(3S)-1-(pyridin-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid | 364070-24-6

• 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: (3S)-1-(pyridin-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
• 英文别名: 1-(pyridin-3-yl)-1,2,3,4-tetrahydro-β-carboline-3-(S)-carboxylic acid；1-(3-pyridyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid；1-(pyridin-3-yl)-3-carboxy-1,2,3,4-tetrahydro-β-carboline；1-(pyridin-3-yl)-β-carboline
• CAS: 364070-24-6
• 化学式: C₁₇H₁₅N₃O₂
• 分子量: 293.325
• InChiKey: XQRUJLXAOIVJQB-MLCCFXAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  78.01
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3S)-1-(pyridin-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid 在 氯化亚砜 、 sodium hydride 、 sulfur 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.33h， 生成 1,5-bis[3-ethoxycarbonyl-1-(pyridyl-3-yl)-β-carboline-9-yl]pentane
  参考文献：
  名称：

  Design, synthesis and in vitro and in vivo antitumor activities of novel bivalent β-carbolines

  摘要：

  A series of bivalent beta-carbolines with a spacer of three to ten methylene units between the indole nitrogen was synthesized and evaluated as antitumor agents. The results demonstrated that compounds 18c, 21b, 25a and 31b exhibited strong cytotoxic activities with IC50 value of lower than 20 mu M against four tumor cell lines. Acute toxicities and antitumor efficacies of the selected compounds in mice were also evaluated, compounds 18b, 21b, 26a and 31b exhibited potent antitumor activities with tumor inhibition rate of over 40% in animal models. Preliminary structure-activity relationships analysis indicated that (1) the spacer length affected antitumor potencies, and four to six methylene units were more favorable; (2) the introduction of appropriate substituent into position-1 of beta-carboline facilitated antitumor potencies. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.033
• 作为产物：
  描述：

  3-吡啶甲醛 、 L-色氨酸 在 溶剂黄146 作用下， 生成 (3S)-1-(pyridin-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
  参考文献：
  名称：

  ビスβ−カルボリン系化合物、その製造方法、医薬組成物および用途

  摘要：

  This invention discloses bis β-carboline compounds, their manufacturing method, pharmaceutical compositions, and applications. Specifically, the bis β-carboline compounds and their pharmaceutically acceptable salts are represented by general formula I, and are produced by condensation of β-carboline intermediates and dihaloalkanes. Furthermore, the invention discloses pharmaceutical compositions containing the bis β-carboline compounds represented by formula I in effective dosages and pharmaceutically acceptable carriers, as well as applications in the manufacturing of antitumor agents using these bis β-carboline compounds. Such tumors include melanoma, gastric cancer, lung cancer, breast cancer, kidney cancer, liver cancer, oral squamous cell carcinoma, cervical cancer, ovarian cancer, pancreatic cancer, prostate cancer, and colon cancer.【Chemical formula 1】

  公开号：

  JP2016500080A

文献信息

• PhI(OAc)₂-mediated one-pot oxidative decarboxylation and aromatization of tetrahydro-β-carbolines: synthesis of norharmane, harmane, eudistomin U and eudistomin I
  作者：Ahmed Kamal、Yellaiah Tangella、Kesari Lakshmi Manasa、Manda Sathish、Vunnam Srinivasulu、Jadala Chetna、Abdullah Alarifi

  DOI：10.1039/c5ob00871a

  日期：——

  A new strategy for synthesis of β-carbolines via one-pot oxidative decarboxylation at room temperature is developed for the first time.

  首次开发了一种在室温下通过一锅法氧化脱羧合成β-咔啉的新策略。

• An efficient one-pot decarboxylative aromatization of tetrahydro-β-carbolines by using N-chlorosuccinimide: total synthesis of norharmane, harmane and eudistomins
  作者：Ahmed Kamal、Manda Sathish、A. V. G. Prasanthi、Jadala Chetna、Yellaiah Tangella、Vunnam Srinivasulu、Nagula Shankaraiah、Abdullah Alarifi

  DOI：10.1039/c5ra16221a

  日期：——

  A mild one-pot synthesis of β-carbolines from their tetrahydro-β-carboline acids has been developed via decorboxylative aromatization using N-chlorosuccinimide (NCS).

  一种从四氢β-咔啉酸合成β-咔啉的温和一锅法已经开发出来，通过使用N-氯代琥珀酰亚胺（NCS）进行脱羧芳构化。