(-)-(S)-5-BROMO-2,3-DIMETHOXY-N-[(1-ETHYL-2-PYRROLIDINYL)METHYL]-BENZAMIDE - CAS 107188-74-9
Category:
Main Product
Product Name:
(-)-(S)-5-BROMO-2,3-DIMETHOXY-N-[(1-ETHYL-2-PYRROLIDINYL)METHYL]-BENZAMIDE
Catalog Number:
107188-74-9
Synonyms:
ISOREMOXIPRIDE; BENZAMIDE, 5-BROMO-2,3-DIMETHOXY-N-[(1-ETHYL-2-PYRROLIDINYL)METHYL]-, (S)-; BENZAMIDE, 5-BROMO-N-[[(2S)-1-ETHYL-2-PYRROLIDINYL]METHYL]-2,3-DIMETHOXY-; FLB 457; (-)-(S)-5-BROMO-2,3-DIMETHOXY-N-[(1-ETHYL-2-PYRROLIDINYL)METHYL]-BENZAMIDE; 5-Bromo
CAS Number:
107188-74-9
Molecular Weight:
371.27
Molecular Formula:
C16H23BrN2O3
Quantity:
Data not available, please inquire.
COA:
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MSDS:
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Canonical SMILES:
CCN1CCCC1CNC(=O)C2=CC(=CC(=C2OC)OC)Br
InChI:
InChI=1S/C16H23BrN2O3/c1-4-19-7-5-6-12(19)10-18-16(20)13-8-11(17)9-14(21-2)15(13)22-3/h8-9,12H,4-7,10H2,1-3H3,(H,18,20)/t12-/m0/s1
InChIKey:
QAECXZXKVURFMR-LBPRGKRZSA-N
Chemical Structure
CAS 107188-74-9 (-)-(S)-5-BROMO-2,3-DIMETHOXY-N-[(1-ETHYL-2-PYRROLIDINYL)METHYL]-BENZAMIDE

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Reference Reading


1.Potential antipsychotic agents. 7. Synthesis and antidopaminergic properties of the atypical highly potent (S)-5-bromo-2,3-dimethoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]benzamide and related compounds. A comparative study.
Högberg T1, de Paulis T, Johansson L, Kumar Y, Hall H, Ogren SO. J Med Chem. 1990 Aug;33(8):2305-9.
(S)-5-Bromo-2,3-dimethoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]benzamide (6) and some related compounds, i.e. the R isomer 7, the 3-hydroxy analogue 8, the desbromo derivative 9, the monomethoxy compound 10, and the 2,4-dimethoxy analogue 11, have been synthesized from the corresponding benzoic acids. The benzamides, lacking o-hydroxy groups, were evaluated for their affinity for the [3H]spiperone binding site and for their inhibition of apomorphine-induced behavioral responses in relation to the effect of the corresponding salicylamides. Besides the 2-hydroxy-3-methoxybenzamide 12 and the related 1,4-benzodioxane (13) and 2,3-dihydrobenzofuran (14), carboxamides were investigated in order to evaluate the stereoelectronic requirements on the 2-methoxy group for the receptor interaction. The study supports the view that the o-methoxy group may adopt coplanar, as well as perpendicular orientations, and maintain the intramolecular hydrogen bonding required in the bioactive conformation.