2514-33-2Relevant academic research and scientific papers
Electrochemical synthesis for benzisothiazol-3(2H)-ones by dehydrogenative N[sbnd]S bond formation
Chen, Junmin,Sheng, Shouri,Xiong, Zhiqiang,Zhong, Qihao
supporting information, (2021/08/26)
Herein, we report an electrochemical method for the synthesis of benzisothiazol-3(2H)-ones from 2-mercaptobenzamides. The electrochemical reaction proceeds through intramolecular N[sbnd]H/S[sbnd]H coupling cyclization reaction by generating H2 as the nonhazardous side product. Moreover, the developed procedure is highly advantageous due to its short reaction time, mild conditions and wide substrate scope without the employment of metal catalyst and exogenous-oxidant.2009 Elsevier Ltd. All rights reserved.
Facile synthesis and in vitro activity of n-substituted 1,2-benzisothiazol-3(2H)-ones against dengue virus NS2BNS3 protease
Batool, Farwa,Saeed, Muhammad,Saleem, Hafiza Nosheen,Kirschner, Luisa,Bodem, Jochen
, (2021/04/28)
Several new N-substituted 1,2-benzisothiazol-3(2H)-ones (BITs) were synthesised through a facile synthetic route for testing their anti-dengue protease inhibition. Contrary to the conventional multistep synthesis, we achieved structurally diverse BITs with excellent yields using a two-step, one-pot reaction strategy. All the synthesised compounds were prescreened for drug-like properties using the online Swiss Absorption, Distribution, Metabolism and Elimination (SwissADME) model, indicating their favourable pharmaceutical properties. Thus, the synthesised BITs were tested for inhibitory activity against the recombinant dengue virus serotype-2 (DENV-2) NS2BNS3 protease. Dose–response experiments and computational docking analyses revealed that several BITs bind to the protease in the vicinity of the catalytic triad with IC50 values in the micromolar range. The DENV2 infection assay showed that two BITs, 2-(2-chlorophenyl)benzo[d]isothiazol-3(2H)-one and 2-(2,6-dichlorophenyl)benzo[d]isothiazol-3(2H)-one, could suppress DENV replication and virus infectivity. These results indicate the potential of BITs for developing new anti-dengue therapeutics.
Bioisosteric investigation of ebselen: Synthesis and in vitro characterization of 1,2-benzisothiazol-3(2H)-one derivatives as potent New Delhi metallo-β-lactamase inhibitors
Jin, Wen Bin,Xu, Chen,Cheung, Qipeng,Gao, Wei,Zeng, Ping,Liu, Jun,Chan, Edward W.C.,Leung, Yun-Chung,Chan, Tak Hang,Wong, Kwok-Yin,Chen, Sheng,Chan, Kin-Fai
, (2020/04/30)
Carbapenem-resistant Enterobacteriaceae (CRE) producing New Delhi metallo-β-lactamase (NDM-1) cause untreatable bacterial infections, posing a significant threat to human health. In the present study, by employing the concept of bioisosteric replacement of the selenium moiety of ebselen, we have designed, synthesized and characterized a small compound library of 2-substituted 1,2-benzisothiazol-3(2H)-one derivatives and related compounds for evaluating their cytotoxicity and synergistic activity in combination with meropenem against the E. coli Tg1 (NDM-1) strain. The most promising compound 3a demonstrated potent synergistic activity against a panel of clinically isolated NDM-1 positive CRE strains with FICI as low as 0.09. Moreover, its IC50 value and inhibition mechanism were also confirmed by using the enzyme inhibition assay and the ESI-MS analysis respectively. Importantly, compound 3a has acceptable toxicity and is not a PAINS. Because of its structural simplicity and potent synergistic activity in combination with meropenem, we propose that compound 3a may be a promising meropenem adjuvant and a new series of such compounds may worth further investigations.
Co-Catalyzed Intramolecular S-N Bond Formation in Water for 1,2-Benzisothiazol-3(2H)-ones and 1,2,4-Thiadiazoles Synthesis
Yang, Liting,Song, Lijuan,Tang, Shanyu,Li, Longjia,Li, Heng,Yuan, Bingxin,Yang, Guanyu
, p. 1281 - 1285 (2019/01/14)
An efficient and versatile Co-catalyzed intramolecular S-N bond formation in water to synthesize 1,2-benzisothiazol-3(2H)-one and 1,2,4-thiadiazoles derivatives in good to excellent yields was developed. The transformation showed great tolerance with a broad range of substituents. The mother liquor was able to be recycled 6 times with minor loss in product yield.
1,2-BENZISOSELENAZOL-3(2H)-ONE AND 1,2-BENZISOTHIAZOL-3(2H)-ONE DERIVATIVES AS BETA-LACTAM ANTIBIOTIC ADJUVANTS
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Paragraph 0282-0285; 0303; 0304, (2019/10/04)
Provided herein are compositions and methods useful in the treatment of beta-lactam antibiotic resistant bacteria.
Method for generating benzisothiazolinone compounds by catalyzing oxidization of molecular oxygen in aqueous phase
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Paragraph 0046; 0048, (2019/01/16)
The invention provides a method for synthesizing benzisothiazolinone compounds by catalyzing oxidization of molecular oxygen in an aqueous phase. A water-soluble transition metal phthalocyanine compound is taken as a catalyst, and a thiosalicylic acid ami
Benzisothiazol-3-ones through a Metal-Free Intramolecular N–S Bond Formation
Yang, Ke,Zhang, Hao,Niu, Ben,Tang, Tiandi,Ge, Haibo
, p. 5520 - 5523 (2018/10/26)
The highly efficient synthesis of benzoisothiazol-3-ones from thiobenzamides has been described with good functional group compatibility and excellent yields. This work represents the first example of selectfluor-promoted N–S bond formation processes. This method provides a facile approach to access various important bioactive benzoisothiazol-3-ones.
Potassium bromide catalyzed N[sbnd]S bond formation via oxidative dehydrogenation
Yu, Tian-Qun,Hou, Yong-Sheng,Jiang, Yi,Xu, Wen-Xuan,Shi, Tao,Wu, Xia,Zhang, Jin-Chao,He, Dian,Wang, Zhen
supporting information, p. 2084 - 2087 (2017/05/10)
N-Substituted benzo[d]isothiazol-3(2H)-ones are a family of compounds with extremely important application. Recently, we have developed a new green pathway to synthesize these compounds via potassium bromide-catalyzed intramolecular oxidative dehydrogenative cyclization. This reaction has high functional group tolerance and affords excellent yield even in gram scale.
Broad spectrum anti-infective properties of benzisothiazolones and the parallels in their anti-bacterial and anti-fungal effects
Gopinath,Yadav,Shukla,Srivastava,Puri,Muraleedharan
, 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.
Preparation of benzisothiazolones from 2-bromobenzamides and sulfur under copper catalysis conditions
Krasikova,Katkevics
, p. 1684 - 1690 (2013/07/04)
A convenient two-stage method has been developed for preparing benz[d]isothiazol-3(2H)-ones from 2-bromobenzamides and sulfur in a one-pot process under copper catalysis conditions. The method is suitable for the synthesis of N-aryl-, benzyl-, and alkyl-substituted benzisothiazolones. The yields of the benzisothiazolones depend on the nature of the starting amide and can reach 91%.
