- Quantification of hydrogen sulfide and methanethiol and the study of their scavenging by biocides of the isothiazolone family
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A sensitive analytical method for the quantification of malodourous hydrogen sulfide (H2S) and methanethiol (CH3SH) was developed and validated. The method consisted of solidphase microextraction with concomitant in-fibre derivatisation of the mercaptan using N-ethylmaleimide. The adducts were analysed by GC-MS using a triple quadrupole in the selected reaction monitoring mode. The limits of detection of solutions of H2S and CH3SH in water were 100 and 10 ngL-1, respectively, below their odour-perception thresholds. The analytical method was used to show the scavenging effect of 1,2-benzisothiazol- 3(2H)-one (Proxel) and 2-methyl-4-isothiazolinone. The mechanism by which H2S and CH3SH are trapped with Proxel was studied by ultraperformance liquid chromatography (UPLC)-MS.
- Frerot, Eric,Bagnoud, Alain,Cicchetti, Esmeralda
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- 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
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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.
- 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
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- Preparation method of dithiobenzamide compound
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The invention provides a preparation method of a dithiobenzamide compound, and relates to the technical field of organic synthesis. The method disclosed by the invention has the advantages that applicable substrates are richer, and the method can be used for synthesizing various dithiodibenzoyl compounds; reaction conditions are mild, the synthesis reaction process is simple to operate, and practicability is achieved; the post-treatment operation is simple and convenient, and the product yield and purity are high; and the reaction process is green and environment-friendly, and the preparationmethod meets the requirements of large-scale industrial production.
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- Preparation method of chemical intermediate 2,2'-dithiobenzamide compound
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The invention provides a preparation method of a chemical intermediate 2,2'-dithiobenzamide compound, which comprises the following steps: reacting a 2-substituted benzamide compound with a sulfur reagent in an aprotic solvent with a high boiling point under the combined action of a metal salt and a ligand to generate a 2,2'-dithiobenzamide compound. The 2,2'-dithiobenzamide compound provided by the invention is an important chemical intermediate, the synthetic process route is simple, and the pollution of three wastes to the environment is reduced while the cost is reduced.
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Paragraph 0041-0050; 0053-0056; 0059-0064; 0079-0088
(2020/07/02)
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- Crucial role of selenium in the virucidal activity of benzisoselenazol- 3(2h)-ones and related diselenides
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Various N-substituted benzisoselenazol-3(2H)-ones and their non-seleniumcontaining analogues have been synthesized and tested against selected viruses (HHV-1, EMCV and VSV) to determine the extent to which selenium plays a role in antiviral activity. The data presented here show that the presence of selenium is crucial for the antiviral properties of benzisoselenazol-3(2H)-ones since their isostructural analogues having different groups but lacking selenium either did not show any antiviral activity or their activity was substantially lower. The open-chain analogues of benzisoselenazol- 3(2H)-ones-diselenides also exhibited high antiviral activity while selenides and disulfides were completely inactive towards model viruses.
- Pietka-Ottlik, Magdalena,Potaczek, Piotr,Piasecki, Egbert,Mlochowski, Jacek
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p. 8214 - 8228
(2011/03/19)
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- A new class of anti-HIV-1 agents targeted toward the nucleocapsid protein NCp7: The 2,2'-dithiobisbenzamides
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As part of the National Cancer Institute's Drug Screening Program, a new class of antiretrovirals active against the human immunodeficiency virus HIV-1 has been identified, and the HIV-1 nucleocapsid protein NCp7 was proposed as the target of antiviral action. The 2,2'-dithiobis-[4'-(sulfamoyl)benzanilide] (3x) and the 2,2'-dithiobis(5-acetylamino)benzamide (10) represented the prototypic lead structures. A wide variety of 2,2'-dithiobisbenzamides were prepared and tested for anti-HIV-1 activity, cytotoxicity, and their ability to extrude zinc from the zinc fingers for NCp7. The structure-activity relationships demonstrated that the ability to extrude zinc from NCp7 resided in the 2,2'-dithiobisbenzamide core structure. The 3,3' and the 4,4' isomers were inactive. While many analogs based upon the core structure retained the zinc extrusion activity, the best overall anti-HIV-1 activity was only found in a narrow set of derivatives possessing carboxylic acid, carboxamide, or phenylsulfonamide functional groups. These functional groups were more important for reducing cytotoxicity than improving antiviral potency or activity vs NCp7. All of the compounds with antiviral activity also extruded zinc from NCp7. From this study several classes of low μM anti-HIV agents with simple chemical structures were identified as possible chemotherapeutic agents for the treatment of AIDS.
- Domagala, John M.,Bader, John P.,Gogliotti, Rocco D.,Sanchez, Joseph P.,Stier, Michael A.,Song, Yuntao,Vara Prasad,Tummino, Peter J.,Scholten, Jeffrey,Harvey, Patricia,Holler, Tod,Gracheck, Steve,Hupe, Donald,Rice, William G.,Schultz, Robert
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p. 569 - 579
(2007/10/03)
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- Alkylation process for preparing azetidinone compound and starting compound therefor
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Novel process for preparing azetidinone compound of the formula [III]: STR1 wherein R1 is H or lower alkyl, R2 and R3 combine together with the adjacent nitrogen to form heterocyclic group, and R4 is protected or unprotected hydroxy-substituted lower alkyl, which comprises reacting an alkanamide compound of the formula [I]: STR2 wherein R1, R2 and R3 are the same as defined above, with a compound of the formula [II]: STR3 wherein L1 is a leaving group and R4 is the same as defined above, in the presence of a base, said compound [III] being useful as synthetic intermediate for 1-methylcarbapenem derivative having excellent antibacterial activity.
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- Azetidinone compound and process for preparation thereof
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There is disclosed an azetidinone compound of the formula [I]: STR1 wherein Ring B is a benzene ring which may have substituent(s), R1 is a hydroxy-substituted lower alkyl group which may have substituent(s), X is oxygen atom and the like, Y is oxygen atom and the like, and Z is a methylene group which may have substituent(s), which is useful as a synthetic intermediate of the 1β-methylcarbapenem-type antibacterial agent.
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- Antithrombotic agent
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Certain 2,2'-dithiobis-N-substituted or unsubstituted benzamides or derivatives thereof are useful as antithrombotic agents because of their ability to suppress aggregation of blood platelets.
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- Photochemical Ring-expansion Reaction of 1,2-Benzisothiazolinones
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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
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p. 3131 - 3136
(2007/10/02)
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- BENZISOTHIAZOLES-1,2 ET -2,1: ETUDES SPECTROSCOPIQUES INFRAROUGE ET RAMAN
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Infrared (4000-2000 cm-1, of vapor, liquid and solution in inert and proton-acceptor solvents) and Raman spectra (4000-100 cm-1, liquid) of 1,2- and 2,1-benzisothiazoles have been recorded.A complete assignment of the fundamental vibrations is proposed.The source of the fundamental vibrational wavenumbers is discussed for a series of benzoheterocycles: benzothiophene, 1,3-benzothiazole, benzisothiazoles and benzisoxazoles.
- Jammal, Tamim El,Guiliano, Michel,Fourneron, Jean Dominique,Mille, Gilbert
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p. 313 - 324
(2007/10/02)
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