紫红孢菌素 | 21879-81-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 紫红孢菌素
• 英文名称: bostrycin
• 英文别名: (5S,6R,7S)-5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-6,8-dihydro-5H-anthracene-1,4-dione
• CAS: 21879-81-2
• 化学式: C₁₆H₁₆O₈
• 分子量: 336.298
• InChiKey: ZQNOLGRKZRDRQO-XHSDSOJGSA-N

物化性质

• 熔点：
  222-224 °C (decomp)
• 沸点：
  618.4±55.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：1mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-甲基-2-丁烯醛 、 紫红孢菌素 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以80%的产率得到2,3-O-(3'-methylbut-2'-enyl)bostrycin
  参考文献：
  名称：

  Studies on the Synthesis of Derivatives of Marine-Derived Bostrycin and Their Structure-Activity Relationship against Tumor Cells

  摘要：

  一系列来源于海洋的bostrycin（1）的新衍生物（5–29）被合成。所有化合物的体外细胞毒活性通过MTT方法在MCF-7、MDA-MB-435、A549、HepG2、HCT-116和MCF-10A细胞上进行评估。在总数中，化合物7、8、22、23、25、28和29显示出与阳性对照表柔比星相当的活性，对测试的癌细胞系有效。然而，这些化合物也对MCF-10A细胞显示出细胞毒性。基于获得的实验数据，还讨论了bostrycin衍生物的结构-活性关系（SAR）。

  DOI：

  10.3390/md10040932
• 作为产物：
  描述：

  5-hydroxy-2,2-diphenylnaphtho<1,2-d>-1,3-dioxole-6,9-dione 在 盐酸 、 四氧化锇 、 四乙酰基二硼氧烷 、 sodium hydrogensulfite 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 31.5h， 生成 紫红孢菌素
  参考文献：
  名称：

  Bostrycin: structure correction and synthesis

  摘要：

  DOI：

  10.1021/jo00220a001

文献信息

• Antibacterial Anthraquinone Derivatives from a Sea Anemone-Derived Fungus <i>Nigrospora</i> sp.
  作者：Kai-Lin Yang、Mei-Yan Wei、Chang-Lun Shao、Xiu-Mei Fu、Zhi-Yong Guo、Ru-Fang Xu、Cai-Juan Zheng、Zhi-Gang She、Yong-Cheng Lin、Chang-Yun Wang

  DOI：10.1021/np300103w

  日期：2012.5.25

  Chemical investigation of a marine-derived fungus Nigrospora sp., isolated from an unidentified sea anemone, yielded two new hydroanthraquinone analogues, 4a-epi-9 alpha-methoxydihydrodeoxybostrycin (1) and 10-deoxybostrycin (2), together with seven known anthraquinone derivatives (3-9). The structures of the two new compounds were established through extensive NMR spectroscopy as well as a single-crystal X-ray diffraction analysis using Cu K alpha radiation. The antibacterial activities of compounds 1-9 and 10 acetyl derivatives (6a, 7a, 8a-8g, 9a) were evaluated in vitro. Compound 6a, the acetylated derivative of 6, exhibited promising activity against Bacillus cereus with an MIC value of 48.8 nM, which was stronger than that of the positive control ciprofloxacin (MIC = 1250 nM). Analysis of the antibacterial screening data for the metabolites and their acetyl derivatives revealed the key structural features required for this activity.
• TOMM6-INTERACTING EXTRACTS AND COMPOUNDS FOR USE IN THE TREATMENT AND PROPHYLAXIS OF NERVOUS SYSTEM DISEASES, ATHEROSCLEROSIS, HEPATITIS B INFECTION AND HUMAN PAPILLOMA VIRUS (HPV) INFECTION
  申请人：ETH ZURICH

  公开号：US20210186947A1

  公开（公告）日：2021-06-24

  The present invention is directed to a TOMM6 (Translocase of Outer Membrane 6 kDa subunit homologue; Mitochondrial import receptor subunit TOM6 homolog)-interacting plant or fungal extract comprising an anthraquinone or anthraquinone derivative, a TOMM6-interacting anthraquinone or anthraquinone derivative, and TOMM6-interacting compounds for use in the treatment or prophylaxis of a nervous system disease, atherosclerosis, Hepatitis B infection and/or human papilloma virus (HPV) infection. Furthermore, the present invention relates to a corresponding method of therapeutic or prophylactic treatment of a nervous system disease or disorder, atherosclerosis, Hepatitis B infection and/or human papilloma virus (HPV) infection, as well as to a method for the identification of a TOMM6-interacting compound or composition. Also, the present invention provides a non-human transgenic animal expressing a transgenic, preferably human TOMM6 or a TOMM6 homolog.
• Studies on the Synthesis of Derivatives of Marine-Derived Bostrycin and Their Structure-Activity Relationship against Tumor Cells
  作者：Hong Chen、Lili Zhong、Yuhua Long、Jia Li、Jueheng Wu、Lan Liu、Shengping Chen、Yongcheng Lin、Mengfeng Li、Xun Zhu、Zhigang She

  DOI：10.3390/md10040932

  日期：——

  A series of new derivatives (5–29) of marine-derived bostrycin (1) were synthesized. The in vitro cytotoxic activities of all compounds were evaluated against MCF-7, MDA-MB-435, A549, HepG2, HCT-116 and MCF-10A cells using the MTT method. The compounds 7, 8, 22, 23, 25, 28 and 29 of the total showed comparable activity to epirubicin, the positive control, against the tested cancer cell lines. However, these compounds also exhibited cytotoxicity towards MCF-10A cells. The structure-activity relationship (SAR) of bostrycin derivatives was also discussed based on the obtained experimental data.

  一系列来源于海洋的bostrycin（1）的新衍生物（5–29）被合成。所有化合物的体外细胞毒活性通过MTT方法在MCF-7、MDA-MB-435、A549、HepG2、HCT-116和MCF-10A细胞上进行评估。在总数中，化合物7、8、22、23、25、28和29显示出与阳性对照表柔比星相当的活性，对测试的癌细胞系有效。然而，这些化合物也对MCF-10A细胞显示出细胞毒性。基于获得的实验数据，还讨论了bostrycin衍生物的结构-活性关系（SAR）。
• Bostrycin: structure correction and synthesis
  作者：T. Ross Kelly、Jayanta K. Saha、Robert R. Whittle

  DOI：10.1021/jo00220a001

  日期：1985.10