88730-73-8Relevant academic research and scientific papers
Lewis acid-promoted synthesis of highly substituted pyrrole-fused benzoxazinones and quinoxalinones
Selvendran, Suresh,Rajendran, Saravanakumar
supporting information, p. 437 - 445 (2020/10/22)
A synthesis of a series of novel fused tricyclic heterocyclic compounds has been achieved in one-pot reaction set up starting from (E)-3-(2-oxo-2-phenylethylidene)indolin-2-one and 1,4-benzoxazinone/quinoxalinone derivatives promoted by tin(IV) chloride.
Oxidative ring expansion of 3-hydroxy-3-phenacyloxindoles using phenyliodine diacetate and molecular iodine: Synthesis of 2-hydroxy-2-aryl/alkyl-2,3-dihydroquinolin-4(1H)-ones
Kavale, Ashish C.,Kalbandhe, Amit H.,Opai, Imran A.,Jichkar, Atul A.,Karade, Nandkishor N.
supporting information, (2020/12/14)
Oxidation of tertiary alcohol of the type 3-hydroxy-3-phenacyloxindoles using the combination of phenyliodine diacetate and molecular iodine in methanol results in oxidative cleavage of C2-C3 bond to form isocyanate as an intermediate with its subsequent
Diastereoselective trans Cyclopropanation of 3-Alkylidene Oxindoles with in Situ Generated α-Diazo Carbonyls or α,β-Unsaturated Diazo Compounds
Pramanik, Sayan,Ray, Suman,Maity, Suvendu,Ghosh, Prasanta,Mukhopadhyay, Chhanda
supporting information, p. 2240 - 2252 (2021/03/18)
An efficient diastereoselective trans cyclopropanation of 3-alkylidene oxindoles with in situ generated α-diazo carbonyl compounds or α,β-unsaturated diazo compounds under metal-free conditions has been developed to synthesize 3-spirocyclopropyl-2-oxindol
MS 4A-PROMOTED AQUEOUS PHOSPHO-ALDOL-BROOK REARRANGEMENT REACTION of ISATINS
Han, Wei,Liu, Fan,Oriyama, Takeshi
, p. 159 - 166 (2022/01/08)
An efficient, simple, environment-friendly, and low-cost protocol for the hydrophosphonation of isatins using inexpensive and non-toxic MS 4A as a recyclable additive in water has been developed. This protocol is also suitable for the aldol reaction of is
The Ligand Free Palladium(II)-Catalyzed Regioselective 1,2-Addition of Enol Silanes to Quinones to Access 4-Hydroxy-4-(2-oxo-2-arylethyl)cyclohexadien-1-ones and Synthetic Applications
Polimera, Subba Rao,A. M. Subbaiah, Murugaiah,Ilangovan, Andivelu
, p. 14356 - 14370 (2021/10/12)
In contrast to the conventional 1,4-addition process, regioselective 1,2-addition of silyl enol ethers to quinones can now be achieved via a palladium(II) enolate pathway that provides access to 4-hydroxy-4-(2-oxo-2-arylethyl)cyclohexa-2,5-dien-1-one derivatives. This quinone alkylation protocol proceeds under mild reaction conditions at ambient temperature under open air and does not require either an external ligand for the palladium or the use of a base. Additionally, the cyclohexadienone products have been exploited as synthetic precursors for the construction of fused heteroaryl systems.
Eco-friendly Polyethylene Glycol-400 as a Rapid and Efficient Recyclable Reaction Medium for the Synthesis of Anticancer Isatin-linked Chalcones and Their 3-Hydroxy Precursor
Gupta, Alpana K.,Bharadwaj, Mausumi,Mehrotra, Ravi
, p. 703 - 709 (2018/12/11)
Isatin chalcones and their 3-hydroxy precursors are shown to possess potential anticancer activity and are also versatile substrates and key intermediates for the synthesis of a large variety of bioactive spiro-oxindoles. An environmental friendly tandem
"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 (2019/06/17)
"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.
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
Glucose-containing imidazolium salt-catalyzed cross-aldol reaction of isatins and unactivated ketones
Wan, Yu,Yuan, Rui,Cui, Hao,Zhang, Xiao-xiao,Li, Ming-qi,Xu, Jiang-biao,Dou, Peng-fei,Zhang, Long-yan,Wu, Hui
, p. 2561 - 2570 (2018/02/16)
Ketone–ketone cross-aldol reaction of isatins and unactivated ketones was catalyzed by glucose-containing imidazolium salt β-1-imidazole-2,3,4,6-tetra-o-hydroxy-d-glucopyranosyl bromide in neutral condition to generate 3-alkyl-3-hydroxyindolin-2-ones in e
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.
