56680-30-9Relevant academic research and scientific papers
Spiro indolone compound as well as, preparation, method and pharmaceutical composition and application thereof
-
Paragraph 0250; 0255-0258, (2020/01/11)
Spiro indolone compounds, a preparing method, a medicine composition and uses of the compounds are disclosed. In particular, the invention provide spiro indolone compounds shown as a formula I or II, a preparing method of the spiro indolone compounds and
Gold(I)-Catalyzed and Nucleophile-Guided Ligand-Directed Divergent Synthesis
Lee, Yen-Chun,Knauer, Lena,Louven, Kathrin,Golz, Christopher,Strohmann, Carsten,Waldmann, Herbert,Kumar, Kamal
supporting information, p. 5688 - 5699 (2018/10/31)
Transition metal catalysts can mediate a plethora of skeleton rearrangements of a range of substrates to construct complex small molecules. Yet, their potential to transform common substrates into distinct molecular scaffolds has not been fully explored to deliver biologically relevant small molecules. Gold(I)-catalyzed transformations of enynes are amongst the most intriguing rearrangements and provide opportunities to access a range of diverse scaffolds efficiently. In ligand-directed divergent synthesis (LDS), variation of ligands in metal complexes determines the fate of substrates during their transformation into distinct scaffolds. For instance, variation of ligands for the gold(I) catalysts helps to transform oxindole derived 1,6-enynes into several distinct molecular frameworks. In this report, we present how ligand variation in gold(I) catalysts, nucleophile-additives and alkyl and alkynyl substitutions on the 1,6-enynes as well as replacement of the oxindole ring with a different privileged ring-system (PRS) influence the LDS approach to access a wider chemical space. Based on the experimental results, we propose several mechanistic pathways in gold(I)-catalyzed cycloisomerizations and cascade reactions of 1,6-enyne substrates leading to structurally distinct chemotypes.
Synthesis of spiro[pyrazolin-3,3′-oxindoles] and 3-arylcarbonylmethyl substituted ylideneoxindoles by 1,3-dipolar cycloadditions of 3-ylideneoxindoles and in-situ-generated α-diazoketones
Jiang, Shan,Guo, Hong-Mei,Yao, Sheng,Shi, De-Qing,Xiao, Wen-Jing
, p. 10433 - 10443 (2018/05/31)
An efficient 1,3-dipolar cycloaddition of 3-ylideneoxindoles with in-situ-generated α-diazoketones to potentially biological active spiro[pyrazolin-3,3′-oxindoles] 4 with excellent regioselectivity and diastereoselectivity and synthetically useful buildin
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),
3-(2-oxoethylidene)indolin-2-one derivatives activate Nrf2 and inhibit NF-κB: Potential candidates for chemoprevention
Nagle, Amrita A.,Reddy, Shridhivya A.,Bertrand, Helene,Tajima, Hisashi,Dang, Truong-Minh,Wong, Siew-Cheng,Hayes, John D.,Wells, Geoffrey,Chew, Eng-Hui
, p. 1763 - 1774 (2014/08/18)
Induction of cytoprotective phase 2 enzymes through inhibition of Keap1, a repressor of transcription factor Nrf2, is a cancer-prevention strategy. Compounds that elicit antiinflammatory and cytoprotective effects are promising candidates for chemoprevent
Design and synthesis of marine natural product-based 1H-indole-2,3-dione scaffold as a new antifouling/antibacterial agent against fouling bacteria
Majik, Mahesh S.,Rodrigues, Cheryl,Mascarenhas, Stacey,D'Souza, Lisette
, p. 89 - 95 (2014/06/23)
Marine organisms such as seaweeds, sponges and corals protect their own surfaces from fouling by their high anesthetic, repellant, and settlement inhibition properties. Within the marine ecosystem, evolution has allowed for the development of certain antifouling properties. Isatin is a biologically active chemical produced by an Alteromonas sp. strain inhibiting the surface of embryos of the cardiean shrimp Palaemon macrodectylus, which protect them from the pathogenic fungus Lagenidium callinectes. In present study, an antibacterial activity of isatin and its synthetic analogues were evaluated against different fouling bacteria in order to explore the structure activity relationships for the first time. The synthesized compounds along with parent isatin were tested against different ecologically relevant marine microorganisms by using the Kirby-Bauer disc diffusion method. Few synthetically modified isatin exhibited potent inhibitory activity at concentration of 2 μg/disc against Planococcus donghaensis, Erythrobacter litoralis, Alivibrio salmonicida, Vibrio furnisii. Overall, the modified analogues showed stronger activity than the parent marine natural product (isatin) and hence 1H-indole-2,3-dione scaffold has immense potential as future antibacterial/antifouling candidate.
Studies on the stereochemical assignment of 3-acylidene 2-oxindoles
Edeson, Steven J.,Jiang, Julong,Swanson, Stephen,Procopiou, Panayiotis A.,Adams, Harry,Meijer, Anthony J. H. M.,Harrity, Joseph P. A.
, p. 3201 - 3210 (2014/05/06)
The designation of E/Z-geometrical isomers in 3-acylidene 2-oxindoles by NMR spectroscopy can lead to erroneous assignment of alkene stereochemistry because of the narrow chemical shift range observed over a large series of analogues. In contrast, UV-Vis spectroscopy offers a convenient and more reliable method for alkene stereochemical assignment. A combination of X-ray crystallography and theoretical studies shows that the observed differences in UV-Vis spectroscopic behaviour relate to the twisted conformation of the Z-isomers that provides reduced conjugation and weaker hypsochromic (blue-shifted) absorbances relative to those of the E-isomers.
New diastereoselective synthesis of 3-alkylidene-1-methyloxindoles
Lopez-Alvarado,Avendano
, p. 104 - 110 (2007/10/03)
Addition of alkyl or aryl α-substituted acetophenones to N-methylisatin in basic media gives diastereomeric mixtures of the corresponding α-substituted 3-benzoylmethyl-3-hydroxy-1-methyloxindole in good yields. Under anhydrous conditions (concentrated sul
THE REACTION OF ISATIN AZOMETHINE YLIDES WITH (Z)- AND (E)-2-OXOINDOLIN-3-YLIDENE ACETOPHENONES: CONCERTED VS APPARENT NON-CONCERTED 1,3-DIPOLAR CYCLOADDITION
Casaschi, Adele,Desimoni, Giovanni,Faita, Giuseppe,Invernizzi, Anna Gamba,Gruenanger, Paolo
, p. 1673 - 1686 (2007/10/02)
The reaction of 1-benzyl-5-bromoisatin with proline, sarcosine, or glycine gives azomethine ylides that can be trapped by (Z)- or (E)-2-oxoindolin-3-ylidene acetophenones acting as dipolarophiles in a 1,3-dipolar cycloaddition.The configuration of the add
An easy Lewis acid-mediated isomerization from (E)- to (Z)-oxoindolin-3-ylidene ketones
Faita, Giuseppe,Mella, Mariella,Righetti, PierPaolo,Tacconi, Gianfranco
, p. 10955 - 10962 (2007/10/02)
(E)-2-Oxoindolin-3-ylidene ketones can be easily isomerized to their (Z)-isomers by AlCl3 at room temperature in CH2Cl2. The behaviour of the unsaturated dicarbonyl framework in the (Z)-configuration as a bidentate ligand
