Synthesis and Bioactivity of Carbohydrate Derivatives of Indigo, Its Isomers and Heteroanalogues

Karapetyan, Gnuni; Chakrabarty, Kuheli; Hein, Martin; Langer, Peter

doi:10.1002/cmdc.201000374

Cited by 30 publications

(9 citation statements)

References 74 publications

(42 reference statements)

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“…Wan, and the synthesis and biological activities of indirubin and its derivatives have been well studied and reviewed [65][66][67][68]. The indirubins are thought to have great potential for pharmaceutical use however, they are plagued by extremely poor aqueous solubility.…”

Section: Indirubin Is the Active Component In The Traditional Chinesementioning

confidence: 99%

Recent Highlights in the Development of Isatin-Based Anticancer Agents

Vine¹,

Matesic²,

Locke³

et al. 2013

Advances in Anticancer Agents in Medicinal Chemistry

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Isatin (1H-indole-2,3-dione) and its derivatives are responsible for a broad spectrum of biological activities. Among these the cytotoxic and antineoplastic properties have been the most widely reported. The synthetic versatility of the isatin, due to its privileged scaffold, has led to the generation of a large number of structurally diverse derivatives which include analogues derived from either mono-, di-, and trisubstitution of the aryl ring A, and/or those obtained by derivatisation of the isatin nitrogen and C2/C3 carbonyl moieties. These compounds inhibit cancer cell proliferation and tumour growth via interaction with a variety of intracellular targets such as DNA, telomerase, tubulin, P-glycoprotein, protein kinases and phosphatases. Herein we review recent highlights in the development of isatin-based compounds as anticancer agents with a particular focus on the cytotoxicity and structure activity relationships. Abstract:Isatin (1H-indole-2,3-dione) and its derivatives are responsible for a broad spectrum of biological activities. Among these the cytotoxic and antineoplastic properties have been the most widely reported. The synthetic versatility of the isatin, due to its privileged scaffold, has led to the generation of a large number of structurally diverse derivatives which include analogues derived from either mono-, di-, and tri-substitution of the aryl ring A, and/or those obtained by derivatisation of the isatin nitrogen and C2/C3 carbonyl moieties. These compounds inhibit cancer cell proliferation and tumour growth via interaction with a variety of intracellular targets such as DNA, telomerase, tubulin, Pglycoprotein, protein kinases and phosphatases. Herein we review recent highlights in the development of isatin-based compounds as anticancer agents with a particular focus on the cytotoxicity and structure activity relationships.

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Section: Indirubin Is the Active Component In The Traditional Chinesementioning

confidence: 99%

Recent Highlights in the Development of Isatin-Based Anticancer Agents

Vine¹,

Matesic²,

Locke³

et al. 2013

Advances in Anticancer Agents in Medicinal Chemistry

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“…9 Carbohydrate tethered indigo dyes are potential candidates for cancer therapy. 10 Isatin derivatives displayed good anti-HIV, 11 anticancer, 12a spermicidal, 12b antimalarial, 13 antiviral, 14 antimicrobial, 15 anticonvulsant 16 and cytotoxic activities. 17 Furthermore, they also exhibit human rhinovirus 3C protease, 18 …”

Section: Introductionmentioning

confidence: 99%

Zinc oxide surface: a versatile nanoplatform for solvent-free synthesis of diverse isatin derivatives

Kothandapani

Ganesan

Mani

et al. 2016

Tetrahedron Letters

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“…Indirubin also inhibits intersegmental vessel growth and induces cellular apoptosis in an in vivo zebrafish model 9 while other indirubin derivatives or analogues, 10 including N-glycosides, show antiproliferative activity against a number of human cancer cell lines. 11,12 Other effects of indirubin or derivatives include anti-protozoal activity 13 as well as inhibition of lipoxygenase.…”

Section: Introductionmentioning

confidence: 99%

A cascade synthetic route to new bioactive spiroindolinepyrido[1,2-a]indolediones from indirubin

et al. 2015

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. (2015). A cascade synthetic route to new bioactive spiroindolinepyrido[1,2-a]indolediones from indirubin. Tetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 71 (43), 8357-8367. A cascade synthetic route to new bioactive spiroindolinepyrido[1,2-a]indolediones from indirubin AbstractThe allylation of indirubin produced the expected indolic N′-allylindirubin and N,N′-diallylindirubin derivatives in moderate yields, together with the corresponding N-substituted isatin products. At higher temperatures, the base-initiated reaction with allylic halides yielded spiroindolinepyrido[1,2-a]indolediones in a one-pot cascade reaction sequence with yields of up to 70%. These readily accessed, new spiro compounds represent the first reported examples of indirubin participating in cascade reactions. Preliminary in vitro biological testing of some of the products indicated promising activity against some cancer cell lines and against Plasmodium falciparum for two spiro derivatives. Computational methods were used to gain a greater understanding of the UV/Vis spectroscopic data for the N′-substituted and N,N′-disubstituted indirubin derivatives.

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Synthesis and Bioactivity of Carbohydrate Derivatives of Indigo, Its Isomers and Heteroanalogues

Cited by 30 publications

References 74 publications

Recent Highlights in the Development of Isatin-Based Anticancer Agents

Recent Highlights in the Development of Isatin-Based Anticancer Agents

Zinc oxide surface: a versatile nanoplatform for solvent-free synthesis of diverse isatin derivatives

A cascade synthetic route to new bioactive spiroindolinepyrido[1,2-a]indolediones from indirubin

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