methyl N-[3-(2-chloro-10H-phenothiazin-10-yl)propanoyl]methionate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: methyl N-[3-(2-chloro-10H-phenothiazin-10-yl)propanoyl]methionate
• 英文别名: methyl (2S)-2-[3-(2-chlorophenothiazin-10-yl)propanoylamino]-4-methylsulfanylbutanoate
• 化学式: C₂₁H₂₃ClN₂O₃S₂
• 分子量: 451.01
• InChiKey: TWKKBFXITFUYGK-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  3-(2-氯吩噻嗪-10-基)丙酸	2-chloro-10-(2-carboxyethyl)-10H-phenothiazine	6853-90-3	C15H12ClNO2S	305.785
  2-氯-10H-吩噻嗪-10-丙腈	3-(2-chloro-10H-phenothiazin-10-yl)propanonitrile	4414-83-9	C15H11ClN2S	286.785

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	N-[3-(2-chloro-10H-phenothiazin-10-yl)propanoyl]methionine	——	C20H21ClN2O3S2	436.983

反应信息

• 作为反应物：
  描述：

  methyl N-[3-(2-chloro-10H-phenothiazin-10-yl)propanoyl]methionate 在 sodium hydroxide 作用下， 以 水 为溶剂， 以82%的产率得到N-[3-(2-chloro-10H-phenothiazin-10-yl)propanoyl]methionine
  参考文献：
  名称：

  Phenothiazine-based CaaX competitive inhibitors of human farnesyltransferase bearing a cysteine, methionine, serine or valine moiety as a new family of antitumoral compounds

  摘要：

  A new family of CaaX competitive inhibitors of human farnesyltransferase based on phenothiazine and carbazole skeleton bearing a L-cysteine, L-methionine, L-serine or L-valine moiety was designed, synthesized and biologically evaluated. Phenothiazine derivatives proved to be more active than carbazole-based compounds. Phenothiazine 1b with cysteine residue was the most promising inhibitor of human farnesyltransferase in the current study. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.008
• 作为产物：
  描述：

  2-氯吩噻嗪 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 65.0h， 生成 methyl N-[3-(2-chloro-10H-phenothiazin-10-yl)propanoyl]methionate
  参考文献：
  名称：

  Phenothiazine-based CaaX competitive inhibitors of human farnesyltransferase bearing a cysteine, methionine, serine or valine moiety as a new family of antitumoral compounds

  摘要：

  A new family of CaaX competitive inhibitors of human farnesyltransferase based on phenothiazine and carbazole skeleton bearing a L-cysteine, L-methionine, L-serine or L-valine moiety was designed, synthesized and biologically evaluated. Phenothiazine derivatives proved to be more active than carbazole-based compounds. Phenothiazine 1b with cysteine residue was the most promising inhibitor of human farnesyltransferase in the current study. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.008

文献信息

• Phenothiazine-based CaaX competitive inhibitors of human farnesyltransferase bearing a cysteine, methionine, serine or valine moiety as a new family of antitumoral compounds
  作者：Gina-Mirabela Dumitriu、Elena Bîcu、Dalila Belei、Benoît Rigo、Joëlle Dubois、Amaury Farce、Alina Ghinet

  DOI：10.1016/j.bmcl.2015.09.008

  日期：2015.10

  A new family of CaaX competitive inhibitors of human farnesyltransferase based on phenothiazine and carbazole skeleton bearing a L-cysteine, L-methionine, L-serine or L-valine moiety was designed, synthesized and biologically evaluated. Phenothiazine derivatives proved to be more active than carbazole-based compounds. Phenothiazine 1b with cysteine residue was the most promising inhibitor of human farnesyltransferase in the current study. (C) 2015 Elsevier Ltd. All rights reserved.