3-Substituted-3-hydroxy-2-oxindole, an Emerging New Scaffold for Drug Discovery with Potential Anti-Cancer and other Biological Activities

Peddibhotla, Satyamaheshwar

doi:10.2174/157340709787580900

Cited by 465 publications

(70 citation statements)

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“…The simple amino acids bearing only an amino group and a carboxyl group could not catalyze this reaction. No expected aldol adducts were observed after direct determination by TLC (Table 1, entries [1][2][3][4][5]. This indicated that it is impossible for the aldol reaction in which these primary amine and secondary amine catalysts unilaterally activate the (E)-4-phenylbut-3-en-2-one (2a) to form an enamine intermediate.…”

Section: Resultsmentioning

confidence: 99%

“…Thin layer chromatography (TLC) was performed on TLC silica gel 60 F254 plates. 1 H-NMR spectra were recorded on a Bruker AVII-400 MHz NMR spectrometer. The chemical shifts were recorded in ppm relative to tetramethylsilane and with the solvent resonance as the internal standard.…”

Section: Generalmentioning

confidence: 99%

“…This kind of compounds have become important synthetic targets as these structural frameworks form the core units of many natural products and pharmaceutically active compounds [1]. Convolutamydines [2], arundaphine [3], donaxaridine [4], dioxibrassinine [5], maremycins [6], paratunamide [7], celogentin K [8], TMC-95A-D [9], flustraminol [10], 3-hydroxy welwitindolinones [11] and CPC-1 [12] are some examples of a growing list of bioactive 3-substituted-3-hydroxy-2-oxindole natural products (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Facile Creation of 3-Substituted-3-Hydroxy-2-Oxindoles by Arginine-Catalyzed Aldol Reactions of α,β-Unsaturated Ketones with Isatins

et al. 2013

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An efficient approach for the synthesis of 3-substituted-3-hydroxy-2-oxindoles has been achieved via an aldol reaction of α,β-unsaturated ketones and isatins using arginine as an organocatalyst. A range of 3-substituted-3-hydroxy-2-oxindoles were obtained in moderate to high (up to 99%) yields. These 3-substituted-3-hydroxy-2-oxindoles with an additional enone moiety provide an opportunity for further elaboration of the products and for potentially interesting biological activities. In addition, the formation of 3-substituted-3-hydroxy-2-oxindole 3a was confirmed by X-ray crystallography. The possible reaction mechanism reveals that the reaction proceeds via a double action process.

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Section: Resultsmentioning

confidence: 99%

Section: Generalmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Facile Creation of 3-Substituted-3-Hydroxy-2-Oxindoles by Arginine-Catalyzed Aldol Reactions of α,β-Unsaturated Ketones with Isatins

et al. 2013

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“…14 As a class of important 3,3-disubstituted oxindoles, 3-substituted 3-hydroxyindolin-2-ones have attracted considerable attention because of their diverse biological activities. 15,16 During recent years several review articles were published on isatins. Singh and Desta reviewed isatin as a privileged molecule in design and synthesis of spiro-fused cyclic frameworks.…”

Section: Introductionmentioning

confidence: 99%

Recent applications of isatin in the synthesis of organic compounds

Moradi¹,

Ziarani²,

Lashgari³

et al. 2017

Arkivoc

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“…This scaffold is present in a large variety of natural and synthetic compounds that exhibit pharmaceutical properties [1][2][3][4][5][6][7][8]. Structure-activity relationship studies have shown that the biological activities of these compounds are significantly affected both by the configuration of the C3 and its substitution pattern [9][10][11].…”

Section: Introductionmentioning

confidence: 99%