ethyl 2-[(2S,3S)-3,4-epoxy-2-(3-methoxy-5-methyl-1-naphthoyl)-3-methylbutyryl]amino-2-[(R)-5-methanesulfonyloxymethylpyrrolidin-2-ylidene]acetate | 228120-02-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 2-[(2S,3S)-3,4-epoxy-2-(3-methoxy-5-methyl-1-naphthoyl)-3-methylbutyryl]amino-2-[(R)-5-methanesulfonyloxymethylpyrrolidin-2-ylidene]acetate
• CAS: 228120-02-3
• 化学式: C₂₈H₃₄N₂O₁₀S
• 分子量: 590.651
• InChiKey: SXFOTVVWXAQMAB-IYAPBYRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  158.86
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(2S,3S)-3,4-epoxy-2-(3-methoxy-5-methyl-1-naphthoyl)-3-methylbutyryl]amino-2-[(R)-5-methanesulfonyloxymethylpyrrolidin-2-ylidene]acetate 在 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 (2S,3S)-3,4-环氧-2-(3-甲氧基-5-甲基-1-萘氧基)-3-甲基丁酰胺
  参考文献：
  名称：

  Synthesis, chemical property, and cytotoxicity of the carzinophilin congeners carrying a 2-(1-acylamino-1-alkoxycarbonyl)methylidene-1-azabicyclo[3.1.0]hexane system

  摘要：

  Synthesis of the title compounds was achieved by employing condensation of the 2-methoxy-1-pyrroline with ethyl nitroacetate and construction of 1-azabicyclo[3.1.0]hexane systems from 5-mesyloxymethylpyrrolidines as key steps. Some of these congeners which carry a C-6-C-11 unit involving the naphthalene part, were found to exhibit prominent cytotoxicity and effectively alkylate nucleophiles at both the aziridine and epoxide moieties.

  DOI：

  10.1016/s0040-4039(00)76798-0
• 作为产物：
  描述：

  Amino-[(R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-acetic acid ethyl ester 在 四丁基氟化铵 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl 2-[(2S,3S)-3,4-epoxy-2-(3-methoxy-5-methyl-1-naphthoyl)-3-methylbutyryl]amino-2-[(R)-5-methanesulfonyloxymethylpyrrolidin-2-ylidene]acetate
  参考文献：
  名称：

  Synthesis, chemical property, and cytotoxicity of the carzinophilin congeners carrying a 2-(1-acylamino-1-alkoxycarbonyl)methylidene-1-azabicyclo[3.1.0]hexane system

  摘要：

  Synthesis of the title compounds was achieved by employing condensation of the 2-methoxy-1-pyrroline with ethyl nitroacetate and construction of 1-azabicyclo[3.1.0]hexane systems from 5-mesyloxymethylpyrrolidines as key steps. Some of these congeners which carry a C-6-C-11 unit involving the naphthalene part, were found to exhibit prominent cytotoxicity and effectively alkylate nucleophiles at both the aziridine and epoxide moieties.

  DOI：

  10.1016/s0040-4039(00)76798-0

文献信息

• Synthetic studies of carzinophilin. Part 1: Synthesis of 2-methylidene-1-azabicyclo[3.1.0]hexane systems related to carzinophilin
  作者：Masaru Hashimoto、Miyoko Matsumoto、Shiro Terashima

  DOI：10.1016/s0040-4020(03)00377-6

  日期：2003.4

  Synthesis of the model compounds of carzinophilin carrying 2-methylidene-1-aza-bicyclo[3.1.0]hexane systems was achieved. Formation of malonylidenes or N-acyl-glycinylidenepyrrolidines was carried out by utilizing Eschenmoser's sulfide contraction or Herdeis's condensation between the 2-methylthio-Δ1-pyrrolone derivatives and ethyl nitroacetate, respectively. The 1-azabicyclo-[3.1.0]hexane systems

  合成了带有2-亚甲基-1-氮杂-双环[3.1.0]己烷体系的卡那菲林模型化合物。malonylidenes或形成ñ酰基-glycinylidenepyrrolidines通过利用Eschenmoser的硫化物的收缩或Herdeis的2-甲硫-Δ之间的缩合进行1个分别-pyrrolone衍生物和硝基乙酸乙酯。1-氮杂双环-[3.1.0]己烷体系是通过碱促进的氮丙啶形成而构建的。
• A Synthetic Azinomycin Analogue with Demonstrated DNA Cross-Linking Activity: Insights into the Mechanism of Action of this Class of Antitumor Agent
  作者：John A. Hartley、Ali Hazrati、Lloyd R. Kelland、Ruzwana Khanim、Michael Shipman、Franck Suzenet、Louise F. Walker

  DOI：10.1002/1521-3773(20001002)39:19<3467::aid-anie3467>3.0.co;2-t

  日期：2000.10.2