(-)-petrosynoic acid B | 1422985-51-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (-)-petrosynoic acid B
• 英文别名: (-)-Petrosynoic Acid B；(4Z,29E,31R)-31-hydroxytritriaconta-4,29-dien-2,18,32-triynoic acid
• CAS: 1422985-51-0
• 化学式: C₃₃H₅₀O₃
• 分子量: 494.758
• InChiKey: QEYHXRJGVIQFQH-VGLFVHPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  36
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-petrosynoic acid B 、 N,O-双(三甲基硅烷基)三氟乙酰胺 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 trimethylsilyl (4Z,29E,31R)-31-trimethylsilyloxytritriaconta-4,29-dien-2,18,32-triynoate
  参考文献：
  名称：

  Structures and Cytotoxic Evaluation of New and Known Acyclic Ene-Ynes from an American Samoa Petrosia sp. Sponge

  摘要：

  Four new compounds, (-)-petrosynoic acids A D (1-4), and five known congeners, pellynols A (5), C (6), D (7), F (8), and I (9), were isolated from a Petrosia sp. marine sponge collected in American Samoa. Isolation work was guided by cytotoxicity against human lung cancer cells (H460). The structures of the C-31-C-33 polyacetylenes (1-9) were determined on the basis of 1D- and 2D-NMR analysis, mass spectrometry, and comparison of specific rotation values. Compounds 1-9 were found to be broadly cytotoxic with limited selectivity for cancer cells, as they were all moderately active against the A2058 (melanoma), H522-T1 (lung), and H460 (lung) human cancer cell lines as well as IMR-90 quiescent human fibroblast cells.

  DOI：

  10.1021/np3008446

文献信息

• Structures and Cytotoxic Evaluation of New and Known Acyclic Ene-Ynes from an American Samoa <i>Petrosia</i> sp. Sponge
  作者：Eric J. Mejia、Lindsay B. Magranet、Nicole J. De Voogd、Karen TenDyke、Dayong Qiu、Young Yongchun Shen、Zhongrui Zhou、Phillip Crews

  DOI：10.1021/np3008446

  日期：2013.3.22

  Four new compounds, (-)-petrosynoic acids A D (1-4), and five known congeners, pellynols A (5), C (6), D (7), F (8), and I (9), were isolated from a Petrosia sp. marine sponge collected in American Samoa. Isolation work was guided by cytotoxicity against human lung cancer cells (H460). The structures of the C-31-C-33 polyacetylenes (1-9) were determined on the basis of 1D- and 2D-NMR analysis, mass spectrometry, and comparison of specific rotation values. Compounds 1-9 were found to be broadly cytotoxic with limited selectivity for cancer cells, as they were all moderately active against the A2058 (melanoma), H522-T1 (lung), and H460 (lung) human cancer cell lines as well as IMR-90 quiescent human fibroblast cells.