ribocyclophane A | 2285440-90-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ribocyclophane A
• 英文别名: (2R,3S,8S,13R,14S,19S)-8,19-dibutyl-3,14-dimethyl-2,13-bis[[(2S,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy]tricyclo[18.2.2.29,12]hexacosa-1(22),9,11,20,23,25-hexaene-10,21,24,26-tetrol
• CAS: 2285440-90-4
• 化学式: C₄₆H₇₂O₁₄
• 分子量: 849.069
• InChiKey: JKEVYZYKIRFEPT-IYGPRKNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  60
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  239
• 氢给体数：
  10
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  ribocyclophane A 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 以0.5 mg的产率得到(-)-cylindrocyclophane A
  参考文献：
  名称：

  Ribocyclophanes A–E, Glycosylated Cyclophanes with Antiproliferative Activity from Two Cultured Terrestrial Cyanobacteria

  摘要：

  The cell extracts of two cultured freshwater Nostoc spp., UIC 10279 and UIC 10366, both from the suburbs of Chicago, showed antiproliferative activity against MDA-MB-231 and MDA-MB-435 cancer cell lines. Bioassay-guided fractionation led to the isolation of five glycosylated cylindrocyclophanes, named ribocyclophanes A-E (1-5) and cylindrocyclophane D (6). The structure determination was carried out by HRESIMS and 1D and 2D NMR analyses and confirmed by single-crystal X-ray crystallography. The structures of ribocyclophanes A-E (1-5) contain a beta-D-ribopyranose glycone in the rare C-1(4) conformation. Among isolated compounds, ribocyclophane D (4) showed antiproliferative activity against MDA-MB-435 and MDA-MB-231 cancer cells with an IC50 value of less than 1 mu M.

  DOI：

  10.1021/acs.jnatprod.7b00954