tert-butyl 4-(1-methyl-4-(1-methyl-4-(3-(methylsulfonyl)propanamido)-1H-pyrrole-2-carboxamido)-1H-pyrrole-2-carboxamido)butanoate | 1335228-85-7

• 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 4-(1-methyl-4-(1-methyl-4-(3-(methylsulfonyl)propanamido)-1H-pyrrole-2-carboxamido)-1H-pyrrole-2-carboxamido)butanoate
• CAS: 1335228-85-7
• 化学式: C₂₄H₃₅N₅O₇S
• 分子量: 537.637
• InChiKey: IVLVGYCRMKELFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  157.6
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(1-methyl-4-(1-methyl-4-(3-(methylsulfonyl)propanamido)-1H-pyrrole-2-carboxamido)-1H-pyrrole-2-carboxamido)butanoate 在 盐酸 、 4-二甲氨基吡啶 、 甲酸 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 生成 N-(4-((6-((7R,13S,17S)-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenathren-7-yl)hexyl)amino)-4-oxobutyl)-1-methyl-4-(1-methyl-4-(3-(methylsulfonyl)propanamido)-1H-pyrrole-2-carboxamido)-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  DNA site-specific N3-adenine methylation targeted to estrogen receptor-positive cells

  摘要：

  A compound that can target cells expressing the estrogen receptor (ER), and produce predominantly 3-MeA adducts in those cells has been designed and synthesized. This compound produces mainly the 3-MeA adduct upon reaction with calf thymus DNA, and binds to the ER with a relative binding affinity of 51% (estradiol = 100%). The compound is toxic to ER-expressing MCF-7 breast cancer cells, and pretreatment with the ER antagonist fulvestrant abrogates the toxicity. Pre-treatment of MCF-7 cells with netropsin, which inhibits N3-adenine methylation by the compound, resulted in a threefold decrease in the toxicity. These results demonstrate the feasibility of this strategy for producing 3-MeA adducts in targeted cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.026
• 作为产物：
  描述：

  1-甲基-4-硝基-2-(三氟乙酰)-1H-吡咯 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、482.64 kPa 条件下， 反应 96.0h， 生成 tert-butyl 4-(1-methyl-4-(1-methyl-4-(3-(methylsulfonyl)propanamido)-1H-pyrrole-2-carboxamido)-1H-pyrrole-2-carboxamido)butanoate
  参考文献：
  名称：

  DNA site-specific N3-adenine methylation targeted to estrogen receptor-positive cells

  摘要：

  A compound that can target cells expressing the estrogen receptor (ER), and produce predominantly 3-MeA adducts in those cells has been designed and synthesized. This compound produces mainly the 3-MeA adduct upon reaction with calf thymus DNA, and binds to the ER with a relative binding affinity of 51% (estradiol = 100%). The compound is toxic to ER-expressing MCF-7 breast cancer cells, and pretreatment with the ER antagonist fulvestrant abrogates the toxicity. Pre-treatment of MCF-7 cells with netropsin, which inhibits N3-adenine methylation by the compound, resulted in a threefold decrease in the toxicity. These results demonstrate the feasibility of this strategy for producing 3-MeA adducts in targeted cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.026