The <sup>13</sup>C NMR spectrum of coumarandione

Winkler, Tammo; Ferrini, P. G.; Haas, Georges

doi:10.1002/mrc.1270120213

Cited by 14 publications

(5 citation statements)

References 11 publications

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“…Different proposals for assignment of the signals have been published 42,[533][534][535] . This question was resolved by the obtention of the HETCOR spectrum, which revealed that the assignment proposed by Galasso, based on quantum mechanical calculations using the CNDO/S wave functions, was correct 534 .…”

Section: C Nmr Spectroscopymentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

858

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: C Nmr Spectroscopymentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

858

447

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“…The acetate carbonyl (6 168.2) is assigned by its two-bond I 3 C -'~ coupling to the acetyl methyl hydrogens (6 2.43). The C-2 carbonyl is assigned on the basis of its chemical shift (8) and its lack of long range coupling.…”

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confidence: 99%

Metabolites produced by the Scleroderris canker fungus, Gremmeniellaabietina. Part 4. Biosynthetic studies

Ayer¹,

Pedras²,

Ward³

1987

Can. J. Chem.

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. J. Chem. 65, 760 (1987).The biosynthetic origin of the carbon atoms of the most highly oxidized, polyketide derived, ring (carbons 1-3) of the Gremmeniella abietina metabolites sclerodione (3), scleroderolide (4), sclerodin (5), and Scleroderris green (6) has been studied. It is shown that both C-1 and C-3 of 3 and 4 are derived from C-1 of acetate, and that C-2 of scleroderolide (4) is derived from C-2 of acetate while C-3 is derived from C-l of acetate. As expected, C-1 and C-3 of Scleroderris green (6) originate from the carboxyl carbon of acetate, while C-2 originates from the methyl carbon of acetate. Complete 13C and 'H nuclear magnetic resonance spectra of these metabolites are reported. It has also been shown that ent-atrovenetin (erzt-7a) is a metabolite of G. abietina.WILLIAM A. AYER, M. SOLEDADE PEDRAS et DALE E. WARD. Can. J. Chem. 65, 760 (1987).On a Ctudit I'origine biosynthitique des atomes de carbone du cycle le plus oxydC (carbones 1-3) et dCrivC d'un polycCtide des mttabolites du Gremrneniella abietina suivants : la sclCrodione (3), le scl6rodCrolide (4), la sclerodine (5) et le vert de ScltrodCrris (6). On a d&montrC que les carbones C-1 ainsi que C-3 des composCs 3 et 4 sont derives du carbone C-l de l'acetate et que le C-2 du sclCrodtrolide (4) est dkrivC du C-2 de l'acetate alors que le C-3 est derive du C-l de I'acCtate. Comme on pouvait s'y attendre, les carbones C-1 et C-3 du vert de Scleroderris (6) ont leur origine dans le groupement carboxyle de I'acCtate alors que le C-2 provient du carbone mkthylique de I'acCtate. On rapporte les spectres de resonance magdtique nucliaire I3c et 'H complets de ces metabolites. On dkmontre aussi que le ent-atroventtine (7a-ent) est un mktabolite du G. abietina.[Traduit par la revue]We have previously reported (1-3) the isolation from Gremmeniella abietina of several metabolites, which contain a phenalenone nucleus fused to a dihydrofuran ring. Several structurally related metabolites have been isolated from other fungi.' Biosynthetic studies on metabolites of Petzicillium herquei (e.g., atrovenetin (1)) have revealed a heptaketide origin for the phenalenone nucleus, whereas the dihydrofuran ring is mevalonate derived (Scheme 1) (5). The metabolites of G. abietina are expected to have a similar biosynthetic origin. Three of the metabolites (3,4, and 5) have one carbon atom less than the parent phenalenones (e.g., 1 and 2). In principle such a degradation could involve the loss of C-1, C-2, or C-3. We have previously speculated (6) that ent-atrovenetinone (2) could be a precursor of sclerodione (3), by loss of C-2. A possible pathway from 2 to 3 is illustrated in Scheme 2. Oxidation of 3 could lead to both sclerodin (5) and scleroderolide (4) (Scheme 3). To follow the labelling pattern of 13C enriched metabolites, it was first necessary to assign the I3C chemical shifts for the metabolites. Since ent-atrovenetinone (2) is produced in small amounts, is unstable in solution (I), and since the stable ethanolate 2 a is a mixture of epimers at C-2, we were...

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“…The ν C = O values are not modified by N-alkylation, N-acetylation leads to a hypsochromic shift of the lactum absorption of about 50-70 cm -1 while the ketone bands shift to 1750 cm -1 as cosenquence of the extension of a conjugation of the nitrogen lone pair with acetyl group [29]. posed by galasso based on quantum mechanical calculations using CNDO/S wave functions was correct [32]. This result allowed the correction of assignment of spectra of 1-acetyl isatin [33,34] and 1-Methylisatin and 3-dicyanomethyleneoxindole [35](▶table 3).…”

Section: Spectral Aspectsmentioning

confidence: 91%

Recent Advancement of Synthesis of Isatins as a Versatile Pharmacophore: A review

Kumar¹,

Singh

Kumar

2020

Drug Res (Stuttg)

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Isatin (1 H-indole-2, 3-Dione) and its derivatives are versatile compounds which acts as a precursor for a large number of pharmacologically active compounds. Therefore isatins have a significant importance in the synthesis of different heterocyclic compounds. Isatins show variety of biological activities. In this review we focus on synthetic methods of isatins and their biological activities such as antimicrobial, anticonvulsant, anti-inflammatory and analgesic activity, antitubercular activity.

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The ¹³C NMR spectrum of coumarandione

Cited by 14 publications

References 11 publications

The chemistry of isatins: a review from 1975 to 1999

The chemistry of isatins: a review from 1975 to 1999

Metabolites produced by the Scleroderris canker fungus, Gremmeniellaabietina. Part 4. Biosynthetic studies

Recent Advancement of Synthesis of Isatins as a Versatile Pharmacophore: A review

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The 13C NMR spectrum of coumarandione

Cited by 14 publications

References 11 publications

The chemistry of isatins: a review from 1975 to 1999

The chemistry of isatins: a review from 1975 to 1999

Metabolites produced by the Scleroderris canker fungus, Gremmeniellaabietina. Part 4. Biosynthetic studies

Recent Advancement of Synthesis of Isatins as a Versatile Pharmacophore: A review

Contact Info

Product

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The ¹³C NMR spectrum of coumarandione