Hoda Z. Shams

Novel Synthesis and Antitumor Evaluation of Polyfunctionally Substituted Heterocyclic Compounds Derived from 2-Cyano-N- (3-cyano-4,5,6,7-tetrahydrobenzo(b)thiophen-2-yl)-acetamide

The reaction of 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene with ethyl cyanoacetate gave 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide. The latter was used to synthesize different heterocyclic derivatives comprising thiophene, thiazole, pyrazole, pyridine, pyrimidine, and coumarin rings. The mechanistic and synthetic pathways depended on regioselective attack and/or cyclization by the cyanoacetamido moiety in the key precursor on various chemical reagents. The competition of the reaction pathways including dipolar cyclization, dinucleophilic-bielectrophilic attack, β-attack, Gewald-type attack, and condensation reactions led to the diversity of the synthesized products. The antitumor activities of the synthesized products were studied and evaluated. Most of the compounds revealed high inhibitory effects when screened in vitro for their antiproliferative activity. Three human cancer cell lines, namely, breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) were used in the screening tests. The simplicity of the synthetic procedures which mainly involved one-pot reactions under mild reaction conditions, the convenience of yield production and the diversity of the reactive sites in the produced systems play a valuable role for further heterocyclic transformations and further biological investigations.

Synthesis, Structure Elucidation, and Biological Evaluation of Some Fused and/or Pendant Thiophene, Pyrazole, Imidazole, Thiazole, Triazole, Triazine, and Coumarin Systems Based on Cyanoacetic 2-[(Benzoylamino)thioxomethyl] Hydrazide

Aiming to produce cyclized systems with potential bioactivity, a variety of fused and/or pendant thiophene, pyrazole, imidazole, thiazole, triazole, triazine, and coumarin systems were synthesized based on a cyanoacetic 2-[(benzoylamino)thi- oxomethyl] hydrazide precursor. The structure of the synthesized compounds was established based on elemental analysis and spectral data. The antibacterial and antifungal activities of the compounds are discussed and evaluated.

THE USES OF 4-PHENYL-3-THIOSEMICARBAZIDE IN HETEROCYCLIC SYNTHESIS: NOVEL SYNTHESIS OF THIAZOLE, PYRAZOLE AND 1,3,4-THIADIAZINE DERIVATIVES

Abstract 4-Phenyl-3-thiosemicarbazide derivatives 1a-c react with phenacylbromide, 3-bromoacetylcoumarin and monochloroacetic acid to afford thiazole derivatives 3a-c, 8a-c and 12a-c respectively. Reaction of 1a with ethyl acetoacetate afford the condensated product 17. Reaction of 3a-c and 8a-c with aromatic diazonium salts afford the 5-arylazothiazole derivatives 5a-f and 9a-f respectively. Most of the synthesized products show high fungicidal and bactericidal activities.

Novel Synthesis of Pyrido[2,1-B]Benzothiazoles and 1,3-Benzothiazole Derivatives

Abstract A variety of new pyrido[2,1-b]benzothiazole and benzothiazoles, have been prepared via the reaction of 2-substituted methylthiazole with α,β-unsaturated nitriles and activated methylene compounds. The structures of the reaction products were established based on the elemental analyses and spectral data (IR, 1H-, 13C-NMR, MS).

SYNTHETIC POTENTIALITIES OF THIOPHENE SYSTEMS IN HETEROCYCLIC SYNTHESIS: A NOVEL SYNTHESIS OF THIENO[2,3-b]PYRIDINE DERIVATIVES

Abstract The reactivity of thiophene derivatives 1,2 and 3 towards active methylene reagents, aryledenernalononitriles were studied to afford several new thieno[2,3-b]pyridine derivatives. The biological activities of the synthesized products showed interesting results.

Synthesis of a new series of polyfunctionally substituted pyrazole azo dye systems for dyeing of synthetic and modified cellulose fibers

Three series of azo dye systems are considered, namely, 5‐oxo‐2‐pyrazoline azo dye systems 9 a‐d,1‐oxo‐pyrazolo pyrazole azo dye systems 10 a, b, c, e, 11 a, b, c, e, 12 a, b, c, e, 13 a‐d and 6‐oxo‐pyranopyrzole azo dye systems 14 a‐d. The shifts of ultraviolet‐visible absorption maxima affected by the structural configuration of the pyrazole dye systems are investigated. The structural effects of the polyfunctionally substituted pyrazole dye systems on the intensity of colour and fastness properties of the dyed fabrics are also discussed. The data of these studies are listed. Colour shades of the synthesized dyes on nylon and acetate fabrics are indicated.

Synthesis of Polyfunctionally Substituted Thiophene, Thieno[2,3-b]pyridine and Thieno[2,3-d]pyrimidine Derivatives

The thiophne derivatives 4a–c were prepared according to the Gewald procedure. Their reactivity towards a variety of chemical reagents was studied to give thienopyridines and pyrimidines. Biological investigations were carried on the newly synthesized products.

A NOVEL SYNTHESIS OF POLYFUNCTIONALLY SUBSTITUTED PYRAZOLO [1,2=a]PYRAZOLE, AND THIENO [3′,2′-3,4]PYRAZOLO [1,2-a]PYRAZOLE SYSTEMS

Abstract A number of fused pyrazole systems, namely, 1-oxopyrazolo[1,2-a]pyrazoles, 6-oxopyrano[2.3-c]pyrazole and l-oxo-thieno[3′,2′-3,4]pyrazolol [1,2-a] pyrazoles are synthesized via new synthetic routes

Synthesis and application of novel disazo pyrazolo[1,2‐a]pyrazole reactive dyes

Purpose – The purpose of this paper is to evaluate the efficiency of modifying reactive azo dyes using pyrazolo[1,2‐a]pyrazole fused systems as the chromophoric moiety which could satisfy many and varied criteria drawn from economic, synthetic, physicochemical and fastness properties.Design/methodology/approach – Six novel heterocyclic disazo reactive dyes were prepared, containing monofunctional sulphatoethylsulphone (SES) and hetero‐bifunctional monochlorotriazine (MCT)/SES reactive groups. Dyes intermediates based on 4‐arylazo‐1,5‐dioxopyrazolo[1,2‐a]pyrazole chromophoric moieties are initially synthesised and coupled with two different diazonium salts having the aforementioned reactive groups, thus yielding the new target reactive dyes. The synthesised dyes are applied to cotton, wool and silk fabrics under the typical exhaust dyeing conditions and their dyeing properties were investigated.Findings – The results assessed for dyeing indicate high‐quality dyeing properties. However, the heterobifunction...

A novel synthesis of 1‐oxo‐thieno[3’,2’‐3,4] pyrazolo[1,2‐a] pyrazole azo dye systems for dyeing of synthetic and modified cellulose fibers

A new series of the title pyrazole azo dye systems has been synthesized. The new dyes are applied on nylon and cellulose acetate fibers to give dyed fabrics with excellent properties of colour intensity and fastness properties. The physical and spectral data of the investigated dyes are illustrated. The shifts of ultraviolet‐visible absorption maxima affected by the structural configuration of the pyrazole dye systems are investigated. The structural effects of the polyfunctionally substituted pyrazole dye systems on the intensity of colour and fastness properties of the dyed fabrics are discussed. The data of these studies are listed. The colour shades of the synthesized dyes on nylon and acetate fabrics are indicated.