Synthesis,Antimicrobial, and Anthelmintic Activities of Some New 3-Chlorobenzothiophene-2-Carbonylchloride Derivatives

3-Chlorobenzothiophene-2-carbonylchloride 1 was prepared from cinnamic acid and then converted into the acid hydrazide 2. Reaction of 3-chloro-1-benzothiophene-2-carbohydrazide 2 with the appropriate isothiocyanate yielded the substituted thiosemicarbazides 3a–b, which are cyclized into thioxotetrahydropyrimidine 4a–b, 1,3,4-thiadiazoles 5a–b, thiazolidine 6a–b, 1,3,4-oxadiazole 7a–b, triazoles 8a–b, 1,2,4-triazole substitutedthioate 9a–f, and 1,3-thiazolylidenes 10a–b, respectively. The structures of the newly synthesized compounds were elucidated on the basis of elemental analyses, IR, ¹H NMR, and mass spectral data and have been screened for antimicrobial and anthelmintic activities.     

Physicochemical studies of (o-vanillin thiosemicarbazonato)-nickel(ii) chelate

Summary Five- and six-membered rings result from the chelation of nickel(II) by the dibasic tridentate Schiff base ligand, o-vanillin thiosemicarbazone(o-VTSC), a new chelate prepared and characterized. The structural results are discussed in the light of spectroscopic and other data.Presented at 29th ICCC, Lausanne, Switzerland, 1992.     

Anticancer activity of silver(I) cyclohexyldiphenylphosphine complexes toward SNO cancer cells

Silver and its derivatives have been and are currently used as antimicrobial and antibacterial agents. However, their use is rather limited to date as anticancer agents. Thus, this study focuses on the synthesis and characterization of three silver(I) complexes which have the ability to adopt different geometries, and to induce cancer cell death in SNO esophageal cancer cells. Silver thiocyanate was reacted in different ratios with cyclohexyldiphenylphosphine to obtain 1:1 (complex 1), 1:2 (complex 2), and 1:3 (complex 3) molar ratios of silver(I):cyclohexyldiphenylphosphine complexes. These complexes were characterized using conventional spectroscopic techniques, which included ¹H, ¹³C, and ³¹P NMR, FTIR, and microanalysis (%C, H, N, S). In addition, the single-crystal X-ray structures of complexes 1 and 2 were determined. Moreover, all three complexes displayed toxic activity toward the malignant SNO cells with IC₅₀ concentrations below 5 μM as determined with an alamarBlue® viability assay. Morphological and flow cytometric analyses were included to identify the possible mode of cancer cell death. These biochemical assays revealed that all three treatments induced apoptosis due to the presence of specific apoptotic markers.     

Synthesis of Benzo[b]thiophene Substituted Carbamates,Ureas, Semicarbazides,and Pyrazoles and Their Antimicrobial and Analgesic Activity

2-Azidocarbonyl-3-chlorobenzo[b]thiophene 3 was obtained from 3-chloro-benzo[b]thiophene-2-carbonyl chloride 1 and 3-chloro-benzo[b]thiophene-2-carboxy hydrazide 2 . The compound 3 on Curtius rearrangement with various alcohols, amines, and hydrazines afforded the corresponding carbamates 4a–b , ureas 5a–j , and semicarbazides 6a–g , respectively. Compound 2 was also utilized for the synthesis of pyrazoles 7a–c by treatment with various chalcones. The structures of the newly synthesized compounds were elucidated on the basis of IR, ¹ H NMR, and mass spectral data and have been screened for antimicrobial and analgesic activities.     

Synthesis and Antimicrobial Activity of Some New 5-(3-Chloro-1-Benzothiophen-2-YL)-1,3,4-Oxadiazole-2-Thiol and Their Derivatives

Abstract

3-Chloro-1-benzothiophene-2-carbonylchloride 1 was made to reacts with hydrazine hydrate afforded 3-chloro-1-benothiophene-2-carbohydrazide 2 in good yield. 5-(3-chloro-1-benzothiophen-2-yl)-1,3,4-oxadiazole-2-thiol 4 was synthesized from 3-chloro-1-benzothiophene-2-carbohydrazide 2. Mannich bases, alkyl halide, and acid chlorides derivatives were then prepared. Compound 4 on condensation with chloroacetone in the presence of NaOH as base and ethanol as solvent gave 1-{[5-(3-chloro-1-benzo[b]thiophen-2-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}propan-2-on 6. Condensation of compound 6 with various aromatic aldehydes afforded a series of chalcones 7a–h. The structures of all the synthesized compounds were confirmed by spectral data and have been screened for antibacterial activity.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

GRAPHICAL ABSTRACT      

Utility of 3-Chlorobenzothiophene-2-Carbonylisothiocyanate for the Synthesis of Some Novel Biheterocycles of Expected Biological Activity

The behavior of 3-chlorobenzothiophene-2-carbonylisothiocyanate 2 towards nitrogen nucleophiles such as primary amines, substituted hydrazines, aryl hydrazines, glycine, anthranilic acid; sulfur nucleophiles such as thioglycolic acid; and oxygen nucleophiles such as substituted phenols has been investigated and found that it proceeds via isothiocyanate heterocyclization to furnish noncondensed heterocyclic compounds containing thiourea, triazole, oxazole, thiazole, and benzoxazole nuclei besides the benzo[b]thiophene nucleus. The structures of the newly synthesized compounds were elucidated on the basis of IR, ¹H NMR, and mass spectral data of the compounds, and they have been screened for antimicrobial, analgesic, and anti-inflammatory activities.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.