9-乙基吡啶并[3,4-b]吲哚-3-羧酸乙酯 | 116524-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 9-乙基吡啶并[3,4-b]吲哚-3-羧酸乙酯
• 英文名称: Ethyl 9-ethylpyrido<3,4-b>indole-3-carboxylate
• 英文别名: ethyl 9-ethyl-β-carboline-3-carboxylate；Ethyl 9-ethyl-9H-beta-carboline-3-carboxylate；ethyl 9-ethylpyrido[3,4-b]indole-3-carboxylate
• CAS: 116524-12-0
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: UHWDCACGLHSYHW-UHFFFAOYSA-N

物化性质

• 熔点：
  117-118 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  398.7±35.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  β-咔啉-3-羧酸乙酯	ethyl 9H-pyrido[3,4-b]indole-3-carboxylate	74214-62-3	C14H12N2O2	240.261

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	9-(3-phenylpropyl)-1-(3,4-dimethoyphenyl)-3-hydroxymethyl-β-carboline	——	C14H12N2O	224.262
  ——	9-ethyl-β-carboline-3-carboxylic acid hydrazide	799821-69-5	C14H14N4O	254.291
  ——	3-azidocarbonyl-9-ethyl-β-carboline	799822-04-1	C14H11N5O	265.274
  ——	9-Ethylpyrido<3,4-b>indole	21373-40-0	C13H12N2	196.252

反应信息

• 作为反应物：
  描述：

  9-乙基吡啶并[3,4-b]吲哚-3-羧酸乙酯 在 盐酸 、 一水合肼 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 8.67h， 生成 3-azidocarbonyl-9-ethyl-β-carboline
  参考文献：
  名称：

  Design, synthesis and in vitro and in vivo antitumor activities of novel β-carboline derivatives

  摘要：

  To further our SAR study on the chemistry and antitumor activity/neurotoxicity of beta-carboline alkaloids. several series of beta-carboline derivatives with various substituents were designed and synthesized from the starting material L-tryptophan on the basis of harmine chemical structure. Cytotoxic activities of these compounds were investigated in vitro. The results showed that some beta-carboline derivatives had significant cytotoxic activities against human tumor cell lines. Among all the synthesized beta-carboline derivatives, the compounds 27, 28 and 32, having a benzyl substituent at both position-2 and 9, respectively, were found to be the most potent compounds with IC50 value lower than 50 mu M against all human tumor cell lines examined. Acute toxicities and antitumor activities of the selected beta-carboline derivatives in mice were also evaluated. The results demonstrated that a benzyl substituent at position-2 increased the antitumor activity as well as acute toxicity significantly. However an (ethoxycarbonyl)amino substituent at position-3 reduced the acute toxicity as well as antitumor activity remarkedly. These data suggested that (1) the antitumor potencies of beta-carboline derivatives were enhanced by the introduction of benzyl substituent into the position-2; (2) the acute toxicity of beta-carboline derivatives reduced dramatically by the introduction of an appropriate substituent into the position-3 and 9; (3) the beta-carboline structure might be an important basis for the design and synthesis of new antitumor drugs with significant antitumor activity and low toxicity. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.04.008
• 作为产物：
  描述：

  (S)-2,3,4,9-四氢-1H-吡啶[3,4-b]吲哚-3-羧酸 在 selenium(IV) oxide 、 氯化亚砜 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 9-乙基吡啶并[3,4-b]吲哚-3-羧酸乙酯
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel .&#946;-Carboline Derivatives as Antiproliferative Agents

  摘要：

  一系列新型β-咔啉衍生物被合成并对其在体外对人肿瘤细胞系的细胞毒活性进行了评估。大多数化合物对测试的细胞系显示出从中等到强大的细胞毒活性，其中化合物12l对KB细胞系表现出最强的抗增殖活性（IC50 = 4.58 μM）。对化合物12l的初步机制研究表明，它能够抑制DNA嵌入和微管蛋白聚合。

  DOI：

  10.2174/15701808113109990009

文献信息

• Synthesis and biological evaluation of piperazine group-linked bivalent β-carbolines as potential antitumor agents
  作者：Rongqin Sun、Rui Liu、Chi Zhou、Zhenghua Ren、Liang Guo、Qin Ma、Wenxi Fan、Liqin Qiu、Huijuan Yu、Guang Shao、Rihui Cao

  DOI：10.1039/c5md00312a

  日期：——

  A series of bivalent β-carbolines with a piperazine group spacer between 3-methylene units were synthesized and their cytotoxic activities in vitro were evaluated. Compounds 7e and 7g exhibited potent cytotoxic activity.

  一系列具有3-亚甲基单元之间的哌嗪基间隔的二价β-咔啉类化合物被合成，并评估了它们的体外细胞毒活性。化合物7e和7g表现出强大的细胞毒活性。
• Synthesis, acute toxicities, and antitumor effects of novel 9-substituted β-carboline derivatives
  作者：Rihui Cao、Qi Chen、Xuerui Hou、Hongsheng Chen、Huaji Guan、Yan Ma、Wenlie Peng、Anlong Xu

  DOI：10.1016/j.bmc.2004.06.038

  日期：2004.9

  A series of novel 9-substituted beta-carboline derivatives was synthesized from harmine and l-tryptophan, respectively. Cytotoxic activities of these compounds in vitro were investigated. The results showed that most compounds of 9-substituted beta-carboline derivatives had more remarkable cytotoxic activities in vitro than their corresponding parent compounds. Acute toxicities and antitumor effects

  分别从甜蜜素和色氨酸合成了一系列新颖的9-取代的β-咔啉衍生物。研究了这些化合物在体外的细胞毒活性。结果表明，大多数9-取代的β-咔啉衍生物的化合物在体外具有比其相应母体化合物更显着的细胞毒活性。还检查了选定的β-咔啉衍生物在小鼠中的急性毒性和抗肿瘤作用。结果表明，位置9处的短烷基或苄基取代基显着提高了抗肿瘤活性，位置3处的乙氧羰基或羧基取代基显着降低了这些β-咔啉衍生物的急性毒性和神经毒性。而且，与其他化合物相比，在第3位具有烷氧基羰基或羧基取代基且在第9位具有短烷基或苄基取代基的化合物均表现出更显着的抗肿瘤活性以及较低的急性毒性和神经毒性。发现分别在第9位和第3位具有正丁基和羧基取代基的化合物8c具有最高的抗肿瘤作用和最低的急性毒性和神经毒性。这些数据表明：（1）β-咔啉衍生物第9位和第3位的适当取代基可能在确定其增强的抗肿瘤活性以及降低的急性毒性和神经毒性作用方面起着至关重要的作用；
• Design of β-carboline derivatives as DNA-targeting antitumor agents
  作者：Huaji Guan、Hongsheng Chen、Wenlie Peng、Yan Ma、Rihui Cao、Xiaodong Liu、Anlong Xu

  DOI：10.1016/j.ejmech.2006.05.004

  日期：2006.10

  This research studied the structure-activity relationship of beta-carboline derivatives as antitumor agents, in which 41 synthesized compounds and their cytotoxicity to tumor and normal cell lines were assayed. It was proved that substituent in position-9 of the beta-carboline ring could reinforce the DNA intercalating ability and consequently cytotoxicity to tumor cell lines, and the amidation of

  本研究研究了β-咔啉衍生物作为抗肿瘤剂的构效关系，分析了41种合成化合物及其对肿瘤和正常细胞系的细胞毒性。事实证明，β-咔啉环第9位的取代基可增强DNA的插入能力，从而增强对肿瘤细胞的细胞毒性，而靶向第3位侧链的DNA末端的氨基酰胺化则会削弱这些化合物的DNA嵌入活性，从而引发了对肿瘤细胞系而不是正常细胞系的细胞毒选择性。此外，这些化合物引起的S和G2-M阻滞证实，它们可以靶向DNA并导致Hela细胞中的DNA破坏。简而言之，
• Harmine derivatives, intermediates used in their preparations, preparation processes and use therefo
  申请人：Wu Jialin

  公开号：US20090227619A1

  公开（公告）日：2009-09-10

  This invention relates to compounds of general formula (I), wherein R 1 , R 2 , R 3 , R 4 and R 5 are as defined in the specification; intermediates used in their preparation, preparation processes and use thereof. The present invention produces new harmine derivatives with enhanced antitumour activity and lower nervous system toxicity by structurally modification of the parent structure of β-carboline of harmines at position 1, 2, 3, 7 and 9. The compounds of the present invention can be prepared easily with high yield. They can be used in manufacture of a variety of antitumour medicines and medicines used in treatment of tumour diseases in combination of light or radiation therapy.

  本发明涉及一般式（I）的化合物，其中R1、R2、R3、R4和R5如规范中所定义；用于它们的制备的中间体，制备方法和使用。本发明通过在β-噻吩类似物的母体结构的1、2、3、7和9位进行结构修饰，产生具有增强抗肿瘤活性和较低神经系统毒性的新的harmine衍生物。本发明的化合物可以轻松高产制备。它们可以用于制造各种抗肿瘤药物和用于结合光或放射治疗治疗肿瘤疾病的药物。
• CALCIUM RECEPTOR MODULATING AGENTS
  申请人：Fotsch Christopher

  公开号：US20110230517A1

  公开（公告）日：2011-09-22

  The present invention relates generally to novel calcimimetic compounds and pharmaceutical compositions comprising them. The invention also relates to methods of treating of diseases or disorders related to the function of the calcium sensing receptor using the compounds represented in Formula (I). Where Cy 1 is pyridinonyl, pyridinyl, quinolinyl or 9-ethyl-9H-beta-carbolinyl, each of which optionally substituted and where Cy 2 is phenyl naphthyl.

  本发明涉及新型钙敏感剂化合物及包含它们的制药组合物。本发明还涉及使用式（I）中所表示的化合物治疗与钙感受受体功能相关的疾病或障碍的方法。其中Cy1为吡啶基、吡啶基、喹啉基或9-乙基-9H-β-咔唑基，每种基团均可选择性地取代，Cy2为苯基萘基。