding hydrazones 13a,b, while the reaction of 1c with 2-(ethoxymethylene)malononitrile (14) or with 2-[bis(methylthio)methylene]malononitrile (16) afforded pyrazole derivatives 15 and 17, respectively.

Thiourea derivatives incorporating a hippuric acid moiety: synthesis and evaluation of antibacterial and antifungal activities.

New series of thiourea derivatives incorporating a hippuric acid moiety have been synthesized through the reaction of 4-hippuric acid isothiocyanate with various nitrogen nucleophiles such as aliphatic amines, aromatic amines, sulfa drugs, aminopyrazoles, phenylhydrazine and hydrazides. The synthesized compounds were tested against bacterial and fungal strains. Most of compounds, such as 2-(4-(3-(3-bromophenyl)thioureido)benzamido)acetic acid and 2-(4-(3-(4-(N-pyrimidin-2-ylsulfamoyl)phenyl)thioureido)benzamido)acetic acid, showed significant antibacterial and antifungal activities.

Synthesis of new 2-substituted 6-bromo-3-methylthiazolo[3,2-alpha]-benzimidazole derivatives and their biological activities.

1-(6-Bromo-3-methyl-1,3-thiazolo[3,2-alpha]benzimidazol-2-yl)ethanone (2) was prepared by bromination at ambient temperature of 1-(3-methylthiazolo[3,2-alpha]benzimidazol-2-yl)ethanone (1). The structure of 2 was determined by single-crystal X-ray diffraction. The precursor 5 was synthesized by heating a mixture of acetyl 2 and bromine.

Modulation of carcinogen metabolizing enzymes by new fused heterocycles pendant to 5,6,7,8-tetrahydronaphthalene derivatives.

The treatment of 2-bromo-1-(5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (1) with pyridine, 2-methylpyridine or 4-methylpyridine afforded their corresponding pyridinum bromides 3a-c. The latter salts reacted with activated acetylene to give the corresponding indolizine derivatives 6a-c. Imidazo[1,2-a]pyridine 9a,b, quinoxaline 15, imidazo[1,2-b][1,2,4]triazole 18 and imidazo[1,2-a]benzimidazole 21 derivatives were prepared from 1 as a starting material.

Immunomodulatory and anticancer activities of some novel 2-substituted-6-bromo-3-methylthiazolo[3,2-a]benzimidazole derivatives.

Ethyl 6-bromo-3-methyl-1,3-thiazolo[3,2-a]benzimidazole-2-carboxylate 2 was prepared by the ambient temperature bromination of ethyl 3-methyl-1,3-thiazolo[3,2-a]benzimidazole-2-carboxylate 1. The acid hydrazide 4 was obtained by the reaction of ester 2 with hydrazine hydrate. Treatment of compound 4 with benzaldehyde or 2-thiophenaldehyde yielded the corresponding hydrazones 6a and 6b, respectively, while the reaction of acid hydrazide 4 with ethoxymethylene malononitrile (7a) or with ethyl ethoxymethylene cyanoacetate (7b) in refluxing ethanol afforded pyrazole derivatives 9a and 9b, respectively.

Synthesis and pharmacological evaluation of 2-substituted benzo[b]thiophenes as anti-inflammatory and analgesic agents.

An efficient method for trapping isocyanate 4, generated from the Curtius rearrangement, with ethyl alcohol to afford the carbamate 5 is reported. 5-Nitrobenzo[b]thiophene-2-carboxylic acid 1 is converted to the corresponding hydrazide 2 by the reaction with hydrazine hydrate and then to the azide 3 with nitrous acid, followed by thermal rearrangement, cooling, and trapping in one pot reaction. The carbamate 5 is treated with hydrazine hydrate to afford the desired, Zileuton analogue, 4-(5-nitrobenzo[b]thiophene-2-yl)semicarbazide 6.

Anti-inflammatory and analgesic activities of newly synthesized chiral peptide derivatives using (3-benzoyl- 4,5-dioxo-2-phenyl-pyrrolidin-1-yl)acetic acid ethyl ester as starting material.

A series of heterocyclic derivatives was synthesized using (3-benzoyl-4,5-dioxo-2-phenyl-pyrrolidin-1-yl)acetic acid ethyl ester 1 as starting material. Treatment of 1 with 1 N NaOH or hydrazine hydrate afford the corresponding acid 2 and acid hydrazides 4 and 5, which were reacted with several reagents to produce some new peptido hetero-organic derivatives 6-12. The pharmacological screening showed that many of these newly synthesized compounds have good anti-inflammatory and analgesic activities comparable to diclofenac potassium and valdecoxib as reference drugs.