N-(3β-acetoxyolean-12-en-28-oyl)-L-valine methyl ester | 851475-53-1

• 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: N-(3β-acetoxyolean-12-en-28-oyl)-L-valine methyl ester
• CAS: 851475-53-1
• 化学式: C₃₈H₆₁NO₅
• 分子量: 611.906
• InChiKey: QAFVIKDRWJUPBE-BOEFQGDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.03
• 重原子数：
  44.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(3β-acetoxyolean-12-en-28-oyl)-L-valine methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N-[3β-hydroxyolean-12-en-28-oyl]-L-valine
  参考文献：
  名称：

  Synthesis and activity of oleanolic acid derivatives, a novel class of inhibitors of osteoclast formation

  摘要：

  Two series of oleanolic acid derivatives were synthesized and their inhibitory activity on the formation of osteoclast-like multinucleated cells (OCLs) induced by 1 alpha,25-dihydroxy vitamin D-3 was evaluated in a co-culture assay system. The structure-activity relationships, together with electronic structure based on the frontier molecular orbitals, for example, HOMO and LUMO, related to different amino acid substituents were studied. Derivatives with proline or phenylalanine showed a tendency to enhance the inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.061
• 作为产物：
  描述：

  L-缬氨酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(3β-acetoxyolean-12-en-28-oyl)-L-valine methyl ester
  参考文献：
  名称：

  Synthesis and activity of oleanolic acid derivatives, a novel class of inhibitors of osteoclast formation

  摘要：

  Two series of oleanolic acid derivatives were synthesized and their inhibitory activity on the formation of osteoclast-like multinucleated cells (OCLs) induced by 1 alpha,25-dihydroxy vitamin D-3 was evaluated in a co-culture assay system. The structure-activity relationships, together with electronic structure based on the frontier molecular orbitals, for example, HOMO and LUMO, related to different amino acid substituents were studied. Derivatives with proline or phenylalanine showed a tendency to enhance the inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.061

文献信息

• Synthesis and evaluation of A-seco type triterpenoids for anti-HIV-1protease activity
  作者：Ying Wei、Chao-Mei Ma、Masao Hattori

  DOI：10.1016/j.ejmech.2009.05.002

  日期：2009.10

  2,3-Seco-dioic acids derived from four different triterpene skeletons were prepared and evaluated for their anti-HIV-1 protease activity. Two A-seco derivatives showed potent inhibitory activity against HIV-1 protease (3c and 3e, IC50 5.7 and 3.9 mu M, respectively), while four other derivatives showed moderate to weak inhibition (3a, 3b, 3d and 3f, IC50 15.7-88.1 mu M). The combination of a 2,3-seco-2,3-dioic acid functional group in ring A and a free acid group at C-28 or C-30 significantly enhanced HIV-1 protease inhibitory activity (3a, 3c-3e, IC50 3.9-17.6 mu M). On the other hand, all A-seco derivatives were found to be very weak inhibitors of HCV, renin and trypsin proteases (IC50 > 80 mu M). These findings indicate that A-seco triterpenes with a carboxyl group at C-28 or C-30 are novel and highly selective HIV-1 protease inhibitors. (C) 2009 Elsevier Masson SAS. All rights reserved.