Novel synthesis of [1]-benzothiepino[5,4-b]pyridine-3-carbonitriles and their anti-inflammatory properties

Girgis, Adel S.; Mishriky, N.; Ellithey, Mohey; Hosni, Hanaa M.; Farag, Hanaa

doi:10.1016/j.bmc.2007.01.015

Cited by 42 publications

(21 citation statements)

References 33 publications

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“…Cyanothioacetamide has found use for the annelation of heterocycles, which can be regarded as a method for "making up" the 3-cyano-2-thioxopyridine ring to structures containing vicinal amino and cyano groups [32,33], or an activated double bond [34,35]. As a result of the transformations triethylammonium 1-cyano-4,5-dioxo-3,4,5,6-tetrahydro[1]benzopyrano [3,4-c]pyridine-2-thiolates 37 [34], 6,7-dihydrothieno[2,3-b]pyridines 38 [33] and 39 [32], and 4-aryl-3-cyano-5,6-dihydro-1-benzothiepino [5,4-b]pyridine-2(1H)-thiones 40 [35] Recyclization as a Method for the Synthesis of Derivatives of 3-cyanopyridine-2-thione.…”

Section: Annelation Of Heterocycles By Cyanothioacetamidementioning

confidence: 99%

“…As a result of the transformations triethylammonium 1-cyano-4,5-dioxo-3,4,5,6-tetrahydro[1]benzopyrano [3,4-c]pyridine-2-thiolates 37 [34], 6,7-dihydrothieno[2,3-b]pyridines 38 [33] and 39 [32], and 4-aryl-3-cyano-5,6-dihydro-1-benzothiepino [5,4-b]pyridine-2(1H)-thiones 40 [35] Recyclization as a Method for the Synthesis of Derivatives of 3-cyanopyridine-2-thione. The cycloacylation of cyanothioacetamide 1 with diketene can be regarded formally as recyclization.…”

Section: Annelation Of Heterocycles By Cyanothioacetamidementioning

confidence: 99%

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Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

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Data from the last six years on the heterocyclization of thioamides containing an active methylene group are analyzed and classified.At the present time there has been a considerable increase in the number of publications on the chemistry of thioamides, and this is explained by the value of the compounds as initial reagents for further transformations and particularly for the synthesis of various sulfur-and nitrogen-containing heterocycles [1][2][3][4][5][6][7][8]. The enormous practical significant of the latter is common knowledge -they have found application as drugs, pesticides, dyes, and preservatives.Thioamides with an active methylene group are attractive synthesis units for the production of heterocycles. These polyfunctional compounds can be represented by the formula R 3 -CH 2 CS-NR 1 R 2 (where R 1 , R 2 = H, Alk, Ar; R 3 is an electron-withdrawing group such as CN, AlkCO, ArCO, (AlkO) 2 PO, AlkSO 2 , ArSO 2 , NO 2 ). The presence of another reaction center (the methylene group) makes it possible to use them as N-С-С and S-C-C components for various condensations [1][2][3][4][5][6][7][8]. A special feature of such substrates is the ability to react both with dinucleophilic and with dielectrophilic and dipolar reagents. As a rule the products of these heterocyclizations contain functional groups, which makes it possible to achieve their modification or annelation. Such characteristics of thioamides with an active methylene group substantially increase their synthetic potential and extend the range of accessible heterosystems, while the use of modern physical methods of investigation (X-ray crystallographic analysis and 1D and 2D NMR spectroscopy) makes it possible to establish the structure of the obtained compounds unambiguously. The presence of biological activity in the products of these transformations also attracts investigators to this subject [5][6][7][8].The reason for the appearance of this review was the increasing need for generalization and classification of new information on the heterocyclization of such thioamides that had not been included in previous reviews [2][3][4][5] and also to define the trends in the study of these processes. Since one of the most important reports in this field is the review [1] we undertook an analysis of the literature that has appeared in the last six years.

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Section: Annelation Of Heterocycles By Cyanothioacetamidementioning

confidence: 99%

Section: Annelation Of Heterocycles By Cyanothioacetamidementioning

confidence: 99%

Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

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“…Anti-inflammatory activity of the synthesized compounds 2a-f,h; 3a-d (at a dose of 50 mg/kg of body weight) was determined in vivo by the acute carrageenan-induced paw oedema standard method in rats [14][15][16][17]. The anti-inflammatory properties were recorded after 4 h of inflammation induction and compared with that of indomethacin (at a dose of 10 mg/kg of body weight) which was used as a reference standard.…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%

Facile synthesis of bis(4,5-dihydro-1H-pyrazole-1-carboxamides) and their thio-analogues of potential PGE2 inhibitory properties

Barsoum

Girgis

2009

European Journal of Medicinal Chemistry

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“…A cyano group bonded to 3-position of pyridine ring of benzothiepinopyridine derivatives was found to be an anticancer as well as an anti-HIV active agent [12]. A methoxy group at the 2-position of benzothiepinopyridine-3-carbonitrile improved total observed pharmacological properties [13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel substituted pyridine derivatives from 3,5‐diacetyl‐2,6‐dimethylpyridine

Zhang

Cao

et al. 2009

Heteroatom Chemistry

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A series of novel (1‐acetyl‐5‐aryl‐4,5‐dihydro)‐1H‐pyrazole substituted pyridine derivatives and poly substituted [2,3′‐bipyridine]‐5‐carbonitrile derivatives were synthesized from 3,5‐diacetyl‐2,6‐dimethylpyridine. The structures of two typical 3,5‐bis[1‐acetyl‐5‐(4‐chlorophenyl)‐4,5‐dihydro‐1H‐pyrazol‐3‐yl]‐2,6‐dimethylpyridines [3b(1) and 3b(2)] were confirmed by X‐ray diffraction analysis. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:123–130, 2009; Published online in Wiley InterScience (http://www.interscience.wiley.com). DOI 10.1002/hc.20522

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Novel synthesis of [1]-benzothiepino[5,4-b]pyridine-3-carbonitriles and their anti-inflammatory properties

Cited by 42 publications

References 33 publications

Heterocyclization of thioamides containing an active methylene group (review)

Heterocyclization of thioamides containing an active methylene group (review)

Facile synthesis of bis(4,5-dihydro-1H-pyrazole-1-carboxamides) and their thio-analogues of potential PGE2 inhibitory properties

Synthesis of novel substituted pyridine derivatives from 3,5‐diacetyl‐2,6‐dimethylpyridine

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