Synthesis of Coumarins (2-Oxo-2<i>H</i>-1-benzopyrans), Thiacoumarins (2-Oxo-2<i>H</i>-1-benzothiopyrans), and Carbostyrils (2-Oxo-1,2-dihydroquinolines)

Manimaran, T.; Thiruvengadam, T. K.; Ramakrishnan, V. T.

doi:10.1055/s-1975-23918

Cited by 29 publications

(7 citation statements)

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“…6- and 7-Substituted 2-aminoquinolines were prepared by methods originally reported by Manimaran et al 37 and Johnson et al 38 In the present study, 7-substituted aminoquinolines ( 5 – 9 and 14 – 16 ) were prepared by a versatile, late-divergent route that began with the preparation of 3′-methylcinnamanilide ( 17 ) by literature procedures. 39 , 40 Compound 17 was subsequently treated with an excess of aluminum chloride in chlorobenzene to affect cyclization and concomitant cleavage of the C-aryl bond to yield the carbostyril 18 as a mixture of the 7-isomer 18a (major) and 5-isomer 18b (minor).…”

Section: Chemistrymentioning

confidence: 96%

Simplified 2-Aminoquinoline-Based Scaffold for Potent and Selective Neuronal Nitric Oxide Synthase Inhibition

Cinelli

Chreifi

et al. 2014

J. Med. Chem.

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Since high levels of nitric oxide (NO) are implicated in neurodegenerative disorders, inhibition of the neuronal isoform of nitric oxide synthase (nNOS) and reduction of NO levels are therapeutically desirable. Nonetheless, many nNOS inhibitors mimic l-arginine and are poorly bioavailable. 2-Aminoquinoline-based scaffolds were designed with the hope that they could (a) mimic aminopyridines as potent, isoform-selective arginine isosteres and (b) possess chemical properties more conducive to oral bioavailability and CNS penetration. A series of these compounds was synthesized and assayed against purified nNOS enzymes, endothelial NOS (eNOS), and inducible NOS (iNOS). Several compounds built on a 7-substituted 2-aminoquinoline core are potent and isoform-selective; X-ray crystallography indicates that aminoquinolines exert inhibitory effects by mimicking substrate interactions with the conserved active site glutamate residue. The most potent and selective compounds, 7 and 15, were tested in a Caco-2 assay and showed good permeability and low efflux, suggesting high potential for oral bioavailability.

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Section: Chemistrymentioning

confidence: 96%

Simplified 2-Aminoquinoline-Based Scaffold for Potent and Selective Neuronal Nitric Oxide Synthase Inhibition

Cinelli

Chreifi

et al. 2014

J. Med. Chem.

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“…have been employed. [111][112][113][114][115][116][117][118] Synthetic methods for the preparation of dihydrocoumarins from phenols and various Michael acceptors via route C are summarized in Table 2. The condensation of phenols with cinnamic acid to give 4-aryl-3,4-dihydrocoumarins using sulfuric acid in acetic acid was first demonstrated by Liebermann and Hartmann.…”

Section: Scheme 39mentioning

confidence: 99%

Syntheses and Biological Activities of Chroman-2-ones. A Review

Kamat

Tilve

Kamat

et al. 2015

Organic Preparations and Procedures International

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“…(12). Prepared in analogy to the cyclization procedure described in [18]: To an ice-cooled suspension of 11 (368 mg, 1 mmol) in 1,2-dichlorobenzene (20 ml) was added in small portions AlCl 3 (3.0 g, 22.5 mmol). The mixture was heated at 1508 for 3 h and was poured after cooling into ice-water (100 ml).…”

Section: Experimental Partmentioning

confidence: 99%

Site Selectivity in [2+2] Photocycloadditions of Tricyclic ‘Diethenylbenzenes' to 2,3-Dimethylbut-2-ene

Bethke

Margaretha

2002

HCA

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Upon irradiation at wavelengths above 390 nm in the presence of 2,3-dimethylbut-2-ene, both the newly synthesized pyranoquinolinedione 8 and thiinobenzopyrandione 9 selectively afford one of two possible photocycloadducts, 23 and 24, respectively.Introduction. ± Crosslinking of thymine units within helical DNA strands can be achieved, for instance, by light-induced reactions of psoralens (2H-furo[3,2-g]benzopyran-2-ones), such as 1, via two consecutive [2 2] photocycloadditions, the first one occuring at the furan double bond [1]. In contrast, photocycloadditions in solution of both linear (1) [2] and angular tricycles (2 and 3) [3] to alkenes selectively occur at the double bond of the six-membered heterocycle. This difference in selectivity has been attributed to the observation that the photocycloaddition to a nucleic acid is preceded by intercalation of a psoralen, the smaller furan moiety fitting into the helix [1] (Scheme 1).

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Synthesis of Coumarins (2-Oxo-2H-1-benzopyrans), Thiacoumarins (2-Oxo-2H-1-benzothiopyrans), and Carbostyrils (2-Oxo-1,2-dihydroquinolines)

Cited by 29 publications

References 0 publications

Simplified 2-Aminoquinoline-Based Scaffold for Potent and Selective Neuronal Nitric Oxide Synthase Inhibition

Simplified 2-Aminoquinoline-Based Scaffold for Potent and Selective Neuronal Nitric Oxide Synthase Inhibition

Syntheses and Biological Activities of Chroman-2-ones. A Review

Site Selectivity in [2+2] Photocycloadditions of Tricyclic ‘Diethenylbenzenes' to 2,3-Dimethylbut-2-ene

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