2-methyl-1,4,5-naphthalenetriol | 58274-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methyl-1,4,5-naphthalenetriol
• 英文别名: 2-methyl-naphthalenetriol-(1,4,5)；2-Methyl-naphthalintriol-(1,4,5)；1,4,5-Naphthalenetriol, 2-methyl-；2-methylnaphthalene-1,4,5-triol
• CAS: 58274-93-4
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: HLGWOMQEFHMMBP-UHFFFAOYSA-N

物化性质

• 沸点：
  335.8±22.0 °C(Predicted)
• 密度：
  1.407±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-1,4,5-naphthalenetriol 在 氧气 作用下， 生成 兰雪醌
  参考文献：
  名称：

  用于立体选择性合成天然萘酮的高效一锅多酶级联反应

  摘要：

  在此，开发了包含稻瘟病菌和 NADPH的烯还原酶 (NostocER) 和萘酚还原酶 (四羟基萘或三羟基萘还原酶) 的生物催化级联反应。将优化后的多酶级联应用于一锅法还原白杨素，获得具有生物活性的顺式-(3 R ,4 R )-异紫荆醇酮，顺式：反式98:2 和 >99% ee，收率 96%。此外，还合成了具有优异立体选择性的天然 (+)-isosclerone、(+)-shinanolone、(-)-shinanolone 和 ( S )-4-hydroxy-3,4-dihydronaphthalen-1(2 H )-one和使用酶级联的高产率（71-89%）。NostocER-T的调查甲萘醌、铅黄素和 5-甲氧基甲萘醌的4 HNR 级联还原揭示了四羟基萘还原酶对这些底物的特异性。此外，动力学研究表明，与其他酶相比， NostocER 和 T 4 HNR 分别对铅黄素和二氢铅黄素具有较高的催化效率。

  DOI：

  10.1021/acscatal.2c02772
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 alkaline aqueous sodium stannite 作用下， 生成 2-methyl-1,4,5-naphthalenetriol
  参考文献：
  名称：

  Madinaveitia; Olay, Anales de la Real Sociedad Espanola de Fisica y Quimica, 1933, vol. 31, p. 134,136

  摘要：

  DOI：

文献信息

• The regioselective synthesis of monomethoxynaphthylene diacetates
  作者：Bhim C. Maiti、Oliver C. Musgrave、Douglas Skoyles

  DOI：10.1016/j.tet.2004.12.034

  日期：2005.2

  Methods for the conversion of 1,4,5-naphthalenetriols into the corresponding monomethoxy diacetates are described. All utilise the formation of peri-bridged intermediates.

  描述了将1,4,5-萘三醇转化为相应的单甲氧基二乙酸酯的方法。所有利用的形成围-bridged中间体。
• 275. Naturally occurring quinones. A new synthesis of plumbagin and a note on the structure of β-hydroplumbagin
  作者：R. H. Thomson

  DOI：10.1039/jr9510001237

  日期：——
• SANKARAM A. V. B.; RAO A. S.; SIDHU G. S., TETRAHEDRON LETT. <TELE-AY>, 1975, NO 42, 3627-3630
  作者：SANKARAM A. V. B.、 RAO A. S.、 SIDHU G. S.

  DOI：——

  日期：——
• ANTI-CANCER LEAD MOLECULE
  申请人：KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY

  公开号：US20140107196A1

  公开（公告）日：2014-04-17

  Derivatives of plumbagin can be selectively cytotoxic to breast cancer cells. Derivative ‘A’ (Acetyl Plumbagin) has emerged as a lead molecule for testing against estrogen positive breast cancer and has shown low hepatotoxicity as well as overall lower toxicity in nude mice model. The toxicity of derivative ‘A’ was determined to be even lower than vehicle control (ALT and AST markers). The possible mechanism of action identified based on the microarray experiments and pathway mapping shows that derivative ‘A’ could be acting by altering the cholesterol-related mechanisms. The low toxicity profile of derivative ‘A’ highlights its possible role'as future anti-cancer drug and/or as an adjuvant drug to reduce the toxicity of highly toxic chemotherapeutic'drugs.
• CHOLESTERYL ESTER TRANSFER PROTEIN (CETP) INHIBITION IN THE TREATMENT OF CANCER
  申请人：KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY

  公开号：US20180049997A1

  公开（公告）日：2018-02-22

  In one embodiment, the invention provides methods of treatment which use therapeutically effective amounts of Cholesteryl Ester Transfer Protein (CETP) inhibitors to treat a variety of cancers. In certain embodiments, the inhibitor is a CETP-inhibiting small molecule, CETP-inhibiting antisense oligonucleotide, CETP-inhibiting siRNA or a CETP-inhibiting antibody. Related pharmaceutical compositions, kits, diagnostics and screens are also provided.