This review describes the reactions of o-aminothiophenol and its derivatives as building blocks for the synthesis of poly-functionalised 1,5-benzothiazepines with pharmacological interest. Annelated 1,5-benzothiazepines were prepared by acyclocondensation reaction of o-aminothiophenol and its derivatives with carbonyl and other functionalities. In case ofcarbonyl function this reaction takes place by a nucleophilic addition, followed by a cyclisation and concomitant elimi-nation of water. The objective of this survey is to provide a comprehensive account of the synthesis of various 1,5-ben-zothiazepines derivatives and their potential to develop better chemotherapeutic agents.
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Curr Top Med Chem
January 2025
School of Chemical Sciences, Indian Association for the Cultivation of Science (IACS), Jadavpur, Kolkata, West Bengal 700 032, India.
The benzothiazole ring system has been recognised with crucial pharmacophoric features being present among various approved drugs and clinical and pre-clinical candidates. The medicinal importance of this privileged scaffold stimulated the interest of synthetic medicinal/ organic chemists for the synthesis of its derivatives due to their diverse biological applications. In most of the reports in the literature, benzothiazoles were synthesized by cyclocondensation of 2- aminothiophenol with either carboxylic acid and its derivatives or aldehydes.
View Article and Find Full Text PDFSpectrochim Acta A Mol Biomol Spectrosc
February 2025
Department of Chemistry, Bharathiar University, Coimbatore 641046, Tamil Nadu, India. Electronic address:
Bioorg Chem
September 2024
Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig 44511, Egypt. Electronic address:
A set of novels 2-thiohydantoin derivatives were synthesized and enaminone function was discussed at position 5 using DMFDMA catalyst which result in formation of pyrazole, isoxazole, benzoxazepine by using reagents such as hydrazine, hydroxylamine and 2-aminothiophenol. These newly synthesized compounds were evaluated for their antioxidant and antiproliferative activity. In vitro studies on the effect of 2-thiohydantoin on scavenging 2,2-diphenyl-1-picrylhydrazyl radical (DPPH•) confirmed the free radical scavenging and antioxidant activity of 2-thiohydantoin.
View Article and Find Full Text PDFOrg Biomol Chem
July 2024
VNU-HCM Key Laboratory of Functional Organic Materials, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City, Vietnam.
The synthesis of medicinally relevant -aryl-substituted 2-aminobenzothiazoles often uses 2-aminothiophenol derivatives, which are not commercially abundant, as starting materials. Herein, we report a method for the annulation of C3-substituted nitroarenes and aryl isothiocyanates towards the synthesis of 2-aminobenzothiazoles. Reactions proceeded in the presence of cobalt ferrite nanoparticles as a catalyst, DABCO as a base, and DMF as a promoter.
View Article and Find Full Text PDFMol Divers
December 2024
Department of Chemistry, Faculty of Science, Sohag University, Sohag, 82524, Egypt.
Dicyandiamide (DCD) reacted with amino acids 1a-f to produce biguanides 2 and 4 and guanidine pyrazolones 3, 5, 6, 7, and 8, according to the reaction. DCD exhibited the following reactions: imidodicarbonimidicdiamide 9, diazocan-2-ylguanidine 10, methyl biguanidylthion 11, N-carbamothioylimidodicarbonimidicdiamide 12, 2-guanidinebenzoimidazole 13a, 2-guanidinylbenzoxazole 13b, and 2-guanidinylbenzothiazol 13c. These reactions were triggered by 6-amino caproic acid, thioacetamide, thiourea, o-aminophenol, o-aminothiophenol, and anthranilic acid, respectively.
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