4299-25-6Relevant academic research and scientific papers
Broad spectrum anti-infective properties of benzisothiazolones and the parallels in their anti-bacterial and anti-fungal effects
Gopinath,Yadav,Shukla,Srivastava,Puri,Muraleedharan
supporting information, p. 1291 - 1295 (2017/06/19)
Various mono- and bis-benzisothiazolone derivatives were synthesized and screened against different strains of bacteria and fungi in order to understand the effect of multiple electrophilic sulfur atoms and substitution pattern in the immediate vicinity of reactive sulfur. Staphyllococcus aureus-ATCC 7000699, MRSA and S. aureus-ATCC 29213 (Quality Control strain) were more susceptible to this class of compounds, and the most potent derivative 1.15 had MIC50 of 0.4?μg/mL (cf. Gentamicin?=?0.78?μg/mL). CLogP value, optimally in the range of 2.5–3.5, appeared to contribute more to the activity than the steric and electronic effects of groups attached at nitrogen. By and large, their anti-fungal activities also followed a similar trend with respect to the structure and CLogP values. The best potency of IC50?=?0.1?μg/mL was shown by N-benzyl derivative (1.7) against Aspergillus fumigatus; it was also potent against Candida albicans, Cryptococcus neoformans, Sporothrix schenckii, and Candida parapsilosis with IC50 values ranging from 0.4 to 1.3?μg/mL. Preliminary studies also showed that this class of compounds have the ability to target malaria parasite with IC50 values in low micromolar range, and improvement of selectivity is possible through structure optimization.
An efficient approach to construct benzisothiazol-3(2: H)-ones via copper-catalyzed consecutive reaction of 2-halobenzamides and carbon disulfide
Li, Ting,Yang, Lei,Ni, Kaidong,Shi, Zhenyu,Li, Fei,Chen, Dongyin
, p. 6297 - 6303 (2016/07/11)
An efficient copper-catalyzed reaction for the synthesis of benzisothiazol-3(2H)-ones has been developed, starting from easily available 2-halobenzamides and carbon disulfide, which gave the corresponding target products in 30-89% yield for 25 examples. The reaction proceeds via a consecutive process with S-C bond and S-N bond formation.
Benzisothiazolones arrest the cell cycle at the G2/M phase and induce apoptosis in HeLa cells
Gopinath, Pushparathinam,Ramalingam, Krishnan,Muraleedharan, Kannoth Manheri,Karunagaran, Devarajan
, p. 749 - 752 (2013/06/04)
Anticancer activities of a series of benzisothiazolones having alkyl, aryl and aralkyl substituents on the nitrogen atom and the mechanistic basis of cytotoxicity are presented. Cellular responses like DNA laddering, disruption of mitochondrial membrane potential and caspase-3 activation on incubation of HeLa cells with representative compounds from this group suggested the induction of apoptosis through an intrinsic pathway. Their ability to arrest the cell cycle at the G2/M phase was confirmed by flow cytometric analysis.
