3-oxo-17β-(1-imidazolyl)carbonyl-28-norlup-20(29)-ene

• 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-(1-imidazolyl)carbonyl-28-norlup-20(29)-ene
• 英文别名: 3-oxobetulinic 1H-imidazole ester；N-[3-oxolup-20(29)-en-28-oyl]-1-imidazole；28-(1H-imidazol-1-yl)-lup-20(29)-en-3,28-dione；(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-(imidazole-1-carbonyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
• 化学式: C₃₃H₄₈N₂O₂
• 分子量: 504.756
• InChiKey: IZTTVFKYKSWHGI-KZDAZGORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  37
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-oxo-17β-(1-imidazolyl)carbonyl-28-norlup-20(29)-ene 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以90%的产率得到
  参考文献：
  名称：

  Synthesis and the antineoplastic activity of imidazolides of betulonic acid

  摘要：

  Lupane C-28-imidazolides containing 3-oxo-, 3-hydroxyimino-, and 2-cyano-2,3-seco-4(23)-ene fragments in cycle A have been synthesized. 3-3-Hydroxyimino-lup-20(29)-en-28-yl-1H-imidazole-1-carboxylate showed the highest antineoplastic activity in experiments in vitro, significantly inhibiting the growth and inducing the death of cells of lung, colon cancer, breast, central nervous system, ovarian, prostate, renal, leukemia, and melanoma cancers. In experiments on mice, it had a moderate antineoplastic effect on inoculated breast adenocarcinoma Ca755 and large intestine adenocarcinoma AKATOL.

  DOI：

  10.1134/s1068162015020065
• 作为产物：
  描述：

  路路通酸 在 草酰氯 作用下， 以 苯 为溶剂， 反应 17.0h， 生成 3-oxo-17β-(1-imidazolyl)carbonyl-28-norlup-20(29)-ene
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Betulonic Acid Amides and Conjugates with Amino Acids

  摘要：

  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.

  DOI：

  10.1023/b:rubi.0000015778.77887.f1

文献信息

• Synthesis of betulonic acid amides
  作者：A. N. Antimonova、N. V. Uzenkova、N. I. Petrenko、M. M. Shakirov、E. E. Shul’ts、G. A. Tolstikov

  DOI：10.1007/s10600-008-9054-7

  日期：2008.5

  Betulonic acid amides of interest as potential biologically active compounds were prepared.

  具有潜在生物活性的贝土洛酸酰胺类化合物被制备出来。
• Novel semisynthetic derivatives of betulin and betulinic acid with cytotoxic activity
  作者：Rita C. Santos、Jorge A.R. Salvador、Silvia Marín、Marta Cascante

  DOI：10.1016/j.bmc.2009.07.050

  日期：2009.9.1

  N-acylimidazole derivatives of betulin and betulinic acid (14–29) have been synthesized. The new compounds were screened for in vitro cytotoxicity activity against human cancer cell lines HepG2, Jurkat and HeLa. A number of compounds have shown IC50 values lower than 2 μM against the cancer cell lines tested and the vast majority has shown a better cytotoxicity profile than betulinic acid, including the

  一系列新的咪唑羧酸酯（氨基甲酸酯）和Ñ桦木醇和桦木酸（的-acylimidazole衍生物14 - 29）已经被合成。筛选了新化合物对人癌细胞HepG2，Jurkat和HeLa的体外细胞毒性活性。许多化合物显示出对测试的癌细胞系的IC 50值低于2μM，并且绝大多数化合物显示出比桦木酸更好的细胞毒性，包括桦木素衍生物。N-酰基咪唑衍生物26和27（HepG2细胞中IC 50为0.8和1.7μM）和C-3氨基甲酸酯衍生物16（IC在HepG2细胞中50 50μM是最有前途的化合物。基于观察到的细胞毒性，已经建立了结构-活性关系。
• Semisynthesis, cytotoxicity, antimalarial evaluation and structure-activity relationship of two series of triterpene derivatives
  作者：Simone Tasca Cargnin、Andressa Finkler Staudt、Patrícia Medeiros、Daniel de Medeiros Sol Sol、Ana Paula de Azevedo dos Santos、Fernando Berton Zanchi、Grace Gosmann、Antonio Puyet、Carolina Bioni Garcia Teles、Simone Baggio Gnoatto

  DOI：10.1016/j.bmcl.2017.12.060

  日期：2018.2

  semisynthesis of two series of ursolic and betulinic acid derivatives through designed by modifications at the C-3 and C-28 positions and demonstrate their antimalarial activity against chloroquine-resistant P. falciparum (W2 strain). Structural modifications at C-3 were more advantageous to antimalarial activity than simultaneous modifications at C-3 and C-28 positions. The ester derivative, 3β-butanoyl betulinic

  在这份报告中，我们描述了通过在C-3和C-28位置进行修饰设计而设计的两个系列的熊草酸和桦木酸衍生物的半合成，并证明了它们对耐氯喹的恶性疟原虫（W2株）具有抗疟活性。与在C-3和C-28位置同时进行修饰相比，在C-3处进行结构修饰更有利于抗疟疾活性。酯衍生物3β-丁酰桦木酸（7b）是活性最高的化合物（IC 50  = 3.4 µM），对VERO和HepG2细胞均无细胞毒性（CC 50  > 400 µM），显示出对寄生虫的选择性（选择性）索引> 117.47）。与青蒿素合用，化合物7b表现出加和效应（CI = 1.14）。对接分析显示7b与疟原虫蛋白酶PfSUB1可能发生相互作用，最佳结合亲和力为-7.02 kcal / mol，地衣芽孢杆菌枯草杆菌蛋白酶A蛋白酶活性测定（IC 50  = 93 µM）和观察到的环形式积累以及滋养体在体外的出现延迟表明，疟原虫上3β-丁酰基桦木酸的主要靶标
• [EN] TRITERPENOID DERIVATIVES USEFUL AS ANTIPROLIFERATIVE AGENTS<br/>[FR] DÉRIVÉS DE TRITERPÉNOÏDE AGENTS ANTIPROLIFÉRATION
  申请人：UNIV DE COIMBRA

  公开号：WO2010134830A1

  公开（公告）日：2010-11-25

  Formule (I) and (II). The present invention relates to the use of a new lupane derivative of general formula (I) or (II), or a pharmaceutically acceptable salt, crystal form, complex, hydrate, or hydrolysable ester thereof, for preventing and/or inhibiting tumor growth and for treating cancer and other proliferative diseases, more particularly for treating leukemia, liver, cervical, colon and prostate cancer. The present invention also relates to the synthesis of these compounds and to pharmaceutical compositions which contain them.

  公式(I)和(II)。本发明涉及使用一种新的通用公式(I)或(II)的鲁班衍生物，或其药学上可接受的盐、晶型、复合物、水合物或可水解酯，用于预防和/或抑制肿瘤生长，并用于治疗癌症和其他增生性疾病，更具体地用于治疗白血病、肝脏、宫颈、结肠和前列腺癌。本发明还涉及这些化合物的合成以及含有它们的药物组合物。
• TRITERPENOID DERIVATIVES USEFUL AS ANTIPROLIFERATIVE AGENTS
  申请人：Ribeiro Salvador Jorge Antonio

  公开号：US20120129901A1

  公开（公告）日：2012-05-24

  Formula (I) and (II). The present invention relates to the use of a new lupane derivative of general formula (I) or (II), or a pharmaceutically acceptable salt, crystal form, complex, hydrate, or hydrolysable ester thereof, for preventing and/or inhibiting tumor growth and for treating cancer and other proliferative diseases, more particularly for treating leukemia, liver, cervical, colon and prostate cancer. The present invention also relates to the synthesis of these compounds and to pharmaceutical compositions which contain them.

  公式（I）和（II）。本发明涉及使用新的熊果苷衍生物的一般公式（I）或（II），或其药学上可接受的盐，晶体形式，复合物，水合物或可水解酯，用于预防和/或抑制肿瘤生长和治疗癌症和其他增生性疾病，更具体地用于治疗白血病，肝癌，宫颈癌，结肠癌和前列腺癌。本发明还涉及这些化合物的合成以及含有它们的制药组合物。