ethyl 1-ethyl-β-carboline-3-carboxylate

• 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: ethyl 1-ethyl-β-carboline-3-carboxylate
• 英文别名: ethyl 1-ethyl-9H-pyrido[3,4-b]indole-3-carboxylate
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: MODVMNWYEZJTIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  DL-色氨酸 在 potassium permanganate 、 氯化亚砜 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.17h， 生成 ethyl 1-ethyl-β-carboline-3-carboxylate
  参考文献：
  名称：

  作为潜在抗利什曼病药物的新型 β-咔啉酯类似物的设计、合成和评价

  摘要：

  摘要 利什曼病是当今最被忽视的疾病之一。新的抗利什曼病疗法的出现强调了由世界卫生组织资助的几个研究小组。目前的研究将集中于确定一些新的β-咔啉酯衍生物抗利什曼病的潜在衍生物的研究。大多数标题化合物的计算机预测 ADMET 特性都在可接受的范围内，并且具有类似药物的特性。在所有测试的类似物中，化合物ES-3（EC 50 3.36 μM；SI > 29.80）显示出与标准药物米替福新（EC 50 4.80 μM；SI > 20.80）对测试的无鞭毛体形式相当且等效的抗利什曼病活性婴儿乳杆菌拉紧。两种化合物ES-6和ES-10表现出显着的活性，EC 50为10.16, 13.56 μM；SI > 4.90, 7.37, 分别。还对具有显着活性的类似物进行了基于计算机模拟的分子对接和动力学研究，以研究目标利什曼原虫锥虫硫酮还原酶活性位点的假定结合模式、相互作用模式以及目标-配体复合物的稳定性。MD

  DOI：

  10.1080/07391102.2021.1973564

文献信息

• Efficient and Practical One-Pot Conversions of N-Tosyltetrahydroisoquinolines into Isoquinolines and of N-Tosyltetrahydro-β-carbolines into β-Carbolines through Tandem β-Elimination and Aromatization
  作者：Jing Dong、Xiao-Xin Shi、Jing-Jing Yan、Jing Xing、Qiang Zhang、Sen Xiao

  DOI：10.1002/ejoc.201001153

  日期：2010.12

  An efficient, practical, and general method for conversions of N-tosyltetrahydroisoquinolines (N-tosyl-THIQs) into isoquinolines and of N-tosyltetrahydro-β-carbolines (N-tosyl-THBCs) into β-carbolines is described. Treatment of N-tosyl-THIQs or N-tosyl-THBCs with base in dimethyl sulfoxide afforded dihydroisoquinolines or dihydro-β-carbolines as intermediates, and these were then oxidized in situ by

  描述了一种将 N-tosyltetrahydroisoquinolines (N-tosyl-THIQs) 转化为异喹啉和将 N-tosyltetrahydro-β-carbolines (N-tosyl-THBCs) 转化为 β-咔啉的有效、实用和通用的方法。在二甲基亚砜中用碱处理 N-tosyl-THIQs 或 N-tosyl-THBCs 得到作为中间体的二氢异喹啉或二氢-β-咔啉，然后这些被分子氧原位氧化得到异喹啉或 β-咔啉。产量。两种一锅法转化都是通过串联β-消除和芳构化发生的。
• Cu-catalyzed mild and efficient oxidation of THβCs using air: application in practical total syntheses of perlolyrine and flazin
  作者：Bo Zheng、Tien Ha Trieu、Tian-Zhuo Meng、Xia Lu、Jing Dong、Qiang Zhang、Xiao-Xin Shi

  DOI：10.1039/c7ra13434g

  日期：——

  friendliness, mildness, very good tolerance of functional groups, high yielding and easy experiment operation. In addition, this new methodology was successfully applied in the efficient and practical total syntheses of β-carboline alkaloids perlolyrine and flazin.

  开发了一种通过Cu( II ) 催化氧化 1,2,3,4-四氢-β-咔啉 (THβCs)合成芳香族 β-咔啉的温和、高效和环保的方法，其中空气 (O 2 )用作清洁氧化剂。该方法具有环境友好、温和、官能团耐受性好、收率高、实验操作简单等优点。此外，该新方法成功应用于高效实用的β-咔啉生物碱perlolyrine和flalazin的全合成。
• 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。
• HARMINE DERIVATIVES, INTERMEDIATES USED IN THEIR PREPARATION, PREPARATION PROCESSES AND USE THEREOF
  申请人：Xinjiang Huashidan Pharmaceutical Research Co., Ltd.

  公开号：EP1634881B1

  公开（公告）日：2011-07-27
• Synthesis and in vitro cytotoxic evaluation of 1,3-bisubstituted and 1,3,9-trisubstituted β-carboline derivatives
  作者：Rihui Cao、Wenlie Peng、Hongsheng Chen、Xuerui Hou、Huaji Guan、Qi Chen、Yan Ma、Anlong Xu

  DOI：10.1016/j.ejmech.2004.11.005

  日期：2005.3

  A series of novel 1,3-bisubstituted and 1, 3,9-trisubstituted beta-carboline derivatives was synthesized from the starting material L-tryptophan. Cytotoxic activities of these compounds were investigated in vitro. The results showed that 1,3,9-trisubstituted beta-carboline derivatives had higher cytotoxic activities in vitro than the corresponding 1,3-bisubstituted compounds. Among all the synthesized 1,3,9-trisubstituted P-carboline derivatives, the compounds with a methyl substituent at position-1 displayed more potent cytotoxic activities, furthermore compound 5e having an ethoxycarbonyl substituent at position-3 and a pentafluorobenzyl at position-9, respectively, was found to be the most potent compounds of this series with IC50 value of 4 uM against BGC-823 cell lines. These data suggested that (1) the cytotoxic potencies of beta-carboline derivatives were enhanced by the introduction of appropriate substituents into position-1 and position-9 in beta-carboline; (2) the beta-carboline structure might be an important basis for the design and synthesis of new antitumor drugs; (3) the methyl substituent at position-1, the pentafluorobenzyl group at position-9 and the ethoxycarbonyl substituent at position-3 were the optimal combination for the improvement of cytotoxic activity of the P-carboline derivatives. (c) 2004 Elsevier SAS. All rights reserved.