8-hydroxy-5-(8'-hydroxynaphthalen-1'-yloxy)-3,4-dihydro-2H-naphthalen-1-one | 208346-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-hydroxy-5-(8'-hydroxynaphthalen-1'-yloxy)-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: 8-hydroxy-5-(8-hydroxynaphthalen-1-yl)oxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 208346-36-5
• 化学式: C₂₀H₁₆O₄
• 分子量: 320.345
• InChiKey: UUCVJERWABTJKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-hydroxy-5-(8'-hydroxynaphthalen-1'-yloxy)-3,4-dihydro-2H-naphthalen-1-one 在 sodium acetate 、 4-甲基苯磺酸吡啶 作用下， 以 苯 为溶剂， 反应 66.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of deoxypreussomerin A and palmarumycin CP1 and related naphthoquinone spiroketals

  摘要：

  Oxidative cyclization of bis-hydroxynaphthyl ethers allows concise total syntheses of palmarumycin CP1 and deoxypreussomerin A in 8-9 steps and 15-35% overall yield from 5-hydroxy-8-methoxy-1-tetralone (8). Polymer-bound triphenyl phosphine was found to be a superior reagent for the rapid preparation of a small library of palmarumycin analogs. Preliminary biological evaluation of naphthoquinone spiroketals against MCF-7 and MDA-MB-231 human breast cancer cells revealed several low-micromolar growth inhibitors. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00936-4
• 作为产物：
  描述：

  5-hydroxy-8-methoxy-1,2,3,4-tetrahydronaphthalene-1-spiro-2'-dioxolane 在 copper(I) oxide 、 三溴化硼 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 吡啶 、 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 8-hydroxy-5-(8'-hydroxynaphthalen-1'-yloxy)-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Total Synthesis of Palmarumycin CP₁ and (±)-Deoxypreussomerin A

  摘要：

  DOI：

  10.1021/jo980576v

文献信息

• Synthesis and methods of use of new antimitotic agents
  申请人：——

  公开号：US20020049221A1

  公开（公告）日：2002-04-25

  Oxidative cyclization of bis-naphthyl ethers allows concise total syntheses of palmarumycin CP, and deoxypreussomerin A in 8-9 steps and 15-35% overall yield from 5-hydroxy-8-methoxy-1 -tetralone. A small library of palmarumycin analogs was created. Biological evaluation of these naphthoquinone spiroketals against MCF-7 and MDA-MB-23 1 human breast cancer cells revealed several low-micromolar growth inhibitors. A number of the analogs inhibit the thioredoxin -thioredoxin reductase system.

  通过双萘醚的氧化环化反应，可以从 5-hydroxy-8-methoxy-1 -tetralone（5-羟基-8-甲氧基-1-四氢萘酮）出发，以 8-9 个步骤和 15-35% 的总收率，简便地全合成出棕榈霉素 CP 和脱氧普鲁索梅林 A。我们建立了一个小型的香豆素类似物库。对这些萘醌螺环酮类化合物针对 MCF-7 和 MDA-MB-23 1 人类乳腺癌细胞进行的生物学评估发现了几种低微摩生长抑制剂。其中一些类似物可抑制硫氧还蛋白-硫氧还蛋白还原酶系统。
• Total Synthesis of Palmarumycin CP₁ and (±)-Deoxypreussomerin A
  作者：Peter Wipf、Jae-Kyu Jung

  DOI：10.1021/jo980576v

  日期：1998.5.1
• US6673937B2
  申请人：——

  公开号：US6673937B2

  公开（公告）日：2004-01-06
• Synthesis and biological evaluation of deoxypreussomerin A and palmarumycin CP1 and related naphthoquinone spiroketals
  作者：Peter Wipf、Jae-Kyu Jung、Sonia Rodrı́guez、John S Lazo

  DOI：10.1016/s0040-4020(00)00936-4

  日期：2001.1

  Oxidative cyclization of bis-hydroxynaphthyl ethers allows concise total syntheses of palmarumycin CP1 and deoxypreussomerin A in 8-9 steps and 15-35% overall yield from 5-hydroxy-8-methoxy-1-tetralone (8). Polymer-bound triphenyl phosphine was found to be a superior reagent for the rapid preparation of a small library of palmarumycin analogs. Preliminary biological evaluation of naphthoquinone spiroketals against MCF-7 and MDA-MB-231 human breast cancer cells revealed several low-micromolar growth inhibitors. (C) 2000 Elsevier Science Ltd. All rights reserved.