allobetulin | 125225-35-6

• 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: allobetulin
• 英文别名: (1R,4R,5R,8R,10S,13R,14R,17R,18S,19R)-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[17.3.2.01,18.04,17.05,14.08,13]tetracosan-10-ol
• CAS: 125225-35-6
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: BZNIIOGSANMIET-KCGIQSLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  allobetulin 在 吗啉 、 五氯化磷 、 sulfur 作用下， 以 甲苯 为溶剂， 生成
  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
• 作为产物：
  描述：

  白桦脂醇 在 montmorrillonite K₁₀ 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以66%的产率得到allobetulin
  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

• Intramolecular cyclization involving O-vinyl or O-vinylketoxime function in a number of pentacyclic triterpenoids in superbasic medium
  作者：A. V. Orlov、N. G. Komissarova、O. V. Shitikova、L. V. Spirikhin、M. S. Yunusov

  DOI：10.1007/s11172-013-0093-2

  日期：2013.3

  28-Triphenylmethoxylup-20(29)-ene-2,3-dione dioxime and 18α(H)-oleanane-3β,19β,28-triol upon reaction with acetylene in superbasic medium KOH-DMSO undergo intramolecular cyclization with the formation of products containing 1,2,5-oxadiazole and tetrahydrofuran fragment, respectively.

  28-三苯甲氧基-20(29)-烯-2,3-二酮二肟和18α(H)-齐墩果烷-3β,19β,28-三醇在超碱性介质KOH-DMSO中与乙炔反应，发生分子内环化，分别形成含有1,2,5-恶二唑和四氢呋喃片段的产品。
• Hase, T. A.; Suokas, E.; Weckman, A., Synthetic Communications, 1981, vol. 11, # 6, p. 489 - 492
  作者：Hase, T. A.、Suokas, E.、Weckman, A.

  DOI：——

  日期：——