22388-07-4Relevant articles and documents
Synthesis, characterization, and antitumor activity of some novel S-functionalized benzo[d]thiazole-2-Thiol derivatives; Regioselective coupling to the-SH group
Ramadan, El Sayed,Abdel Hamid, Hamida M.,Noureddin, Sawsan A.,Badahdah, Khadija O.
, p. 647 - 654 (2018)
Several 2-substituted sulfanyl benzo[d]thiazoles were regioselectively synthesized by the reaction of benzo[d]thiazole-2-Thiol (1a) with a variety of reagents under different basic conditions. Some 2-(2,3-disubstituted propyl sulfanyl)benzo[d]thiazoles were obtained from 2-(allylthio)benzo[d]thiazole, which was prepared by the allylation of 1a with allyl bromide in the presence of sodium hydride in dry N,N-dimethylformamide. Reaction of 1a with various pyrazolyl-quinoxaline derivatives was also investigated. Better yields and shorter reaction time were achieved for the synthesis of some derivatives by using ultrasound irradiation. The structural elucidation of all compounds was based on both analytical and spectroscopic data. The newly synthesized compounds were tested in vitro for their antitumor activity against Ehrlich ascites carcinoma (EAC) cells grown in albino mice. Doxorubicin was used as a standard antitumor antibiotic, and some compounds showed half maximal inhibitory concentration (IC50) in the range 40-68 μg mL-1.
Unexpected cis-selectivity in (Sylvestre) Julia Olefinations with Bu 3Sn-containing allyl benzothiazolyl sulfones: Stereoselective synthesis of 1,3-butadienyl- and 1,3,5-hexatrienylstannanes
Sorg, Achim,Brückner, Reinhard
, p. 289 - 293 (2005)
Bu3Sn-substituted benzothiazolyl sulfones 1c, 1d, and 1f were subjected to Julia olefmation reactions with a variety of aldehydes. cis-Selectivities up to 97:3 were obtained by using KHMDS as base in THF.
A New Approach to the Synthesis of Benzothiazole, Benzoxazole, and Pyridine Nucleosides as Potential Antitumor Agents
Khodair, Ahmed I.,Al-Masoudi, Najim A.,Gesson, Jean-Pierre
, p. 2061 - 2076 (2003)
A modified nitrogen and sulfur glycosylation reaction involving benzothiazole benzoxazole and pyridine nucleoside bases with furanose and pyranose sugars are described. Conformational analysis has been studied by homo- and heteronuclear two-dimensional NMR methods (2D DFQ-COSY, HMQC and HMBC). The N and S sites of glycosylation were determined from the 1H, 13C heteronuclear multiple-quantum coherence (HMQC) experiments. All the deprotected nucleosides were tested for their potential antitumor activity.
Selective and mild sulfoxidation of 2-sulfylbenzothiazole using hydroperoxides derived from cyclohexanone in the absence of catalyst
Shi, Wenjun,Yu, Chunmian,Zhou, Xinrui,Zhu, Shihao
, (2021/05/26)
Alkyl hydroperoxides derived from cyclohexanone are attractive oxidants because they are easily available, more reactive than TBHP but much less acidic than m-CPBA. Wherein 1,1′-peroxybis(1-hydroperoxycyclohexane) (C) can be generated by the current simply method and displays the excellent reactivity and selectivity based on oxidative reactions of various benzothiazolyl sulfides substituted by different function groups. The research found that the reactions can be performed in the absence of catalyst and under very mild conditions optimized. Yields of sulfoxides is higher than 90%, no or a little reaction happened at the proximal double bond、 N and S atoms in the benzothiazolyl moiety. Phenyl sulfide as the substrates was also examined for the reaction scope test. The results show that they were uniquely and completely oxidized to sulfoxides in 1 h. A mild, environmentally friendly, catalyst-free aryl sulfide sulfoxidation method has been developed.
Three-Component Synthesis of 2-Substituted Thiobenzoazoles Using Tetramethyl Thiuram Monosulfide (TMTM) as Thiocarbonyl Surrogate
Wang, Xi,Wu, Chun-Yan,Li, Yue-Sheng,Dong, Zhi-Bing
, p. 6770 - 6775 (2020/11/23)
A metal-free synthesis of 2-benzyl/allyl-substituted thiobenzoazoles was developed starting from tetramethyl thiuram monosulfide (TMTM) which served as thiocarbonyl surrogate. By using 2-aminophenols (or 2-aminothiophenols, or 1,2-phenylenediamines) and TMTM as starting materials, 2-mercaptobenzoazoles could be synthesized efficiently. The subsequent C–S bond formation with benzyl/allyl halides gave the final products (2-benzyl/allyl-substituted thiobenzoazoles) with good to excellent yields. The metal-free conditions, inexpensive and easily available starting materials, and broad substrate scope are the advantageous features of this protocol.
