6-hydroxy-dehydro-α-lapachone | 116513-69-0

• 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-dehydro-α-lapachone
• 英文别名: 6-hydroxy-2,2-dimethyl-2H-benzo[g]chromene-5,10-dione；6-hydroxy-2,2-dimethyl-2H,5H,10H-benzo[g]chromene-5,10-dione；6-hydroxy-2,2-dimethylbenzo[g]chromene-5,10-dione
• CAS: 116513-69-0
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: HSXZMRFWNYJCEM-UHFFFAOYSA-N

物化性质

• 熔点：
  156-158 °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：

  6-hydroxy-dehydro-α-lapachone 在 palladium on activated charcoal 作用下， 以 四氢呋喃 为溶剂， 生成 6-hydroxy-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
• 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 6-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

• WO2008/115804
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.
• 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：——
• NOVEL IDO INHIBITORS AND METHODS OF USE THEREOF
  申请人：Lankenau Institute for Medical Research

  公开号：EP2137168B1

  公开（公告）日：2016-09-14
• Methods and Compositions for the Treatment of Rheumatoid Arthritis and Other Inflammatory Diseases
  申请人：Muller Alexander J.

  公开号：US20090253706A1

  公开（公告）日：2009-10-08

  Compositions and methods for the treatment of inflammatory diseases are disclosed.