6-chloro-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid | 837381-09-6

• 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: 6-chloro-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid
• 英文别名: 6-chloro-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylic acid；6-Chloro-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-1-carboxylic acid
• CAS: 837381-09-6
• 化学式: C₁₂H₁₁ClN₂O₂
• 分子量: 250.685
• InChiKey: CMQSGMXGIWWFHN-UHFFFAOYSA-N

物化性质

• 沸点：
  525.4±50.0 °C(Predicted)
• 密度：
  1.483±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 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：
  65.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 以82%的产率得到6-chloro-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride
  参考文献：
  名称：

  WO2020037155A5

  摘要：

  公开号：

  WO2020037155A5
• 作为产物：
  描述：

  5-氯-1H-吲哚-3-乙胺盐酸盐 、 乙醛酸 在 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 16.0h， 以80%的产率得到6-chloro-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid
  参考文献：
  名称：

  WO2020037155A5

  摘要：

  公开号：

  WO2020037155A5

文献信息

• Discovery of Indoles as Potent and Selective Inhibitors of the Deacetylase SIRT1
  作者：Andrew D. Napper、Jeffrey Hixon、Thomas McDonagh、Kenneth Keavey、Jean-Francois Pons、Jonathan Barker、Wei Tsung Yau、Patricia Amouzegh、Adam Flegg、Estelle Hamelin、Russell J. Thomas、Michael Kates、Stephen Jones、Manuel A. Navia、Jeffrey O. Saunders、Peter S. DiStefano、Rory Curtis

  DOI：10.1021/jm050522v

  日期：2005.12.1

  against the human sirtuin SIRT1 led to the discovery of a series of indoles as potent inhibitors that are selective for SIRT1 over other deacetylases and NAD-processing enzymes. The most potent compounds described herein inhibit SIRT1 with IC50 values of 60-100 nM, representing a 500-fold improvement over previously reported SIRT inhibitors. Preparation of enantiomerically pure indole derivatives allowed

  针对人类sirtuin SIRT1的高通量筛选导致发现了一系列吲哚，它们是对SIRT1选择性强于其他脱乙酰基酶和NAD加工酶的有效抑制剂。本文描述的最有效的化合物以60-100 nM的IC50值抑制SIRT1，这比以前报道的SIRT抑制剂提高了500倍。对映体纯的吲哚衍生物的制备使其能够在体外和体内表征。动力学分析表明，这些抑制剂在烟酰胺从酶中释放后结合，并阻止了脱乙酰肽和O-乙酰-ADP-核糖的释放，O-乙酰-ADP-核糖是酶催化的脱乙酰产物。这些SIRT1抑制剂是低分子量的，细胞可渗透的，口服可生物利用的和代谢稳定的。
• 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。
• 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.
• 1,3,4,9-TETRAHYDRO-2H-PYRIDO[3,4-B]INDOLE DERIVATIVE COMPOUNDS AND USES THEREOF
  申请人：Recreo Pharmaceuticals Inc.

  公开号：EP3836919A1

  公开（公告）日：2021-06-23
• [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.