1-(3,4,5-三甲氧基苯基)乙烷-1,2-二醇 | 116673-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-(3,4,5-三甲氧基苯基)乙烷-1,2-二醇
• 英文名称: 1-(3,4,5-trimethoxyphenyl)-1,2-dihydroxyethane
• 英文别名: 1,2-Ethanediol, 1-(3,4,5-trimethoxyphenyl)-；1-(3,4,5-trimethoxyphenyl)ethane-1,2-diol
• CAS: 116673-46-2
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: VRYUDXCGWXDNLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  hexa-2,4-dienoyl chloride 、 1-(3,4,5-三甲氧基苯基)乙烷-1,2-二醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 [2-hexa-2,4-dienoyloxy-2-(3,4,5-trimethoxyphenyl)ethyl] hexa-2,4-dienoate
  参考文献：
  名称：

  1-(3,4,5-Trimethoxyphenyl)ethane-1,2-diyl esters, a novel compound class with potent chemoreversal activity

  摘要：

  1-(3,4,5-Trimethoxyphenyl)ethane-1,2-diyl esters, which share a fragment from (+/-)-3'-O-4'-O-bis(3,4-dimethoxycinnamoyl)-cis-khellactone (DMDCK) and 3'R,4'R-disubstituted-2',2'-dimethyldihydropyrano[2,3-f]chromone (DSP), exhibited remarkable chemoreversal activity on multidrug resistant human nasopharyngeal carcinoma (KB) when combined with three anticancer drugs, paclitaxel, vincristine and doxorubicin. Among 15 novel synthesized analogs, bis-trimethoxybenzoyl derivative 15 was the most active (340-fold more active than verapamil when used with vincristine) followed by two di-cinnamoyl derivatives, 10 and 11, and then di-cyclohexanecarbonyl derivative 9. All aliphatic chain derivatives, 3-5, showed no activity. Structure-activity relationship study indicated that a di-ester structure was critical to enhance the activity resulting from the maintenance of the spatial arrangement proposed by the pharmacophore based on the verapamil-binding site. Further mechanism of action study showed 15 inhibited mainly P-glycoprotein efflux pump function, while 13 exhibited an additional multidrug resistance-associated protein efflux pump function. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.096
• 作为产物：
  描述：

  3,4,5-trimethoxy styrene 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 为溶剂， 生成 1-(3,4,5-三甲氧基苯基)乙烷-1,2-二醇
  参考文献：
  名称：

  1-(3,4,5-Trimethoxyphenyl)ethane-1,2-diyl esters, a novel compound class with potent chemoreversal activity

  摘要：

  1-(3,4,5-Trimethoxyphenyl)ethane-1,2-diyl esters, which share a fragment from (+/-)-3'-O-4'-O-bis(3,4-dimethoxycinnamoyl)-cis-khellactone (DMDCK) and 3'R,4'R-disubstituted-2',2'-dimethyldihydropyrano[2,3-f]chromone (DSP), exhibited remarkable chemoreversal activity on multidrug resistant human nasopharyngeal carcinoma (KB) when combined with three anticancer drugs, paclitaxel, vincristine and doxorubicin. Among 15 novel synthesized analogs, bis-trimethoxybenzoyl derivative 15 was the most active (340-fold more active than verapamil when used with vincristine) followed by two di-cinnamoyl derivatives, 10 and 11, and then di-cyclohexanecarbonyl derivative 9. All aliphatic chain derivatives, 3-5, showed no activity. Structure-activity relationship study indicated that a di-ester structure was critical to enhance the activity resulting from the maintenance of the spatial arrangement proposed by the pharmacophore based on the verapamil-binding site. Further mechanism of action study showed 15 inhibited mainly P-glycoprotein efflux pump function, while 13 exhibited an additional multidrug resistance-associated protein efflux pump function. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.096

文献信息

• CN-assisted oxidative cyclization of cyano cinnamates and styrene derivatives: a facile entry to 3-substituted chiral phthalides
  作者：R. Santhosh Reddy、I. N. Chaithanya Kiran、Arumugam Sudalai

  DOI：10.1039/c2ob25409c

  日期：——

  of o-cyano cinnamates and styrene derivatives leads to efficient construction of chiral phthalide frameworks in high optical purities. This unique reaction is characterized by unusual synergism between CN and osmate groups resulting in rate enhancement of the AD process. The method is amply demonstrated by the synthesis and the structural/stereochemical assignment of the natural products.

  邻氰基肉桂酸酯和苯乙烯衍生物的不对称二羟基化（AD）导致高光学纯度的手性邻苯二甲酸酯骨架的有效构建。这种独特的反应的特征在于CN和渗透酸基团之间异常的协同作用，从而导致AD过程的速率提高。天然产物的合成和结构/立体化学分配充分证明了该方法。
• Synthesis of 2-hydroxy-2-phenylethylamino derivatives as potential α-adrenergic blocking agents
  作者：M. Alvarez、R. Granados、R. Lavilla、M. Salas

  DOI：10.1002/jhet.5570220326

  日期：1985.5

  synthesis of N,N'-bis[6-(2-hydroxy-2-phenylethylamino)hexyl] cystamines 4, and N-(2-hydroxy-2-phenylethyl)-1,6-hexanediamines 6 are described. Compounds 4 were obtained by condensation of the requisite epoxide 2 with 3-(6-aminohexyl)-1,3-thiazolidine followed by dimerization with opening of the thiazolidine ring. A similar method was used for the preparation of compounds 6. In order to prepare 4j (N,N'-bis6-[2-hydroxy-2(3

  合成N，N'-双[6-（2-羟基-2-苯乙氨基）己基] cystamines 4，和N-（2-羟基-2-苯乙基）-1,6- hexanediamines 6中描述。通过将必需的环氧化物2与3-（6-氨基己基）-1，3-噻唑烷缩合，然后通过打开噻唑烷环进行二聚来获得化合物4。用类似的方法制备化合物6。为了制备4j（N，N′-双6- [2-羟基-2（3，4-二羟基苯基）乙基氨基]己基}胱胺），有几种方法。经过测试 选择的方法涉及使用两个羟基都被保护为甲氧基甲基醚的3，4-二羟基苯甲醛。
• Dual binding modes to the receptor for platelet activating factor (PAF) of anti-paf trans-2,5-diarylfurans
  作者：E.J Corey、Chung-Pin Chen、M.J Parry

  DOI：10.1016/0040-4039(88)85042-1

  日期：1988.1

  The trans-2,5-diaryltetrahydrofurans 2 and 4 are equiactive with their enantiomers 3 and 5 as antagonists of platelet activating factor (PAF, 1), an indication of dual binding modes to the PAF receptor, further supported by the anti-PAF activity of the 1,3-dioxolane 6.

  的反式-2,5- diaryltetrahydrofurans 2和4是与equiactive其对映体3和5作为激活因子（PAF，血小板的拮抗剂1），双结合模式到PAF受体的指示，由抗PAF活性的进一步支持1,3-二氧戊环6。
• New Antimitotic Agents with Activity in Multi-Drug-Resistant Cell Lines and in Vivo Efficacy in Murine Tumor Models
  作者：Bruce G. Szczepankiewicz、Gang Liu、Hwan-Soo Jae、Andrew S. Tasker、Indrani W. Gunawardana、Thomas W. von Geldern、Stephen L. Gwaltney、J. Ruth Wu-Wong、Laura Gehrke、William J. Chiou、R. Bruce Credo、Jeffery D. Alder、Michael A. Nukkala、Nicolette A. Zielinski、Ken Jarvis、Karl W. Mollison、David J. Frost、Joy L. Bauch、Yu Hua Hui、Akiyo K. Claiborne、Qun Li、Saul H. Rosenberg

  DOI：10.1021/jm010231w

  日期：2001.12.1

  During a screen for compounds that could inhibit cell proliferation, a series of new tubulin-binding compounds was identified with the discovery of oxadiazoline 1 (A-105972). This compound showed good cytotoxic activity against non-multi-drug-resistant and multi-drug-resistant cancer cell lines, but its utility in vivo was limited by a short half-life. Medicinal chemistry efforts led to the discovery of indolyloxazoline 22g (A-259745), which maintained all of the in vitro activity seen with oxadiazoline 1, but also demonstrated a better pharmacokinetic profile, and dose-dependent in vivo activity. Over a 28 day study, indolyloxazoline 22g increased the life span of tumor-implanted mice by up to a factor of 3 upon oral dosing. This compound, and others of its structural class, may prove to be useful in the development of new chemotherapeutic agents to treat human cancers.
• COREY, E. J.;CHEN, CHUNG-PIN;PARRY, M. J., TETRAHEDRON LETT., 29,(1988) N 24, C. 2899-2902
  作者：COREY, E. J.、CHEN, CHUNG-PIN、PARRY, M. J.

  DOI：——

  日期：——