70097-11-9Relevant academic research and scientific papers
Hydrogen-bonding patterns in 3-alkyl-3-hydroxy-indolin-2-ones
Becerra, Diana,Insuasty, Braulio,Cobo, Justo,Glidewell, Christopher
, p. o79-o86 (2010)
The mol-ecules of racemic 3-benzoyl-methyl-3-hydroxy-indolin-2-one, C 16H13NO3, (I), are linked by a combination of N-H...O and O-H...O hydrogen bonds into a chain of centrosymmetric edge-fused R 2 2(10) and R 4
"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.
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.
Green catalytic synthesis method of isatin derivative
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Paragraph 0013; 0014; 0022; 0023; 0024, (2018/01/17)
The invention discloses a green catalytic synthesis method of isatin derivative. The method comprises the following steps: adopting isatin compound and ketone containing alpha-hydrogen as raw materials, adopting water as a solvent to perform Aldol reactio
DABCO-catalyzed synthesis of 3-substituted-3-hydroxyindolin-2-ones in aqueous media
Tiwari, Keshri Nath,Bora, Darshana,Chauhan, Garima,Yadav, Deepika,Sharma, Kavita,Thakur, Ashima,Singh, Lachhman,Tripathi, Vishwadeep
, p. 620 - 625 (2016/06/06)
An efficient and greener protocol for easy access to 3-susbstituted-3-hydroxy-2-oxindoles by the reaction with various substituted isatins and acetophenones is described. This protocol is widely applicable for a variety of isatins and acetophenones using
Synthesis and biological evaluation of spiro[cyclopropane-1,3′-indolin]-2′-ones as potential anticancer agents
Reddy, Chada Narsimha,Nayak, V. Lakshma,Mani, Geeta Sai,Kapure, Jeevak Sopanrao,Adiyala, Praveen Reddy,Maurya, Ram Awatar,Kamal, Ahmed
, p. 4580 - 4586 (2015/10/12)
Libraries of spiro[cyclopropane-1,3′-indolin]-2′-ones were synthesized and evaluated for their biological activity against five different human cancer cell lines HT-29 (colon cancer), DU-145 (prostate cancer), Hela (cervical cancer), A-549 (Lung cancer),
Chalcone based azacarboline analogues as novel antitubulin agents: Design, synthesis, biological evaluation and molecular modelling studies
Sharma, Sahil,Kaur, Charanjit,Budhiraja, Abhishek,Nepali, Kunal,Gupta, Manish K.,Saxena,Bedi
, p. 648 - 660 (2014/09/17)
The present study involves the design of a series of 3-aryl-9-acetyl- pyridazino[3,4-b]indoles as constrained chalcone analogues. A retrosynthetic route was proposed for the synthesis of target compounds. All the synthesized compounds were evaluated for in-vitro cytotoxicity against THP-1, COLO-205, HCT-116 and A-549 human cancer cell lines. The results indicated that 2a, 3a, 5a and 6a possessed significant cytotoxic potential with an IC50 value ranging from 1.13 to 5.76 μM. Structure activity relationship revealed that the nature of both Ring A and Ring B influences the activity. Substitution of methoxy groups on the phenyl ring (Ring A) and unsubstituted phenyl ring (Ring B) were found to be the preferred structural features. The most potent compound 2a was further tested for tubulin inhibition. Compound 2a was found to significantly inhibit the tubulin polymerization (IC50 value - 2.41 μM against THP-1). Compound 2a also caused disruption of microtubule assembly as evidenced by Immunoflourescence technique. The significant cytotoxicity and tubulin inhibition by 2a was rationalized by molecular modelling studies. The most potent structure was docked at colchicine binding site (PDB ID-1SA0) and was found to be stabilized in the cavity via various hydrophobic and hydrogen bonding interactions.
Photophysical study of some 3-benzoylmethyleneindol-2-ones and estimation of ground and excited states dipole moments from solvatochromic methods using solvent polarity parameters
Saroj, Manju K.,Sharma, Neera,Rastogi, Ramesh C.
experimental part, p. 73 - 86 (2012/04/04)
3-Benzoylmethyleneindol-2-ones, isatin based chalcones containing donor and acceptor moieties that exhibit excited-state intramolecular charge transfer, have been studied in different solvents by absorption and emission spectroscopy. The excited state beh
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
