Nb-acetyltryptamine-4,5-dione | 172983-04-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Nb-acetyltryptamine-4,5-dione
• 英文别名: N-acetyltryptamine-4,5-dione；N-[2-(4,5-dioxo-1H-indol-3-yl)ethyl]acetamide
• CAS: 172983-04-9
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: WNKIXYMIBXISAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Nb-acetyltryptamine-4,5-dione 在 三乙胺 、 锌 作用下， 反应 0.33h， 生成
  参考文献：
  名称：

  Preparations of Tryptamine-4,5-dinones, and Their Diels-Alder and Nucleophilic Addition Reactions

  摘要：

  Syntheses of Nb-acetyltryptamine-4,5-dione and (+/-)-Nb-acetyltryptophan-4,5-dione methyl ester are reported. They were excellent dienophiles as well as good electrophiles, and produced 6,7-disubstituted indoles in Diels-Alder reaction and various 7-substituted indoles with nucleophiles.

  DOI：

  10.3987/com-95-7189
• 作为产物：
  描述：

  N-乙酰-5-羟色胺 在 potassium nitrososulfonate 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以99%的产率得到Nb-acetyltryptamine-4,5-dione
  参考文献：
  名称：

  Preparations of Tryptamine-4,5-dinones, and Their Diels-Alder and Nucleophilic Addition Reactions

  摘要：

  Syntheses of Nb-acetyltryptamine-4,5-dione and (+/-)-Nb-acetyltryptophan-4,5-dione methyl ester are reported. They were excellent dienophiles as well as good electrophiles, and produced 6,7-disubstituted indoles in Diels-Alder reaction and various 7-substituted indoles with nucleophiles.

  DOI：

  10.3987/com-95-7189

文献信息

• Further insights into the reaction of melatonin with hydroxyl radical
  作者：Joseph A. Horstman、Monika Z. Wrona、Glenn Dryhurst

  DOI：10.1016/s0045-2068(02)00511-4

  日期：2002.10

  Recent interest has focused on the use of exogenous melatonin as an antioxidant, particularly to scavenge the highly cytotoxic hydroxyl radical (HO.) which may be generated in many pathological conditions. However, in vitro and in vivo studies aimed at assessing the antioxidant properties of melatonin have produced conflicting results. While it is known that HO, reacts with melatonin at a diffusion limited rate, very little is known about the products of this reaction. In this investigation it is shown that incubation of melatonin with a Fenton-type HO.-generating system at pH 7.4 forms a complex mixture of primary products. These include 2-hydroxymelatonin, which was isolated as its more stable oxindole tautomer, 4- and 6-hydroxymelatonin, N-acetyl-N-2-formyl-5-methoxykynurenine and 7,7'-bi-(5-methoxy-N-acetyltryptamine-4-one). Reaction pathways that might lead to these products are described. The differing biological effects of these products, while currently incompletely understood, might account for the controversy concerning the antioxidant properties of melatonin. (C) 2002 Published by Elsevier Science (USA).
• Preparations of Tryptamine-4,5-dinones, and Their Diels-Alder and Nucleophilic Addition Reactions
  作者：Masanori Somei、Yoshikazu Fukui、Masakazu Hasegawa

  DOI：10.3987/com-95-7189

  日期：——

  Syntheses of Nb-acetyltryptamine-4,5-dione and (+/-)-Nb-acetyltryptophan-4,5-dione methyl ester are reported. They were excellent dienophiles as well as good electrophiles, and produced 6,7-disubstituted indoles in Diels-Alder reaction and various 7-substituted indoles with nucleophiles.