betulonic acid chloride 3-oxime | 628308-26-9

• 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: betulonic acid chloride 3-oxime
• CAS: 628308-26-9
• 化学式: C₃₀H₄₆ClNO₂
• 分子量: 488.154
• InChiKey: LXFNFEAPGZGJRE-SVAFSPIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.24
• 重原子数：
  34.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  49.66
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  betulonic acid chloride 3-oxime 在 sodium azide 作用下， 以 丙酮 、 苯 为溶剂， 反应 8.0h， 生成 17β-[N'-(pyridin-2-yl)ureido]-28-norlup-20(29)-ene 3-oxime
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Ureides and Carbamates of Betulinic Acid and Its Derivatives

  摘要：

  Ureides and carbamates of betulinic acid and its derivatives were prepared in good yields by interaction of betulinic acid, betulonic acid, and betulonic acid 3-oxime with amines, amino acids, and alcohols. Ureides of betulonic acid containing L-Val and L-Met residues were found to be effective against herpes simplex type 1 virus.

  DOI：

  10.1023/b:rubi.0000008902.36604.97
• 作为产物：
  描述：

  白桦脂醇 在 chromium(VI) oxide 、 草酰氯 、 硫酸 、 盐酸羟胺 作用下， 以 吡啶 、 丙酮 、 苯 为溶剂， 反应 2.0h， 生成 betulonic acid chloride 3-oxime
  参考文献：
  名称：

  Lupane triterpenes and derivatives with antiviral activity

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(03)00714-5

文献信息

• ——
  作者：O. B. Flekhter

  DOI：10.1023/a:1023948919315

  日期：——

  New nitrogen-containing derivatives of betulinic and betulonic acids, hydrazides and N'-benzalhydrazides, were synthesized. Their antiviral activities toward of influenza A virus, herpes simplex type I virus, enterovirus ECHO6, and HIV-1 were studied in vitro. Betulinic acid 3-oxime was found to have the highest activity against the influenza virus. Betulonic acid, betulinic acid 4-chlorobenzalhydrazide

  合成了新的桦木酸和丁二酸的含氮衍生物酰肼和N'-苯甲酰肼。在体外研究了它们对甲型流感病毒，I型单纯疱疹病毒，肠病毒ECHO6和HIV-1的抗病毒活性。发现贝特林酸3-肟对流感病毒的活性最高。苯丁酸，桦木酸4-氯苯甲酰肼，桦木酸3-肟苯甲酰肼和桦木酸酰肼抑制单纯疱疹I型病毒的复制。桦木酸酰肼还显示出对HIV-1的抗病毒活性。所研究的桦木酸的所有衍生物对肠病毒ECHO6的抗病毒活性均较低。
• Synthesis and evaluation of antiviral activities of triterpenic conjugates with 2-aminobutan-1-ol as potent microbicidal agents
  作者：Irina A. Tolmacheva、Ekaterina V. Igosheva、Olga V. Savinova、Eugene I. Boreko、Vladimir F. Eremin、Victoria V. Grishko

  DOI：10.1007/s00044-019-02401-w

  日期：2019.10

  triterpenic A ring on the level of antiviral activity of triterpenic C3, C28 amides with a residue of racemic, (S), or (R)-enantiomeric 2-aminobutan-1-ol against herpes simplex viruses type I (HSV-I) and type II (HSV-II), as well as against human immunodeficiency virus type I (HIV-1) was investigated. The 2,3-secolupane racemic amide 5a was selected as a potent microbicidal agent with the highest virus inhibitory

  三萜A环的合成修饰对三萜C3，C28酰胺具有外消旋，（S）或（R）-对映异构体2-氨基丁烷-1-醇残基的抗病毒活性水平对单纯疱疹病毒的影响研究了I型（HSV-I）和II型（HSV-II）以及针对人类I型免疫缺陷病毒（HIV-1）的病毒。选择2,3-seculupane消旋酰胺5a作为有效的杀微生物剂，具有最高的病毒抑制作用（针对HSV-I和HSV-II）和杀病毒（针对HSV-1和HIV-1），其抗病毒活性由（S）-对映体共轭5b提供。
• 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.