Crystal and molecular structure of isatin

Frolova, N. A.; Kravtsov, Victor Ch.; Biyushkin, V. N.; Chumakov, Yu. M.; Bel'kova, O. N.; Malinovskii, T. I.

doi:10.1007/bf00744014

Cited by 14 publications

(19 citation statements)

References 1 publication

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“…1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one (ODQ) was dissolved in dimethyl sulfoxide and diluted 1:10,000 from a working stock. Isatin (1H-indole-2,3-dione; Frolova et al, 1988) was dissolved in hot ethanol (70°C) and diluted 1:100,000 from a working stock. Dimethyl sulfoxide at a final concentration of 0.01% or ethanol at 0.001% did not have any effect on contraction.…”

Section: Methodsmentioning

confidence: 99%

Agonist-Specific Compartmentation of cGMP Action in Myometrium

Buxton

Milton²,

Barnett³

et al. 2010

J Pharmacol Exp Ther

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Nitric oxide relaxes myometrium in a cGMP-independent manner. Although cGMP activates its cognate kinase, this is not required for the inhibitory effect of nitric oxide. Thus, nitric oxide-mediated cGMP elevation does not enjoy the same set of substrates as it does in other smooth muscles. To further understand the regulation of relaxation of uterine muscle by cGMP, we have studied the actions of peptide-mediated cGMP action in guinea pig myometrium. We used both functional and biochemical studies of the action of the particulate guanylyl cyclase activator uroguanylin and its receptor, particulate guanylyl cyclase type C, to address the relationship between cGMP elevation acting in the membrane signaling domain to that of the nonmembrane region of the cell. Uroguanylin relaxed oxytocin-induced contractions in a dose-dependent fashion only in pregnant myometrium. Both relaxation and cGMP accumulation after uroguanylin stimulation were blocked by the putative particulate guanylyl cyclase type C inhibitors 2-chloro-ATP and isatin (1H-indole-2,3-dione), but not by the soluble guanylyl cyclase inhibitor 1H-[1,2,4]oxadiazolo[4,3-A]quinoxalin-1-one (ODQ). Uroguanylin stimulated cGMP accumulation only in the pregnant myometrium. Caveolin-1 expression increased in pregnancy toward term. In the caveolin-1-containing membrane domain, uroguanylin, but not the nitric-oxide donor, led to the elevation of cGMP that was insensitive to ODQ. Particulate guanylyl cyclase C was expressed and prouroguanylin was detected in pregnant myometrium. We conclude that a uroguanylin-particulate cyclase-cGMP relaxation pathway is present and cGMP is compartmented in myometrium. The agonist-mediated selectivity of relaxation to cGMP is of fundamental pharmacological interest in understanding signal transduction in smooth muscle.

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Section: Methodsmentioning

confidence: 99%

Agonist-Specific Compartmentation of cGMP Action in Myometrium

Buxton

Milton²,

Barnett³

et al. 2010

J Pharmacol Exp Ther

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“…This large value was attributed to lone pair electron repulsion between the two oxygen atoms 516,517 . This interpretation was however, subsequently refuted by comparison of bond lengths of cis and trans 1,2-diketones where no systematic or substantial difference between the bond lengths was observed 518 .…”

Section: Crystallographic Datamentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

834

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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“…The crystallographic data represents that it is planar; with a large bond length of 1.55 Å between the two carbonyls. The lone pair electron repulsion between the oxygen atoms [20,21] was responsible for such a large bond length which was subsequently checked by comparison of bond length between cis and trans 1, 2-diketones and no difference was observed [22]. A similar bond length was observed for 1-acetylisatin [23], 1-α-chloroacetylisatin [24] , diethyl (2,3-dihydro-2-oxo-3-indolylidene) propanedioate [25] , 1,1'-oxalylbisisatin [26] and 1-methylisatin [27], as well as in derivatives where C-3 is tetrahedral, such as 3,3-dichloro-1H-indol-2(3H)-one [28] and 5'bromospiro-[1,3-dioxolano-2,3-indolin]-2'-one [29], as well as in 3-methyleneoxindoles [30] (Table 1) and in products obtained by nucleophilic ring opening of 1-acetylisatin, where the 1,2-dicarbonyl system assumes a s-trans conformation [31].…”

Section: Crystallographic Datamentioning

confidence: 99%

Recent Advancement in Synthesis of Isatin as Anticonvulsant Agents: A Review

Nain¹

2014

Med chem

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Isatin (1H-indole-2,3-dione) and its analog, are versatile substrates which acts as a precursor for large number of pharmacologically active compounds, thus having a significant importance in the synthesis of different heterocyclic compound.Isatin shows varity of biological activities such as antimicrobial, anticancer, antiviral, anticonvulsant, antiinflammatory and analgesic.This review focused on isatin synthetic methods and its biological activity as anticonvulsant. An Isatin derivative shows potent anticonvulsant activity at low concentration among all the derivatives, Schiff bases are found to be most potent anticonvulsant agent.

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Crystal and molecular structure of isatin

Cited by 14 publications

References 1 publication

Agonist-Specific Compartmentation of cGMP Action in Myometrium

Agonist-Specific Compartmentation of cGMP Action in Myometrium

The chemistry of isatins: a review from 1975 to 1999

Recent Advancement in Synthesis of Isatin as Anticonvulsant Agents: A Review

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