O-(2-methoxy-α-phenylbenzyl)hydroxylamine | 1221398-71-5

• 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: O-(2-methoxy-α-phenylbenzyl)hydroxylamine
• 英文别名: O-((2-methoxyphenyl)phenylmethyl)hydroxylamine；O-[(2-methoxyphenyl)-phenylmethyl]hydroxylamine
• CAS: 1221398-71-5
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: PNPDSKOEXKULSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O-(2-methoxy-α-phenylbenzyl)hydroxylamine 在 盐酸 作用下， 以 乙醚 、 水 为溶剂， 以89%的产率得到O-(2-methoxy-α-phenylbenzyl)hydroxylamine hydrochloride
  参考文献：
  名称：

  Diaryl hydroxylamines as pan or dual inhibitors of indoleamine 2,3-dioxygenase-1, indoleamine 2,3-dioxygenase-2 and tryptophan dioxygenase

  摘要：

  Tryptophan (Trp) catabolizing enzymes play an important and complex role in the development of cancer. Significant evidence implicates them in a range of inflammatory and immunosuppressive activities. Whereas inhibitors of indoleamine 2,3-dioxygenase-1 (IDO1) have been reported and analyzed in the clinic, fewer inhibitors have been described for tryptophan dioxygenase (TDO) and indoleamine 2,3-dioxygenase-2 (IDO2) which also have been implicated more recently in cancer, inflammation and immune control. Consequently the development of dual or pan inhibitors of these Trp catabolizing enzymes may represent a therapeutically important area of research. This is the first report to describe the development of dual and pan inhibitors of IDO1, TDO and IDO2. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.11.010
• 作为产物：
  描述：

  2-甲氧基二苯甲醇 在 N-羟基邻苯二甲酰亚胺 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 O-(2-methoxy-α-phenylbenzyl)hydroxylamine
  参考文献：
  名称：

  Diaryl hydroxylamines as pan or dual inhibitors of indoleamine 2,3-dioxygenase-1, indoleamine 2,3-dioxygenase-2 and tryptophan dioxygenase

  摘要：

  Tryptophan (Trp) catabolizing enzymes play an important and complex role in the development of cancer. Significant evidence implicates them in a range of inflammatory and immunosuppressive activities. Whereas inhibitors of indoleamine 2,3-dioxygenase-1 (IDO1) have been reported and analyzed in the clinic, fewer inhibitors have been described for tryptophan dioxygenase (TDO) and indoleamine 2,3-dioxygenase-2 (IDO2) which also have been implicated more recently in cancer, inflammation and immune control. Consequently the development of dual or pan inhibitors of these Trp catabolizing enzymes may represent a therapeutically important area of research. This is the first report to describe the development of dual and pan inhibitors of IDO1, TDO and IDO2. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.11.010

文献信息

• Discovery of novel and potent benzhydryl-tropane trypanocides highly selective for Trypanosoma cruzi
  作者：G.A. Holloway、J.P. Parisot、P.M. Novello、K.G. Watson、T. Armstrong、R.C.A. Thompson、I.P. Street、J.B. Baell

  DOI：10.1016/j.bmcl.2010.02.022

  日期：2010.3

  A benzhydryl tropinone oxime that is potently toxic to Trypanosoma cruzi has been previously identified. An SAR investigation determined that no part of the original compound was superfluous and all early SAR probes led to significant drops in activity. The only alteration that could be achieved without loss of activity was replacement of the aryl chloride substituent with chloro homologues. This led to the discovery of a trifluoromethyl-containing analogue with an EC50 against T. cruzi of 30 nM and a cytotoxicity selectivity index of over 1000 relative to rat skeletal myoblast L-6 cells. (C) 2010 Elsevier Ltd. All rights reserved.