9-hydroxy-dehydro-α-lapachone | 22333-57-9

• 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: 9-hydroxy-dehydro-α-lapachone
• 英文别名: α-caryopterone；9-hydroxy-2,2-dimethyl-2H,5H,10H-benzo[g]chromene-5,10-dione；9-hydroxy-2,2-dimethylbenzo[g]chromene-5,10-dione
• CAS: 22333-57-9
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: VDVJFNSKGHGQBS-UHFFFAOYSA-N

物化性质

• 熔点：
  160-165 °C
• 沸点：
  462.1±45.0 °C(Predicted)
• 密度：
  1.39±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：
  0.2
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-hydroxy-dehydro-α-lapachone 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 9-甲氧基-alpha-拉帕醌
  参考文献：
  名称：

  一些天然存在的烯丙基化的朱古龙衍生物的合成

  摘要：

  从juglone到2,8，已经开始合成α-头蝶烯酮（I），α-二氢头蝶烯酮II），9-甲氧基-α-lapachone（III）和4,9-二羟基-α-lapachone（IV）。 -二羟基-1,4-萘醌。

  DOI：

  10.1016/s0040-4039(00)71140-3
• 作为产物：
  描述：

  1,5-二羟基萘 在 三乙胺 盐酸 、 cupric complex of oxygen and acetonitrile 作用下， 以 水 、 苯 为溶剂， 生成 9-hydroxy-dehydro-α-lapachone
  参考文献：
  名称：

  天然存在的萘-z.sfnc; 2,3-bz.sfnc;吡喃-5,10-醌α-炔opter酮，二氢-α-炔opter酮及其异构体6-羟基-脱氢-α-lapachone和6-羟基-α-拉帕酮

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)80040-4

文献信息

• 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。
• Indoleamine 2,3-Dioxygenase Is the Anticancer Target for a Novel Series of Potent Naphthoquinone-Based Inhibitors
  作者：Sanjeev Kumar、William P. Malachowski、James B. DuHadaway、Judith M. LaLonde、Patrick J. Carroll、Daniel Jaller、Richard Metz、George C. Prendergast、Alexander J. Muller

  DOI：10.1021/jm7014155

  日期：2008.3.1

  Indoleamine 2,3-dioxygenase (IDO) is emerging as an important new therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. While small molecule inhibitors of IDO exist, there remains a dearth of high-potency compounds offering in vivo efficacy and clinical translational potential. In this study, we address this gap by defining a new class of naphthoquinone-based IDO inhibitors exemplified by the natural product menadione, which is shown in mouse tumor models to have similar antitumor activity to previously characterized IDO inhibitors. Genetic validation that IDO is the critical in vivo target is demonstrated using IDO-null mice. Elaboration of menadione to a pyranonaphthoquinone has yielded low nanomolar potency inhibitors, including new compounds which are the most potent reported to date (K-i = 61-70 nM). Synthetic accessibility of this class will facilitate preclinical chemical-genetic studies as well as further optimization of pharmacological parameters for clinical translation.
• Synthesis of dehydro-α-lapachones, α- and β-lapachones, and screening against cancer cell lines
  作者：Caroline dos S. Moreira、Caroline D. Nicoletti、Daniel P. Pinheiro、Leonardo G. C. de Moraes、Debora O. Futuro、Vitor F. Ferreira、Claudia do Ó Pessoa、David R. da Rocha

  DOI：10.1007/s00044-019-02439-w

  日期：2019.12

  14 new naphthoquinones were prepared and tested against human cancer cell lines PC-3 (prostate), HCT-116 (colon carcinoma), SNB-19 (glioblastoma), HL-60 (leukemia) and MCF-7 (breast), and a nontumor cell line L929 (murine fibroblasts) to determine cytotoxicity with the MTT assay. 8-OH-beta -lapachones (14a, 14c, 14d) presented best results, showing low IC50 values and high selectivity for HCT-116 and HL-60 tumor cells.
• Kapoor, N. K.; Gupta, R. B.; Khanna, R. N., Acta Chimica Hungarica, 1983, vol. 112, # 2, p. 163 - 166
  作者：Kapoor, N. K.、Gupta, R. B.、Khanna, R. N.

  DOI：——

  日期：——