Prenisatin (5-(3-Methyl-2-butenyl)-indole-2,3-dione): an Antifungal Isatin Derivative from Chaetomium globosum.

Breinholt, Jens; Demuth, Helle; Heide, Morten; Jensen, Georg W.; Møller, Inge L.; Nielsen, Ruby I.; Olsen, Carl Erik; Rosendahl, Connie N.; Haugg, Monika; Trabesinger-Rüf, Nathalie; Weinhold, Elmar G.

doi:10.3891/acta.chem.scand.50-0443

Cited by 37 publications

(19 citation statements)

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“…6 , and has also been found as a component of the secretion from the parotid gland of Bufo frogs 7 , and in humans as it is a metabolic derivative of adrenaline [8][9][10] . Substituted isatins are also found in plants, for example the melosatin alkaloids (methoxy phenylpentyl isatins) obtained from the Caribbean tumorigenic plant Melochia tomentosa [11][12][13] as well as from fungi: 6-(3'-methylbuten-2'-yl)isatin was isolated from Streptomyces albus 14 and 5-(3'-methylbuten-2'-yl)isatin from Chaetomium globosum 15 . Isatin has also been found to be a component of coal tar 16 .…”

Section: Introductionmentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

860

447

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Isatinas (1H-indol-2,3-diona) são compostos de grande versatilidade sintética, podendo ser utilizados na obtenção de diversos sistemas heterociclos, como derivados indólicos e quinolínicos, o que as tornam importantes matérias-primas na síntese de fármacos. Isatinas também têm sido detectadas em tecidos de mamíferos, o que tem despertado o interesse em seu estudo como moduladores em diversos processos bioquímicos. Os avanços na aplicação de isatinas em síntese orgânica, bem como na compreensão de seus efeitos biológicos e farmacológicos nos últimos vinte e cinco anos encontram-se relatados nesta revisão e seus respectivos materiais suplementares.Isatins (1H-indole-2,3-dione) are synthetically versatile substrates, where they can be used for the synthesis of a large variety of heterocyclic compounds, such as indoles and quinolines, and as raw material for drug synthesis. Isatins have also been found in mammalian tissue and their function as a modulator of biochemical processes has been the subject of several discussions. The advances in the use of isatins for organic synthesis during the last twenty-five years, as well as a survey of its biological and pharmacological properties are reported in this review and in the accompanying supplementary information.

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Section: Introductionmentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

860

447

View full text Add to dashboard Cite

show abstract

“…So, the structure of this pigment was established as the new 7-(3-methyl-but-2-enyl)-isatin (168). Two structural analogues, 5-prenylisatin and 6-isopentensylisatin are naturally occurring in Chaetomium globosum [264] and Streptomyces albus [265] , respectively. Recently, three further new isatins derivatives, 6-hydroxyisatin (170), 6-hydroxy-5-methoxy-isatin (171) and 5-hydroxy-6-methoxy-isatin (173) were isolated [266] in our group from Streptomyces spp., however, the structures could not un-equivocally be confirmed, due to the small amounts.…”

Section: Marine Streptomyces Sp B7874mentioning

confidence: 99%

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

Ueda¹,

Hashimoto²,

Yamamura³

et al. 2011

J Antibiot

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“…Various substituted isatins have been isolated from plants, e.g. melosatin alkaloids from Melochia tomentosa, a Caribbean tumorigenic plant 4 ; 6-(3 0 -methylbuten-2 0 -yl)isatin from fungi, Streptomyces albus 5 and 5-(3 0 -methylbuten-2 0 -yl)isatin from Chaetomium globosum 6 . It is also known that isatins act as endogenous biological regulators, found in the brain, peripheral tissues, and body fluids of humans and animals 7 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and anti-inflammatory activity evaluation of novel triazolyl-isatin hybrids

Sharma

Balwani

Mathur

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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New isatin-triazole based hybrids have been synthesized and evaluated for their inhibitory activity of TNF-a induced expression of Intercellular Adhesion Molecule-1 (ICAM-1) on the surface of human endothelial cells. Structure-activity relationship (SAR) studies revealed that the presence of the electron-attracting bromo substituent at position-5 of the isatin moiety played an important role in enhancing the anti-inflammatory potential of the synthesized compounds. Z-1-[3-(1H-1,2,4-Triazol-1-yl)propyl]-5-bromo-3-[2-(4-methoxyphenyl)-hydrazono]indolin-2-one (19) with an IC 50 ¼ 20 mM and 89% ICAM-1 inhibition with MTD at 200 mM was found to be the most potent of all the synthesized derivatives. Introduction of 1,2,4-triazole ring and electron-donating methoxy group on the phenylhydrazone moiety resulted in four-fold increase of the anti-inflammatory activity.

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Prenisatin (5-(3-Methyl-2-butenyl)-indole-2,3-dione): an Antifungal Isatin Derivative from Chaetomium globosum.

Cited by 37 publications

References 0 publications

The chemistry of isatins: a review from 1975 to 1999

The chemistry of isatins: a review from 1975 to 1999

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

Synthesis and anti-inflammatory activity evaluation of novel triazolyl-isatin hybrids

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