3-chloro-1-(10H-phenoxazin-10-yl)propan-1-one | 92433-61-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 3-chloro-1-(10H-phenoxazin-10-yl)propan-1-one
• 英文别名: 10-<3-Chlor-propionyl>-phenoxazin；10-(3-chloro-propionyl)-10H-phenoxazine；3-Chloro-1-phenoxazin-10-ylpropan-1-one；3-chloro-1-phenoxazin-10-ylpropan-1-one
• CAS: 92433-61-9
• 化学式: C₁₅H₁₂ClNO₂
• 分子量: 273.719
• InChiKey: UAZVMKQSSWBCHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 3-chloro-1-(10H-phenoxazin-10-yl)propan-1-one 以 丁酮 为溶剂， 反应 10.0h， 生成 10-[3-(4-methyl-piperazin-1-yl)-propionyl]-10H-phenoxazine
  参考文献：
  名称：

  De Antoni,J., Bulletin de la Societe Chimique de France, 1963, p. 2874 - 2877

  摘要：

  DOI：
• 作为产物：
  描述：

  吩噁嗪 、 3-氯丙酰氯 以 甲苯 为溶剂， 反应 4.0h， 以79%的产率得到3-chloro-1-(10H-phenoxazin-10-yl)propan-1-one
  参考文献：
  名称：

  Inhibitory effect of phenothiazine- and phenoxazine-derived chloroacetamides on Leishmania major growth and Trypanosoma brucei trypanothione reductase

  摘要：

  A number of phenothiazine-, phenoxazine- and related tricyclics-derived chloroacetamides were synthesized and evaluated in vitro for antiprotozoal activities against Leishmania major (L. major) promastigotes. Several analogs were remarkably potent inhibitors, with antileishmanial activities being comparable or superior to those of the reference antiprotozoal drugs. Furthermore, we explored the structure activity relationships of N-10 haloacetamides that influence the potency of such analogs toward inhibition of L major promastigote growth in vitro. With respect to the mechanism of action, selected compounds were evaluated for time -dependent inactivation of Trypanosoma brucei trypanothione reductase. Our results are indicative of a covalent interaction which could account for potent antiprotozoal activities. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.023

文献信息

• Inhibitory effect of phenothiazine- and phenoxazine-derived chloroacetamides on Leishmania major growth and Trypanosoma brucei trypanothione reductase
  作者：Ana Marcu、Uta Schurigt、Klaus Müller、Heidrun Moll、R. Luise Krauth-Siegel、Helge Prinz

  DOI：10.1016/j.ejmech.2015.11.023

  日期：2016.1

  A number of phenothiazine-, phenoxazine- and related tricyclics-derived chloroacetamides were synthesized and evaluated in vitro for antiprotozoal activities against Leishmania major (L. major) promastigotes. Several analogs were remarkably potent inhibitors, with antileishmanial activities being comparable or superior to those of the reference antiprotozoal drugs. Furthermore, we explored the structure activity relationships of N-10 haloacetamides that influence the potency of such analogs toward inhibition of L major promastigote growth in vitro. With respect to the mechanism of action, selected compounds were evaluated for time -dependent inactivation of Trypanosoma brucei trypanothione reductase. Our results are indicative of a covalent interaction which could account for potent antiprotozoal activities. (C) 2015 Elsevier Masson SAS. All rights reserved.
• De Antoni,J., Bulletin de la Societe Chimique de France, 1963, p. 2874 - 2877
  作者：De Antoni,J.

  DOI：——

  日期：——