2-[2-(2-bromo-1,1-dimethoxyethyl)-1,3-oxazol-4-yl]-N-[(2R,3S)-1-[[(2S)-1-[[(1S)-1-[4-(4-carbamothioyl-1,3-oxazol-2-yl)-1,3-oxazol-2-yl]-2-[(2-methylpropan-2-yl)oxy]ethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]-5-phenyl-1,3-oxazole-4-carboxamide | 1064766-42-2

• 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: 2-[2-(2-bromo-1,1-dimethoxyethyl)-1,3-oxazol-4-yl]-N-[(2R,3S)-1-[[(2S)-1-[[(1S)-1-[4-(4-carbamothioyl-1,3-oxazol-2-yl)-1,3-oxazol-2-yl]-2-[(2-methylpropan-2-yl)oxy]ethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]-5-phenyl-1,3-oxazole-4-carboxamide
• CAS: 1064766-42-2
• 化学式: C₄₁H₅₁BrN₈O₁₀S
• 分子量: 927.874
• InChiKey: MCIFJQSPRUYOHX-FQZUIQCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  61
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  277
• 氢给体数：
  4
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2-[2-(2-bromo-1,1-dimethoxyethyl)-1,3-oxazol-4-yl]-N-[(2R,3S)-1-[[(2S)-1-[[(1S)-1-[4-(4-carbamothioyl-1,3-oxazol-2-yl)-1,3-oxazol-2-yl]-2-[(2-methylpropan-2-yl)oxy]ethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]-5-phenyl-1,3-oxazole-4-carboxamide 在 甲酸 作用下， 反应 1.0h， 生成 2-[2-(2-bromoacetyl)-1,3-oxazol-4-yl]-N-[(2R,3S)-1-[[(2S)-1-[[(1S)-1-[4-(4-carbamothioyl-1,3-oxazol-2-yl)-1,3-oxazol-2-yl]-2-hydroxyethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]-5-phenyl-1,3-oxazole-4-carboxamide
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Mechercharmycin A Analogues

  摘要：

  Several analogues of the cytotoxic thiopeptide IB-01211 or mechercharmycin A (1) have been synthesized. The cytotoxicity of 1 and the synthesized analogues were evaluated against a panel of three human tumor cell lines. Thiopeptide 1 and the most active derivatives 2 and 3c were chosen for further studies on effects on cell cycle progression and induction of apoptosis. Interestingly, the inhibition of cell division and activation of a programmed cell death by apoptosis were detected.

  DOI：

  10.1021/jm800513w
• 作为产物：
  描述：

  (2S)-2-[[(2R,3S)-2-[[2-[2-(2-bromo-1,1-dimethoxyethyl)-1,3-oxazol-4-yl]-5-phenyl-1,3-oxazole-4-carbonyl]amino]-3-methylpentanoyl]amino]-3-methylbutanoic acid 、 2-[2-[(1S)-1-amino-2-[(2-methylpropan-2-yl)oxy]ethyl]-1,3-oxazol-4-yl]-1,3-oxazole-4-carbothioamide 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 2-[2-(2-bromo-1,1-dimethoxyethyl)-1,3-oxazol-4-yl]-N-[(2R,3S)-1-[[(2S)-1-[[(1S)-1-[4-(4-carbamothioyl-1,3-oxazol-2-yl)-1,3-oxazol-2-yl]-2-[(2-methylpropan-2-yl)oxy]ethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]-5-phenyl-1,3-oxazole-4-carboxamide
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Mechercharmycin A Analogues

  摘要：

  Several analogues of the cytotoxic thiopeptide IB-01211 or mechercharmycin A (1) have been synthesized. The cytotoxicity of 1 and the synthesized analogues were evaluated against a panel of three human tumor cell lines. Thiopeptide 1 and the most active derivatives 2 and 3c were chosen for further studies on effects on cell cycle progression and induction of apoptosis. Interestingly, the inhibition of cell division and activation of a programmed cell death by apoptosis were detected.

  DOI：

  10.1021/jm800513w

文献信息

• Synthesis and Antitumor Activity of Mechercharmycin A Analogues
  作者：Delia Hernández、Marta Altuna、Carmen Cuevas、Rosa Aligué、Fernando Albericio、Mercedes Álvarez

  DOI：10.1021/jm800513w

  日期：2008.9.25

  Several analogues of the cytotoxic thiopeptide IB-01211 or mechercharmycin A (1) have been synthesized. The cytotoxicity of 1 and the synthesized analogues were evaluated against a panel of three human tumor cell lines. Thiopeptide 1 and the most active derivatives 2 and 3c were chosen for further studies on effects on cell cycle progression and induction of apoptosis. Interestingly, the inhibition of cell division and activation of a programmed cell death by apoptosis were detected.