1-(3-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

• 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: 1-(3-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• 英文别名: 1-(3-Fluor-phenyl)-1.2.3.4-tetrahydro-β-carbolin；1-(3-fluoro-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline；Pyrido[3,4-b]indole, 1,2,3,4-tetrahydro-1-(3-fluorophenyl)-
• 化学式: C₁₇H₁₅FN₂
• 分子量: 266.318
• InChiKey: XRGMJPZNCWYTRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 在 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 432.0h， 生成 dimethyl 3-ethyl-6-(3-fluorophenyl)-2,3,6,7-tetrahydro-1H-azocino[5,4-b]indole-4,5-dicarboxylate
  参考文献：
  名称：

  Synthesis of 6-aryl-Substituted Azocino-[5,4-b]indoles from 1-aryl-Substituted 2-Ethyltetrahydro-β-Carbolines

  摘要：

  We optimized the reaction of tetrahydropyridine ring expansion in 1-aryl-substituted tetrahydro-beta-carbolines by the action of activated alkynes and achieved higher than 70% yields of the target indoloazocines. The substituents in the 1-aryl ring and at the indole nitrogen atom were shown to affect the rate and selectivity of this transformation.

  DOI：

  10.1007/s10593-014-1518-z
• 作为产物：
  描述：

  rac-1-(3-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride 在 sodium carbonate 作用下， 以 水 为溶剂， 生成 1-(3-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  通过“底物行走”实现1-芳基四氢-β-咔啉的不对称生物催化合成

  摘要：

  色胺和醛的 Pictet-Spengler 反应的立体选择性催化剂可能允许简单快速地制备手性 1-取代四氢-β-咔啉。尽管生物催化剂以前曾用于皮克泰-斯宾格勒反应，但没有一种生物催化剂接受苯甲醛及其取代衍生物。为了应对这一挑战，结合底物行走和不同野生型主链之间有益突变的转移，将来自萝芙木( Rs STR) 的胡豆苷合酶开发成适合色胺和苯甲醛不对称 Pictet-Spengler 缩合的酶衍生物。双变体Rs STR V176L/V208A 接受各种邻位、间位和对位取代的苯甲醛，并产生相应的手性 1-芳基-四氢-β-咔啉，对映体过量高达 99%。

  DOI：

  10.1002/chem.202004449

文献信息

• N-Bromo-succinimide promoted synthesis of β-carbolines and 3,4-dihydro-β-carbolines from tetrahydro-β-carbolines
  作者：Santanu Hati、Subhabrata Sen

  DOI：10.1016/j.tetlet.2016.01.081

  日期：2016.3

  Herein, we report a facile synthesis of 3,4-dihydro-β-carbolines and aromatic β-carbolines from tetrahydro-β-carbolines, mediated by N-bromosuccinimide in toluene at 0 °C to room temperature (rt), in good to moderate yields.

  本文中，我们报道了由N-溴琥珀酰亚胺在0°C到室温（rt）的介导下，由N-溴琥珀酰亚胺在四氢-β-咔啉中轻松合成3,4-二氢-β-咔啉和芳香族β-咔啉。中等产量。
• Cerium Chloride Catalyzed, 2-Iodoxybenzoic Acid Mediated Oxidative Dehydrogenation of Multiple Heterocycles at Room Temperature
  作者：Santanu Hati、Subhabrata Sen

  DOI：10.1002/ejoc.201601419

  日期：2017.3.3

  Catalytic cerium chloride was found to activate 2-iodoxybenzoic acid (IBX) for the oxidative dehydrogenation of tetrahydroisoquinolines, tetrahydro-β-carbolines, and thiazolidines to their dehydrogenated and aromatic forms at room temperature in moderate to excellent yields. The robustness of the protocol was demonstrated by scaling up the reactions to multigram quantities.

  发现催化氯化铈活化 2-碘氧基苯甲酸 (IBX)，用于在室温下将四氢异喹啉、四氢-β-咔啉和噻唑烷氧化脱氢为其脱氢和芳族形式，产率中等至极好。该协议的稳健性通过将反应放大到数克数量来证明。
• Metal-Free Access to (<i>Spirocyclic</i>)Tetrahydro-β-carbolines in Water Using an Ion-Pair as a Superacidic Precatalyst
  作者：Zhenguo Zhang、Xiaoxiao Liu、Liang Ji、Ting Zhang、Zhenhua Jia、Teck-Peng Loh

  DOI：10.1021/acscatal.1c05546

  日期：2022.2.4

  The unprecedented triarylcarbonium ion-pair-catalyzed Pictet–Spengler reaction of tryptamines with aromatic aldehydes and cyclic ketones in water was disclosed. Under metal-free conditions, diverse tetrahydro-β-carbolines and spirocyclic tetrahydro-β-carbolines were obtained in good yields with excellent functional group tolerance, including late-stage modification of natural products and small molecular

  公开了前所未有的三芳基碳离子对催化的色胺与芳香醛和环酮在水中的 Pictet-Spengler 反应。在无金属条件下，以良好的收率获得了多种四氢-β-咔啉和螺环四氢-β-咔啉，具有优异的官能团耐受性，包括天然产物和小分子药物的后期修饰。该协议的实用性还体现在 Komavine 和其他几种功能化合物的克级合成中。初步机理研究表明，在水介质中，碳鎓离子对与水原位生成的超酸性物质对于促进 Pictet-Spengler 反应至关重要。
• Design, synthesis and biological evaluation of a novel library of antimitotic C2-aroyl/arylimino tryptamine derivatives that are also potent inhibitors of indoleamine-2, 3-dioxygenase (IDO)
  作者：Jyoti Chauhan、Moumita Dasgupta、Tania Luthra、Akanksha Awasthi、Sayantan Tripathy、Anindyajit Banerjee、Santanu Paul、Debasish Nag、Saikat Chakrabarti、Gopal Chakrabarti、Subhabrata Sen

  DOI：10.1016/j.ejps.2018.08.033

  日期：2018.11

  products. The molecular docking of the designed compounds indicated that they bind to the colchicin binding site of tubulin. They were synthesized by a unique iodine catalysed oxidative ring opening reaction of 1-aryltetrahydro-β-carbolines. Among the compounds synthesized quite a few compounds induced cytotoxicity on the cancer cells by disrupting the tubulin polymerization. They were found to be non-toxic

  设计，合成并筛选了具有抗有丝分裂特性的，具有C2取代色胺（基于不同的C2-芳酰基/芳基吲哚和吲哚-二酮哌嗪杂种）的新型文库，针对其对微管蛋白聚合以及对A549肺癌HeLa的抑制作用子宫颈癌，MCF7乳腺癌和HePG2肝癌细胞系。分子的设计灵感来自已知的抗有丝分裂化合物和天然产物。设计化合物的分子对接表明它们与微管蛋白的秋水仙素结合位点结合。它们是通过独特的碘催化1-芳基四氢-β-咔啉的氧化开环反应合成的。在合成的化合物中，相当多的化合物通过破坏微管蛋白聚合来诱导癌细胞的细胞毒性。发现它们对健康细胞无毒。针对A549和HeLa细胞的最具活性的分子（浓度约6μM之间）的免疫荧光研究表明，微管结构完全被破坏和收缩。这些化合物还以低微摩尔IC50抑制吲哚胺2，3-二加氧酶。
• Novel tricyclic heterocycle compound
  申请人：Ohmoto Kazuyuki

  公开号：US20060154944A1

  公开（公告）日：2006-07-13

  The present invention relates to the compound represented by formula (I) A—X—Y-Z-B  (I) (wherein A is a cyclic group which may have a substituent(s); X is a single bond or a spacer; Y is a single bond or a spacer; Z is a single bond or a spacer; B is a hydrocarbon group which may have a substituent(s) or a cyclic group which may have a substituent(s)), a salt thereof, a solvate thereof or a prodrug thereof. The compound represented by formula (I), a salt thereof, a solvate thereof or a prodrug thereof is useful for preventive and/or therapeutic agent for a disease caused by stress.

  本发明涉及由式(I)A—X—Y-Z-B所表示的化合物（其中A是可能具有取代基的环状基团；X是单键或间隔物；Y是单键或间隔物；Z是单键或间隔物；B是可能具有取代基的碳氢基团或环状基团），其盐、溶剂化物或前药。该式(I)化合物、其盐、溶剂化物或前药可用作预防和/或治疗由压力引起的疾病的药物。