tert-butyl N-[4-[bis[2-[3-[4-bromo-2-[3-(4-methylpiperazin-1-yl)propanoylamino]phenyl]sulfanylanilino]-2-oxoethyl]amino]-4-oxobutyl]carbamate | 354815-11-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl N-[4-[bis[2-[3-[4-bromo-2-[3-(4-methylpiperazin-1-yl)propanoylamino]phenyl]sulfanylanilino]-2-oxoethyl]amino]-4-oxobutyl]carbamate
• CAS: 354815-11-5
• 化学式: C₅₃H₆₈Br₂N₁₀O₇S₂
• 分子量: 1181.13
• InChiKey: WTFSRXQSGQCPSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  74
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  239
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[4-[bis[2-[3-[4-bromo-2-[3-(4-methylpiperazin-1-yl)propanoylamino]phenyl]sulfanylanilino]-2-oxoethyl]amino]-4-oxobutyl]carbamate 在 sodium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 9H-fluoren-9-ylmethyl N-[4-[bis[2-[3-[4-bromo-2-[3-(4-methylpiperazin-1-yl)propanoylamino]phenyl]sulfanylanilino]-2-oxoethyl]amino]-4-oxobutyl]carbamate
  参考文献：
  名称：

  Potent and specific inhibitors of trypanothione reductase from Trypanosoma cruzi

  摘要：

  In order to optimise the activity of bis(2-aminodiphenylsulfides) upon trypanothione reductase (TR) from Trypanosoma cruzi, a new series of bis(2-aminodiphenylsulfides) possessing three side chains was synthesized. Various moieties were introduced at the end of the third side chain. including acridinyl or biotinyl moieties for fluorescent labeling studies. TR inhibition was improved: the most potent inhibitor (IC50 = 200 nM) was selective towards TR versus human glutathione reductase and corresponded to a single myristyl group. Compounds were also tested in vitro upon Trypanosoma cruzi and Leishmania infantum amastigotes, upon Trypanosoma brucei trypomastigotes, and for their cytotoxicity upon human MRC-5 cells. In the presence of serum, acridine derivative was no longer detectable in mass spectrometry and its antitrypanosomal activity no longer observed. This transformation might explain the absence of correlation between the potent TR inhibition and the in vitro and in vivo antiparasitic activity with both of the first generation of 2-aminodiphenylsulfides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00312-6
• 作为产物：
  描述：

  2-(9-fluorenylmethyloxycarbonyl)imino-N,N'-[3-(2-amino-4-bromo)phenylsulfanyl]phenyldiacetylamide 在 N-乙基哌啶 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.17h， 生成 tert-butyl N-[4-[bis[2-[3-[4-bromo-2-[3-(4-methylpiperazin-1-yl)propanoylamino]phenyl]sulfanylanilino]-2-oxoethyl]amino]-4-oxobutyl]carbamate
  参考文献：
  名称：

  Potent and specific inhibitors of trypanothione reductase from Trypanosoma cruzi

  摘要：

  In order to optimise the activity of bis(2-aminodiphenylsulfides) upon trypanothione reductase (TR) from Trypanosoma cruzi, a new series of bis(2-aminodiphenylsulfides) possessing three side chains was synthesized. Various moieties were introduced at the end of the third side chain. including acridinyl or biotinyl moieties for fluorescent labeling studies. TR inhibition was improved: the most potent inhibitor (IC50 = 200 nM) was selective towards TR versus human glutathione reductase and corresponded to a single myristyl group. Compounds were also tested in vitro upon Trypanosoma cruzi and Leishmania infantum amastigotes, upon Trypanosoma brucei trypomastigotes, and for their cytotoxicity upon human MRC-5 cells. In the presence of serum, acridine derivative was no longer detectable in mass spectrometry and its antitrypanosomal activity no longer observed. This transformation might explain the absence of correlation between the potent TR inhibition and the in vitro and in vivo antiparasitic activity with both of the first generation of 2-aminodiphenylsulfides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00312-6