2,2-dimethyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)but-3-en-1-ol | 145668-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2-dimethyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)but-3-en-1-ol
• CAS: 145668-11-7
• 化学式: C₂₀H₂₆O₅
• 分子量: 346.423
• InChiKey: RTIQTQPXKZCNFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)but-3-en-1-ol 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 0.15h， 以75%的产率得到2,2-dimethyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)but-3-ene-1-thiol
  参考文献：
  名称：

  6-取代的1,4-萘醌肟衍生物的合成及细胞毒性（II）

  摘要：

  在本研究中，已经合成了一系列的1,4-萘醌肟衍生物。通过光谱法确认了结构。评价新合成的化合物的体外细胞毒性。在这些化合物中，化合物8c，8d，8e，12a和12b表现出与参考药物5-Fu相当的有效细胞毒性。

  DOI：

  10.1134/s1070363217120416
• 作为产物：
  描述：

  1-溴代异戊烷 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 2,2-dimethyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)but-3-en-1-ol
  参考文献：
  名称：

  Synthesis and Cytotoxicity of 1,4-Naphthoquinone Oxime Derivatives

  摘要：

  A series of hydroxylated 1,4-naphthoquinone oximes were designed and synthesized. The in vitro cytotoxicity of these compounds was evaluated against five human cancer cell lines and human skin fibroblast cell line. Among them, compounds (1E,4E)-6-{1-[(5-Hydroxypentyl)oxy]-2,2-dimethylbut-3-en-1-yl}-5,8- dimethoxynaphthalene-1,4-dione dioxime and (1E,4E)-6-{1-[(6-Hydroxyhexyl)oxy]-2,2-dimethylbut-3-en-1-yl}-5,8-dimethoxynaphthalene-1,4-dione dioxime displayed higher cytotoxicity in three cancer cell lines than the positive drug 5-fluorouracil

  DOI：

  10.1134/s1070363218110221

文献信息

• Cerium (IV) ammonium nitrate (CAN)-mediated regioselective synthesis and anticancer activity of 6-substituted 5,8-dimethoxy-1,4-naphthoquinone
  作者：Guang Huang、Hui-Ran Zhao、Qing-Qing Meng、Wen Zhou、Qi-Jing Zhang、Jin-Yun Dong、Jia-Hua Cui、Shao-Shun Li

  DOI：10.1016/j.cclet.2016.10.034

  日期：2017.7

  2-substituted 1,4,5,8-tetramethoxynaphthalenes with CAN in EtOAc/H2O in comparatively high yields. An interesting finding was that apart from the reported electron-withdrawing effects of substituents on position 2 of naphthalene ring, regioselective synthesis of 6-DMNQ was largely dependent on the steric effects in CAN-mediated oxidation. The selective cytotoxicities of 6-DMNQ from the in vitro cell-based assays

  摘要6-取代的5,8-O-二甲基-1,4-萘醌（6-DMNQ）是一种有前途的抗癌支架，是通过2-取代的1,4,5,8-四甲氧基萘与CAN的氧化脱甲基作用选择性制备的。 EtOAc / H 2 O的产率较高。一个有趣的发现是，除了已报道的取代基在萘环2位上的吸电子作用外，6-DMNQ的区域选择性合成很大程度上取决于CAN介导的氧化反应中的空间位阻作用。在癌细胞和正常细胞之间表现出了基于体外细胞试验的6-DMNQ的选择性细胞毒性。而且，大多数含硫的6-DMNQ衍生物显示出比相应的含氧衍生物更好的抗癌活性，
• An improved and practical synthesis route to antiproliferative (±)-shikonin and its <i>O</i>-acyl derivatives
  作者：Mana Ono、Shouki Abe、Koji Higai、Shoko Higashi、Setsuo Saito、Ryota Saito

  DOI：10.1080/00397911.2020.1853171

  日期：2021.3.4

  Shikonin and its O-acyl derivatives are attracting increasing levels of attention among medicinal chemists due to their potencies as highly selective cytotoxic agents against cancer cells. However,...

  紫草素及其 O-酰基衍生物由于其作为抗癌细胞的高选择性细胞毒性剂的效力而受到药物化学家越来越多的关注。然而，...
• Synthesis of shikalkin and certain related compounds
  作者：V. L. Novikov、N. N. Balaneva、A. M. Moiseenkov、G. B. Elyakov

  DOI：10.1007/bf00864352

  日期：1992.8

  A successful total synthesis of a biologically active pigment from plants of the Boraginaceae family was carried out with naphthazarine as the starting material, and using the 1,4,5,8-tetramethoxynaphthalene, the corresponding 2-vinyl derivative and its epoxide or a cyclopropane adduct with diazoacetic ester at the key stages. In the course of developing the scheme of the synthesis of shikalkin, its three analogs were obtained, differing in the nature of the monoterpenoid side chain.
• Discovery of Dimethyl Shikonin Oxime 5a, a Potent, Selective Bombesin Receptor Subtype-3 Agonist for the Treatment of Type 2 Diabetes Mellitus
  作者：Lehao Wu、Jiahua Cui、Chunxiao Zhao、Zeyuan Wang、Jihong Lu、Shaoshun Li、Jinping Jia、Hua Xiao、Yan Zhang

  DOI：10.1021/acs.jmedchem.3c00323

  日期：2023.6.22
• CN114181179
  申请人：——

  公开号：——

  公开（公告）日：——