21591-87-7Relevant articles and documents
Studies on potential antiviral compounds. XXIV. New 1-substituted isatin β-thiosemicarbazones
Ferranti,Garuti,Giovanninetti,Katz
, p. 415 - 421 (1985)
Some new 1-substituted isatin β-thiosemicarbazones were examined for their ability to inhibit the growth of the wild-type strain of vaccinia virus and the isatin β-thiosemicarbazone (IBT) resistant mutant of this virus. Also investigated was the capabilit
Selective C?N Bond Cleavage of N-Acylisatins: Towards High Performance Acylation/Arylation/Transamination Reagents
Xiong, Li,Deng, Rong,Liu, Tingting,Luo, Zhongfeng,Wang, Zijia,Zhu, Xiao-Feng,Wang, Hui,Zeng, Zhuo
supporting information, p. 5383 - 5391 (2019/11/03)
New multipurpose arylation/acylation/transamination reagents, N-acylisatins, have been developed by selective ‘inside-outside’ C?N bond cleavage under different catalytic conditions. As activated amides, N-acylisatins undergo Rh-catalyzed C?H arylation and Pd-catalyzed acylation by cleavage outside the C?N bond, and the desired biaryls and diaryl ketones were obtained in good to excellent yields. Generally, the combination of N-acylisatins with amines leads to a ring-opening reaction and formation of transamination products in a predictable manner through inside C?N bond cleavage. Interestingly, treatment of N-acylisatins with amines lead to unexpected outer-ring transamination products when CsF is added, which shows that CsF can favor the outside C?N bond cleavage path. Notably, this work presents a new strategy for multiple chemical transformations of a single amide to achieve various products by selective C?N bond cleavage. (Figure presented.).
Synthesis, in vitro, and in cell studies of a new series of [Indoline-3,2′-thiazolidine]-based p53 modulators
Bertamino, Alessia,Soprano, Maria,Musella, Simona,Rusciano, Maria Rosaria,Sala, Marina,Vernieri, Ermelinda,Di Sarno, Veronica,Limatola, Antonio,Carotenuto, Alfonso,Cosconati, Sandro,Grieco, Paolo,Novellino, Ettore,Illario, Maddalena,Campiglia, Pietro,Gomez-Monterrey, Isabel
, p. 5407 - 5421 (2013/07/26)
Analogues of the previously described spiro[imidazo[1,5-c]thiazole-3, 3′-indoline]-2′,5,7(6H,7aH)-trione p53 modulators were prepared to explore new structural requirements at the thiazolidine domain for the antiproliferative activity and p53 modulation. In cell, antiproliferative activity was evaluated against two human tumor cell lines. Derivative 5-bromo-3′-(cyclohexane carbonyl)-1-methyl-2-oxospiro[indoline-3,2′- thiazolidine] (4n) emerged as the most potent compound of this series, inhibiting in vitro 30% of p53-MDM2 interaction at 5 μM and the cell growth of different human tumor cells at nanomolar concentrations. Docking studies confirmed the interactions of 4n with the well-known Trp23 and Phe19 clefts, explaining the reasons for its binding affinity for MDM2. 4n at 50 nM is capable of inducing the accumulation of p53 protein, inducing significant apoptotic cell death without affecting the cell cycle progression. Comparative studies using nutlin in the same cellular system confirm the potential of 4n as a tool for increasing understanding of the process involved in the nontranscriptional proapoptotic activities of p53.
