[4-[(2R,3S)-4-[3,4-bis(methoxycarbonyloxy)phenyl]-2,3-dimethyl-butyl]-2-methoxycarbonyloxy-phenyl] methyl carbonate | 1024713-81-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 英文名称: [4-[(2R,3S)-4-[3,4-bis(methoxycarbonyloxy)phenyl]-2,3-dimethyl-butyl]-2-methoxycarbonyloxy-phenyl] methyl carbonate
• 英文别名: [4-[(2S,3R)-4-[3,4-bis(methoxycarbonyloxy)phenyl]-2,3-dimethylbutyl]-2-methoxycarbonyloxyphenyl] methyl carbonate
• CAS: 1024713-81-2
• 化学式: C₂₆H₃₀O₁₂
• 分子量: 534.517
• InChiKey: CFYOLPDZDDSSGT-IYBDPMFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  38
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  nordihydroguairetic acid 、 氯甲酸甲酯 在 吡啶 作用下， 以83%的产率得到[4-[(2R,3S)-4-[3,4-bis(methoxycarbonyloxy)phenyl]-2,3-dimethyl-butyl]-2-methoxycarbonyloxy-phenyl] methyl carbonate
  参考文献：
  名称：

  Heterocyclic and carbonate derivatives of NDGA and their use as new anti-HIV and anti-cancer agents

  摘要：

  在碱性条件下，Nordihydroguaiaretic酸与各种烷基氯化物、1-哌啶甲酰氯、氯甲酸甲酯或1,1'-卡邦二咪唑反应，分别产生相应的酚醚、氨基甲酸酯和碳酸酯，收率为67-83％（图1和图2）。在这些衍生物中，含氮化合物被转化为相应的盐酸盐。这些NDGA衍生物在水溶液中具有良好的溶解性和稳定性。这些新化合物对HIV Tat调控的cos-7细胞中的转录激活具有强效活性。该系列中最活跃的转录抑制剂化合物5b（P4N，四哌啶基NDGA，meso-2,3-二甲基-1,4-双（3,4-[2-(哌啶基)乙氧基]苯基）丁烷四盐酸盐）的IC50为0.88μM。

  公开号：

  US07741357B1

文献信息

• Heterocyclic and carbonate derivatives of NDGA and their use as new anti-HIV and anti-cancer agents
  申请人：Johns Hopkins University

  公开号：US07741357B1

  公开（公告）日：2010-06-22

  Reaction of nordihydroguaiaretic acid with various alkyl chlorides, 1-piperidinecarbonyl chloride, methyl chloroformate, or 1,1′-carbonyldiimidazole under alkaline conditions produced the corresponding phenol ethers, carbamates and carbonates, respectively, in 67-83% yields (Scheme 1 and Scheme 2). Among these derivatives, the nitrogen-containing compounds were converted to the corresponding hydrochloride salts. Having good solubility, these NDGA derivatives were found to be stable in aqueous solution. These new compounds exerted potent activities against HIV Tat-regulated transactivation in cos-7 cells. The most active transcription inhibitor compound of this series 5b (P4N, Tetrapiperidino NDGA, meso-2,3-dimethyl-1,4-bis(3,4-[2-(piperidino)ethoxyphenyl])butane tetrakishydrochloride salt) has an IC50 of 0.88 μM.

  在碱性条件下，Nordihydroguaiaretic酸与各种烷基氯化物、1-哌啶甲酰氯、氯甲酸甲酯或1,1'-卡邦二咪唑反应，分别产生相应的酚醚、氨基甲酸酯和碳酸酯，收率为67-83％（图1和图2）。在这些衍生物中，含氮化合物被转化为相应的盐酸盐。这些NDGA衍生物在水溶液中具有良好的溶解性和稳定性。这些新化合物对HIV Tat调控的cos-7细胞中的转录激活具有强效活性。该系列中最活跃的转录抑制剂化合物5b（P4N，四哌啶基NDGA，meso-2,3-二甲基-1,4-双（3,4-[2-(哌啶基)乙氧基]苯基）丁烷四盐酸盐）的IC50为0.88μM。
• New nordihydroguaiaretic acid derivatives as anti-HIV agents
  作者：Jih Ru Hwu、Ming-Hua Hsu、Ru Chih C. Huang

  DOI：10.1016/j.bmcl.2008.02.018

  日期：2008.3

  Reaction of nordihydroguaiaretic acid with various alkyl chloride, 1-piperidinecarbonyl chloride, methyl chloroformate, or 1,1'-carbonyldiimidazole under alkaline conditions produced the corresponding phenol ethers, carbamates and carbonates, respectively, in 67 - 83% yields. Among these derivatives, the nitrogen-containing compounds were converted to the corresponding hydrochloride salts. Having good solubility, these NDGA derivatives were found stable in aqueous solution. These new compounds exerted appealing activity against HIV Tat-regulated transactivation in human epithelial cells. The most potent compound meso-2,3dimethyl- 1,4-bis( 3,4-[2-(piperdino) ethoxyphenyl]) butane tetrakishydrochloride salt (5b) showed IC50 value of 0.88 mu M. (C) 2008 Elsevier Ltd. All rights reserved.