3-amino-lup-20(29)-en-28-oic acid | 212773-15-4

• 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-amino-lup-20(29)-en-28-oic acid
• 英文别名: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-amino-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• CAS: 212773-15-4
• 化学式: C₃₀H₄₉NO₂
• 分子量: 455.725
• InChiKey: ZZWDPHKXZJTXKA-FZFNOLFKSA-N

物化性质

• 沸点：
  541.0±33.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-lup-20(29)-en-28-oic acid 在 三氟化硼乙醚 、 N,N'-羰基二咪唑 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 10.17h， 生成 (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-(piperidine-3-carbonylamino)-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
  参考文献：
  名称：

  白桦脂酸衍生物及其制备方法和在制备抗肿 瘤药物中的应用

  摘要：

  本发明公开了一种式(1)、式(2)所示白桦脂酸衍生物及其制备方法。将白桦脂胺、白桦脂酸分别和各种杂环羧酸进行缩合反应得到杂环修饰的白桦脂酸衍生物。本发明还提供了所述白桦脂酸衍生物在制备抗肿瘤药物中的应用。

  公开号：

  CN104744549B
• 作为产物：
  描述：

  白桦脂酸 在 吡啶 、 lithium aluminium tetrahydride 、 Jones reagent 、 盐酸羟胺 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 79.0h， 生成 3-amino-lup-20(29)-en-28-oic acid
  参考文献：
  名称：

  熊果酸衍生物的合成和抗白血病活性：与伊马替尼联合使用的潜在联合药物

  摘要：

  伊马替尼是一种特异性Bcr-Abl酪氨酸激酶抑制剂，是治疗慢性粒细胞白血病最常用的药物。然而，高达 33% 的患者未达到最佳反应。因此，开发慢性粒细胞白血病的新治疗策略至关重要。桦木酸 (1) 和熊果酸 (2) 是天然五环三萜，具有抗白血病活性。在本研究中，我们评估了桦木酸和熊果酸三萜部分 C-3 位置的药物调节对其抗 K562 白血病细胞活性的影响。合成了六种新衍生物 (1a-2c)，并评估了其在哺乳动物和白血病细胞中的促凋亡和抗增殖作用。熊果酸C-3位含有胺基的2c衍生物对白血病细胞活性最强，处理48小时后IC 50值为5.2 μM。 2c 对 VERO 和 HepG2 细胞以及人淋巴细胞没有表现出细胞毒性作用，与正常细胞相比，对癌症表现出良好的选择性指数。通过半胱天冬酶 3 和 8 凋亡诱导细胞死亡，并且还导致细胞周期停滞，如 G1 期细胞积累和 G2 期细胞数量减少所证明的那样。此

  DOI：

  10.1016/j.cbi.2021.109535

文献信息

• [EN] ENHANCED NEOGLYCOSIDES THROUGH NEOGLYCOSYLATION AND METHODS OF USE THEREOF<br/>[FR] NÉO-GLYCOSIDES AMÉLIORÉS PAR NÉO-GLYCOSYLATION ET LEURS PROCÉDÉS D'UTILISATION
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2010080863A1

  公开（公告）日：2010-07-15

  Using neoglycosylation, the impact of differential glycosylation upon the divergent anticancer and anti-HIV properties of the triterpenoid betulinic acid (BA) was examined. Each member from a library of 37 differentially glycosylated BA variants was tested for anticancer and anti-HIV activities. Enhanced analogs for both desired activities were discovered with the corresponding antitumor or antiviral enhancements diverging, based upon the appended sugar, into two distinct compound subsets.

  通过新糖基化技术，研究了巴西诺酸（BA）的不同糖基化对其抗癌和抗HIV特性的影响。对包含37种不同糖基化BA变体的库中的每个成员进行了抗癌和抗HIV活性测试。发现了增强的类似物，对于这两种期望的活性，根据附加的糖，分化为两个不同的化合物子集，分别具有抗肿瘤或抗病毒增强效果。
• Enhancing the Divergent Activities of Betulinic Acid via Neoglycosylation
  作者：Randal D. Goff、Jon S. Thorson

  DOI：10.1021/ol8025704

  日期：2009.1.15

  Using neoglycosylation, the impact of differential glycosylation upon the divergent anticancer and anti-HIV properties of the triterpenoid betulinic acid (BA) was examined. Each member from a library of 37 differentially glycosylated BA variants was tested for anticancer and anti-HIV activities. Enhanced analogs for both desired activities were discovered with the corresponding antitumor or antiviral enhancements diverging, on the basis of the appended sugar, into two distinct compound subsets.
• Antimicrobial properties of amine- and guanidine-functionalized derivatives of betulinic, ursolic and oleanolic acids: Synthesis and structure/activity evaluation
  作者：Anna Yu. Spivak、Rezeda R. Khalitova、Darya A. Nedopekina、Rinat R. Gubaidullin

  DOI：10.1016/j.steroids.2019.108530

  日期：2020.2

  A series of 34 new amine- and guanidine-functionalized derivatives of betulinic, ursolic, and oleanolic acids were synthesized and tested for their antimicrobial activity against the growth of four bacterial strains (Escherichia colt Acinetobacter baumannii, Pseudomonas aeruginosa, and Staphylococcus aureus (MESA)) and two fungal strains (Candida albicans and Cryptococcus neoformans). The obtained compounds were also tested for the cytotoxic effect against HEK293 human embryonic kidney cell line and hemolytic activity against human red blood cells. Most of the prepared amino and guanidinium derivatives of betulinic, ursolic, and oleanolic acids showed a considerably higher bacteriostatic activity against methicillin-resistant S. aureus than the parent compounds. The most active compounds (MICs <= 0.25 mu g/ml or 0.4-0.5 mu M) were superior over the clinically used antibiotic vancomycin in the antibacterial effect (MIC of 1 mu g/ml or 0.7 mu M). Apart from antibacterial activity, new triterpene acid derivatives exhibited excellent antifungal activity against Cryptococcus neoformans, with MICs values being as low as 0.25 mu g/ml (0.4 mu M), and were approximately 65 times as active as fluconazole, a known antifungal agent. Four most promising compounds we identified (7, 13, 24, and 33) showed not only high bacteriostatic effect, but also low cytotoxicity against mammalian HEK293 cells and high hemolytic selectivity.
• Synthesis of heterocycle-modified betulinic acid derivatives as antitumor agents
  作者：Hai-Wei Cui、Yuan He、Jinhua Wang、Wei Gao、Ting Liu、Min Qin、Xue Wang、Cheng Gao、Yan Wang、Ming-Yao Liu、Zhengfang Yi、Wen-Wei Qiu

  DOI：10.1016/j.ejmech.2015.03.048

  日期：2015.5

  A series of novel heterocycle-modified betulinic acid (BA) derivatives were synthesized and investigated for their activity against the growth of eight non-drug resistant and one multidrug-resistant tumor cell line using a sulforhodamine B (SRB) assay. The most active compound 17 showed an average IC50 1.19 mu M, which was about 20 times more potent than the lead compound BA. It is amazing that for most synthetic saturated N-heterocycle derivatives, MCF-7/ADR was the most sensitive tumor cells, especially 17 showed the most potent antitumor activity (IC50 = 0.33 mu M) on this multidrug-resistant tumor cell line, that was 117 times more potent than BA. Most of the tested compounds displayed less toxic on human fibroblasts (HAF) in comparison with the tumor cell lines. The cytometry and transwell migration assays were used to test the ability of 17 to induce apoptosis and inhibit metastasis on tumor cell lines respectively. (C) 2015 Published by Elsevier Masson SAS.
• [EN] SYNTHETIC PENTACYCLIC TRITERPENOIDS AND DERIVATIVES OF BETULINIC ACID AND BETULIN<br/>[FR] TRITERPENOIDES PENTACYCLIQUES SYNTHETIQUES ET DERIVES D'ACIDE BETULINIQUE ET DE BETULINE
  申请人：ADVANCED LIFE SCIENCES INC

  公开号：WO2007112043A2

  公开（公告）日：2007-10-04

  [EN] The present invention comprises small molecule inhibitors of cell proliferative conditions, in particular cancer and conditions associated with cancer. For example, associated malignancies include ovarian cancer, cervical cancer, breast cancer, colorectal cancer, and glioblastomas, among others. Accordingly, the compounds of the present invention are useful for treating, preventing, and/or inhibiting these diseases. Thus, the present invention also comprising pharmaceutical formulations comprising the compounds and methods of using the compounds and formulations to inhibit cancer and treat, prevent, or inhibit the foregoing diseases.
  [FR] La présente invention concerne des inhibiteurs à petite molécule d'affections de la prolifération cellulaire, en particulier du cancer et des affections associées au cancer. Par exemple, les malignités associées incluent le cancer de l'ovaire, le cancer du col de l'utérus, le cancer du sein, le cancer colorectal et les glioblastomes, entre autres. Les composés de la présente invention sont par conséquent utiles pour le traitement, la prévention et/ou l'inhibition de ces maladies. Ainsi, la présente invention concerne également des formulations pharmaceutiques comprenant ces composés, et les procédés d'utilisation des composés et des formulations afin d'inhiber le cancer et traiter, prévenir, ou inhiber les maladies susmentionnées.