3-Benzo[b]furyl- and 3-benzo[b]thienylaminobutyric acids as GABAB ligands. Synthesis and structure-activity relationship studies

Ansar, Mohamed; Ebriki, S Al Akoum; Mouhoub, Rahima; Berthelot, Pascal; Vaccher, Claude; Vaccher, Marie‐Pierre; Flouquet, Nathalie; Caignard, D. H.; Renard, Pierre; Pirard, Bernard; Rettori, Marie-Claire; Evrard, G.; Durant, François; Debaert, M.

doi:10.1016/0223-5234(96)85165-8

Cited by 14 publications

(4 citation statements)

References 20 publications

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“…Compound 7a was synthesized from 2-methylphenol ( 2a ) following the representative procedure described as method A and obtained as a pale yellow solid in 9% yield (three steps): mp 58−59 °C; 1 H NMR (CDCl 3 ) δ 2.58 (s, 3H), 7.24 (t, J = 7.6 Hz, 1H), 7.32 (d, J = 7.6 Hz, 1H), 7.56 (s, 1H), 7.57 (d, J = 7.6 Hz, 1H), 9.88 (s, 1H). The proton NMR spectral data were identical with those reported …”

Section: Methodssupporting

confidence: 78%

“…The second method 17 of benzofuran synthesis involved the treatment of the salicylaldehyde 5 with bromoac-etaldehyde diethyl acetal in the presence of potassium carbonate to afford the diethyl acetal 6. Compound 6 was then cyclized with acetic acid to give the carbaldehyde 7 (method B).…”

Section: Chemistrymentioning

confidence: 99%

“…The proton NMR spectral data were identical with those reported. 17 4,7-Dichlorobenzofuran-2-carbaldehyde (7c). Compound 7c was synthesized from 2,5-dichlorophenol (2c) following the representative procedure described as method A and obtained as a pale yellow solid in 31% yield (three steps): mp 155-159 °C; 1 H NMR (CDCl3) δ 7.29 (d, J ) 8.4 Hz, 1H), 7.46 (d, J ) 8.4 Hz, 1H), 9.84 (s, 1H).…”

Section: -Fluoro-4-trifluoromethylbenzofuran-2-carbaldehyde (7f)mentioning

confidence: 99%

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Discovery of Novel and Potent Retinoic Acid Receptor α Agonists: Syntheses and Evaluation of Benzofuranyl-pyrrole and Benzothiophenyl-pyrrole Derivatives

et al. 2000

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In the course of our studies on retinoic acid receptor (RAR) agonists, we have designed and synthesized a series of benzofuran and benzothiophene derivatives. Some of these compounds (1a,b,e,f,j) markedly inhibited LPS-induced B-lymphocyte proliferation and exerted RARalpha selectivity. One of them, 4-[5-(4,7-dimethylbenzofuran-2-yl)pyrrol-2-yl]benzoic acid (1b), when orally administered significantly inhibited mouse antibody production and delayed type hypersensitivity (DTH) responses from a dose of 0.1 mg/kg.

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Section: Methodssupporting

confidence: 78%

Section: Chemistrymentioning

confidence: 99%

Section: -Fluoro-4-trifluoromethylbenzofuran-2-carbaldehyde (7f)mentioning

confidence: 99%

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Discovery of Novel and Potent Retinoic Acid Receptor α Agonists: Syntheses and Evaluation of Benzofuranyl-pyrrole and Benzothiophenyl-pyrrole Derivatives

et al. 2000

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“…General Procedure for the Formylation of Phenols I and III. 43 A solution of the appropriate phenol (4.09 mmol) in 2.5 mL of 10 N NaOH was heated to 65 °C. After that, 1 mL of CHCl 3 was slowly added to the mixture, which was then heated at reflux in chloroform for 2 h. After cooling, the mixture was acidified to pH 1 with concentrated HCl, the organic layer collected, and the aqueous phase extracted with CHCl 3 .…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Potent Nematicidal Activity of Phthalaldehyde, Salicylaldehyde, and Cinnamic Aldehyde against Meloidogyne incognita

Caboni

Aissani

Cabras

et al. 2013

J. Agric. Food Chem.

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The nematicidal activity of selected aromatic aldehydes was tested against the root knot nematode Meloidogyne incognita. The most active aldehyde was phthalaldehyde (1) with an EC(50) value of 11 ± 6 mg/L followed by salicylaldehyde (2) and cinnamic aldehyde (3) with EC(50) values of 11 ± 1 and 12 ± 5 mg/L, respectively. On the other hand, structurally related aldehydes such as 2-methoxybenzaldehyde (21), 3,4-dimethoxybenzaldehyde, and vanillin (23) were not active at the concentration of 1000 mg/L. By liquid chromatography-mass spectrometry the reactivity of tested aldehydes against a synthetic peptide resembling the nematode cuticle was characterized. At the test concentration of 1 mM, the main adduct formation was observed for 3,4-dihydroxybenzaldehyde (22), 2-methoxybenzaldehyde (21), and 3,4-dimethoxybenzaldehyde. Considering that 2-methoxybenzaldehyde (21) and 3,4-dimethoxybenzaldehyde were not active against M. incognita in in vitro experiments led us to hypothesize a different mechanism of action rather than an effect on the external cuticle modification of nematodes. When the toxicity of the V-ATPase inhibitor pyocyanin (10) was tested against M. incognita J2 nematodes, an EC(50) at 24 h of 72 ± 25 mg/L was found. The redox-active compounds such as phthalaldehyde (1) and salicylaldehyde (2) may share a common mode of action inhibiting nematode V-ATPase enzyme. The results of this investigation reveal that aromatic redox-active aldehydes can be considered as potent nematicides, and further investigation is needed to completely clarify their mode of action.

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Theoretical approach to the pharmacophoric pattern of GABAB analogs

Lorenzini

Bruno-Blanch

Estiú

1998

Int. J. Quant. Chem.

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ABSTRACT:In order to determine the structural requirements that are important for GABA binding affinity, a quantum-chemical-based conformational study has been B performed, followed by a similarity analysis which includes 12 GABA analogs. Due B w Ž . to the flexibility of the structures, a semigrid GABA analog 2RS-5,5-dimethyl B x morpholinyl-acetic acid has been used as a template for the amonium moiety in order to help to identify the active conformation. Both in vacuo, and solvent-simulated calculations, for the physiological media modeled as water molecules, have been compared, for this Ž Ž . . Ž . analog, at ab initio G94, 6-31 q G d,p and semiempirical PM3 levels, respectively. On the basis of this comparison, the results of in vacuo PM3 calculations have been chosen for the similarity analysis. We have included, in the calculations, a group of molecules heterogeneous enough to become representative of the different families that can bind to the GABA receptor site. Following their comparison we report the leading characteristics B that can be related to their binding capability and define a pharmacophoric pattern for GABA analogs. The latter is compared with the one previously found for the binding B affinity at the GABA receptor site.

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3-Benzo[b]furyl- and 3-benzo[b]thienylaminobutyric acids as GABAB ligands. Synthesis and structure-activity relationship studies

Cited by 14 publications

References 20 publications

Discovery of Novel and Potent Retinoic Acid Receptor α Agonists: Syntheses and Evaluation of Benzofuranyl-pyrrole and Benzothiophenyl-pyrrole Derivatives

Discovery of Novel and Potent Retinoic Acid Receptor α Agonists: Syntheses and Evaluation of Benzofuranyl-pyrrole and Benzothiophenyl-pyrrole Derivatives

Potent Nematicidal Activity of Phthalaldehyde, Salicylaldehyde, and Cinnamic Aldehyde against Meloidogyne incognita

Theoretical approach to the pharmacophoric pattern of GABAB analogs

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