1-甲基-3-硝基-5H-吡啶并[4,3-b]吲哚 | 75567-58-7

• 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: 1-甲基-3-硝基-5H-吡啶并[4,3-b]吲哚
• 英文名称: 3-nitro-1-methyl-5H-pyrido[4,3-b]indole
• 英文别名: 1-methyl-3-nitro-5H-pyrido<4,3-b>indole；1-methyl-3-nitro-5H-pyrido[4,3-b]indole
• CAS: 75567-58-7
• 化学式: C₁₂H₉N₃O₂
• 分子量: 227.222
• InChiKey: MVHWCKZQGXOVJX-UHFFFAOYSA-N

物化性质

• 沸点：
  505.0±45.0 °C(Predicted)
• 密度：
  1.444±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-甲基-3-硝基-5H-吡啶并[4,3-b]吲哚 在 palladium on activated charcoal 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 2.5h， 生成 N-(1-甲基-5H-吡啶并[4,3-b]吲哚-3-基)-乙酰胺
  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：

  3-氨基-1-甲基-5H-吡啶[4,3-b]吲哚 在 hexacarbonyl molybdenum 双氧水 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 以40%的产率得到1-甲基-3-硝基-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

文献信息

• Deoxyribonucleic acid modification by mutagenic 3-amino-1-methyl-5H-pyrido(4,3-b)indole: The chemical events.
  作者：YUICHI HASHIMOTO、KOICHI SHUDO、TOSHIHIKO OKAMOTO

  DOI：10.1248/cpb.32.4300

  日期：——

  3-Amino-1-methyl-5H-pyrido [4, 3-b] indole (Trp-P-2) is a mutagen/carcinogen isolated from a pyrolysate of L-tryptophan. The active metabolite of Trp-P-2, 3-hydroxyamino-1-methyl-5H-pyrido [4, 3-b] indole (N-OH-Trp-P-2), was synthesized and the chemical reactions of N-OH-Trp-P-2 with deoxyribonucleic acid were investigated. The structure of the nucleic acid base covalently bound with Trp-P-2 was elucidated as 3-(C8-guanyl) amino-1-methyl-5H-pyrido [4, 3-b] indole (Gua-Trp-P-2) by comparison with a synthetic sample. The initial chemical events in carcinogenesis caused by Trp-P-2 were established.

  3-氨基-1-甲基-5H-吡啶并[4，3-b]吲哚（Trp-P-2）是从 L-色氨酸的热解产物中分离出来的一种诱变剂/致癌物质。研究人员合成了 Trp-P-2 的活性代谢物--3-羟基氨基-1-甲基-5H-吡啶并[4，3-b]吲哚（N-OH-Trp-P-2），并研究了 N-OH-Trp-P-2 与脱氧核糖核酸的化学反应。通过与合成样品的对比，阐明了与 Trp-P-2 共价结合的核酸碱基的结构为 3-(C8-鸟嘌呤基)氨基-1-甲基-5H-吡啶并[4, 3-b] 吲哚（Gua-Trp-P-2）。确定了 Trp-P-2 致癌的最初化学事件。
• 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
  作者：Sridharan Rajagopal、Michael E Brooks、Thach-Mien Nguyen、Michael Novak

  DOI：10.1016/j.tet.2003.08.005

  日期：2003.9

  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.