(R)-(+)-1-(2-METHOXYBENZOYL)-2- - CAS 207511-15-7
Category:
Main Product
Product Name:
(R)-(+)-1-(2-METHOXYBENZOYL)-2-
Catalog Number:
207511-15-7
Synonyms:
(R)-(+)-1-(2-Methoxybenzoyl)-2-pyrrolidinemethanol; 207511-15-7; AC1LELFC; AC1Q4EBT; AC1Q4EBU; 345598_ALDRICH
CAS Number:
207511-15-7
Molecular Weight:
235.281
Molecular Formula:
C13H17NO3
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
COC1=CC=CC=C1C(=O)N2CCCC2CO
InChI:
InChI=1S/C13H17NO3/c1-17-12-7-3-2-6-11(12)13(16)14-8-4-5-10(14)9-15/h2-3,6-7,10,15H,4-5,8-9H2,1H3/t10-/m1/s1
InChIKey:
ZPRSXRGRMZPZQY-SNVBAGLBSA-N
Chemical Structure
CAS 207511-15-7 (R)-(+)-1-(2-METHOXYBENZOYL)-2-

Reference Reading


1.Synthesis and structure-activity relationships of 4-amino-5-chloro-N-(1,4-dialkylhexahydro-1,4-diazepin-6-yl)-2-methoxybenzamide derivatives, novel and potent serotonin 5-HT3 and dopamine D2 receptors dual antagonist.
Hirokawa Y1, Harada H, Yoshikawa T, Yoshida N, Kato S. Chem Pharm Bull (Tokyo). 2002 Jul;50(7):941-59.
In search of a dopamine D2 and serotonin 5-HT3 receptors dual antagonist as a potential broad antiemetic agent, a number of benzamides were prepared from 4-amino-5-chloro-2-methoxybenzoic acid derivatives and 6-amino-1,4-dialkylhexahydro-1,4-diazepines and evaluated for their binding affinity for the dopamine D2 and the serotonin 5-HT3 receptors using rat brain synaptic and rat cortical membranes, respectively. From the results of both in vitro receptor binding and in vivo biological assays for the dopamine D2 receptor, 1-ethyl-4-methylhexahydro-1,4-diazepine ring was selected as an optimum amine moiety. Introduction of one methyl group on the nitrogen atom at the 4-position and/or modification of the substituent at the 5-position of the 4-amino-5-chloro-2-methoxybenzoyl moiety caused a marked increase in the dopamine D2 receptor binding affinity along with a potent 5-HT3 receptor binding affinity. Among the compounds, 5-chloro-N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)-2-methoxy-4-methylaminobenzamide (82), 5-bromo (110), and 5-iodo (112) analogues exhibited a much higher affinity for the dopamine D2 receptor than that of metoclopramide (IC50=17.
2.Radioimmunoassay for the novel platelet activating factor receptor antagonist E5880.
Suzuki H1, Asano O, Tadano K, Horie T. J Pharm Sci. 1994 May;83(5):657-61.
A direct radioimmunoassay for E5880, 1-ethyl-2-[[N-(2-methoxybenzoyl)-N-[[(2R)-2-methoxy-3-[[[4- [(octadecylcarbamoyl)- oxy]piperidino]carbonyl]oxy]propoxy]carbonyl]amino]methyl] pyridinium chloride, a novel analogue-type antagonist of platelet activating factor (PAF), was developed. In this procedure, [3H]E5880 was used as the radioligand, and the antiserum was obtained from rabbits immunized with hapten covalently bound to bovine serum albumin. The hapten represents a structural analogue of E5880, with a carboxyl group on the terminal carbon of the 3-position side chain. A metabolite of E5880, deacyl-E5880, cross-reacted weakly (1.8%) with this antiserum. The assay buffer for the radioimmunoassay consisted of PBS, pH 6.5, containing 1% BSA to prevent the degradation of E5880 in aqueous solution and its adsorption to the tube. The detection limit of the assay was 200 pg/mL when a 0.1-mL plasma sample was used. The radioimmunoassay was used for the direct analysis of E5880 in dog plasma.
3.Role of orexin-1 receptor mechanisms on compulsive food consumption in a model of binge eating in female rats.
Piccoli L1, Micioni Di Bonaventura MV, Cifani C, Costantini VJ, Massagrande M, Montanari D, Martinelli P, Antolini M, Ciccocioppo R, Massi M, Merlo-Pich E, Di Fabio R, Corsi M. Neuropsychopharmacology. 2012 Aug;37(9):1999-2011. doi: 10.1038/npp.2012.48. Epub 2012 May 9.
Orexins (OX) and their receptors (OXR) modulate feeding, arousal, stress, and drug abuse. Neural systems that motivate and reinforce drug abuse may also underlie compulsive food seeking and intake. Therefore, the effects of GSK1059865 (5-bromo-N-[(2S,5S)-1-(3-fluoro-2-methoxybenzoyl)-5-methylpiperidin-2-yl]methyl-pyridin-2-amine), a selective OX(1)R antagonist, JNJ-10397049 (N-(2,4-dibromophenyl)-N'-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]urea), a selective OX(2)R antagonist, and SB-649868 (N-[((2S)-1-{[5-(4-fluorophenyl)-2-methyl-1,3-thiazol-4-yl]carbonyl}-2-piperidinyl)methyl]-1-benzofuran-4-carboxamide), a dual OX(1)/OX(2)R antagonist were evaluated in a binge eating (BE) model in female rats. BE of highly palatable food (HPF) was evoked by three cycles of food restriction followed by stress, elicited by exposing rats to HPF, but preventing them from having access to it for 15 min. Pharmacokinetic assessments of all compounds were obtained under the same experimental conditions used for the behavioral experiments.