6-hydroxy-α-lapachone | 104556-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 6-hydroxy-α-lapachone
• 英文别名: 6-Hydroxy-alpha-lapachone；6-hydroxy-2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione
• CAS: 104556-24-3
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: YSVRJLIAIDMDKD-UHFFFAOYSA-N

物化性质

• 熔点：
  122-124 °C
• 沸点：
  436.4±45.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ALPHA-拉杷醌 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 三氟乙酸 、 三氟乙酸酐 、 [双(三氟乙酰氧基)碘]苯 作用下， 反应 12.0h， 以51%的产率得到6-hydroxy-α-lapachone
  参考文献：
  名称：

  Ruthenium-catalyzed C–H oxygenation of quinones by weak O-coordination for potent trypanocidal agents

  摘要：

  对醌的C-H氧化通过多功能钌（II）催化实现，具有广泛的底物范围，并且还发现了抗锥虫化合物。

  DOI：

  10.1039/c8cc07572g

文献信息

• Synthesis of the naturally occurring naphtho-z.sfnc;2,3-bz.sfnc;pyran-5,10-quinones α-caryopterone,dihydro-α-caryopterone and their isomers 6-hydroxy-dehydro-α-lapachone and 6-hydroxy-α-lapachone
  作者：Alaíde B. de Oliveira、Dalva T. Ferreira、Délio Soares Raslan

  DOI：10.1016/s0040-4039(00)80040-4

  日期：1988.1

  Isomeric 6- and 9-hydroxy-naphtho-z.sfnc;2,3-bz.sfnc;pyran-5,10-quinones were synthesised by alkylation-cyclisation of 2- and 3-hydroxyjuglone in a single step and can be distinguished by UV-visible spectra in the presence of additives and 1HNMR.

  异构6-和9-羟基萘-z.sfnc; 2,3-bz.sfnc; pyran-5,10-醌是通过2-和3-羟基juglone的烷基化环化一步合成的，可以区分在添加剂和1 HNMR存在下通过紫外可见光谱测定。
• Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol
  作者：Evelyn L. Bonifazi、Carla Ríos-Luci、Leticia G. León、Gerardo Burton、José M. Padrón、Rosana I. Misico

  DOI：10.1016/j.bmc.2010.02.032

  日期：2010.4

  A series of 5-hydroxy-1,4-naphthoquinones analogues was synthesized from juglone (6) and their antiproliferative activity against a representative panel of six human solid tumor cell lines has been investigated. The 2,5-dihydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione (4) and 2,3-dihydro-5-hydroxy-2-(prop-1-en-2-yl)naphtho[2,3-b]furan-4,9-dione (27) were the most potent antiproliferative agents

  从juglone（6）合成了一系列5-hydroxy-1,4-naphthoquinones类似物，并研究了它们对代表6种人类实体瘤细胞系的抗增殖活性。2,5-二羟基-3-（3-甲基丁-2-烯基）萘-1,4-二酮（4）和2,3-二氢-5-羟基-2-（丙-1-烯-2- yl）naphtho [2,3 - b ] furan-4,9-dione（27）是最有效的抗增殖剂，其GI 50值分别为0.42-8.1和0.80-2.2μM。结果为5-羟基萘醌的某些结构性质与其抗增殖活性之间的相关性提供了见识。
• Two New Syntheses of the Pyranojuglone Pigment ?-Caryopterone
  作者：Takeshi Matsumoto、Akitami Ichihara、Mitsutoshi Yanagiya、Tamio Yuzawa、Akiyoshi Sannai、Hideaki Oikawa、Sadao Sakamura、Conrad Hans Eugster

  DOI：10.1002/hlca.19850680827

  日期：1985.12.18

  process, 3-methoxyjuglone (= 8-hydroxy-2-methoxy-1,4-naphthoquinone; 9) has been synthesized from 1,2,4-trimethoxybenzene (5) and converted, after prenylation, to α-caryopterone (1; Scheme 1), a pyranojuglone pigment from Caryopteris clandonensis. On the other hand, juglone (= 5-hydroxy-1,4-naphthoquinone; 12) was regioselectively prenylated at C(2) via its 1-methoxy-cyclohexa-1,3-diene adduct 15(Scheme

  通过一个简单的方法，由1,2,4-三甲氧基苯（5）合成了3-甲氧基juglone（= 8-羟基-2-甲氧基-1,4-萘醌; 9），并在异戊二烯化后转化为α-环戊烯酮（1；方案1），来自Caryopteris clandonensis的吡喃juglone颜料。另一方面，通过其1-甲氧基-环己-1,3-二烯加合物15 （方案2），在C（2）上对juglone（= 5-hydroxy-1,4-naphthoquinone; 12）进行区域选择性炔丙基化。如此形成的2-异戊烯基胡克隆酮（4）在氧化和其他反应后导致1。
• β-Lapachone analogs with enhanced antiproliferative activity
  作者：Carla Ríos-Luci、Evelyn L. Bonifazi、Leticia G. León、Juan C. Montero、Gerardo Burton、Atanasio Pandiella、Rosana I. Misico、José M. Padrón

  DOI：10.1016/j.ejmech.2012.04.008

  日期：2012.7

  In this study, we describe the synthesis of a series of alpha- and beta-lapachone containing hydroxyl or methoxyl groups on the benzene ring, by means of the selective acid promoted cyclization of the appropriate lapachol analog. The evaluation of the antiproliferative activity in human solid tumor cell lines provided 7-hydroxy-beta-lapachone as lead with enhanced activity over the parent drug beta-lapachone. Cell cycle studies, protein expression experiments, and reactive oxygen species analysis revealed that, similarly to beta-lapachone, ROS formation and DNA damage are critical factors in the cellular toxicity of 7-hydroxy-beta-lapachone. (C) 2012 Elsevier Masson SAS. All rights reserved.
• DE, OLIVEIRA ALAIDE B.;FERREIRA, DALVA T.;RASLAN, DELIO SOARES, TETRAHEDRON LETT., 29,(1988) N 2, 155-158
  作者：DE, OLIVEIRA ALAIDE B.、FERREIRA, DALVA T.、RASLAN, DELIO SOARES

  DOI：——

  日期：——