beta-Carboline, 1,2,3,4-tetrahydro-1-carboxy-6-methoxy-1-methyl- | 29573-11-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: beta-Carboline, 1,2,3,4-tetrahydro-1-carboxy-6-methoxy-1-methyl-
• 英文别名: 6-methoxy-1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-1-carboxylic acid
• CAS: 29573-11-3
• 化学式: C₁₄H₁₆N₂O₃
• 分子量: 260.293
• InChiKey: BETCVGLWCYMGME-UHFFFAOYSA-N

物化性质

• 沸点：
  503.7±50.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  beta-Carboline, 1,2,3,4-tetrahydro-1-carboxy-6-methoxy-1-methyl- 在 palladium on activated charcoal 盐酸 、 异丙苯 、 氢溴酸 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,9-dimethyl-9H-pyrido[3,4-b]indol-6-ol
  参考文献：
  名称：

  6-Hydroxy- and 6-methoxy-β-carbolines as acetyl- and butyrylcholinesterase inhibitors

  摘要：

  In the course of studies directed toward the discovery of novel acetyl- and butyrylcholinesterase (AChE and BChE) inhibitors for the treatment of Alzheimer's disease, we focused on beta-carbolines (BCs). 6-Oxygenated P-carboline and P-carbolinium derivatives based on the serotonin template were synthesized and tested in vitro for their ability to inhibit AChE and BChE, respectively. Particularly the carbolinium salts, which can be formed by intracerebral methylation out of the tertiary-BC prodrugs, show inhibitory activity levels reaching those of galantamine, physostigmine, and rivastigmine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.067
• 作为产物：
  描述：

  5-甲氧基色胺 、 丙酮酸 以 甲醇 、 水 为溶剂， 生成 beta-Carboline, 1,2,3,4-tetrahydro-1-carboxy-6-methoxy-1-methyl-
  参考文献：
  名称：

  Novel tetrahydro-β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)

  摘要：

  A structure-activity relationship study was conducted on a series of tetrahydro-beta-carboline-1-carboxylic acid analogs in order to identify the key functionality responsible for activity against the mitogen-activated protein kinase-activated protein kinase 2 enzyme (MK-2). The compounds were further evaluated for their ability to inhibit TNF alpha production in U937 cells and in vivo. These compounds represent a novel structural class of compounds capable of inhibiting MK-2 with remarkable selectivity. (c) 2007 Elsevier Ltd. All rialuts reserved.

  DOI：

  10.1016/j.bmcl.2007.05.070

文献信息

• Beta-carboline compounds and analogues thereof as mitogen-activated protein kinase-activated protein kinase-2 inhibitors
  申请人：Anderson R. David

  公开号：US20050137220A1

  公开（公告）日：2005-06-23

  A method is described for inhibiting mitogen activated protein kinase-activated protein kinase-2 in a subject in need of such inhibition, where the method involves administering to the subject a beta-carboline MK-2 inhibiting compound, or a pharmaceutically acceptable salt thereof.

  本文描述了一种用于抑制需要这种抑制的受试者中的有丝分裂原活化蛋白激酶激活蛋白激酶-2的方法，其中该方法涉及向受试者施用一种β-喀啉MK-2抑制化合物或其药学上可接受的盐。
• [EN] BETA-CARBOLINE COMPOUNDS AND ANALOGUES THEREOF AND THEIR USE AS MITOGEN-ACTIVATED PROTEIN KINASE-ACTIVATED PROTEIN KINASE-2 INHIBITORS<br/>[FR] COMPOSES DE BETA-CARBOLINE AINSI QUE LEURS ANALOGUES ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE PROTEINE KINASE-2 ACTIVEE PAR PROTEINE KINASE ACTIVEE PAR DES MITOGENES
  申请人：PHARMACIA CORP

  公开号：WO2005009370A2

  公开（公告）日：2005-02-03

  Novel methods and compositions are described for inhibiting mitogen activated protein kinase-activated protein kinase-2 in a subject. The method involves administering to the subject a beta-carboline MK-2 inhibiting compound, or a pharmaceutically acceptable salt, or isomer thereof. The novel compositions are capable of inhibiting mitogen activated protein kinase-activated protein kinase-2 and analogues thereof. Pharmaceutical compositions and kits that include these compounds are also described.
• Novel tetrahydro-β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)
  作者：John I. Trujillo、Marvin J. Meyers、David R. Anderson、Shridhar Hegde、Matthew W. Mahoney、William F. Vernier、Ingrid P. Buchler、Kun K. Wu、Syaluan Yang、Susan J. Hartmann、David B. Reitz

  DOI：10.1016/j.bmcl.2007.05.070

  日期：2007.8

  A structure-activity relationship study was conducted on a series of tetrahydro-beta-carboline-1-carboxylic acid analogs in order to identify the key functionality responsible for activity against the mitogen-activated protein kinase-activated protein kinase 2 enzyme (MK-2). The compounds were further evaluated for their ability to inhibit TNF alpha production in U937 cells and in vivo. These compounds represent a novel structural class of compounds capable of inhibiting MK-2 with remarkable selectivity. (c) 2007 Elsevier Ltd. All rialuts reserved.
• 6-Hydroxy- and 6-methoxy-β-carbolines as acetyl- and butyrylcholinesterase inhibitors
  作者：Yvonne Schott、Michael Decker、Hans Rommelspacher、Jochen Lehmann

  DOI：10.1016/j.bmcl.2006.08.067

  日期：2006.11

  In the course of studies directed toward the discovery of novel acetyl- and butyrylcholinesterase (AChE and BChE) inhibitors for the treatment of Alzheimer's disease, we focused on beta-carbolines (BCs). 6-Oxygenated P-carboline and P-carbolinium derivatives based on the serotonin template were synthesized and tested in vitro for their ability to inhibit AChE and BChE, respectively. Particularly the carbolinium salts, which can be formed by intracerebral methylation out of the tertiary-BC prodrugs, show inhibitory activity levels reaching those of galantamine, physostigmine, and rivastigmine. (c) 2006 Elsevier Ltd. All rights reserved.