96136-57-1

Basic information

• Product Name: 1H-Pyrido[3,4-b]indole-3-carboxylic acid, 2,3,4,9-tetrahydro-4-(methoxymethyl)-6-(phenylmethoxy)-, ethyl ester
• CAS NO: 96136-57-1
• Molecular Formula: C23H26N2O4
• Molecular Weight: 394.47
• Mol File: 96136-57-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1H-Pyrido[3,4-b]indole-3-carboxylic acid, 2,3,4,9-tetrahydro-4-(methoxymethyl)-6-(phenylmethoxy)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrido[3,4-b]indole-3-carboxylic acid, 2,3,4,9-tetrahydro-4-(methoxymethyl)-6-(phenylmethoxy)-, ethyl ester(96136-57-1)
• EPA Substance Registry System: 1H-Pyrido[3,4-b]indole-3-carboxylic acid, 2,3,4,9-tetrahydro-4-(methoxymethyl)-6-(phenylmethoxy)-, ethyl ester(96136-57-1)

Safety Data

• Hazardous Substances Data: 96136-57-1(Hazardous Substances Data)

Upstream product

• 210160-48-8 3-[5-(benzyloxy)indole-3-yl]-4-methoxy-2-nitrobutanoic acid ethyl ester 
• 169525-70-6 2-amino-3-[5-(benzyloxy)indole-3-yl]-4-methoxybutanoic acid ethyl ester 
• 1215-59-4 5-benzyloxy-1H-indole 
• 210160-59-1 6-Benzyloxy-4-methoxymethyl-2,3,4,9-tetrahydro-1H-β-carboline-1,3-dicarboxylic acid 3-ethyl ester 

Downstream Products

• 147742-37-8 6-benzyloxy-4-methoxymethyl-β-carboline-3-carboxylic acid-hydrazide 
• 210160-77-3 6-Benzyloxy-3-isothiocyanato-4-methoxymethyl-9H-β-carboline 
• 124563-47-9 6-Benzyloxy-4-methoxymethyl-9-methyl-9H-β-carboline-3-carboxylic acid ethyl ester 
• 83910-44-5 3-carboethoxy-4-methoxymethyl-6-benzyloxy-β-carboline 

Relevant articles and documents

Synthesis and evaluation of analogues of the partial agonist 6- (propyloxy)-4-(methoxymethyl)-β-carboline-3-carboxylic acid ethyl ester (6- PBC) and the full agonist 6-(benzyloxy)-4-(methoxymethyl)-β-carboline-3- carboxylic acid ethyl ester (Zk 93423) at wild type and recombinant GABA(A) receptors

A pharmacophore and an alignment rule have previously been reported for BzR agonist ligands. The design and synthesis of 6-(propyloxy)-4- (methoxymethyl)-β-carboline-3-carboxylic acid ethyl ester (6-PBC, 24, IC50 = 8.1 nM) was based on this pharmacophore. When evaluated in vivo this ligand exhibited anticonvulsant/anxiolytic activity but was devoid of the muscle relaxant/ataxic effects of 'classical' 1,4-benzodiazepines (i.e., diazepam). Significantly, 6-PBC 24 also reversed diazepam-induced muscle relaxation in mice. The 3-substituted analogues 40-46 and 48 of 6-PBC 24 and Zk 93423 27 (IC50 = 1 nM) were synthesized and evaluated in vitro to determine what affect these modifications would have on the binding affinity at recombinant BzR subtypes. With the exception of the 3-amino ligands 40 and 41, all the β-carbolines were found to exhibit high binding affinity at BzR sites. The 3-propyl ether derivative 45 was also evaluated in vivo and found to be devoid of any proconvulsant or anticonvulsant activity at doses up to 40 mg/kg. The 6-(1-naphthylmethylexy) and 6-octyloxy analogues 25, 26, 28, and 29 of 6-PBC 24 were synthesized to further evaluate the proposed alignment of agonists vs inverse agonists in the pharmacophore of the BzR. In addition, ligands 26 and 29 were designed to probe the dimensions of lipophilic pocket L3 at the agonist site. The activity of 29 was evaluated in vivo; however, this analogue elicited no pharmacological effects at doses up to 80 mg/kg. These and other related β-carbolines were also examined in five recombinant GABA(A) receptor subtypes. Ligands 52-61 all exhibited moderate to high affinity at GABA(A) receptors containing α1 subunits. These ligands will be useful in further defining the pharmacophore at α1β3γ2 receptors.