6-methoxycomaparvin-5-methyl ether | 111397-49-0

• 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-methoxycomaparvin-5-methyl ether
• 英文别名: 8-hydroxy-5,6,10-trimethoxy-2-propylbenzo[h]chromen-4-one
• CAS: 111397-49-0
• 化学式: C₁₉H₂₀O₆
• 分子量: 344.364
• InChiKey: JUNIOWHVNDZWCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-methoxycomaparvin-5-methyl ether 、 三甲基硅烷化重氮甲烷 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以73.5%的产率得到6-methoxycomaparvin 5,8-dimethyl ether
  参考文献：
  名称：

  Comatulins A–E, Taurine-Conjugated Anthraquinones from the Australian Crinoid Comatula rotalaria

  摘要：

  Chemical investigations of two specimens of the Australian crinoid Comatula rotalaria afforded five new taurine-conjugated anthraquinones, comatulins A-E (1-5), together with 11 known marine natural products (6-16). The chemical structures of all the compounds were elucidated by detailed spectroscopic and spectrometric data analysis. The first X-ray crystal structure of a crinoid-derived acyl anthraquinone, rhodocomatulin 5,7- dimethyl ether (8), is reported here. Compounds 1, 2, 6-13, and two additional naphthopyrone derivatives, 17 and 18, were evaluated for their ability to inhibit HIV-1 replication in vitro; none of the compounds were active at 100 mu M. Furthermore, compounds 1, 2, 6-10, 14, 15, 17, and 18 were screened for nematocidal activity against exsheathed third-stage larvae of Hemonchus contortus, a highly pathogenic parasite nematode of ruminants. Compound 17, known as 6-methoxycomaparvin 5,8-dimethyl ether, showed an inhibitory effect on larval motility (IC50 = 30 mu M) and development (IC50 = 31 mu M) and induced the eviscerated (Evi) phenotype.

  DOI：

  10.1021/acs.jnatprod.0c00267

文献信息

• METHOD OF INHIBITING ABCG2 AND OTHER TREATMENT METHODS
  申请人：The United States of America, as represented by the Secretary, Department of Health and Human

  公开号：US20130274323A1

  公开（公告）日：2013-10-17

  Disclosed are methods of enhancing the chemotherapeutic treatment of tumor cells, reducing resistance of a cancer cell to a chemotherapeutic agent, a method of inhibiting ABCG2, Pgp, or MRP1 in a mammal afflicted with cancer, and a method of increasing the bioavailability of an ABCG2 substrate drug in a mammal. The methods comprise administering effective amounts of certain compounds to the mammal, for example, a compound of the formula (I): wherein R 1 , R 2 , R 3 , X 1 , X 2 , X 3 , a, and b are as described herein. Uses of these compounds in the preparation of a medicament are also disclosed. Also disclosed are compounds of formula (II), pharmaceutical compositions comprising such compounds and uses thereof.
• US8470888B2
  申请人：——

  公开号：US8470888B2

  公开（公告）日：2013-06-25
• US9314448B2
  申请人：——

  公开号：US9314448B2

  公开（公告）日：2016-04-19
• Comatulins A–E, Taurine-Conjugated Anthraquinones from the Australian Crinoid <i>Comatula rotalaria</i>
  作者：Kah Yean Lum、Aya C. Taki、Robin B. Gasser、Ian Tietjen、Merrick G. Ekins、Jonathan M. White、Russell S. Addison、Sasha Hayes、James St John、Rohan A. Davis

  DOI：10.1021/acs.jnatprod.0c00267

  日期：2020.6.26

  Chemical investigations of two specimens of the Australian crinoid Comatula rotalaria afforded five new taurine-conjugated anthraquinones, comatulins A-E (1-5), together with 11 known marine natural products (6-16). The chemical structures of all the compounds were elucidated by detailed spectroscopic and spectrometric data analysis. The first X-ray crystal structure of a crinoid-derived acyl anthraquinone, rhodocomatulin 5,7- dimethyl ether (8), is reported here. Compounds 1, 2, 6-13, and two additional naphthopyrone derivatives, 17 and 18, were evaluated for their ability to inhibit HIV-1 replication in vitro; none of the compounds were active at 100 mu M. Furthermore, compounds 1, 2, 6-10, 14, 15, 17, and 18 were screened for nematocidal activity against exsheathed third-stage larvae of Hemonchus contortus, a highly pathogenic parasite nematode of ruminants. Compound 17, known as 6-methoxycomaparvin 5,8-dimethyl ether, showed an inhibitory effect on larval motility (IC50 = 30 mu M) and development (IC50 = 31 mu M) and induced the eviscerated (Evi) phenotype.