Soad M. Abdel-Gawad

Synthesis of Some New Biologically Active Sulfur Compounds Containing Pyrazolo[3,4-d] pyrimidine Moiety

A novel series of the pyrazolo[3,4-d]pyrimidines having biologically active sulfur moieties 3-20 were prepared via reaction of 4-mercapto-1-phenyl-1 H -pyrazolo[3,4-d]pyrimidine 3 with different reagents. Identification of the new compounds was established by elemental analyses, IR, 1 H-NMR, and mass spectral data. Some of the obtained compounds showed the interesting antimicrobial activity comparable to antibiotic chloramphenicol as standard antibacterial agent and Terbinafin as a standard antifungal agent.

Synthesis and Biological Activity of Some Novel Thieno[2,3-b]quinoline, Quinolino[3′,2′:4,5] thieno[3,2-d]pyrimidine and Pyrido[2′,3′:4,5] thieno[2,3-b]quinoline Derivatives

Thieno [2,3-b] quinoline derivative 5 was synthesized by the cycloalkylation of compound bi 3a with chloro acetonitrile. Interaction of compound 5 with formic acid, formamide, and thioacetamide furnished the corresponding quinolino[3′,2′:4,5]thieno[3,2- d]pyrimidine derivatives 7 , 8 , and 9 , respectively. Also, quinolinothienopyrimidine 11 was obtained in good yield by cyclization of compound 5 with phenyl isothiocyanate under reflux in pyridine. Triethyl orthoformate reacted with compound 5 to form the ethoxymethylene derivative 12 . Refluxing of 5 with acetic anhydride for a short time afforded acetamide derivative 16 , whereas when refluxed for a long time furnished the diacetyl derivative 17 . Fusion of compound 5 with urea and thiourea yielded the corresponding quinolinothienopyrimidines 19 and 20 , respectively. When compound 5 was reacted with urea in the presence of sodium ethoxide, the corresponding ureado derivative 18 was obtained. Treatment of 5 with sulfuric acid at r.t. furnished the novel thienoquinoline 6 , while on heating gave the acid derivative 21 . Pyrido [2′,3′: 4,5]thieno [2,3- d] quinoline 23–25 were synthesized by the interaction of 5 with ethyl cyanoacetate, benzylidenemalononitrile, and acetaldehyde/malononitrile, respectively. On preliminary screening, compounds 22 and 25 exhibited in vitro growth that was inhibitory activity against Saccharomyces Cerevisiae when compared with the standard fungicide Mycostatine. The structure of the biologically active compounds 22 and 25 remain unchanged when exposed to gamma irradiation up to 40 KGy.

Reactions of Hydrazonoyl Halides 33 1 : Synthesis of Some New 2,3-Dihydro-1,3,4-thiadiazoles Containing Pyrazol-3-yl, Indolin-2-one-2-yl and Indan-1,3-dione-2-yl Moieties

Some new 2,3-dihydro-1,3,4-thiadiazoles containing pyrazol-3-yl, indolin-2-one-2-yl and indan-1,3-dione-2-yl moieties in a good yields obtained from the reaction of hydrazonoyl halides with thiocarbamate and carbodithioate in ethanolic triethylamine respectively. In contrast, pyrazolylthiourea reacts with hydrazonoyl halides under the same condition afford corresponding hydrazonoyl sulfide derivatives.

Synthesis of Thiazolidine and Thiophene Derivatives for Evaluation as Anticancer Agents

The non-isolated adducts (3a,b) were used as key intermediates to synthesize some novel thiazolidine and thiophene derivatives. Compound (4) exhibited a remarkable antitumor activity against EAC cells compared with the Doxorubicin as a positive control.

Synthesis of Some New Thieno[2,3-b]pyridines, Pyrimidino[4′,5′:4,5]thieno[2,3-b]-pyridines, and 2,3-Dihydro-1,3,4-thiadiazoles

Thieno[2,3-b]pyridines were synthesized from 6-benzofuran-2-yl-4-phenyl-2-sulfanylpyridine-3-carbonitrile and each of chloro acetone, ethyl chloroacetate, ω -bromoacetophenone, and chloroacetonitrile. These compounds were conveniently converted into novel pyrido[4′,5′:4,5]thieno[3,2-d]pyrimidines. Also, 2,3-dihydro-1,3,4-thiadiazole was synthesized from hydrazonoyl halides and 2-benzofuran-2-yl-3-(phenylamino)-3-thioxopropanenitrile. The structures of the products have been elucidated by elemental analyses, spectral data studies, and alternative syntheses whenever possible. The newly synthesized compounds were tested towards microorganisms.

Novel Antitumor Acetamide, Pyrrole, Pyrrolopyrimidine, Thiocyanate, Hydrazone, Pyrazole, Isothiocyanate and Thiophene Derivatives Containing a Biologically Active Pyrazole Moiety

4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)-benzenesulfonamide (sulfaphenazole) 1 was selected as strategic starting material for the synthesis of some novel acetamide 2, pyrrole 4, pyrrolo[2,3-d]pyrimidine 5, thiocyanate 6, hydrazone 7a,b pyrazole 8, isothiocyanate 9 and thiophene 12 derivatives to evaluate theantitumor activity. Compound 4 was more effective than the reference drug, doxorubicin (CAS 23214-92-8) as positive control.

Reactions with hydrazonoyl halides 46 1: Synthesis of some new 2,3-dihydro-1,3,4-thiadiazoles and triazolino[4,3- a]pyrimidines as antimicrobial agents

2,3-Dihydro-1,3,4-thiadiazoles and triazolino[4,3- a]pyrimidines were synthesized in a good yields from reactions of hydrazonoyl halides with alkyl carbodithioate and pyrimidine-2-thione, respectively. All structures of the newly synthesized compounds were elucidated by elemental analysis, spectral data and alternative synthesis methods. Some of the new compounds were tested against bacteria and some fungi.

Synthesis, structural characterization and anticancer evaluation of pyrazole derivatives

The utility of 4-isothiocyanato-N-(1-phenyl-1H-pyrazol-5-yl)benzene sulfonamide 2 in the synthesis of some novel thiosemicarbazide, carbamothioate,1,3,4-thiadiazole, azomethine, thiourea, bisthiourea and imidazole derivatives is reported. The structure of the newly synthesized compounds was confirmed on the basis of analytical and spectral data. Some of the prepared compounds were evaluated for their in vitro anticancer activity against Ehrlich ascites carcinoma cells (EAC). It was found that the corresponding 2-acetyl-N-(4-(N-(1-phenyl-1H-pyrazol-5-yl) sulfamoyl)phenyl) hydrazinecarbothioamide 7 with IC50 value (2.14 µg/ml) showed better activity than doxorubicin with IC50 value (43.6 µg/ml) as reference drug.Graphical AbstractNew thiosemicarbazide,carbamothioate,1,3,4-thiadiazole, azomethine, thiourea, bisthiourea and imidazole derivatives containing pyrazole moiety have been synthesized and evaluated for their anticancer activity.

Utility of 2-[4-Benzo[d]furan-2,1,3-thiazol-2-yl)] Ethane-Nitrile in Synthesis of Thiazole, Coumarin, Thiphene, and Thiadiazoline Derivatives

Coumarine, thiazole, thiophene and 2,3-dihydro-1,3,4-thiadiazole derivatives were synthesized from 2-[4-(4-methyl-2-phenyl-1,3-thiazol.-5-yl)-1,3-thiazol-2-yl]ethanenitrile and salicylaldehyde, chloroacetone, ethyl chloroacetate, or hydrazonoyl halides, respectively.