quinoxalino[2,3-b]-28-hydroxy-20(29)-lupene

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: quinoxalino[2,3-b]-28-hydroxy-20(29)-lupene
• 英文别名: [(1R,2R,5R,6R,7R,10S,13R,14R,17R)-1,13,14,18,18-pentamethyl-7-prop-1-en-2-yl-20,27-diazaheptacyclo[15.12.0.02,14.05,13.06,10.019,28.021,26]nonacosa-19,21,23,25,27-pentaen-10-yl]methanol
• 化学式: C₃₆H₅₀N₂O
• 分子量: 526.806
• InChiKey: UWZPURHOYQHEGS-FLKOHOBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  39
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  46
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  白桦脂酸 在 吗啉 、 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 sulfur 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 quinoxalino[2,3-b]-28-hydroxy-20(29)-lupene
  参考文献：
  名称：

  Triterpenoid Pyrazines and Benzopyrazines with Cytotoxic Activity

  摘要：

  Twelve lupane, 18 alpha-oleanane, and des-E-lupane derivatives (1a-5b) were either extracted from natural sources or synthesized from betulinic acid (1a) and betulin (2). Compounds 1b, 1c, 3b, 3c, 4b, 4c, 5a, and 5b were then used as starting materials for further synthesis of a series of pyrazines and benzopyrazines (6a-18); 20 of them are new (6a-6e, 7a-7d, and 10a-18). Activity of pyrazine 6a against the T-lymphoblastic leukemia cell line CEM encouraged us to synthesize several new esters (6b-6d) to study structure-activity relationships with respect to substitution of the carboxyl group at position 28. The synthesized compounds were tested for cytotoxicity against a variety of cancer cell lines of different histogenetic origin, and the results were compared with cytotoxicity of the known starting compounds. Significant cytotoxic activity against A 549, K 562, and multidrug-resistant K 562-tax cell lines was found in pyrazines 6a, 6d, and 6e.

  DOI：

  10.1021/np060436d

文献信息

• ——
  作者：A. V. Korovin、A. V. Tkachev

  DOI：10.1023/a:1009598805986

  日期：——

  Oxidation of triterpenoids methyl ursonate, acetylbetulone, and allobetulone with atmospheric oxygen in the presence of (BuOK)-O-t in (BuOH)-O-t afforded the corresponding 2,3-diketo derivatives in 90-97% yields. These derivatives exist predominantly as tautomers containing the enolized keto group at the C(2) atom. Their reactions with o-phenylenediamine gave rise to the corresponding quinoxalines in 85-95% yields.
• Triterpenoid Pyrazines and Benzopyrazines with Cytotoxic Activity
  作者：Milan Urban、Jan Sarek、Miroslav Kvasnica、Iva Tislerova、Marian Hajduch

  DOI：10.1021/np060436d

  日期：2007.4.1

  Twelve lupane, 18 alpha-oleanane, and des-E-lupane derivatives (1a-5b) were either extracted from natural sources or synthesized from betulinic acid (1a) and betulin (2). Compounds 1b, 1c, 3b, 3c, 4b, 4c, 5a, and 5b were then used as starting materials for further synthesis of a series of pyrazines and benzopyrazines (6a-18); 20 of them are new (6a-6e, 7a-7d, and 10a-18). Activity of pyrazine 6a against the T-lymphoblastic leukemia cell line CEM encouraged us to synthesize several new esters (6b-6d) to study structure-activity relationships with respect to substitution of the carboxyl group at position 28. The synthesized compounds were tested for cytotoxicity against a variety of cancer cell lines of different histogenetic origin, and the results were compared with cytotoxicity of the known starting compounds. Significant cytotoxic activity against A 549, K 562, and multidrug-resistant K 562-tax cell lines was found in pyrazines 6a, 6d, and 6e.