methyl 1-cyclohexyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate | 569642-61-1

• 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: methyl 1-cyclohexyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• 英文别名: 1-cyclohexyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester；cis methyl 1,2,3,4-tetrahydro-1-cyclohexyl-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 569642-61-1
• 化学式: C₁₉H₂₄N₂O₂
• 分子量: 312.412
• InChiKey: KOLPHMYBGCHLFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  methyl 1-cyclohexyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 生成 Cis-2-benzyl-5-cyclohexyl-5,6,11,11a-tetrahydro-1H-imidazo[1',5':1,6]pyrido[3,4-b]indole-1,3(2H)-dione
  参考文献：
  名称：

  Chemical compounds

  摘要：

  通用结构式##STR1##的化合物及其盐和溶剂合物的使用作为治疗剂。

  公开号：

  US06143757A1
• 作为产物：
  描述：

  (S)-2-{[1-Cyclohexyl-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester 在 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以86%的产率得到methyl 1-cyclohexyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Highly efficient Lewis acid-catalysed Pictet–Spengler reactions discovered by parallel screeningElectronic supplementary information (ESI) available: full experimental procedures. See http://www.rsc.org/suppdata/cc/b2/b212063a/

  摘要：

  高产量的路易斯酸催化的一锅法Pictet–Spengler反应，采用色氨酸甲酯和色氨酸与脂肪族和芳香族醛在微波辐射的帮助下，在短反应时间内完成。

  DOI：

  10.1039/b212063a

文献信息

• Sodium periodate oxidation of tetrahydro-β-carboline derivatives
  作者：Franco Gatta、Domenico Misiti

  DOI：10.1002/jhet.5570260302

  日期：1989.5

  The oxidation of some 3-(methoxy- and ethoxycarbonyl)tetrahydro-β-carboline derivatives with sodium periodate led to the formation of 1, 4-benzodiazonine derivatives or fully aromatic β-carbolines depending on both nature and number of substituents at 1-position.

  某些3-（甲氧基-和乙氧基羰基）四氢-β-咔啉衍生物与高碘酸钠的氧化作用会导致生成1,4-苯二重氮衍生物或完全芳族的β-咔啉，具体取决于1位上取代基的性质和数量。
• Phytochemical meanings of tetrahydro-β-carboline moiety in strictosidine derivatives
  作者：Nicole Sudžuković、Johann Schinnerl、Lothar Brecker

  DOI：10.1016/j.bmc.2015.12.028

  日期：2016.2

  Synthesis of 13 different tetrahydro-beta-carbolines (THBC) was accomplished by applying the Pictet-Spengler reaction with seven aldehydes, which have been coupled with tryptamine (6) and L-tryptophan methyl ester (7), respectively. The resulting products represent analogues of strictosidine (1) and carboxystrictosidine (5). They were investigated with respect to possible effects on herbivores in feeding bioassays upon the generalist Spodoptera littoralis. Maximum inhibition averages were 42% after four and 46% after six days for the most effective product (19) at 1000 ppm. Additionally, the frass of this particular bioassay was investigated via HPLC-UV for THBC digestion. All synthesized THBCs were also tested for their radical scavenger activity by monitoring their interaction with 2,2-diphenyl-1-picrylhydrazyl (DPPH). Compounds 16-20, 24 and 25 exhibited radical scavenging activity, ranging from 50% to 74% compared to that of a-tocopherol. All results were discussed with respect to possible contributions of tetrahydro-beta-carboline moieties in bioactivities of strictosidine (1) and its biodegradation products. (c) 2015 Elsevier Ltd. All rights reserved.
• US6001847
  申请人：——

  公开号：——

  公开（公告）日：——
• SANDRIN J.; SOERENS D.; HUTCHINS L.; RICHFIELD E.; UNGEMACH F.; COOK J. M+, HETEROCYCLES, 1976, 4, NO 6, 1101-1105
  作者：SANDRIN J.、 SOERENS D.、 HUTCHINS L.、 RICHFIELD E.、 UNGEMACH F.、 COOK J. M+

  DOI：——

  日期：——
• TETRAHYDROIMIDAZOPYRIDOINDOLEDIONES AS INHIBITORS OF cGMP SPECIFIC PDE
  申请人：ICOS CORPORATION

  公开号：EP0859778B1

  公开（公告）日：2001-12-19