meso-2,3-dimethyl-1,4-bis(3,4-[2-(piperidino)ethoxyphenyl])butane | 859634-52-9

• 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-2,3-dimethyl-1,4-bis(3,4-[2-(piperidino)ethoxyphenyl])butane
• 英文别名: meso-2,3-dimethyl-1,4-bis(3,4-di[2-(1-piperidino)ethoxy]phenyl)butane；1-[2-[4-[(2R,3S)-4-[3,4-bis[2-(1-piperidyl)ethoxy]phenyl]-2,3-dimethyl-butyl]-2-[2-(1-piperidyl)ethoxy]phenoxy]ethyl]piperidine；1-[2-[4-[(2S,3R)-4-[3,4-bis(2-piperidin-1-ylethoxy)phenyl]-2,3-dimethylbutyl]-2-(2-piperidin-1-ylethoxy)phenoxy]ethyl]piperidine
• CAS: 859634-52-9
• 化学式: C₄₆H₇₄N₄O₄
• 分子量: 747.118
• InChiKey: AWQGURYAWGEYJU-LQDDJWCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  54
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  nordihydroguairetic acid 、 1-(2-氯乙基)哌啶盐酸盐 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 meso-2,3-dimethyl-1,4-bis(3,4-[2-(piperidino)ethoxyphenyl])butane
  参考文献：
  名称：

  New nordihydroguaiaretic acid derivatives as anti-HIV agents

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.02.018

文献信息

• IN VIVO AMELIORATION OF ENDOGENOUS ANTI-TUMOR AUTOANTIBODIES TARGETING SURFACE TUMOR ANTIGENS VIA LOW-DOSE P4N
  申请人：THE JOHNS HOPKINS UNIVERSITY

  公开号：US20190111040A1

  公开（公告）日：2019-04-18

  In accordance with the present invention, the immunoregulatory activity of low doses of P 4 N was investigated. Unlike previously described antitumor drugs, low dose P 4 N, in doses of about 1 to 10 mg/kg, or at concentrations of about 10 to 100 nM, was surprisingly found to contribute to humoral immunity by raising the titers and activities of autoantibodies against GRP78 and F1F0 ATP synthase on the surface of CT26 cells, and inducing B cell proliferation and differentiation of plasma cells. Methods for inducing endogenous antitumor autoantibodies (EAA) in a subject having a neoplasia comprising administering to the subject an effective amount of the nordihydroguaiaretic acid (NDGA) derivative P4N, or salts, solvates and stereoisomers thereof, as well as methods for inducing B cell proliferation, inducing BAFF stimulated B cell proliferation, and suppressing or inhibition growth of a neoplasia are also provided.
• FORMULATIONS OF TERAMEPROCOL AND TEMOZOLOMIDE AND THEIR USE IN STIMULATION OF HUMORAL IMMUNITY IN TUMORS
  申请人：The Johns Hopkins University

  公开号：US20220409552A1

  公开（公告）日：2022-12-29

  The present invention provides novel pharmaceutical formulations comprising derivatives of NDGA, including M 4 N (tetra-0-methyl nordihydroguaiaretic acid) and temozolomide and their use in the inhibition and treatment of neoplastic diseases, including glioblastoma multiforme, lung and other cancers.
• 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.