The stereochemistry of 2‐oxoindolin‐3‐ylidene derivatives

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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“…2-Oxindolin-3-ylideneacetonitrile exists as a separable E,Z-pair, but the Z-isomer slowly isomerises when dissolved in dimethylsulfoxide 436 .…”

Section: Scheme 103mentioning

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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“…To date, the reactivity of 5-alkylidene-1,2,3-dithiazoles is rarely explored with triphenylphosphine [ 58 ], and is never described with strong bases. By analogy with our previous work on N -arylimino-1,2,3-dithiazole ring opening via nucleophilic attack at S1 and/or S2, we expected to obtain 3-alkenyl-oxindoles functionalized by a thiol and a carbonitrile function ( Figure 1 , III ) [ 59 , 60 ].…”

Section: Resultsmentioning

confidence: 84%

“…We previously showed that attack of some N -arylimino-1,2,3-dithiazoles with sodium hydride or methyl magnesium bromide led, in each case, to one product: N -aryl isothiocyanate and cyanothioformamide [ 59 , 60 ]. Treatment of 3-(1,2,3-dithiazolylidene)indololin-2-ones ( Scheme 3 , 3a – 3d ) by two equivalents of sodium hydride or methyl magnesium bromide in tetrahydrofuran led to the expected 2-mercapto-2-(2-oxoindolin-3-ylidene)acetonitrile derivatives ( Scheme 3 , 4a – 4d ) with modest to good yields (23–88%) ( Scheme 3 ; Table 2 and Table 3 ).…”

Section: Resultsmentioning

confidence: 99%

“…The stereochemistry of the products ( Table 4 , 6b – 6d ) was unambiguously determined using 1 H-NMR, and through comparison with data from the literature [ 60 , 61 ]. Osman et al previously reported the synthesis and the stereochemistry of 2-(2-oxoindolin-3-ylidene)acetonitrile isomers ( Table 4 , 6a ) via a Wittig reaction between an isatin and a phosphorus ylide [ 61 ].…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of 2-Mercapto-(2-Oxoindolin-3-Ylidene)Acetonitriles from 3-(4-Chloro-5H-1,2,3-Dithiazol-5-Ylidene)Indolin-2-ones

et al. 2018

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Alkylidene oxindoles are important functional moieties and building blocks in pharmaceutical and synthetic chemistry. Our interest in biologically active compounds focused our studies on the synthesis of novel oxindoles, bearing on the exocyclic double bond at the C8, CN, and S groups. Extending the potential applications of Appel’s salt, we developed a new synthetic approach by investigating the reactions of C5-substituted 2-oxindoles with 4,5-dichloro-1,2,3-dithiazolium chloride (Appel’s salt) to give original (Z)-3-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)indolin-2-one derivatives, and new 2-mercapto-(2-oxoindolin-3-ylidene)acetonitriles via a dithiazole ring-opening reaction. The work described in this article represents further applications of Appel’s salt in the conception of novel heterocyclic rings, in an effort to access original bioactive compounds. Fifteen new compounds were prepared and fully characterized.

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“…The synthesis and characterization of the carbamates C1–C4 has been reported previously 25 . The precursors for the synthesis of the carbamates, namely pre‐C5, 18 pre‐C6 26 and pre‐C7, 27 are known compounds and were prepared according to the methods detailed in previous publications. The carbamates C5–C7 were prepared from pre‐C5–C7 as detailed below.…”

Section: Methodsmentioning

confidence: 99%

Vasodilatory Activity of Novel Carbamate Derivatives of Isatin

Maronas

Sudo

Côrrea

et al. 2008

Clin Exp Pharma Physio

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Isatin (1H-indole-2,3 dione) is an endogenous compound that may act as a physiological regulator of muscle contraction by reducing cGMP production by inhibition of guanylyl cyclase (GC) activity. Intracellular cGMP levels can regulate the contractile response of smooth muscle. Therefore, in the present study we investigated the effects of seven novel carbamate derivatives of isatin, namely C1-C7, on the contractility of aortic rings from Wistar rats. Carbamates C1 and C6 most effectively promoted endothelium-dependent relaxation of aortic rings pretreated with 10 micromol/L phenylephrine (PE) to induce contraction. The concentration of the C1 and C6 carbamates necessary to reduce PE-induced aortic contraction by 50% (IC(50)) was 5.6 +/- 1.0 and 48.4 +/- 3.4 micromol/L, respectively. Carbamate derivative-induced vasodilation required an intact endothelium, which is responsible for nitric oxide (NO) release. Pretreatment of rings with 100 micromol/L naloxone or 10 micromol/L atropine prevented the C1- and C6-mediated vascular relaxation, indicating that the vasodilatory activity was dependent on the activation of opioid or muscarinic receptors, respectively. The results of our studies provide insights into the role of novel carbamates in the regulation of vascular tone. Carbamates could stimulate NO synthesis, which induces vasodilation primarily by stimulation of GC and cGMP production. Taken together, our findings suggest that carbamate derivative-induced vasodilation may be considered an alternative treatment for primary and/or secondary hypertension.

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The stereochemistry of 2‐oxoindolin‐3‐ylidene derivatives

Abstract: The stereochemistry of a number of functionally‐substituted 2‐oxoindolin‐3‐ylidene derivatives has been established by a study of pmr and ir spectroscopy. These compounds have been shown to exist as one isomer with the exception of the substituted acetonitriles.

Cited by 33 publications

References 29 publications

The chemistry of isatins: a review from 1975 to 1999

The chemistry of isatins: a review from 1975 to 1999

Synthesis of 2-Mercapto-(2-Oxoindolin-3-Ylidene)Acetonitriles from 3-(4-Chloro-5H-1,2,3-Dithiazol-5-Ylidene)Indolin-2-ones

Vasodilatory Activity of Novel Carbamate Derivatives of Isatin

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