3-氨基-1-甲基-5H-吡啶[4,3-b]吲哚 | 75074-77-0

• 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
• 中文名称: 3-氨基-1-甲基-5H-吡啶[4,3-b]吲哚
• 中文别名: 3-氨基-1-甲基-5H-吡啶并[4,3-b]吲哚；3-氨基-1-甲基-5h-吡啶[4,3-b]吲哚
• 英文名称: Trp-P-2 acetate
• 英文别名: 3-amino-1-methyl-5H-pyrido[4,3-b]indole acetate；Tryptophan p 2 acetate；1-methyl-5H-pyrido[4,3-b]indol-2-ium-3-amine;acetate
• CAS: 75074-77-0
• 化学式: C₂H₄O₂*C₁₂H₁₁N₃
• 分子量: 257.292
• InChiKey: AASZBFHIHXZWRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  92
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氨基-1-甲基-5H-吡啶[4,3-b]吲哚 在 palladium on activated charcoal 、 hexacarbonyl molybdenum 双氧水 、 一水合肼 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-羟基氨基-1-甲基-5H-吡啶并(4,3-b)吲哚
  参考文献：
  名称：

  Synthesis and characterization of the aqueous solution chemistry of the food-derived carcinogen model N-acetoxy-N-(1-methyl-5H-pyrido[4,5-b]indol-3-yl)acetamide and its N-pivaloyloxy analogue

  摘要：

  We report the synthesis of N-acetoxy-N-(1-methyl-5H-pyrido[4,5-b]indol-3-yl)acetamide, 7, its N-pivaloyloxy analogue, 9, and improved synthesis of indole-2-acetonitrile, 3 (70% in five steps from indole-2-carboxylic acid), the carcinogenic amine Trp-P-2, 4 (40% from 3), and the nitro compound, 5 (40% from 4 by oxidation with H,02 using MO(CO)6 catalyst). In aqueous solution at neutral pH, 7 primarily undergoes C-O bond cleavage to yield the hydroxamic acid, 8, but under the same conditions the sterically hindered 9 decomposes predominately by N-O bond cleavage with a pH independent rate constant that is 7.5-fold smaller than that for 7. In the pH range 0.5-7.0 three different processes for the decomposition of 9 were detected by kinetics. Only the process that dominates at neutral pH generates a nitrenium species that can be trapped by N ((3)) over bar. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.08.005
• 作为产物：
  描述：

  1,2-二氢-2-氰基喹啉-1-羧酸乙酯 在 三氯化铝 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 3-氨基-1-甲基-5H-吡啶[4,3-b]吲哚
  参考文献：
  名称：

  Synthesis of mutagens isolated from tryptophan pyrolysate and of some analogs, 3-amino-5H-pyrido(4,3-b)indoles.

  摘要：

  一种强效的诱变剂3-氨基-1-甲基-5H-吡啶[4,3-b]吲哚，来自于色氨酸热解物，并合成了一些类似物。关键反应是AlCl3催化的2-氰基甲基吲哚与烷基（或苯基）氰化物的缩合反应。

  DOI：

  10.1248/cpb.29.1280

文献信息

• γ-Carboline derivatives with anti-bovine viral diarrhea virus (BVDV) activity
  作者：Kumiko Sako、Hiroshi Aoyama、Shinichi Sato、Yuichi Hashimoto、Masanori Baba

  DOI：10.1016/j.bmc.2008.01.052

  日期：2008.4.1

  Based on anti-viral screening of our heteroaromatics derived from thalidomide, the gamma-carboline skeleton has been identified as a superior scaffold structure for compounds with potent anti-bovine viral diarrhea virus (BVDV) activity. Structural development studies led to a potent anti-viral agent, SK5M (5-methyl-gamma-carboline), with the EC50 of 0.26 mu M. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of genotoxic heterocyclic amines Trp-P-1 and Trp-P-2
  作者：Satoshi Hibino、Eiichi Sugino、Takeshi Kuwada、Naoki Ogura、Kohichi Sato、Tominari Choshi

  DOI：10.1021/jo00048a026

  日期：1992.10

  Trp-P-1 (1a) and Trp-P-2 (1b) possessing a pyrido[4,3-b]indole system have been newly synthesized. The key reaction step in the synthetic sequence has been the thermal electrocyclic reaction of the 1-azahexa-1,3,5-triene system 3 involving the indole [b] bond derived from 2-vinylindoles 4. 2-Vinylindole 4a has been derived from N-(benzenesulfonyl)indole (5) in a four-step sequence. 2-Vinylindole 4b has been synthesized by two routes using either ethoxymethylidene Meldrum's acid (6b) or diethyl ethoxymethylidenemalonate (10) as Michael acceptors to the 2-lithio-N-(benzenesulfonyl)indole.
• AKIMOTO, HIROSHI;KAWAI, AKIYOSHI;NOMURA, HIROAKI, BULL. CEM. SOC. JAP., 1985, 58, N 1, 123-130
  作者：AKIMOTO, HIROSHI、KAWAI, AKIYOSHI、NOMURA, HIROAKI

  DOI：——

  日期：——
• US8226992B1
  申请人：——

  公开号：US8226992B1

  公开（公告）日：2012-07-24
• Synthesis of mutagens isolated from tryptophan pyrolysate and of some analogs, 3-amino-5H-pyrido(4,3-b)indoles.
  作者：KEI TAKEDA、KOICHI SHUDO、TOSHIHIKO OKAMOTO、TAKUO KOSUGE

  DOI：10.1248/cpb.29.1280

  日期：——

  A potent mutagen, 3-amino-1-methyl-5H-pyrido [4, 3-b] indole, isolated from tryptophan pyrolysate, and some analogs were synthesized. The key reaction was the AlCl3-catalyzed condensation of 2-cyanomethylindole and alkyl (or phenyl) cyanide.

  一种强效的诱变剂3-氨基-1-甲基-5H-吡啶[4,3-b]吲哚，来自于色氨酸热解物，并合成了一些类似物。关键反应是AlCl3催化的2-氰基甲基吲哚与烷基（或苯基）氰化物的缩合反应。