27337-45-7Relevant articles and documents
Pd/Cu-Catalyzed C-H/C-H Cross Coupling of (Hetero)Arenes with Azoles through Arylsulfonium Intermediates
Lin, Zeng-Hui,Tian, Ze-Yu,Zhang, Cheng-Pan
, p. 4400 - 4405 (2021/06/27)
A highly efficient method for the selective formal C-H/C-H cross-coupling of azoles and (hetero)arenes was established through arylsulfonium intermediates under transition-metal catalysis, which produced a variety of 2-(hetero)aryl azoles in good to excellent yields. Advantages of the reaction included mildness, a good functional group tolerance, a wide range of substrates, a high regio- and chemoselectivity, one-pot procedures, and the late-stage functionalization of complex molecules without the use of oxidants, offering a promising strategy for the transition-metal-catalyzed C-H arylation of azoles.
A green route for the synthesis of 2-substituted benzoxazole derivatives catalyzed by Al3+-exchanged K10 clay
Suresh, Dhanusu,Dhakshinamoorthy, Amarajothi,Pitchumani, Kasi
supporting information, p. 6415 - 6419 (2013/11/19)
A new, simple, and efficient protocol is developed for the synthesis of 2-substituted benzoxazole derivatives through N-C-O bond formation using Al 3+-exchanged K10 clay (Al3+-K10) as catalyst. A wide range of benzoxazole derivatives
Antitumor benzothiazoles. 7. Synthesis of 2-(4- acylaminophenyl)benzothiazoles and investigations into the role of acetylation in the antitumor activities of the parent amines
Chua, Mei-Sze,Shi, Dong-Fang,Wrigley, Samantha,Bradshaw, Tracey D.,Hutchinson, Ian,Shaw, P. Nicholas,Barrett, David A.,Stanley, Lesley A.,Stevens, Malcolm F. G.
, p. 381 - 392 (2007/10/03)
2-(4-Aminophenyl)benzothiazoles display potent and selective antitumor activity against inter alia breast, ovarian, colon, and renal cell lines, but their mechanism of action, though yet to be defined, may be novel. Metabolism is suspected to play a central role in the mode of action of these benzothiazoles since drug uptake and biotransformation were observed in sensitive cell lines (e.g., breast MCF-7 and MDA 468 cells) in vitro, whereas insensitive cell lines (e.g., prostate PC 3 cells) showed negligible uptake and biotransformation. N-Acyl derivatives of the arylamines have been synthesized, and in vitro studies confirm N-acetylation and oxidation as the main metabolic transformations of 2-(4-aminophenyl)benzothiazoles. With the predominant process being dictated by the nature of the 3'-substituent. The prototype amine 3 underwent mainly N-acetylation in vitro, while 3'- substituted analogues 4 and 5 were primarily oxidized. N-Acetylation of 4 to 11 exerts a drastic dyschemotherapeutic effect in vitro, but acetylation of the halogeno congeners 5-7 gave acetylamines 12-14 which substantially retain selective antitumor activity. In vivo pharmacokinetic studies in rats confirmed rapid and exclusive N-acetylation of the 3'-methyl analogue 4, but less acetylation with the 3'-chloro analogue 5. Distinct expression patterns of N-acetyltransferase NAT1 and NAT2 have been demonstrated in our panel of cell lines.
