183180-67-8

Basic information

• Product Name: (R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl]-1H-indole
• CAS NO: 183180-67-8
• Molecular Weight: 348.401
• Mol File: 183180-67-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl]-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl]-1H-indole(183180-67-8)
• EPA Substance Registry System: (R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl]-1H-indole(183180-67-8)

Safety Data

• Hazardous Substances Data: 183180-67-8(Hazardous Substances Data)

Upstream product

• 120-72-9 indole 
• 61350-62-7 N-benzyloxycarbonyl-D-proline acid chloride 

Downstream Products

• 244122-44-9 (R)-1-(4-Fluorophenylsulfonyl)-3-(1-methyl-2-pyrrolidinylmethyl)indole 
• 244122-49-4 (R)-1-(4-Methoxybenzoyl)-3-(1-methyl-2-pyrrolidinylmethyl)indole 
• 244122-50-7 (R)-1-(4-Fluorobenzoyl)-3-(1-methyl-2-pyrrolidinylmethyl)indole 
• 244122-48-3 (R)-1-Benzoyl-3-(1-methyl-2-pyrrolidinylmethyl)indole 
• 881833-41-6 2-(1-benzenesulfonyl-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 143322-55-8 (R)-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indole 
• 143321-81-7 (R)-3-(N-Benzyloxycarbonylpyrrolidin-2-ylmethyl)-1H-indole 

Relevant articles and documents

Conformationally constrained N1-arylsulfonyltryptamine derivatives as 5-HT6 receptor antagonists

Several series of conformationally constrained N1- arylsulfonyltryptamine derivatives were prepared and tested for 5-HT6 receptor binding affinity and ability to modulate cAMP production in a cyclase assay. The 3-piperidin-3-yl-, 3-(1-methylpyrrolidin-2-ylmethyl)-, and 3-pyrrolidin-3-yl-1H-indole arrays (8-13) appear to be able to adopt a conformation that allows high affinity 5-HT6 receptor binding, while the β-carboline array 14 binds with a significantly weaker (10- to 100-fold) affinity. N1-Benzenesulfonyl-3-piperidin-3-yl-1H-indole 9a is a high affinity full agonist with EC50 = 24 nM. Several of the N1-arylsulfonyl-3-(1-methylpyrrolidin-2-ylmethyl)-1H-indole derivatives behave as very potent antagonists ((S)-11r, (S)-11t; IC50 = 0.8, 1.0 nM).

Pyrrolidine-indole compounds having 5-HT6 affinity

Described herein are compounds with affinity for the 5-HT 6 receptor, which have the general formula: STR1 wherein: R 1 is selected from the group consisting of H and C 1-4 alkyl;R 2 is selected from the group consisting of H, C 1-4 alkyl and benzyl;R 3 is selected from the group consisting of COR 5, SO 2 R 5, CONHC 1-4 alkyl and C(S)SR 6 ;R 4a is selected from the group consisting of H, OH, halo, C 1-4 alkyl and C 1-4 alkoxy;R 4b is selected from the group consisting of H, hydroxy, halo, C 3-7 cycloalkyloxy, C 1-4 alkoxy, C 1-4 alkyl, benzyloxy, phenoxy, trifluoromethyl, trifluoromethoxy and vinyl;R 4c is selected from the group consisting of H, OH, halo, C 1-4 alkyl and C 1-4 alkoxy;R 4d is selected from the group consisting of H, OH, halo, C 1-4 alkyl and C 1-4 alkoxy;R 5 is selected from the group consisting of phenyl, pyridyl, thienyl, quinolinyl and naphthyl which are optionally substituted with 1-4 substituents selected from C 1-4 alkoxy, C 1-4 alkyl, halo, nitro, trifluoromethyl, trifluoromethoxy, 1,2-methylenedioxy, C 1-4 alkylcarbonyl, C 1-4 alkoxycarbonyl and C 1-4 alkylS--; andR 6 is selected from C 1-4 alkyl, allyl, propargyl and optionally substituted benzyl wherein the benzyl group is optionally substituted with 1-4 substituents selected from cyano, C 1-4 alkyl and halo.Also described is the use of these compounds as pharmaceuticals to treat indications where inhibition of the 5-HT 6 receptor is implicated, such as schizophrenia.