(1R,3R)-methyl 1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate | 34368-38-2

• 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: (1R,3R)-methyl 1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• 英文别名: methyl (1R,3R)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 34368-38-2
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: WZHYQHKXXRMALW-PRHODGIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (1R,3R)-methyl 1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 在 一水合肼 作用下， 以 甲苯 为溶剂， 反应 25.0h， 生成 (1R,3R)-N'-(4-chlorobenzylidene)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carbohydrazide
  参考文献：
  名称：

  抗病毒剂NK0209的四种旋光异构体的合成及其构型和对植物病毒活性的测定。

  摘要：

  以前，我们首次报道了harmala生物碱harmine和tetrahydroharmine具有对抗植物病毒的活性，并且我们开发了类似物NK0209，可有效预防和控制植物病毒疾病。在这里，为了研究NK0209的空间构型对其抗病毒活性的影响，我们合成了其四个光学异构体，确定了它们的构型，并评估了它们对烟草花叶病毒的活性。这四种异构体的活性均明显优于宁南霉素，后者是最成功的商业抗病毒药物之一，在500μg/ mL浓度下的体内失活，治愈和保护率分别为57.3±1.9、54.2±3.3和55.0±4.1％。 。此外，

  DOI：

  10.1021/acs.jafc.9b07694
• 作为产物：
  描述：

  D-色氨酸 在 氯化亚砜 、 硫酸 作用下， 反应 14.0h， 生成 (1R,3R)-methyl 1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel tryptoline derivatives as indoleamine 2,3-dioxygenase (IDO) inhibitors

  摘要：

  Indoleamine 2,3-dioxygenase (IDO) plays a significant role in several disorders such as Alzheimer's disease, age-related cataracts and tumors. A series of novel tryptoline derivatives were synthesized and evaluated for their inhibitory activity against IDO. Substituted tryptoline derivatives (11a, 11c, 11e, 12b and 12c) were demonstrated to be more potent than known inhibitor MTH-Trp. Suzuki-Miyaura cross-coupling reaction of 11a-d with phenylboronic acid proceeded in high yields. In most cases, C5 and C6 substitutions on the corresponding indole ring were well tolerated. The tryptoline derivative 11c is a promising chemical lead for the discovery of novel IDO inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.028

文献信息

• Synthesis and Antiviral/Fungicidal/Insecticidal Activities Study of Novel Chiral Indole Diketopiperazine Derivatives Containing Acylhydrazone Moiety
  作者：Jialin Xie、Wentao Xu、Hongjian Song、Yuxiu Liu、Jingjing Zhang、Qingmin Wang

  DOI：10.1021/acs.jafc.0c00875

  日期：2020.5.20

  order to systematically study the effect of the spatial configuration of the compounds on the antiviral activity, four compounds with different spatial configurations at C6 and C12a were also prepared. The bioassay results indicated that most of these new compounds displayed moderate to good antiviral activity, among which compounds 23, 25, 27, 28, 31, and 5d showed a significantly higher activity than

  根据酰基hydr化合物抑制TMV CP装配的机理和二酮哌嗪环独特的结构特征，设计合成了一系列光学纯的吲哚二酮哌嗪酰基hydr。为了系统地研究化合物的空间构型对抗病毒活性的影响，还制备了四种在C6和C12a处具有不同空间构型的化合物。生物测定结果表明，这些新化合物中的大多数显示出中等至良好的抗病毒活性，其中化合物23、25、27、28、31和5d的活性明显高于市售的病毒唑。深入的结构-活性关系研究表明，空间构象是调节抗病毒活性的最重要因素之一。研究结果提供了有关该分子与其靶蛋白相互作用的可能最佳构型的信息。同时，这些新化合物还对14种植物致病真菌表现出广谱杀真菌活性。而且，这些化合物中的一些对小菜蛾和淡色库蚊具有良好的杀虫活性。
• A new method for the preparation of 3,4-dihydro - and 1,2,3,4-tetrahydro-.BETA.-carbolines.
  作者：AKIHIKO ISHIDA、TOHRU NAKAMURA、KUNIHIKO IRIE、TOKURO OHISHI

  DOI：10.1248/cpb.33.3237

  日期：——

  N-Alkylthiocarbonyltryptophan (2a-i) and tryptamine (2j-m) derivatives can be converted into the corresponding 3, 4-dihydro-β-carbolines (3) under mild conditions by the use of alkylating or acylating agents. The NaBH4 reduction of 1, 3-disubstituted 3, 4-dihydro-β-carbolines (3a-i) gave cis- (5) or trans-1, 2, 3, 4-tetrahydro-β-carbolines (6) with satisfactory stereoselectivity. The synthesis of optically active 3a, b and 5a, b is also described.

  N-烷基硫羰基色氨酸（2a-i）和色氨酸（2j-m）衍生物可以在温和条件下通过烷基化或酰基化剂转化为相应的3, 4-二氢-β-氨基吲哚（3）。1, 3-二取代的3, 4-二氢-β-氨基吲哚（3a-i）经过NaBH4还原，得到了具有满意立体选择性的顺式（5）或反式-1, 2, 3, 4-四氢-β-氨基吲哚（6）。本文还描述了外消旋活性3a, b和5a, b的合成。
• Syntheses of chiral 1,3-disubstituted tetrahydro-β-carbolines via CIAT process: highly stereoselective Pictet–Spengler reaction of d-tryptophan ester hydrochlorides with various aldehydes
  作者：Sen Xiao、Xia Lu、Xiao-Xin Shi、Yu Sun、Li-Li Liang、Xin-Hong Yu、Jing Dong

  DOI：10.1016/j.tetasy.2009.01.026

  日期：2009.3

  A highly stereoselective Pictet-Spengler reaction of D-tryptophan methyl ester hydrochloride 1-HCl with various aldehydes via a CIAT (crystallization-induced asymmetric transformation) process is described. It was revealed that the CIAT process should be performed in a mixed solvent of nitromethane and toluene, and a fine tuning of the ratio of nitromethane and toluene for each epimer Mixture of 2-HCl was necessary in order to get as high yields and stereoselectivities as possible. Enantiomerically pure cis (or trans) 1,3-disubstituted tetrahydro-beta-carbolines 2a-2v were obtained by recrystallization or flash chromatography after neutralization of the corresponding hydrochloride salts cis-2-HCl or trans-2-HCl. (c) 2009 Elsevier Ltd. All rights reserved.
• SANDRIN, JOSEPH;HOLLINSHEAD, SEAN P.;COOK, JAMES M., J. ORG. CHEM., 54,(1989) N3, C. 5636-5640
  作者：SANDRIN, JOSEPH、HOLLINSHEAD, SEAN P.、COOK, JAMES M.

  DOI：——

  日期：——
• SALVI, N. A.;CHOUGHULEY, A. S. U., INDIAN J. CHEM. B , 29,(1990) N0, C. 986-988
  作者：SALVI, N. A.、CHOUGHULEY, A. S. U.

  DOI：——

  日期：——