ChemInform Abstract: SYNTHESIS OF SOME 1,5‐BENZODIAZEPINES. I

Kulkarni, Surendra U.; Thakar, K. A.

doi:10.1002/chin.197610210

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“…Purification was made by recrystallization from EtOH to give yellow crystals in a yield of 35%. Spectroscopic data were identical with those previously reported …”

Section: Methodssupporting

confidence: 70%

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Refinement and Evaluation of a Pharmacophore Model for Flavone Derivatives Binding to the Benzodiazepine Site of the GABA_A Receptor

et al. 2002

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To further develop and evaluate a pharmacophore model previously proposed by Cook and co-workers (Drug Des. Discovery 1995, 12, 193-248) for ligands binding to the benzodiazepine site of the GABA(A) receptor, 40 new flavone derivatives have been synthesized and their affinities for the benzodiazepine site have been determined. Two new regions of steric repulsive interactions between ligand and receptor have been characterized, and the receptor region in the vicinity of 6- and 3'-substituents has been mapped out. 2'-Hydroxy substitution is shown to give a significant increase in affinity, which is interpreted in terms of a novel hydrogen bond interaction with the previously proposed hydrogen bond-accepting site A2. On the basis of the results of these studies and the refined pharmacophore model, 5'-bromo-2'-hydroxy-6-methylflavone, the highest affinity flavone derivative reported so far (K(i) = 0.9 nM), was successfully designed. A comparison of the pharmacophore model with a recently proposed alternative model (Marder; et al. Bioorg. Med. Chem., 2001, 9, 323-335) has been made.

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“…Purification was made by recrystallization from EtOH to give yellow crystals in a yield of 35%. Spectroscopic data were identical with those previously reported …”

Section: Methodssupporting

confidence: 70%

“…Spectroscopic data were identical with those previously reported. 32 8-Methylflavone (6). The compound was prepared according to the procedure described for 3.…”

Section: Methodsmentioning

confidence: 99%

Refinement and Evaluation of a Pharmacophore Model for Flavone Derivatives Binding to the Benzodiazepine Site of the GABA_A Receptor

et al. 2002

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ChemInform Abstract: SYNTHESIS OF SOME 1,5‐BENZODIAZEPINES. I

Abstract: Die aus den entsprechenden Estern durch Baker‐Venkataraman‐Umlagerung zugänglichen 1,3‐Dione (I) geben bei der Kondensation mit o‐Phenylendiamin (II) die 1,5‐Benzodiazepine (III), die während oder nach einer Protonierung teilweise zu (IV) tautomerisieren.

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Refinement and Evaluation of a Pharmacophore Model for Flavone Derivatives Binding to the Benzodiazepine Site of the GABA_A Receptor

Refinement and Evaluation of a Pharmacophore Model for Flavone Derivatives Binding to the Benzodiazepine Site of the GABA_A Receptor

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ChemInform Abstract: SYNTHESIS OF SOME 1,5‐BENZODIAZEPINES. I

Abstract: Die aus den entsprechenden Estern durch Baker‐Venkataraman‐Umlagerung zugänglichen 1,3‐Dione (I) geben bei der Kondensation mit o‐Phenylendiamin (II) die 1,5‐Benzodiazepine (III), die während oder nach einer Protonierung teilweise zu (IV) tautomerisieren.

Cited by 1 publication

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Refinement and Evaluation of a Pharmacophore Model for Flavone Derivatives Binding to the Benzodiazepine Site of the GABAA Receptor

Refinement and Evaluation of a Pharmacophore Model for Flavone Derivatives Binding to the Benzodiazepine Site of the GABAA Receptor

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Refinement and Evaluation of a Pharmacophore Model for Flavone Derivatives Binding to the Benzodiazepine Site of the GABA_A Receptor

Refinement and Evaluation of a Pharmacophore Model for Flavone Derivatives Binding to the Benzodiazepine Site of the GABA_A Receptor