3-oxo-17β-carbamoyl-28-norlup-20(29)-ene | 628308-25-8

• 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: 3-oxo-17β-carbamoyl-28-norlup-20(29)-ene
• 英文别名: 3-oxolup-20(29)-en-28-amide；betulonic acid amide；(1R,3AS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxamide；(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxamide
• CAS: 628308-25-8
• 化学式: C₃₀H₄₇NO₂
• 分子量: 453.709
• InChiKey: YUVRHNHDLXYOHO-SVAFSPIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-oxo-17β-carbamoyl-28-norlup-20(29)-ene 在 吡啶 、 lithium aluminium tetrahydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 25.0h， 生成 3β-acetoxy-28-oxo-28-[N'-acetyl-(3-aminopropyl)-amino]lup-20(29)-ene
  参考文献：
  名称：

  Synthesis of aminopropylamino derivatives of betulinic and oleanolic acids

  摘要：

  Triterpenoids with the following amine fragments in C3 and C28 positions were synthesized on the basis of betulinic and oleanolic acids: (3-aminopropoxy)-, 3-acetyl-(3-aminopropyl)amino-, 6-[bis(3-aminopropyl)amino]hexylamino-, and (3-aminopropyl)-4-aminophenylsulfonyl-4-phenylamino. Amide of betulonic acid with 4,4'-diaminodiphenylsulfonic substituent was shown to exhibit no antitumor effect, but to have a pronounced anti-inflammatory activity.

  DOI：

  10.1134/s1068162013020064
• 作为产物：
  描述：

  路路通酸 在 草酰氯 、 氨 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以84.1%的产率得到3-oxo-17β-carbamoyl-28-norlup-20(29)-ene
  参考文献：
  名称：

  Betulinic acid derived hydroxamates and betulin derived carbamates are interesting scaffolds for the synthesis of novel cytotoxic compounds

  摘要：

  The betulinic acid-derived hydroxamates 5-18, the amides 19-24, and betulin-derived bis-carbamates 25-28 as well as the carbamates 31-40 and 44-48 were prepared and evaluated for their anti-proliferative activity in a photometric sulforhodamine B (SRB) assay against several human cancer cell lines and nonmalignant mouse fibroblasts (NIH 3T3). While for 3-O-acetyl hydroxamic acid 5 EC50 values as low as EC50 = 1.3 mu M were found, N,O-bis-alkyl substituted hydroxamates showed lowered cytotoxicity (EC50 = 16-20 mu M). In general, hydroxamic acid derivatives showed only reduced selectivity for tumor cells, except for allyl substituted compound 13 (EC50 = 5.9 mu M for A2780 human ovarian carcinoma cells and EC50 > 30 mu M for nonmalignant mouse fibroblasts). The cytotoxicity of betulinic acid derived amides 19-24 and of betulin derived bis-carbamates 25-28 was low, except for N-ethyl substituted 25. Hexyl substituted 39 showed EC50 = 5.6 mu M (518A2 cells) while for mouse fibroblasts EC50 > 30 was determined. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.043

文献信息

• Lupane triterpenes and derivatives with antiviral activity
  作者：L.A. Baltina、O.B. Flekhter、L.R. Nigmatullina、E.I. Boreko、N.I. Pavlova、S.N. Nikolaeva、O.V. Savinova、G.A. Tolstikov

  DOI：10.1016/s0960-894x(03)00714-5

  日期：2003.10

  Betulin and betulinic acid have been modified at the C-3 and C-28 positions and the antiviral activity of derivatives has been evaluated in vitro. It was found that simple modifications of the parent structure of lupane triterpenes produced highly effective agents against influenza A and herpes simplex type 1 viruses. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis and Antiviral Activity of Betulonic Acid Amides and Conjugates with Amino Acids
  作者：O. B. Flekhter、E. I. Boreko、L. R. Nigmatullina、E. V. Tret'yakova、N. I. Pavlova、L. A. Baltina、S. N. Nikolaeva、O. V. Savinova、V. F. Eremin、F. Z. Galin、G. A. Tolstikov

  DOI：10.1023/b:rubi.0000015778.77887.f1

  日期：2004.1

  Betulonic acid amides with aliphatic and heterocyclic amines and with L-amino acids were synthesized by the acid chloride method. Betulonic acid amide and L-methionine derivatives of betulonic acid and its 3-oxime effectively inhibit the influenza A virus. Betulonic acid octadecylamide is active against the herpes simplex type I virus. The conjugate of betulonic acid 3-oxime with L-methionine is also active toward HIV-1. The tested compounds mainly show no activity toward the ECHO6 virus, which is devoid of a coat.
• Synthesis of squalamine analogues on the basis of lupane triterpenoids
  作者：Gulnara V. Giniyatullina、Oxana B. Flekhter、Genrikh A. Tolstikov

  DOI：10.1016/j.mencom.2009.01.013

  日期：2009.1

  The first synthesis of a family of betulin-based triterpene-polyamine conjugates, which are structurally related to the potential antibiotic squalamine, is demonstrated.