(3S)-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid benzyl ester | 102130-85-8

• 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
• 英文名称: (3S)-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid benzyl ester
• 英文别名: (3S)-2,3,4,9-tetrahydro-β-carbolin-3-carboxylic acid benzyl ester；benzyl (3S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 102130-85-8
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: PSTDRLUXXSVTJJ-KRWDZBQOSA-N

物化性质

• 熔点：
  180-182 °C
• 沸点：
  499.5±45.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid benzyl ester 在 盐酸 、 copper(l) iodide 、 palladium on activated charcoal 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 6.17h， 生成 N-((1-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)-1H-1,2,3-triazol-4-yl)methyl)-1-((S)-2-((S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carbonyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carbonyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Indole-TEMPO conjugates alleviate ischemia-reperfusion injury via attenuation of oxidative stress and preservation of mitochondrial function

  摘要：

  Mitochondrial oxidative damage contributes to a wide range of pathologies including ischemia/reperfusion injury. Accordingly, protecting mitochondria from oxidative damage should possess therapeutic relevance. In the present study, we have designed and synthesized a series of novel indole-TEMPO conjugates that manifested good anti-inflammatory properties in a murine model of xylene-induced ear edema. We have demonstrated that these compounds can protect cells from simulated ischemia/reperfusion (s-I/R)-induced reactive oxygen species (ROS) overproduction and mitochondrial dysfunction. Furthermore, we have demonstrated that indole-TEMPO conjugates can attenuate organ damage induced in rodents via intestinal I/R injury. We therefore propose that the pharmacological profile and mechanism of action of these indole-TEMPO conjugates involve convergent roles, including the ability to decrease free radical production via lipid peroxidation which couples to an associated decrease in ROS-mediated activation of the inflammatory process. We further hypothesize that the protective effects of indole-TEMPO conjugates partially reside in maintaining optimal mitochondrial function. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2017.03.033
• 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 盐酸 、 caesium carbonate 作用下， 以 乙酸乙酯 为溶剂， 生成 (3S)-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis and Thrombolytic Activity of Pseudopeptides Related to Fibrinogen Fragment

  摘要：

  Two kinds of linkers consisting of 3-(S)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid, ARPAK, GRPAK and QRPAK were synthesized. The thrombolytic activities in vivo indicated that the coupling position of 3-(S)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid in the peptides effected on the potencies significantly. When the C-terminal of the peptides was amidated by 3-(S)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid, the thrombolytic potency of the peptides was enhanced or kept. When the N-terminal of the peptides was acylated by 3-(S)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid, however, the thrombolytic effect of the peptides was banished. The expected specific beta II'-turn conformation and the stability to trypsin in the pseudopeptides with 3-(S)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid in its C-terminal may be responsible for the enhanced thrombolytic potency. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00403-1

文献信息

• A new class of anti-thrombosis hexahydropyrazino-[1′,2′:1,6]pyrido-[3,4-b]-indole-1,4-dions: Design, synthesis, logK determination, and QSAR analysis
  作者：Jiawang Liu、Guofeng Wu、Guohui Cui、Wei-Xuan Wang、Ming Zhao、Chao Wang、Ziding Zhang、Shiqi Peng

  DOI：10.1016/j.bmc.2007.06.012

  日期：2007.9.1

  (tetrahydro-beta-carboline-3-carboxy-l-amino acid benzylesters, 2-aminoacyltetrahydro-beta-carboline-3-carboxylic acid benzylesters) were prepared and used for the cyclization to form 5a-t. Coupling hydrochloric acid salt of tetrahydro-beta-carboline-3-carboxylic acid esters and Boc-amino acids in the reported literature usually generates very low yield products accompanied by racemization. However, in our case, the

  基于N-[（3S）]-1,2,3,4-四氢-β-咔啉-3-羧基] -1-赖氨酸在乙酸水溶液（5％）和大鼠中的环化血浆给出了相同的产物，并假设环化产物具有抗血栓活性，我们报道了20种六氢吡嗪并[1'，2'：1,6]吡啶并[ 3,4-b]吲哚-1,4-dion（5a-t）作为潜在的抗血栓形成剂。制备了两种中间体（四氢-β-咔啉-3-羧基-1-氨基酸苄酯，2-氨基酰基四氢-β-咔啉-3-羧酸苄酯），并用于环化形成5a-t。在已报道的文献中，四氢-β-咔啉-3-羧酸酯的盐酸盐与Boc-氨基酸的偶联通常产生非常低的收率产物，并伴随着消旋作用。然而，在我们的情况下，四氢-β-咔啉-3-羧酸苄酯的游离碱以高收率且没有外消旋作用产生了所需的产物。来自体外和体内研究的抗血栓形成结果表明，5a-t可能是一类新型的抗血栓形成剂，口服有效有效浓度为0.5μmol/ kg。此外，使用e-dragon服务器生成的分子
• Carboline-3-carboxylic acid modified related sequences of Ala-Arg-Pro-Ala-Lys, their synthesis and use as thromobolytic agent
  申请人：Peng Shiqi

  公开号：US20050080015A1

  公开（公告）日：2005-04-14

  The present invention relates to the protected intermediates and the deprotected products of P6A, related to the protected pseudopeptides introducing the protected intermediateds of P6A to 3S-(2-Boc)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid and the deprotected pseudopeptides, related to the protected pseudopeptides introducing the protected intermediateds of P6A to 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid benzyl ester, related to the methods for their preparation, and related to their use as the thrombolytic agents.

  本发明涉及P6A的保护中间体和去保护产物，涉及将P6A的保护伪肽引入到3S-(2-Boc)-1,2,3,4-四氢-β-咔啉-3-羧酸的保护中间体和去保护伪肽，涉及将P6A的保护伪肽引入到3S-1,2,3,4-四氢-β-咔啉-3-羧酸苄酯的保护中间体，涉及它们的制备方法，以及它们作为溶栓剂的用途。
• 氨基酸和氨基正己酸修饰的咔啉羧酸苄酯 ,其 制备 ,活性和应用
  申请人：首都医科大学

  公开号：CN109912590B

  公开（公告）日：2020-06-19

  本发明公开了下面结构的(3S)‑N‑(6‑氨基酰氨基正己酰)‑2,3,4,9‑四氢‑β‑咔啉‑3‑羧酸苄酯(式中AA选自L‑Phe,L‑Gly,L‑Ile,L‑Val和L‑Tyr残基)。公开了它们的制备方法和其抗肿瘤作用，阐明了它们在制备抗肿瘤作用的药物中的应用。
• [EN] AGENTS FOR DIFFERENTIATING STEM CELLS AND TREATING CANCER<br/>[FR] AGENTS POUR DIFFÉRENCIER DES CELLULES SOUCHES ET TRAITER UN CANCER
  申请人：MINERVA BIOTECHNOLOGIES CORP

  公开号：WO2018183654A1

  公开（公告）日：2018-10-04

  The present application discloses a method for identifying an agent for the treatment or prevention of cancer or metastatic cancer comprising the steps of contacting stem cell with a potential agent, and identifying an agent that induces differentiation, or inhibits stem cell pluripotency or growth of the stem cell, wherein such agent is determined to be an anti-cancer agent.

  本申请公开了一种用于识别治疗或预防癌症或转移性癌症的药剂的方法，包括以下步骤：将干细胞与潜在药剂接触，并识别诱导分化的药剂，或抑制干细胞多能性或干细胞生长的药剂，其中这种药剂被确定为抗癌药剂。
• 6-氨基酰氨基正己酰咔啉羧酸苄酯 ,其制备 , 活性和应用
  申请人：首都医科大学

  公开号：CN110551120B

  公开（公告）日：2020-10-20

  本发明公开了下面结构的(3S)‑N‑(6‑AA‑氨基正己酰)‑2,3,4,9‑四氢‑β‑咔啉‑3‑羧酸苄酯(式中AA选自Gly残基,L‑Asn残基,L‑Thr残基,L‑Trp残基)。公开了它们的制备方法和其抗肿瘤转移作用，阐明了它们在制备抗肿瘤转移作用药物中的应用。