865072-69-1Relevant articles and documents
"on Water" Catalytic Aldol Reaction between Isatins and Acetophenones: Interfacial Hydrogen Bonding and Enamine Mechanism
Han, Jinsong,Zhang, Jin-Lei,Zhang, Wei-Qiang,Gao, Ziwei,Xu, Li-Wen,Jian, Yajun
, p. 7642 - 7651 (2019)
"On water" catalytic aldol reaction catalyzed by polyetheramine (D230) has been developed for easy access to 3-substituted 3-hydroxyindolin-2-ones through the reaction between various substituted isatins and acetophenones/cyclic ketones in high yields under room temperature. Systematic mechanism investigation uncovers the secret for the on water catalytic aldol reaction: comparison of the heterogeneous and homogeneous reaction circumstances with yields of 95 and 20%, respectively, indicates the on-water reaction dominating; interfacial hydrogen bonding between isatin with H2O is tested based on the downfield shift of the C2 and C3's 13C NMR signals when water was added to the CDCl3 solution of isatin; Lewis base polyetheramine D230 catalyzes the aldol reaction via the enamine mechanism verified by in situ NMR and ESI-MS analysis.
Design, synthesis and QSAR study of novel isatin analogues inspired Michael acceptor as potential anticancer compounds
Wang, Jiabing,Yun, Di,Yao, Jiali,Fu, Weitao,Huang, Fangyan,Chen, Liping,Wei, Tao,Yu, Cuijuan,Xu, Haineng,Zhou, Xiaoou,Huang, Yanqing,Wu, Jianzhang,Qiu, Peihong,Li, Wulan
, p. 493 - 503 (2018/01/01)
Molecular hybridization is considered as an effective tactic to develop drugs for the treatment of cancer. A series of novel hybrid compounds of isatin and Michael acceptor were designed and synthesized on the basis of association principle. These hybrid compounds were tested for cytotoxic potential against human cancer cell lines namely, BGC-823, SGC-7901 and NCI-H460 by MTT assay. Most compounds showed good anti-growth activities in all tested human cancer cells. SAR and QSAR analysis may provide vital information for the future development of novel anti-cancer inhibitors. Notably, compound 6a showed potent growth inhibition on BGC-823, SGC-7901 and NCI-H460 with the IC50 values of 3.6 ± 0.6, 5.7 ± 1.2, 3.2 ± 0.7 μM, respectively. Besides, colony formation assays, wound healing assays and flow cytometry analysis indicated 6a exhibited a potent anti-growth and anti-migration ability in a concentration-dependence manner through arrested cells in the G2/M phase of cell cycle. Moreover, 6a significantly repressed tumor growth in a NCI-H460 xenograft mouse model. Overall, our findings suggested isatin analogues inspired Michael acceptor may provide promising lead compounds for the development of cancer chemotherapeutics.
Hit optimization studies of 3-hydroxy-indolin-2-one analogs as potential anti-HIV-1 agents
Chander, Subhash,Tang, Cheng-Run,Penta, Ashok,Wang, Ping,Bhagwat, Deepak P.,Vanthuyne, Nicolas,Albalat, Muriel,Patel, Payal,Sankpal, Sanskruti,Zheng, Yong-Tang,Sankaranarayanan, Murugesan
, p. 212 - 222 (2018/05/24)
In the current study, twenty-two compounds based upon 3-hydroxy-3-(2-oxo-2-phenylethyl)indolin-2-one nucleus were designed, synthesized and in vitro evaluated for HIV-1 RT inhibition and anti-HIV-1 activity. Compounds 3d, 5c and 5e demonstrated encouragin
Catalyst-free aldol condensation of ketones and isatins under mild reaction conditions in DMF with molecular sieves 4 A as additive
Chen, Wen-Bing,Liao, Yu-Hua,Du, Xi-Lin,Zhang, Xiao-Mei,Yuan, Wei-Cheng
experimental part, p. 1465 - 1476 (2010/05/18)
In the presence of molecular sieve (MS) 4 A in DMF, a catalyst-free aldol condensation of a variety of aromatic and aliphatic ketones with isatins under mild reaction conditions has been developed. This approach may provide access to a wide range of 3-sub
