- Potassium bromide catalyzed N[sbnd]S bond formation via oxidative dehydrogenation
-
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.
- Yu, Tian-Qun,Hou, Yong-Sheng,Jiang, Yi,Xu, Wen-Xuan,Shi, Tao,Wu, Xia,Zhang, Jin-Chao,He, Dian,Wang, Zhen
-
-
Read Online
- Electrochemical synthesis for benzisothiazol-3(2H)-ones by dehydrogenative N[sbnd]S bond formation
-
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.
- Chen, Junmin,Sheng, Shouri,Xiong, Zhiqiang,Zhong, Qihao
-
supporting information
(2021/08/26)
-
- Co-Catalyzed Intramolecular S-N Bond Formation in Water for 1,2-Benzisothiazol-3(2H)-ones and 1,2,4-Thiadiazoles Synthesis
-
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.
- Yang, Liting,Song, Lijuan,Tang, Shanyu,Li, Longjia,Li, Heng,Yuan, Bingxin,Yang, Guanyu
-
p. 1281 - 1285
(2019/01/14)
-
- Domino Reactions Initiated by Copper-Catalyzed Aryl-I Bond Thiolation For the Switchable Synthesis of 2,3-Dihydrobenzothiazinones and Benzoisothiazolones
-
The three-component reactions of o-iodobenzamides, elemental sulfur and dichloromethane (DCM) providing 2,3-dihydro-4H-benzo[e][1,3]thiazin-4-ones (2,3-dihydrobenzothiazinones) are accomplished via copper-catalyzed aryl C?I thiolation and subsequent N-, S-hetero ring formation. In addition, the in situ aryl C?I bond thiolation is also employed for the switchable synthesis of benzo[d]isothiazol-3(2H)-ones (benzoisothiazolones) by subjecting o-iodobenzamides, elemental sulfur to the copper-catalyzed condition with microwave irradiation. (Figure presented.).
- Xiong, Jin,Zhong, Guofeng,Liu, Yunyun
-
supporting information
p. 550 - 555
(2018/12/14)
-
- Ebsulfur as a potent scaffold for inhibition and labelling of New Delhi metallo-β-lactamase-1 in vitro and in vivo
-
The superbug infection caused by New Delhi metallo-β-lactamase (NDM-1) has grown into an emerging threat, labelling and inhibition of NDM-1 has proven challenging due to its shuttling between pathogenic bacteria. Here, we report a potent covalent scaffold, ebsulfur, for targeting the protein in vitro and in vivo. Enzymatic kinetic study indicated that eighteen ebsulfurs gained except 1a–b and 1f inhibited NDM-1, exhibiting an IC50 value ranging of 0.16–9 μM, and 1g was found to be the best, dose- and time-dependent inhibitor with an IC50 of 0.16 μM. Also, these ebsulfurs effectively restored the antibacterial activity of cefazolin against E. coli expressing NDM-1, and the best effect was observed to be from 1g, 1i and 1n, resulting in an 256-fold reduction in MIC of the antibiotic at a dose of 16 μg/mL. The equilibrium dialysis study implied that the ebsulfur disrupted the coordination of one Zn(II) ion at active site of NDM-1. Labelling of NDM-1 using a constructed fluorescent ebsulfur Ebs-R suggested that the inhibitor covalently bound to the target through SDS-PAGE analysis in vitro. Also, labelling NDM-1 in living E. coli cells with Ebs-R by confocal microscopic imaging showed the real-time distribution change process of intracellular recombinant protein NDM-1. Moreover, the cytotoxicity of these ebsulfurs against L929 mouse fibroblastic cells was tested, and their capability to restore antibacterial activity of antibiotic against clinical strains E. coli EC08 producing NDM-1 was determined. The ebsulfur scaffold proposed here is valuable for development of the covalent irreversible inhibitors of NDM-1, and also for labelling the target in vitro and in vivo.
- Su, Jianpeng,Liu, Jiayun,Chen, Cheng,Zhang, Yuejuan,Yang, Kewu
-
p. 192 - 201
(2018/12/02)
-
- Broad spectrum anti-infective properties of benzisothiazolones and the parallels in their anti-bacterial and anti-fungal effects
-
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.
- Gopinath,Yadav,Shukla,Srivastava,Puri,Muraleedharan
-
p. 1291 - 1295
(2017/06/19)
-
- Design, synthesis and evaluation of benzoisothiazolones as selective inhibitors of PHOSPHO1
-
We report the discovery and characterization of a series of benzoisothiazolone inhibitors of PHOSPHO1, a newly identified soluble phosphatase implicated in skeletal mineralization and soft tissue ossification abnormalities. High-throughput screening (HTS)
- Bravo, Yalda,Teriete, Peter,Dhanya, Raveendra-Panickar,Dahl, Russell,Lee, Pooi San,Kiffer-Moreira, Tina,Ganji, Santhi Reddy,Sergienko, Eduard,Smith, Layton H.,Farquharson, Colin,Millan, Jose Luis,Cosford, Nicholas D.P.
-
p. 4308 - 4311
(2014/09/17)
-
- Copper-catalyzed intramolecular N-S bond formation by oxidative dehydrogenative cyclization
-
Copper-catalyzed synthesis of benzo[d]isothiazol-3(2H)-ones and N-acyl-benzothiazetidine by intramolecular dehydrogenative cyclization is described. In this reaction, a new nitrogen-sulfur (N-S) bond is formed by N-H/S-H coupling. The present reaction has
- Wang, Zhen,Kuninobu, Yoichiro,Kanai, Motomu
-
p. 7337 - 7342
(2013/08/15)
-
- Preparation of benzisothiazolones from 2-bromobenzamides and sulfur under copper catalysis conditions
-
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%.
- Krasikova,Katkevics
-
p. 1684 - 1690
(2013/07/04)
-
- Benzisothiazolones arrest the cell cycle at the G2/M phase and induce apoptosis in HeLa cells
-
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.
- Gopinath, Pushparathinam,Ramalingam, Krishnan,Muraleedharan, Kannoth Manheri,Karunagaran, Devarajan
-
p. 749 - 752
(2013/06/04)
-
- Design, synthesis and evaluation of 1,2-benzisothiazol-3-one derivatives as potent caspase-3 inhibitors
-
A number of 1,2-benzisothiazol-3-one derivatives were prepared through structural modification of the original compound from high-throughput screening. Some analogues (e.g., 6b, 6r, 6s and 6w) were identified as novel and potent caspase inhibitors with IC50 of nanomolar. Structure-activity relationship (SAR) studies for caspase-3 inhibition were evaluated in vitro. Molecular modeling studies provided further insight into the interaction of this class of compounds with activated caspase-3. The present small molecule caspase-3 inhibitor with novel structures different from structures of known caspase inhibitors revealed a new direction for therapeutic strategies directed against diseases involving abnormally up-regulated apoptosis.
- Liu, Dazhi,Tian, Zhen,Yan, Zhihui,Wu, Lixin,Ma, Yan,Wang, Quan,Liu, Wei,Zhou, Honggang,Yang, Cheng
-
p. 2960 - 2967
(2013/07/28)
-
- Synthesis of 1,2-benzisothiazolin-3-ones by ring transformation of 1,3-benzoxathiin-4-one 1-oxides
-
1,2-Benzisothiazolin-3-ones were synthesized from 1,3-benzoxathiin-4-one 1-oxides by means of a nonhazardous and inexpensive method. The 1,3-benzoxathiin-4-one 1-oxides were prepared by oxidation of 1,3-benzoxathiin-4-ones with hydrogen peroxide in the presence of a catalyst. Attack of amines on the carbonyl groups of the 1,3-benzoxathiin-4-one 1-oxides and subsequent elimination of carbonyl compounds likely produced sulfenic acids, which then underwent ring closure to afford the 1,2-benzisothiazolin-3-ones.
- Shimizu, Masao,Shimazaki, Teruaki,Yoshida, Tetsuya,Ando, Wataru,Konakahara, Takeo
-
experimental part
p. 3932 - 3936
(2012/07/14)
-
- Potent, selective, and orally available benzoisothiazolone phosphomannose isomerase inhibitors as probes for congenital disorder of glycosylation Ia
-
We report the discovery and validation of a series of benzoisothiazolones as potent inhibitors of phosphomannose isomerase (PMI), an enzyme that converts mannose-6-phosphate (Man-6-P) into fructose-6-phosphate (Fru-6-P) and, more importantly, competes wit
- Dahl, Russell,Bravo, Yalda,Sharma, Vandana,Ichikawa, Mie,Dhanya, Raveendra-Panickar,Hedrick, Michael,Brown, Brock,Rascon, Justin,Vicchiarelli, Michael,Mangravita-Novo, Arianna,Yang, Li,Stonich, Derek,Su, Ying,Smith, Layton H.,Sergienko, Eduard,Freeze, Hudson H.,Cosford, Nicholas D. P.
-
experimental part
p. 3661 - 3668
(2011/06/27)
-
- BENZOISOTHIAZOLONES AS INHIBITORS OF PHOSPHOMANNOSE ISOMERASE
-
The disclosure provides new compounds and compositions thereof, and methods for treating or ameliorating a disorder relating to CDG-Ia. In particular, the disclosure provides benzoisothiazolone inhibitors of PMI, which have been synthesized and their abil
- -
-
Page/Page column 35
(2011/10/10)
-
- Phenyliodine(III) bis(trifluoroacetate) mediated synthesis of 2-aryl-1,2-benzisothiazol-3(2H)-ones in ionic liquid
-
Treatment of N-aryl-2-(benzylthio)benzamides with phenyliodine(III) bis(trifluoroacetate) containing trifluoroacetic acid resulted in an interrupted Pummerer-type reaction in ionic liquid 1-n-butyl-3-methylimidazolium hexafluorophosphate, [bmim][PF6
- Wang, Huey-Min,Liang, I.-Chian,Hou, Rei-Sheu,Huang, Hsin-Yu,Chen, Ling-Ching
-
p. 127 - 130
(2008/02/11)
-
- A practical synthesis of N-substituted 1,2-benzisothiazolin-3-ones from N,N′-disubstituted 2,2′-dithiodibenzamides
-
A variety of N-substituted 1,2-benzisothiazolin-3-ones were easily synthesized from N,N′-disubstituted 2,2′-dithiodibenzamides in the presence of O-methylhydroxylamine hydrochloride. Derivatives with a primary, secondary, or tertiary alkyl group or an aryl group on the N-1 nitrogen of the 1,2-benzisothiazolin-3-one were obtained.
- Sano, Tomohumi,Takagi, Toshiyuki,Gama, Yasuo,Shibuya, Isao,Shimizu, Masao
-
p. 1585 - 1588
(2007/10/03)
-
- Synthesis of 1,2-benzisothiazolin-3-one by transamination of sulfenamides
-
N-Substituted sulfenamoylbenzoates were synthesized by transamination of N-unsubstituted sulfenamoylbenzoates with amines. The reaction did not always proceed by simple amine exchange between the amines and ammonia on the sulfur atom of the sulfenamides. In reactions with aliphatic amines, the sulfenamides cyclized to form N-substituted 1,2-benzisothiazolin-3-ones. The synthesis of 1,2-benzisothiazolin-3-ones by intramolecular transamination was also investigated by S-amination of 2-mercaptobenzamides.
- Shimizu, Masao,Takeda, Ayanobu,Fukazawa, Hidenori,Abe, Yoshimoto,Shibuya, Isao
-
p. 1855 - 1864
(2007/10/03)
-
- An effective synthesis of N-substituted 2-sulfenamoylbenzoates and 1,2-benzisothiazolin-3-ones that uses 1,2-benzisothiazolin-3-one as a leaving group
-
N-Substituted 2-sulfenamoylbenzoates and 1,2-benzisothiazolin-3-ones were effectively synthesized by the substitution reaction between S-[2-(3-oxo-1,2-benzisothiazolinyl)]-2-mercaptobenzoates (2) and primary amines. The substitution reaction occurred on the sulfur atom of the 2-sulfenamoyl group of 2, and 1,2-benzisothiazolin-3-one behaved as a leaving group. The eliminated 1,2-benzisothiazolin-3-one could be reused as a starting material for the synthesis of 2. N,N-Disubstituted 2-sulfenamoylbenzoates were prepared by the reaction of 2 with secondary amines.
- Shimizu, Masao,Sugano, Yoshinori,Konakahara, Takeo,Gama, Yasuo,Shibuya, Isao
-
p. 3779 - 3783
(2007/10/03)
-
- Method for producing alkylsulfinylbenzamides and 1,2-benzisothiazol-3-ones
-
A method for producing an alkylthiobenzamide by carrying out a reaction of a halobenzamide with an alkanethiol in the presence of a base in a heterogeneous solvent; a method for producing an alkylsulfinylbenzamide by carrying out a reaction of an alkylthi
- -
-
-
- Reactions of 3H-1,2-benzodithiol-3-one 1-oxide with amines and anilines
-
Reaction of 3H-1,2-benzodithiol-3-one 1-oxide with primary amines or anilines provides reasonable yields (40-70%) of the corresponding 1,2-benzisothiazolin-3(2H)-ones. These reactions may have relevance to the biological chemistry of 1,2-dithiolan-3-one 1-oxides and also offer a new method for the preparation of certain 1,2-benzisothiazolin-3(2H)-ones.
- Kim, Woongki,Dannaldson, Jeffrey,Gates, Kent S.
-
p. 5337 - 5340
(2007/10/03)
-
- Photochemical Ring-expansion Reaction of 1,2-Benzisothiazolinones
-
The photochemical reaction of a series of 2-aryl-1,2-benzisothiazol-3(2H)-ones (1) under deaerated conditions was found to give dibenzothiazepin-11(10H)-ones (2).A mechanism through a biradical species is proposed for the photoreaction.When the photolysis of 1 was carried out in the presence of oxygen, 2-aryl-1,2-benzisothiazol-3(2H)-one-1-oxides (11) were formed together with compounds 2.
- Kamigata, Nobumasa,Hashimoto, Satoshi,Kobayashi, Michio,Nakanishi, Hiroshi
-
p. 3131 - 3136
(2007/10/02)
-
- A Novel Route to 2-Substituted 1,2-Benzisothiazol-3(2H)-ones
-
2-Alkyl- and 2-aryl-1,2-benzisothiazol-3(2H)-ones were synthesized in high yields by the cyclization of 2-(methylsulphinyl)benzamides with thionyl chloride.
- Uchida, Yuzuru,Kozuka, Seizi
-
p. 510 - 511
(2007/10/02)
-