bis(2,3,11,13-tetrahydrohelenalinyl) malonate | 77928-58-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: bis(2,3,11,13-tetrahydrohelenalinyl) malonate
• 英文别名: Bis-tetrahydro-helenalinylmalonate；bis[(3aR,5R,5aS,8aR,9S,9aR)-1,5,8a-trimethyl-2,8-dioxo-3a,4,5,5a,6,7,9,9a-octahydro-1H-azuleno[6,5-b]furan-9-yl] propanedioate
• CAS: 77928-58-6
• 化学式: C₃₃H₄₄O₁₀
• 分子量: 600.706
• InChiKey: MZLXYISZAFBQFV-VBQUAAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  心菊内酯 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 、 苯 为溶剂， 反应 41.0h， 生成 bis(2,3,11,13-tetrahydrohelenalinyl) malonate
  参考文献：
  名称：

  Antitumor agents. 44. Bis(helenalinyl) esters and related derivatives as novel potent antileukemic agents

  摘要：

  Bis(helenalinyl), bis(plenolinyl), bis(2,3-dihydrohelenalinyl), and bis(2,3,11,13-tetrahydrohelenalinyl) esters have been synthesized in an effort to elucidate the role of the two enone alkylating centers, beta-unsubstituted cyclopentenone and alpha-methylene gamma-lactone, as well as the significance of the diester linkage with respect to the enhanced in vivo P-388 lymphocytic leukemia antileukemic activity of bis(helenalinyl) malonate (2) against P-388 lymphocytic leukemia in the mouse. The bisesters (2-5; 7, 8; 10, 11) are, in general, more potent and less toxic than their corresponding parent alcohols (1, 6; 9; 14). The beta-unsubstituted cyclopentenone ring and the alpha-methylene gamma-lactone moiety in the bisesters play important roles for the enhancement of the P-388 antileukemic activity. Removal of the enone double bonds in both alkylating centers of 2 gave rise to inactive compounds. Except for 2, the potent antileukemic activity of the bis(helenalinyl) esters (3-5) appears to be independent of the ester chain length.

  DOI：

  10.1021/jm00140a003

文献信息

• Antitumor agents. 44. Bis(helenalinyl) esters and related derivatives as novel potent antileukemic agents
  作者：Kuo-Hsiung Lee、Toshiro Ibuka、Donald Sims、Osamu Muraoka、Hiroshi Kiyokawa、Iris H. Hall、Hyeong L. Kim

  DOI：10.1021/jm00140a003

  日期：1981.8

  Bis(helenalinyl), bis(plenolinyl), bis(2,3-dihydrohelenalinyl), and bis(2,3,11,13-tetrahydrohelenalinyl) esters have been synthesized in an effort to elucidate the role of the two enone alkylating centers, beta-unsubstituted cyclopentenone and alpha-methylene gamma-lactone, as well as the significance of the diester linkage with respect to the enhanced in vivo P-388 lymphocytic leukemia antileukemic activity of bis(helenalinyl) malonate (2) against P-388 lymphocytic leukemia in the mouse. The bisesters (2-5; 7, 8; 10, 11) are, in general, more potent and less toxic than their corresponding parent alcohols (1, 6; 9; 14). The beta-unsubstituted cyclopentenone ring and the alpha-methylene gamma-lactone moiety in the bisesters play important roles for the enhancement of the P-388 antileukemic activity. Removal of the enone double bonds in both alkylating centers of 2 gave rise to inactive compounds. Except for 2, the potent antileukemic activity of the bis(helenalinyl) esters (3-5) appears to be independent of the ester chain length.