meso-1,4-bis-(3,4-dihydroxyphenyl)-2,3-dimethylbutane bis-cyclic carbonate

• 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: meso-1,4-bis-(3,4-dihydroxyphenyl)-2,3-dimethylbutane bis-cyclic carbonate
• 英文别名: meso-2,3-dimethyl-1,4-bis-(2-oxo-benzo[1,3]dioxol-5-yl)-butane；meso-2,3-Dimethyl-1,4-bis-(2-oxo-benzo[1,3]dioxol-5-yl)-butan；5-[(2R,3S)-2,3-dimethyl-4-(2-oxo-1,3-benzodioxol-5-yl)butyl]-1,3-benzodioxol-2-one
• 化学式: C₂₀H₁₈O₆
• 分子量: 354.359
• InChiKey: ZDJMWUXXZFFQGO-TXEJJXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 五氯化磷 、 甲苯 作用下， 生成 meso-1,4-bis-(3,4-dihydroxyphenyl)-2,3-dimethylbutane bis-cyclic carbonate
  参考文献：
  名称：

  去甲二氢愈创木酸的合成。

  摘要：

  DOI：

  10.1021/ja01198a513

文献信息

• Synthesis, characterization, and anti-melanoma activity of tetra-O-substituted analogs of nordihydroguaiaretic acid
  作者：Ross O. Meyers、Joshua D. Lambert、Nicole Hajicek、Alan Pourpak、John A. Kalaitzis、Robert T. Dorr

  DOI：10.1016/j.bmcl.2009.06.063

  日期：2009.8

  Synthesis of seven semi-synthetic analogs of NDGA is described. An approach to NDGA derivatization is described in which the ortho-phenolic groups are tethered together by one atom, forming a 5-membered heterocyclic ring. The analogs were evaluated for cytotoxicity in four cancer cell lines and compared to NDGA and tetra-O-methyl-NDGA (M4N) (1a). NDGA bis-cyclic sulfate (2a), NDGA bis-cyclic carbonate

  描述了七种 NDGA 半合成类似物的合成。描述了一种 NDGA 衍生化方法，其中邻苯酚基团由一个原子连接在一起，形成 5 元杂环。在四种癌细胞系中评估类似物的细胞毒性，并与 NDGA 和四-O-甲基-NDGA (M4N) ( 1a ) 进行比较。NDGA 双环硫酸盐 ( 2a )、NDGA 双环碳酸酯 ( 2b ) 和亚甲二氧苯基-NDGA ( 2d ) 和 NDGA 四乙酸酯 ( 1b ) 显示出体外抗癌活性。两种化合物，( 1b ) 和 ( 2b ))，在人类黑色素瘤的小鼠异种移植模型中评估了抗癌活性，并显示出剂量依赖性活性。
• 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.
• US7741357B1
  申请人：——

  公开号：US7741357B1

  公开（公告）日：2010-06-22
• US8420692B1
  申请人：——

  公开号：US8420692B1

  公开（公告）日：2013-04-16