Synthesis and Evaluation of Thioamide and Bromo Derivatives of 1,3-Diphenylpropane-1,3-dione as 5α-Reductase Inhibitors.

Background: 1,3-Diphenylpropane-1,3-dione (1) is an acetylacetone β-diketone in which both of the methyl groups have been replaced with phenyl groups. It is a component of licorice root extract (Glycyrrhiza glabra) and has anti-mutagenic and anti-cancer properties. It functions as a metabolite, an anti-mutagen, and an anti-neoplastic agent.

Evaluation of cytotoxic properties of two fluorescent -Re(CO) complexes bearing an ,-bidentate benzimidazole coligand.

The reaction between 1-benzimidazol-2-ylmethyl-(-aryl)amine derivatives (L) and [ReBr(CO)] afforded octahedral Re(i) complexes of the general formula of [ReBr(CO)L] (R = 4-Cl and 4-COOCH). The Re(i) complexes were screened for their potential cytotoxicity against three malignant cell lines and one normal cell line of different origins. The solvatochromic characteristics of the complexes were examined by UV/vis.

An Exhaustive Compilation on the Synthesis of Heterocycles Pendant on the Fatty Acid Alkyl Chains.

Fatty acids derived from oils and fats of different plant and animal resources are considered one of the most valuable renewable precursors of the synthetic chemical and pharmaceutical industries. On the other hand, heterocyclic compounds are well known nowadays by their constitution of many commercialized drugs due to their unique biological activities. Combination between fatty acids and heterocyclic compounds has made important advances in the construction of valuable biologically relevant molecules in pharmaceutical industry.

Light-activated cytotoxicity of dicarbonyl Ru(II) complexes with a benzimidazole coligand towards breast cancer.

Reaction between [RuCl(CO)] and 1-benzimidazol-2-ylmethyl-(-phenyl)amine ligands (L) functionalized with various electron-donating and electron-withdrawing substituents on the phenyl ring (R = H, 4-CH, 4-Cl, 4-COOCH, and 3-COOCH) afforded the dark-stable photoactivatable carbon monoxide prodrugs of the general formula [RuCl(CO)L]. Release of the CO molecules from the Ru(II) compounds was examined by monitoring the electronic and IR spectra upon illumination at 365 nm. A noticeable decrease in the intensities of the two characteristic (CO) modes for Ru(CO)II2 species, and the growth of two new bands for the mono-carbonyl species and free CO, were the main features of the photolysis profiles.

Synthesis, antimicrobial, anti-proliferative activities, molecular docking and DFT studies of novel pyrazolo[5,1-c][1, 2, 4]triazine-3-carboxamide derivatives.

In this investigation, we studied the reactivity of 5-aminouracil () with ethyl cyanoacetate () utilizing microwave irradiation to afford the corresponding 2-cyano--(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide () in excellent yield. The electrophilic azo-coupling reaction of acetamide with aromatic diazonium salts afforded the corresponding hydrazone derivatives The Michael addition cyclization of hydrazone in pyridine to give pyrazolo[5,1-c][1, 2, 4]triazine-3-carboxamide derivatives. The obtained compounds were elucidated against antimicrobial activity and antitumor activity breast cancer cells (MCF-7) and liver cancer cells (HepG2) utilized MTT assay.

Removal of hazardous pollutants using bifunctional hydrogel obtained from modified starch by grafting copolymerization.

The removal of industrial pollutants from wastewater is important to protect human health and the environment. For this reason, bifunctional hydrogel was synthesized by radiation-induced grafting copolymerization of 2-acrylamido-2-methylpropane-1-sulphonic acid (AMPS) and dimethylaminoethyl methacrylate (DMAEMA) onto starch and subsequent chemical modification of the prepared hydrogel by benzyl chloride. The physical and chemical properties of the hydrogel AMPS co DMAEMA modified with ion-exchange groups were investigated by FT-IR, DSC and SEM techniques.

Novel pyridine-based Pd(II)-complex for efficient Suzuki coupling of aryl halides under microwaves irradiation in water.

Suzuki C-C cross-coupling of aryl halides with aryl boronic acids using new phosphene-free palladium complexes as precatalysts was investigated. A pyridine-based Pd(II)-complex was used in open air under thermal as well as microwave irradiation conditions using water as an eco-friendly green solvent.

Synthesis, biological evaluation, and molecular docking studies of new pyrazol-3-one derivatives with aromatase inhibition activities.

A new series derived from 4-(2-chloroacetyl)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one was synthesized, characterized and its pharmacological activity toward aromatase enzyme inhibition was screened and compared to the reference native ligand letrozole. The most active compound of the series was 16, showing IC value of 0.0023 ± 0.

Novel Benzo[d]imidazole-based Heterocycles as Broad Spectrum Anti-viral Agents: Design, Synthesis and Exploration of Molecular Basis of Action.

The design and synthesis of a novel series of benzo[d]imidazole-based heterocycles and their biological evaluation as antiviral agents are reported herein. 1-(1-Methyl-1H-benzo[d]imidazol- 2-yl)-2-thiocyanatoethanone 2 was used as a key intermediate for the synthesis of the thiazolylhydrazine 4, the thiazolylamine 5 and the methylthiazole 7. Coupling of compounds 5 or 7 with the appropriate diazotized aromatic amines gave the diazenyl derivatives 6a-c and 8a-c, respectively.

Regioselective synthesis and ab initio calculations of fused heterocycles thermally and under microwave irradiation.

Pyrazolo[1,5-a]pyrimidine, triazolo[1,5-a]pyrimidine, and pyrimido[1,2-a]benzimidazole, pyrido[1,2-a]benzimidazole ring systems incorporating phenylsulfonyl moiety were synthesized via the reaction of 3-(N,N-dimethylamino)-1-(thiophen-2-yl)-2-(phenylsulfonyl)prop-2-en-1-one derivatives with the appropriate aminoazoles as 1,3-binucleophiles and 1H-benzimidazol-2-ylacetonitrile using conventional methods as well as microwave irradiation. The regioselectivity of the cyclocondensation reactions was confirmed both experimentally by alternative synthesis of reaction products and theoretically using ab initio quantum chemical calculations namely the Density Functional Theory (DFT). The theoretical work was carried out using the Becke, three parameter, Lee-Yang-Parr hybrid functional (B3LYP) combined with the 6-311++G(d,p) basis set.

Development of two reference materials for all trans-retinol, retinyl palmitate, α- and γ-tocopherol in milk powder and infant formula.

Vitamins are important food constituents that can be present in almost every foodstuff. Food quality and safety depends on food surveillance by reliable quantitative analysis enabled by appropriate quality control. Certified matrix reference materials are versatile tools to support quality assurance and control.

Synthesis and antimicrobial activity of some new thieno[2,3-b]thiophene derivatives.

A series of thieno[2,3-b]thiophene moiety-containing bis-cyanopyrazoles 5a-c, bis-aminopyrazole 9 and bis-pyridazine derivatives 11 were synthesized and evaluated in vitro for their antimicrobial potential. The antimicrobial activity of some selected products was evaluated and showed good results. 5,5'-(3,4-Dimethylthieno[2,3-b]thiophene-2,5-diyl)bis(3-acetyl-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile) (5d) was found to be more potent than the standard drug amphotericin B against Geotricum candidum and equipotent to amphotericin B against Syncephalastrum racemosum.

Recent advances in the therapeutic applications of pyrazolines.

Introduction: Pyrazolines are well-known and important nitrogen-containing five-membered ring heterocyclic compounds. Various methods have been worked out for their synthesis. Several pyrazoline derivatives have been found to possess diverse biological properties, which has stimulated research activity in this field.

Single step synthesis of new fused pyrimidine derivatives and their evaluation as potent Aurora-A kinase inhibitors.

A simple, facile, efficient and one pot three-component procedure for the synthesis of pyrazolo[1,5-a]pyrimidines, triazolo[1,5-a]pyrimidines and pyrimido[1,2-a]benzimidazoles ring systems incorporating phenylsulfonyl moiety was developed via the reaction of 1-aryl-2-(phenylsulfonyl)ethanone derivatives 1a-d with the appropriate heterocyclic amine and triethyl orthoformate and evaluated as Aurora-A kinase inhibitors. The cytotoxic activity of the newly synthesized compounds against HST116 colon tumor cell line was investigated. 2,7-Diphenyl-6-(phenylsulfonyl)pyrazolo[1,5-a]pyrimidine (4b) and its p-methoxy analogue 4c were found to be equipotent to Doxorubicin as a reference drug.

Design, synthesis and structure-activity relationship study of novel pyrazole-based heterocycles as potential antitumor agents.

The versatile hitherto unreported 3-[(E)-3-(dimethylamino)acryloyl]-1,5-diphenyl-1H-pyrazole-4-carbonitrile (3) was prepared via the reaction of 3-acetyl-1,5-diphenyl-1H-pyrazole-4-carbonitrile (1) with dimethylformamid-dimethylacetal (DMF-DMA). The latter product and 3-((E)-3-morpholin-4-yl-acryloyl)-1,5-diphenyl-1H-pyrazole-4-carbonitrile (4) underwent regioselective 1,3-dipolar cycloaddition with nitrilimines to afford the corresponding pyrazole derivatives. In vivo anti-estrogenic activity and acute toxicity after single oral dose of the newly synthesized compounds were evaluated.

Synthesis and structure-activity relationship studies of pyrazole-based heterocycles as antitumor agents.

Several 4-cyano-1,5-diphenylpyrazoles attached to different heterocyclic ring systems at position 3 were synthesized starting from ethyl 4-cyano-1,5-diphenyl-1H-pyrazole-3-carboxylate 1. The newly synthesized compounds were tested in vivo for their anti-estrogenic effects and evaluated in vitro for their cytotoxic properties against estrogen-dependent tumors. 3-(5-Mercapto-1,3,4-oxadiazole-2-yl)-1,5-diphenyl-1H-pyrazole-4-carbonitrile 13 revealed the highest cytotoxic activity with a GI(50) value equal to 40 nM against the IGROVI ovarian tumor cell line.

Radiation-induced grafting of glycidyl methacrylate onto cotton fabric waste and its modification for anchoring hazardous wastes from their solutions.

Ion exchange adsorbents based on cellulosic fabric wastes carrying sulfonic acid and amine functional groups were synthesized by radiation-induced graft polymerization of glycidyl methacrylate (GMA) with subsequent chemical modification of the epoxy groups of poly-GMA graft chains with sodium sulfite/H(2)SO(4) and triethylamine, respectively. The conversion of epoxy groups into the functional groups was investigated. Factors affecting on grafting process such as radiation dose, monomer concentration and solvent were studied.

Synthesis of new N-phenylpyrazole derivatives with potent antimicrobial activity.

The versatile synthons 4-(2-bromoacetyl)-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole (3) and 4-[(E)-3-(dimethylamino)acryloyl]-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole (2) were used as precursors for the synthesis of a series of phenylpyrazoles with different aromatic ring systems at position 4. The antimicrobiological evaluation of the newly synthesized compounds was carried out in vitro assays for antifungal and antibacterial activities. Amongst the tested compounds, 4-acetyl-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole (1), 4-[(E)-3-(dimethylamino)acryloyl]-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole (2), 4-(2-bromoacetyl)-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole (3) and 4-(2-aminothiazol-4-yl)-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole (17) showed interesting antimicrobial properties.

Synthesis of new 3-pyridinecarboxylates of potential vasodilation properties.

2-(alicyclic-amino)-4,6-diaryl-3-pyridinecarboxylates 5a-d were prepared via aromatic nucleophilic substitution reaction of secondary amines (piperidine or morpholine) with 2-bromo-3-pyridinecarboxylate derivatives 3a,b. The latters were obtained through bromination of 3-aryl-4-benzoyl-2-cyanobutyrates 2a and 2b, which were obtained from the base promoted addition of ethyl cyanoacetate to 2-propen-1-ones 1a and 1b, with bromine in glacial acetic acid. Reaction of 3 with piperazine hexahydrate in 2:1 molar ratio afforded 1,4-bis[(ethyl 4,6-diaryl-3-pyridinecarboxylate)-2-yl]piperazines 6a,b.

Regioselective synthesis and antitumor screening of some novel N-phenylpyrazole derivatives.

The versatile, hitherto unreported 4-acetyl-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole (3) was prepared via the reaction of 2-(2-phenylhydrazono)-2-chloro-N-phenylacetamide with pentan-2,4-dione in the presence of sodium ethoxide. Reaction of 3 with dimethylformamide-dimethylacetal (DMF-DMA) furnished the corresponding 4-[(E)-3-(dimethylamino)acryloyl]-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole (5). The latter product underwent regioselective 1,3-dipolar cycloaddition with some nitrilimines to afford the non-isolable dihydropyrazole intermediates which then lose dimethylamine yielding the corresponding pyrazole derivatives.