93835-05-3Relevant articles and documents
Synthesis of aza and carbocyclic β-carbolines for the treatment of alcohol abuse. Regiospecific solution to the problem of 3,6-disubstituted β- And aza-β-carboline specificity
Phani Babu Tiruveedhula,Methuku, Kashi Reddy,Deschamps, Jeffrey R.,Cook, James M.
, p. 10705 - 10715 (2015/11/17)
A novel two step protocol was developed to gain regiospecific access to 3-substituted β- and aza-β-carbolines, 3-PBC (1), 3-ISOPBC (2), βCCt (3), 6-aza-3-PBC (4) and 6-aza-3-ISOPBC (5). These β-carbolines (1-3) are potential clinical agents to reduce alco
Development of a two-step route to 3-PBC and βcCt, two agents active against alcohol self-administration in rodent and primate models
Namjoshi, Ojas A.,Gryboski, Angelica,Fonseca, German O.,Van Linn, Michael L.,Wang, Zhi-Jian,Deschamps, Jeffrey R.,Cook, James M.
experimental part, p. 4721 - 4727 (2011/07/08)
To gain access to 3-propoxy-β-carboline hydrochloride (3-PBC·HCl) (1·HCl) and β-carboline-3-carboxylate-tert-butyl ester (βCCt) (2), potential clinical agents active against alcohol self-administration, a two-step route was developed. This process involve
Design, synthesis, and subtype selectivity of 3,6-disubstituted β-carbolines at Bz/GABA(A)ergic receptors. SAR and studies directed toward agents for treatment of alcohol abuse
Yin, Wenyuan,Majumder, Samarpan,Clayton, Terry,Petrou, Steven,Vanlinn, Michael L.,Namjoshi, Ojas A.,Ma, Chunrong,Cromer, Brett A.,Roth, Bryan L.,Platt, Donna M.,Cook, James M.
experimental part, p. 7548 - 7564 (2011/01/04)
A series of 3,6-disubstituted β-carbolines was synthesized and evaluated for their in vitro affinities at αxβ 3γ2 GABAA/benzodiazepine receptor subtypes by radioligand binding assays in search of α1 s
Synthesis of bivalent ligands of β-carboline-3-carboxylates via a palladium-catalyzed homocoupling process
Yin, Wenyuan,Sarma, P. V. V. Srirama,Ma, Jun,Han, Dongmei,Chen, Jessica L.,Cook, James M.
, p. 6363 - 6368 (2007/10/03)
The first synthesis of bivalent ligands of β-carboline-3-carboxylates has been achieved from β-carboline-3-carboxylate tert-butyl ester (βCCt) via Sonogashira and palladium-catalyzed homocoupling processes. The Boc protected intermediate, an iodo-β-carboline-3-carboxylate, was employed to provide a general entry into a series of bivalent ligands structurally similar to βCCt.
Bz1 Receptor Subtype Specific Ligands. Synthesis and Biological Properties of BCCt, a Bz1 Receptor Subtype Specific Antagonist
Cox, Eric D.,Hagen, Timothy J.,Mckernan, Ruth M.,Cook, James M.
, p. 710 - 718 (2007/10/03)
Receptor subtype selectivity studies at five major GABAA/BzR subtypes of some selected β-carbolines are reported. In addition, receptor subtype selectivity has been correlated to the in vivo biological profiles of these ligands. The antagonist βCCt 4 is the most Bz1 selective ligand reported to date. In comparison to the agonist zolpidem and the antagonist flumazenil, βCCt is 3.5 and 20 fold more selective, respectively, at Bz1 sites. βCCt has been shown to selectively antagonize the effects of diazepam on punished behavior as well as the anticonvulsant effects, while it failed to antagonize the rate-decreasing muscle-relaxant, ataxic, and sedative effects of this benzodiazepine. The unique biological activity of βCCt combined with its Bz1 subtype selectivity distinguishes it from the antagonist flumazenil (Ro15-1788), Consequently this ligand may be an important tool in identifying Bz1 receptor subtypes in vivo. In addition, an improved synthesis of this 3-substituted β-carboline is described.
SYNTHESIS OF 3,6-DISUBSTITUTED &β-CARBOLINES WHICH POSSESS EITHER BENZODIAZEPINE ANTAGONIST OR AGONIST ACTIVITY
Hagen, Timothy J.,Guzman, Filadelfo,Schultz, Christopher,Cook, James M.,Skolnick, Phil,Shannon, Harlan E.
, p. 2845 - 2855 (2007/10/02)
A series of 3-substituted and 3,6-disubstituted β-carbolines have been synthesized.These compounds have been screened in vitro in order to determine the size of substituents which benzodiazepine receptors will tolerate at positions -3 and -6 of the β-carboline nucleus.It has been found that the receptor will tolerate ester alkyl groups at position-3 as large as cyclohexyl 1g but not as large as adamantyl 5d.Moreover, N-aryl substituents as large as naphthobenzylamino 8b can be introduced at position-6 without significant loss of receptor binding affinity.
