2,3-dihydrohelenalin | 35412-73-8

• 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: 2,3-dihydrohelenalin
• 英文别名: (3aR,5R,5aS,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,6,7,9,9a-octahydroazuleno[6,7-b]furan-2,8-dione
• CAS: 35412-73-8
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: IOUNDPHKKPZPKB-XEPQRQSNSA-N

物化性质

• 沸点：
  460.1±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-dihydrohelenalin 、 丁二酰氯 以 苯 为溶剂， 反应 36.0h， 以250 mg的产率得到bis(2,3-dihydrohelenalinyl) succinate
  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
• 作为产物：
  描述：

  心菊内酯 在 sodium cyanoborohydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以76%的产率得到2,3-dihydrohelenalin
  参考文献：
  名称：

  几种倍半萜内酯在胃细胞保护作用中的构效关系。

  摘要：

  报道了几种倍半萜内酯对胃细胞保护活性的结构要求。对潜在活跃中心进行了理论实验研究。还原类似物的生物学评估以及这些化合物与内源性半胱氨酸残基之间的分子相互作用的模拟表明，非空间阻碍的迈克尔受体的存在似乎是该化合物家族中细胞保护活性的基本结构要求。该观察结果表明，细胞保护作用是通过粘膜中含巯基的肽与研究分子中存在的迈克尔受体之间的迈克尔反应介导的。这种作用机制是对我们先前论文中提出的机制的补充，并且与之不同。

  DOI：

  10.1021/jm00091a013

文献信息

• COMPOUNDS AND COMPOSITIONS FOR TREATING INFECTION
  申请人：Chepkwony Paul Kiprono

  公开号：US20120190734A1

  公开（公告）日：2012-07-26

  Compounds from 14 Kenyan plants, including from the root of Dovyalis abyssinica and Clutia robusta have been characterized and isolated, and their uses are disclosed.

  来自14种肯尼亚植物的化合物已经被鉴定和分离，包括来自阿比西尼亚多维亚利斯和强健小簇花的根部，它们的用途已经被披露。
• Structure-activity relationship in the gastric cytoprotective effect of several sesquiterpene lactones
  作者：Oscar S. Giordano、Mauricio J. Pestchanker、Eduardo Guerreiro、Jose R. Saad、Ricardo D. Enriz、Ana M. Rodriguez、Esteban A. Jauregui、Jorge Guzman、Alejandra O. M. Maria、Graciela H. Wendel

  DOI：10.1021/jm00091a013

  日期：1992.6

  a non sterically hindered Michael acceptor seems to be an essential structural requirement for the cytoprotective activity in this family of compounds. This observation suggests that cytoprotection is mediated through a Michael reaction between the sulfhydryl-containing peptides of the mucosa and Michael acceptors present in the molecules under study. This mechanism of action is in addition to and

  报道了几种倍半萜内酯对胃细胞保护活性的结构要求。对潜在活跃中心进行了理论实验研究。还原类似物的生物学评估以及这些化合物与内源性半胱氨酸残基之间的分子相互作用的模拟表明，非空间阻碍的迈克尔受体的存在似乎是该化合物家族中细胞保护活性的基本结构要求。该观察结果表明，细胞保护作用是通过粘膜中含巯基的肽与研究分子中存在的迈克尔受体之间的迈克尔反应介导的。这种作用机制是对我们先前论文中提出的机制的补充，并且与之不同。
• 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.