92-36-4Relevant articles and documents
Discovery and Characterization of Benzimidazole Derivative XY123 as a Potent, Selective, and Orally Available RORγ Inverse Agonist
Wu, Xishan,Shen, Hui,Zhang, Yan,Wang, Chao,Li, Qiu,Zhang, Cheng,Zhuang, Xiaoxi,Li, Chenchang,Shi, Yudan,Xing, Yanli,Xiang, Qiuping,Xu, Jinxin,Wu, Donghai,Liu, Jinsong,Xu, Yong
, p. 8775 - 8797 (2021/06/30)
Receptor-related orphan receptor γ (RORγ) has emerged as an attractive therapeutic target for the treatment of cancer and inflammatory diseases. Herein, we report our effort on the discovery, optimization, and evaluation of benzothiazole and benzimidazole derivatives as novel inverse agonists of RORγ. The representative compound27h(designated as XY123) potently inhibited the RORγ transcription activity with a half-maximal inhibitory concentration (IC50) value of 64 nM and showed excellent selectivity against other nuclear receptors.27halso potently suppressed cell proliferation, colony formation, and the expression of androgen receptor (AR)-regulated genes in AR-positive prostate cancer cell lines. In addition,27hdemonstrated good metabolic stability and a pharmacokinetic property with reasonable oral bioavailability (32.41%) and moderate half-life (t1/2= 4.98 h). Significantly, oral administration of compound27hachieved complete and long-lasting tumor regression in the 22Rv1 xenograft tumor model in mice. Compound27hmay serve as a new valuable lead compound for further development of drugs for the treatment of prostate cancer.
A water-soluble benzo thiazole synthesis of dye method
-
Paragraph 0010; 0037; 0039; 0042; 0044; 0047; 0049; 0052, (2017/10/07)
The present invention discloses a water-soluble benzothiazole dye synthesis method, which comprises: mixing p-toluidine, sodium sulfide and a catalyst, carrying out a cyclization reaction to produce 2-(4-anilino)-6-methyl-benzothiazole, carrying out a sulfonation reaction on the 2-(4-anilino)-6-methyl-benzothiazole and a sulfonation agent to produce 2-(4-anilino)-6-methyl-7-sulfonic-benzothiazole, adding the 2-(4-anilino)-6-methyl-7-sulfonic-benzothiazole (III) and a sodium hydroxide aqueous solution to a solvent, adding a carbonyl-containing compound, and carrying out a reaction to obtain the water-soluble benzothiazole dye. Compared with the synthesis method in the prior art, the synthesis method of the present invention has characteristics of cheap and readily available raw materials, simple process, safety and environmental protection, and is suitable for large-scale industrial production.
Synthesis of 2-(4-aminophenyl)benzothiazoles using MF resin supported H+ under solvent free conditions
Lei, Yingjie,Wu, Xinshi,Zhang, Guochun,Ai, Cuiling
, p. 679 - 682 (2015/05/05)
Abstract A simple and convenient approach to 2-(4-aminophenyl)benzothiazole derivatives by condensation of o-aminothiophenol with (un)substituted p-aminobenzoic acid under the action of melamine formaldehyde resin (MFR) supported sulfuric acid under microwave irradiation (MW) and solvent-free conditions has been developed. Structures of the corresponding products were elucidated by IR, 1H NMR spectra, and elemental analysis. The resin could be easily recovered and reused for subsequent reactions.