1-Carboxy-6-hydroxy-1,2,3,4-tetrahydro-2-carbolin | 17994-20-6

• 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: 1-Carboxy-6-hydroxy-1,2,3,4-tetrahydro-2-carbolin
• 英文别名: 6-hydroxy-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid；6-hydroxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylic acid
• CAS: 17994-20-6
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: KDTKEEBTTHBVSR-UHFFFAOYSA-N

物化性质

• 沸点：
  573.6±50.0 °C(Predicted)
• 密度：
  1.494±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  85.4
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Carboxy-6-hydroxy-1,2,3,4-tetrahydro-2-carbolin 生成 2,3,4,9-四氢-1H-吡啶并[3,4-b]吲哚-6-醇
  参考文献：
  名称：

  YAMANO, TOSHIO;MIURA, RETSU;KANASHIRO, MASARKU;UEMURA, TOMIHIKO, BIOORG. CHEM., 16,(1988) N 2, 189-205

  摘要：

  DOI：
• 作为产物：
  描述：

  5-苄氧基色胺 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 12.0h， 生成 1-Carboxy-6-hydroxy-1,2,3,4-tetrahydro-2-carbolin
  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。
• YAMANO, TOSHIO;MIURA, RETSU;KANASHIRO, MASARKU;UEMURA, TOMIHIKO, BIOORG. CHEM., 16,(1988) N 2, 189-205
  作者：YAMANO, TOSHIO、MIURA, RETSU、KANASHIRO, MASARKU、UEMURA, TOMIHIKO

  DOI：——

  日期：——
• [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.