3-oxolupan-28-oyl chloride | 1007345-49-4

• 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-oxolupan-28-oyl chloride
• 英文别名: dihydrobetulonic acid chloride；(1S,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-propan-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carbonyl chloride
• CAS: 1007345-49-4
• 化学式: C₃₀H₄₇ClO₂
• 分子量: 475.155
• InChiKey: UXGGEPVHJRMQAG-SVAFSPIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-oxolupan-28-oyl chloride 在 吡啶 、 4-二甲氨基吡啶 、 硫酸 、 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 生成 3-[(3S,4S,5R,8R,9R,10R,13S,14R,15S)-13-(7-acetamidoheptylcarbamoyl)-4,9,10-trimethyl-15-propan-2-yl-3-prop-1-en-2-yl-2,3,5,6,7,8,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-4-yl]propanoic acid
  参考文献：
  名称：

  A-ring modified betulinic acid derivatives as potent cancer preventive agents

  摘要：

  Ten new 3,4-seco betulinic acid (BA) derivatives were designed and synthesized. Among them, compounds 7-15 exhibited enhanced chemopreventive ability in an in vitro short-term 12-O-tetradecanoylphorbol- 13-acetate (TPA) induced Epstein-Barr virus early antigen (EBV-EA) activation assay in Raji cells. Specifically, analogs with a free C-28 carboxylic acid, including 7, 8, 11, and 13, inhibited EBV-EA activation significantly. The most potent compound 8 displayed 100% inhibition at 1 x 10(3) mol ratio/TPA and 73.4%, 35.9%, and 8.4% inhibition at 5 x 10(2), 1 x 10(2), and 1 x 10 mol ratio/TPA, respectively, comparable with curcumin at high concentration and better than curcumin at low concentration. The potent chemopreventive activity of novel seco A-ring BAs (8 and 11) was further confirmed in an in vivo mouse skin carcinogenesis assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.041
• 作为产物：
  描述：

  白桦脂醇 在 palladium 10% on activated carbon Jones reagent 、 草酰氯 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 100.0 ℃ 、10.13 MPa 条件下， 生成 3-oxolupan-28-oyl chloride
  参考文献：
  名称：

  N'--3-AMINO-3-PHENYLPROPEONIC ACID AND THE PHARMACEUTICALLY ACCEPTABLE DERIVATIVES THEREOF, A METHOD FOR THE PRODUCTION AND THE USE THEREOF IN THE FORM OF A MEDICINAL AGENT

  摘要：

  该发明涉及有机化学和医学领域，特别是病毒学。更具体地说，该发明涉及一种新型化合物N′-{N-[3-氧代-鲁班-28-酰基]-9-氨基壬酰基}-3-氨基-3-苯丙酸，其化学式为1，以及该化合物的药用盐和前药形式，具有抗病毒（抗HIV）和免疫刺激活性。还公开了一种制备化合物1的方法以及将其用于制造具有抗病毒（抗HIV）和免疫刺激活性的药物的用途。

  公开号：

  US20100087539A1

文献信息

• [EN] C-28 AMIDES OF MODIFIED C-3 BETULINIC ACID DERIVATIVES AS HIV MATURATION INHIBITORS<br/>[FR] AMIDES C-28 DE DÉRIVÉS D'ACIDE BÉTULINIQUE MODIFIÉS EN C-3, UTILISÉS COMME INHIBITEURS DE MATURATION DU VIH
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2011153319A1

  公开（公告）日：2011-12-08

  Compounds having drug and bio-affecting properties, their pharmaceutical compositions and methods of use are set forth. In particular, modified C-3 and C-28 betulinic acid derivatives that possess unique antiviral activity are provided as HIV maturation inhibitors. These compounds are useful for the treatment of HIV and AIDS.

  具有药物和生物活性的化合物、其药物组合物及其使用方法。特别是，提供了一种具有独特抗病毒活性的改性C-3和C-28桦木酸衍生物，用作HIV成熟抑制剂。这些化合物可用于治疗HIV和艾滋病。
• Synthesis and Evaluation of Anticancer Activities of Novel C-28 Guanidine-Functionalized Triterpene Acid Derivatives
  作者：Anna Spivak、Rezeda Khalitova、Darya Nedopekina、Lilya Dzhemileva、Milyausha Yunusbaeva、Victor Odinokov、Vladimir D’yakonov、Usein Dzhemilev

  DOI：10.3390/molecules23113000

  日期：——

  Triterpene acids, namely, 20,29-dihydrobetulinic acid (BA), ursolic acid (UA) and oleanolic acid (OA) were converted into C-28-amino-functionalized triterpenoids 4–7, 8a, 15, 18 and 20. These compounds served as precursors for the synthesis of novel guanidine-functionalized triterpene acid derivatives 9b–12b, 15c, 18c and 20c. The influence of the guanidine group on the antitumor properties of triterpenoids

  三萜酸，即 20,29-二氢桦木酸 (BA)、熊果酸 (UA) 和齐墩果酸 (OA) 被转化为 C-28-氨基官能化的三萜类化合物 4-7、8a、15、18 和 20。这些化合物用作合成新型胍官能化三萜酸衍生物 9b-12b、15c、18c 和 20c 的前体。研究了胍基对三萜类化合物抗肿瘤特性的影响。在五种人类肿瘤细胞系（Jurkat、K562、U937、HEK 和 Hela）上测试了细胞毒性，并与对正常人成纤维细胞的测试进行了比较。大多数测试的胍衍生物的抗肿瘤活性低于相应的胺类，但带有胍基团的三萜类化合物对人成纤维细胞的毒性较小。无论三萜骨架类型如何，将三（羟甲基）氨基甲烷部分引入三萜酸分子都显着增强了所得缀合物 15、15c、18b、c 和 20b、c 的细胞毒活性。选择二氢桦木酸胺 15、其胍衍生物 15c 以及熊果酸和齐墩果酸的胍衍生物 18c 和 20c 用于在 Jurkat
• Antitumor activity of amides of dihydrobetulonic acid in vitro and in vivo
  作者：I. V. Sorokina、I. Ya. Mainagashev、N. A. Zhukova、D. V. Korchagina、T. G. Tolstikova、V. P. Nikolin、N. A. Popova、M. A. Pokrovskii、A. G. Pokrovskii、N. F. Salakhutdinov

  DOI：10.1134/s106816201302012x

  日期：2013.3

  Amides containing homopiperidine and piperazine cycles were synthesized from dihydrobetulonic acid obtained by the oxidation of dihydrobetulin. All substances were shown to have a high antitumor activity (CCID50 = 3.5-36.2 mu M) in vitro in lymphoid (CEM-13, U-937) and monocytic (MT-4) human cell lines. Amides containing the methyl- and ethylpiperazine residues do not influence the viability of Lung Lewis Carcinoma cells in culture and do not have a significant effect on its transplants in C57BL/6 mice. However, these amides efficiently inhibit the development of metastases in lungs of these mice. The antimetastatic activity of the studied amides increases with changing the methyl by ethyl aliphatic residue in the piperazine cycle.