inophyllum E | 17312-31-1

• 物质功能分类: 天然产物 - 木脂素
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: inophyllum E
• 英文别名: (16R,17S)-10,10,16,17-tetramethyl-6-phenyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(14),2(7),5,8(13),11-pentaene-4,18-dione
• CAS: 17312-31-1
• 化学式: C₂₅H₂₂O₅
• 分子量: 402.447
• InChiKey: YRHQANFINIANSK-UONOGXRCSA-N

物化性质

• 熔点：
  186-188 °C
• 沸点：
  608.7±55.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  inophyllum E 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 6.0h， 生成 inophyllum A 4-bromobenzoate
  参考文献：
  名称：

  The inophyllums, novel inhibitors of HIV-1 reverse transcriptase isolated from the Malaysian tree, Calophyllum inophyllum Linn

  摘要：

  As part of a search for novel inhibitors of HIV-1 reverse transcriptase, the acetone extract of the giant African snail, Achatina fulica, was shown to be active. Fractionation of the extract yielded inophyllums A, B, C, and E and calophyllolide (1a, 2a, 3a, 3b, and 6), previously isolated from Calophyllum inophyllum Linn., a known source of nutrition for A. fulica. From a methanol/ methylene chloride extract of C. inophyllum, the same natural products in considerably greater yield were isolated in addition to a novel enantiomer of soulattrolide (4), inophyllum P (2b), and two other novel compounds, inophyllums G-1 (7) and G-2 (8). The absolute stereochemistry of inophyllum, A (1a) was determined to be 10(R), 11(S), 12(S) from a single-crystal X-ray analysis of its 4-bromobenzoate derivative, and the relative stereochemistries of the other inophyllums isolated from C. inophyllum were established by a comparison of their H-1 NMR NOE values and coupling constants to those of inophyllum A (1a). Inophyllums B and P (2a and 2b) inhibited HIV reverse transcriptase with IC50 values of 38 and 130 nM, respectively, and both were active against HIV-1 in cell culture (IC50 of 1.4 and 1.6 mu M). Closely related inophyllums A, C, D, and E, including calophyllic acids, were significantly less active or totally inactive, indicating certain structural requirements in the chromanol ring. Altogether, 11 compounds of the inophyllum class were isolated from C. inophyllum and are described together with the SAR of these novel anti-HIV compounds.

  DOI：

  10.1021/jm00078a001
• 作为产物：
  描述：

  inophyllum A 在 chromium trioxide-pyridine complex 作用下， 生成 inophyllum E
  参考文献：
  名称：

  来自斯里兰卡的两组化学性质不同的 calophyllum 物种

  摘要：

  摘要 对Calophyllum moonii 和C. walkeri 的叶提取物进行了研究。前者含有新黄酮类化合物，而后者含有calozeylanic酸。已经审查了七种 Calophyllum 物种的叶提取物中天然产物的分布，并且已经认识到 Calophyllum 物种中存在两个化学上不同的群体。

  DOI：

  10.1016/s0031-9422(00)85494-1

文献信息

• Synthesis of the calophyllum coumarins
  作者：Christopher J. Palmer、Jonathan L. Josephs

  DOI：10.1016/s0040-4039(00)73500-3

  日期：1994.7

  Synthetic routes leading to the synthesis of the natural 4-alkyl and 4-phenyl coumarins isolated from Calophyllum sp. are reported. The reported structures of calanolides C and D and oblongulide are incorrect and have been corrected by unambiguous synthesis.
• Palmer, Christopher; Josephs, Jonathan, Journal of the Chemical Society. Perkin transactions I, 1995, # 24, p. 3135 - 3152
  作者：Palmer, Christopher、Josephs, Jonathan

  DOI：——

  日期：——
• Sekino, Etsuko; Kumamoto, Takuya; Tanaka, Tomohiro, Journal of Organic Chemistry, 2004, vol. 69, # 8, p. 2760 - 2767
  作者：Sekino, Etsuko、Kumamoto, Takuya、Tanaka, Tomohiro、Ikeda, Tomoko、Ishikawa, Tsutomu

  DOI：——

  日期：——
• EP0674643A4
  申请人：——

  公开号：EP0674643A4

  公开（公告）日：1995-08-08
• COUMARIN DERIVATIVES AS RETROVIRAL INHIBITORS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0674643A1

  公开（公告）日：1995-10-04

表征谱图