4-aza-6-oximotryptanthrin | 1224882-72-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 4-aza-6-oximotryptanthrin
• 英文别名: 11-(hydroxyimino)pyrido[2',3':4,5]pyrimido[1,2-α]indol-5(11H)-one
• CAS: 1224882-72-7
• 化学式: C₁₄H₈N₄O₂
• 分子量: 264.243
• InChiKey: OAYVXFMPXXTMHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.37
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  靛红 在 吡啶 、 盐酸羟胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.17h， 生成 4-aza-6-oximotryptanthrin
  参考文献：
  名称：

  AZA-TRYPTANTHRIN DERIVATIVES AS IDO1 AND/OR TDO INHIBITORS

  摘要：

  公开号：

  EP3421472B1

文献信息

• NITROGEN HETEROCYCLIC TRYPTAMINE KETONE DERIVATIVE AND APPLICATION AS IDO1 AND/OR TDO INHIBITOR
  申请人：Peking University

  公开号：EP3421472A1

  公开（公告）日：2019-01-02

  This invention discloses the use of aza-tryptanthrin derivatives as an IDO1 and/or TDO inhibitors, and the derivatives are represented by the general Formula (I). The compounds represented by the Formula (I) have inhibitory effects on indoleamine-2,3-dioxygenase 1 (IDO1) and/or tryptophan-2,3-dioxygenase (TDO), and can be used for treating diseases having the pathological features of IDO1 and/or TDO-mediated tryptophan metabolism, including but not limited to tumors, autoimmune disease, infectious diseases, Alzheimer's disease, depression, anxiety.

  本发明公开了氮杂色蒽衍生物作为IDO1和/或TDO抑制剂的用途，其衍生物由通式（I）表示。由式（I）表示的化合物对吲哚胺-2,3-二氧合酶1（IDO1）和/或色氨酸-2,3-二氧合酶（TDO）具有抑制作用，可用于治疗具有IDO1和/或TDO介导的色氨酸代谢病理特征的疾病，包括但不限于肿瘤、自身免疫性疾病、传染性疾病、阿尔茨海默病、抑郁症、焦虑症等。
• Use of aza-tryptanthrin derivatives as inhibitors of IDO1 and/or TDO
  申请人：Peking University

  公开号：US10669273B2

  公开（公告）日：2020-06-02

  This invention discloses the use of aza-tryptanthrin derivatives as an IDO1 and/or TDO inhibitors, and the derivatives are represented by the general Formula (I). The compounds represented by the Formula (I) have inhibitory effects on indoleamine-2,3-dioxygenase 1 (IDO1) and/or tryptophan-2,3-dioxygenase (TDO), and can be used for treating diseases having the pathological features of IDO1 and/or TDO-mediated tryptophan metabolism, including but not limited to tumors, autoimmune disease, infectious diseases, Alzheimer's disease, depression, anxiety.

  本发明公开了氮杂色蒽衍生物作为IDO1和/或TDO抑制剂的用途，其衍生物由通式（I）表示。由式（I）表示的化合物对吲哚胺-2,3-二氧合酶1（IDO1）和/或色氨酸-2,3-二氧合酶（TDO）具有抑制作用，可用于治疗具有IDO1和/或TDO介导的色氨酸代谢病理特征的疾病，包括但不限于肿瘤、自身免疫性疾病、传染性疾病、阿尔茨海默病、抑郁症、焦虑症等。
• Antimicrobial Activity of Tryptanthrins in <i>Escherichia coli</i>
  作者：Pooja P. Bandekar、Keir Alekseii Roopnarine、Virali J. Parekh、Thomas R. Mitchell、Mark J. Novak、Richard R. Sinden

  DOI：10.1021/jm901847f

  日期：2010.5.13

  Tryptanthrins have potential therapeutic activity against a wide variety of pathogenic organisms, although little is known about their mechanism. Activity against Escherichia colt, however, has not been examined. The effects of tryptanthrin (indolo[2,1-b]quinazolin-6,12-dione) and nine derivatives on growth, survival, and mutagenesis in E. colt were examined. Analogues with a nitrogen atom at the 4-position of tryptanthrin stopped log phase growth of E. coli cultures at concentrations as low as 5 mu M. Tryptanthrins decreased viability during incubation with cells in buffer by factors of 10(-2) to < 10(-6) at 0.2-40 mu M. Derivatives with an oxime group at the 6-position exhibited the greatest bactericidal activity. Most tryptanthrins were not mutagenic in several independent assays, although the 4-aza and 4 aza-8-fluoro derivatives increased frameshift mutations about 22- and 4-fold, respectively. Given the structure of trypanthrins, binding to DNA may occur by intercalation. From analysis using a sensitive linking number assay, several tryptanthrins, especially the 4-aza and 6-oximo derivatives, intercalate into DNA.
• Use of Aza-Tryptanthrin Derivatives as Inhibitors of IDO1 and/or TDO
  申请人：Peking University

  公开号：US20190112308A1

  公开（公告）日：2019-04-18

  This invention discloses the use of aza-tryptanthrin derivatives as an IDO1 and/or TDO inhibitors, and the derivatives are represented by the general Formula (I). The compounds represented by the Formula (I) have inhibitory effects on indoleamine-2,3-dioxygenase 1 (IDO1) and/or tryptophan-2,3-dioxygenase (TDO), and can be used for treating diseases having the pathological features of IDO1 and/or TDO-mediated tryptophan metabolism, including but not limited to tumors, autoimmune disease, infectious diseases, Alzheimer's disease, depression, anxiety.