4-amino-N-(3-bromophenyl)-N'-hydroxy-1,2,5-oxadiazole-3-carboximidamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-amino-N-(3-bromophenyl)-N'-hydroxy-1,2,5-oxadiazole-3-carboximidamide
• 英文别名: 4-Amino-N-(3-bromophenyl)-N''-hydroxy-1,2,5-oxadiazole-3-carboximidamide；4-amino-N'-(3-bromophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide
• 化学式: C₉H₈BrN₅O₂
• 分子量: 298.099
• InChiKey: HVSMGKDKCTVBDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氨基-1,2,5-恶二唑-3-氯化甲醛肟 、 间溴苯胺 以 乙醇 为溶剂， 反应 2.0h， 生成 4-amino-N-(3-bromophenyl)-N'-hydroxy-1,2,5-oxadiazole-3-carboximidamide
  参考文献：
  名称：

  在小鼠黑素瘤模型中发现具有吲哚胺2,3-双加氧酶的强效竞争性抑制剂的体内药效学活性和功效

  摘要：

  在吲哚胺2，3-二加氧酶（IDO）的新型抑制剂中，已发现羟am的化学型是关键药效团。优化导致鉴定出5l，这是IDO的一种有力（HeLa IC 50 = 19 nM）竞争性抑制剂。小鼠中5l的测试证明IDO具有药效学抑制作用，这是通过血浆中犬尿氨酸水平降低（> 50％）和携带分泌GM-CSF的B16黑色素瘤肿瘤的小鼠的剂量依赖性功效来衡量的。

  DOI：

  10.1021/jm900518f

文献信息

• Modulators of indoleamine 2,3-dioxygenase and methods of using the same
  申请人：Combs P. Andrew

  公开号：US20060258719A1

  公开（公告）日：2006-11-16

  The present invention is directed to modulators of indoleamine 2,3-dioxygenase (IDO), as well as compositions and pharmaceutical methods thereof.

  本发明涉及色氨酸2,3-二氧化酶（IDO）的调节剂，以及其组合物和药用方法。
• MODULATORS OF INDOLEAMINE 2,3-DIOXYGENASE AND METHODS OF USING THE SAME
  申请人：Combs Andrew P.

  公开号：US20110311479A1

  公开（公告）日：2011-12-22

  The present invention is directed to modulators of indoleamine 2,3-dioxygenase (IDO), as well as compositions and pharmaceutical methods thereof.

  本发明涉及吲哚胺2,3-二氧化酶(IDO)的调节剂，以及其组成物和制药方法。
• Discovery of phosphonamidate IDO1 inhibitors for the treatment of non-small cell lung cancer
  作者：Qianming Du、Xi Feng、Yinuo Wang、Xi Xu、Yan Zhang、Xinliang Qu、Zhiyu Li、Jinlei Bian

  DOI：10.1016/j.ejmech.2019.111629

  日期：2019.11

  Targeting indoleamine 2,3-dioxygenase 1 (IDO1) has been identified as an attractive approach for the development of cancer immunotherapy. In this study, a series of phosphonamidate ester containing compounds were designed, synthesized and evaluated for their inhibitory activities against IDOL. Among them, compounds 16,17, and 26 with good IDO1 inhibitory (HeLa IDO1 IC50 = 10-21 nM, hIDO1 IC50 = 78 -121 nM) activities were selected for further investigation and showed good physicochemical properties. Furthermore, based on comparable PK profile and excellent IDO2/TDO inhibitory potency, representative compound 16 was selected for further bio-evaluation and characterized with good efficacy in suppressing lung metastasis (77% inhibition rate) of Lewis cells in vivo. Thus, compound 16 could be a potential and efficacious agent for further evaluation. (C) 2019 Elsevier Masson SAS. All rights reserved.
• US8034953B2
  申请人：——

  公开号：US8034953B2

  公开（公告）日：2011-10-11
• US8372870B2
  申请人：——

  公开号：US8372870B2

  公开（公告）日：2013-02-12