3-hydroxyxestoquinol dimethyl ether | 99463-23-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3-hydroxyxestoquinol dimethyl ether
• 英文别名: (1S,17R)-17-hydroxy-5,8-dimethoxy-1-methyl-14-oxapentacyclo[11.6.1.02,11.04,9.016,20]icosa-2,4,6,8,10,13(20),15-heptaen-12-one
• CAS: 99463-23-7
• 化学式: C₂₂H₂₀O₅
• 分子量: 364.398
• InChiKey: HFYHSHFEGQOCDL-ZHRRBRCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxyxestoquinol dimethyl ether 生成 (3R,12bS)-3-(tert-Butyl-dimethyl-silanyloxy)-8,11-dimethoxy-12b-methyl-1,2,3,12b-tetrahydro-5-oxa-benzo[k]acephenanthrylen-6-one
  参考文献：
  名称：

  通过CD光谱的理论计算确定，来自冲绳海洋海绵Xestospongia sapra的卤代喹啉和硫酸卤代喹啉，五环对苯二酚的绝对立体结构

  摘要：

  通过CD光谱的理论计算，确定了来自冲绳海洋海绵Xestospongia sapra的两个五环对苯二酚，对苯二酚和硫酸对苯二酚的绝对立体结构。

  DOI：

  10.1016/s0040-4039(00)89263-1
• 作为产物：
  描述：

  (+)-Halenaquinol dimethyl ether 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 3-hydroxyxestoquinol dimethyl ether
  参考文献：
  名称：

  通过CD光谱的理论计算确定，来自冲绳海洋海绵Xestospongia sapra的卤代喹啉和硫酸卤代喹啉，五环对苯二酚的绝对立体结构

  摘要：

  通过CD光谱的理论计算，确定了来自冲绳海洋海绵Xestospongia sapra的两个五环对苯二酚，对苯二酚和硫酸对苯二酚的绝对立体结构。

  DOI：

  10.1016/s0040-4039(00)89263-1

文献信息

• Synthesis of biotinylated xestoquinone that retains inhibitory activity against Ca2+ ATPase of skeletal muscle myosin
  作者：Mitsuhiro Nakamura、Takahiko Kakuda、Yuichi Oba、Makoto Ojika、Hideshi Nakamura

  DOI：10.1016/s0968-0896(03)00276-1

  日期：2003.7

  Xestoquinone isolated from a marine sponge binds to skeletal muscle myosin and inhibits its Ca2+ ATPase activity. In this study, we first examined xestoquinone and its analogues to assess the relationships between structure and myosin Ca2+ ATPase inhibitory activity. On the basis of the resultant data, we then designed a biotinylated xestoquinone analogue. Xestoquinone and its analogues were derived from extracts of the marine sponge Xestospongia sapra. Four xestoquinone analogues with a quinone structure significantly inhibited Ca2+ ATPase activity. In contrast, four xestoquinone analogues in which the quinone structure was converted to a quinol dimethyl ether did not inhibit Ca2+ ATPase activity. This suggests that the quinone moiety is essential for inhibitory activity. Then, we synthesized a biotinylated xestoquinone in which a biotin tag was introduced to a site far from the quinone moiety, and this molecule exhibited stronger inhibitory activity than that of xestoquinone. This biotinylated xestoquinone could be useful as a probe in studies of the xestoquinone-myosin binding mode. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Absolute stereochemistry of the halenaquinol family, marine natural products with a novel pentacyclic skeleton, as determined by the theoretical calculation of circular dichroism spectra
  作者：Nobuyuki Harada、Hisashi Uda、Motomasa Kobayashi、Nobuyoshi Shimizu、Isao Kitagawa

  DOI：10.1021/ja00197a025

  日期：1989.7