1-ethyl 4-methyl 2-hydroxy-2-(4-methoxyphenyl)-3-methylenesuccinate | 1173565-49-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-ethyl 4-methyl 2-hydroxy-2-(4-methoxyphenyl)-3-methylenesuccinate
• 英文别名: 1-O-ethyl 4-O-methyl 2-hydroxy-2-(4-methoxyphenyl)-3-methylidenebutanedioate
• CAS: 1173565-49-5
• 化学式: C₁₅H₁₈O₆
• 分子量: 294.304
• InChiKey: JUKHJPZMGOLDTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-ethyl 4-methyl 2-hydroxy-2-(4-methoxyphenyl)-3-methylenesuccinate 、 R(+)-alpha-甲基苄胺 在 三氟乙酸 作用下， 以 甲醇 、 1,4-二氧六环 为溶剂， 反应 72.0h， 生成 (3R,4R)-methyl 4-hydroxy-4-(4-methoxyphenyl)-5-oxo-1-((R)-1-phenylethyl)pyrrolidine-3-carboxylate
  参考文献：
  名称：

  Studies on the structure–activity relationship of 1,3,3,4-tetra-substituted pyrrolidine embodied CCR5 receptor antagonists. Part 2: Discovery of highly potent anti-HIV agents

  摘要：

  Modification of 1,3,3,4-tetra-substituted pyrrolidine embodied CCR5 receptor antagonists revealed that introducing a fluoro group at the 3-position of the 3-phenyl group to reduce metabolism did not adversely affect the high potency against HIV infection, and that replacing the piperidine ring with a tropane ring could deliver the most potent anti-HIV agents. Stereochemistry of the substituted tropane ring is essential for maintaining the potent anti-HIV activity because only exo-isomers displayed subnanomolar whole cell activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.046
• 作为产物：
  描述：

  乙酯4-甲氧基苯并基甲酸盐 、 丙烯酸甲酯（MA） 在 三乙烯二胺 作用下， 反应 240.0h， 以75%的产率得到1-ethyl 4-methyl 2-hydroxy-2-(4-methoxyphenyl)-3-methylenesuccinate
  参考文献：
  名称：

  [EN] PYROLLIDINE-BASED COMPOUNDS
  [FR] COMPOSÉS À BASE DE PYROLLIDINE

  摘要：

  本发明揭示了式（I）的化合物或其药学上可接受的衍生物、盐或前药，可以抑制HIV复制。

  公开号：

  WO2009089659A1

文献信息

• [EN] PYROLLIDINE-BASED COMPOUNDS<br/>[FR] COMPOSÉS À BASE DE PYROLLIDINE
  申请人：SHANGHAI TARGETDRUG CO LTD

  公开号：WO2009092293A1

  公开（公告）日：2009-07-30

  A compound of formula (I) or a pharmaceutically acceptable derivative, salt or prodrug thereof, which can inhibit HIV replication.

  一种化合物，其化学式为（I），或其药学上可接受的衍生物、盐或前药，能够抑制HIV的复制。
• A Facile One-Pot Transformation of Baylis-Hillman Adducts into Unsymmetrical Disubstituted Maleimide and Maleic Anhydride Frameworks: A Facile Synthesis of Himanimide A
  作者：Deevi Basavaiah、Badugu Devendar、Kunche Aravindu、Ainelly Veerendhar

  DOI：10.1002/chem.200902887

  日期：2010.2.15

  Unsymmetrical, disubstituted maleimide and maleic anhydride frameworks have been accessed from Baylis–Hillman adducts in an operationally simple three‐step (Friedel–Crafts reaction, selective hydrolysis, and cyclization), one‐pot strategy. This strategy has been successfully extended to the synthesis of a representative bioactive compound, himanimide A (see scheme).

  不对称，二取代的马来酰亚胺和顺丁烯二酸酐骨架可通过操作简单的三步操作（弗里德-克拉夫茨反应，选择性水解和环化），一锅法从拜利斯-希尔曼加合物中获得。该策略已成功地扩展到代表性生物活性化合物喜马拉尼A（参见方案）的合成。
• Studies on the structure–activity relationship of 1,3,3,4-tetra-substituted pyrrolidine embodied CCR5 receptor antagonists. Part 2: Discovery of highly potent anti-HIV agents
  作者：Ben Li、Eric Dale Jones、Enkun Zhou、Li Chen、Dean Cameron Baylis、Shanghai Yu、Miao Wang、Xing He、Jonathan Alan Victor Coates、David Ian Rhodes、Gang Pei、John Joseph Deadman、Xin Xie、Dawei Ma

  DOI：10.1016/j.bmcl.2010.05.046

  日期：2010.9

  Modification of 1,3,3,4-tetra-substituted pyrrolidine embodied CCR5 receptor antagonists revealed that introducing a fluoro group at the 3-position of the 3-phenyl group to reduce metabolism did not adversely affect the high potency against HIV infection, and that replacing the piperidine ring with a tropane ring could deliver the most potent anti-HIV agents. Stereochemistry of the substituted tropane ring is essential for maintaining the potent anti-HIV activity because only exo-isomers displayed subnanomolar whole cell activity. (C) 2010 Elsevier Ltd. All rights reserved.