(S)-2-tert-Butoxycarbonylamino-6-[((1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-icosahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-hexanoic acid methyl ester | 880129-61-3

• 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: (S)-2-tert-Butoxycarbonylamino-6-[((1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-icosahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-hexanoic acid methyl ester
• 英文别名: methyl (2S)-6-[[(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-carbonyl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 880129-61-3
• 化学式: C₄₂H₆₈N₂O₆
• 分子量: 697.012
• InChiKey: CBWKRSOJNJAYJE-BHJZPSHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  50
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-tert-Butoxycarbonylamino-6-[((1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-icosahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-hexanoic acid methyl ester 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 7.0h， 生成 BOC-lysinated Betulonic acid
  参考文献：
  名称：

  PURIFICATION METHODS FOR BETULONIC ACID AND BOC-LYSINATED BETULONIC ACID, AND ORGANIC SYNTHESIS OF BETULONIC ACID AMIDES WITH PIPERAZINE DERIVATIVES

  摘要：

  本发明提供了一种纯化白桦树皮提取的树脂酸与有机合成琼斯氧化试剂反应产物中含有的方法，一种制备哌嗪树脂酸酰胺衍生物的方法，该衍生物用作具有抗菌功能的化学品，使用通过纯化方法获得的高纯度树脂酸和通过该方法制备的衍生物，一种纯化有机合成赖氨酸和高纯度树脂酸（起始物质）反应产物中含有的Boc-赖氨酸树脂酸单体酯的方法，以及纯化高纯度Boc-赖氨酸树脂酸单体酯的反应产物中含有的Boc-赖氨酸树脂酸的方法。

  公开号：

  US20140243527A1
• 作为产物：
  描述：

  白桦脂醇 在 Jones reagent 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 4.0h， 生成 (S)-2-tert-Butoxycarbonylamino-6-[((1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-icosahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-hexanoic acid methyl ester
  参考文献：
  名称：

  PURIFICATION METHODS FOR BETULONIC ACID AND BOC-LYSINATED BETULONIC ACID, AND ORGANIC SYNTHESIS OF BETULONIC ACID AMIDES WITH PIPERAZINE DERIVATIVES

  摘要：

  本发明提供了一种纯化白桦树皮提取的树脂酸与有机合成琼斯氧化试剂反应产物中含有的方法，一种制备哌嗪树脂酸酰胺衍生物的方法，该衍生物用作具有抗菌功能的化学品，使用通过纯化方法获得的高纯度树脂酸和通过该方法制备的衍生物，一种纯化有机合成赖氨酸和高纯度树脂酸（起始物质）反应产物中含有的Boc-赖氨酸树脂酸单体酯的方法，以及纯化高纯度Boc-赖氨酸树脂酸单体酯的反应产物中含有的Boc-赖氨酸树脂酸的方法。

  公开号：

  US20140243527A1

文献信息

• Boc-lysinated-betulonic acid: A potent, anti-prostate cancer agent
  作者：B SAXENA、L ZHU、M HAO、E KISILIS、M KATDARE、O OKTEM、A BOMSHTEYN、P RATHNAM

  DOI：10.1016/j.bmc.2006.05.048

  日期：2006.9.15

  Betulonic acid, derived from betulinol, a pentacyclic styrene, has shown a highly specific anti-prostate cancer activity in in vitro cell cultures. However, due to the lack of solubility of betulonic acid in aqueous medium, its potent anti-cancer activity in vivo has not been determined to the fullest extent. The present study describes the chemical synthesis of hydrophilic Boc-lysinated-betulonic acid, which has improved its solubility in an aqueous biocompatible solvent. Evaluation in cytotoxicity assays, Boc-lysinated-betulonic acid dissolved in phosphate-buffered saline (PBS) containing 22% ethanol and 4% human serum albumin, has shown 95.7% inhibition of LNCaP prostate cancer cells in culture after 72 h incubation at a concentration of 100 mu M, but with little effect on normally proliferating fibroblast cells. In the in vivo assay, male athymic mice transplanted with human prostate LNCaP xenografts were injected with Boc-lysinated-betulonic acid intraperitoneally at a dose of 30 mg/kg daily for 17 days. The treated mice exhibited 92% inhibition of tumor growth as compared to controls. Histological sections of the tumors showed that Boc-lysinated-betulonic acid arrested mitosis and induced apoptosis, which was confirmed by TUNEL assay, Yo-Pro-1 staining, and the release of cleaved caspase-3 from the ex vivo in tumor culture. These studies, for the first time, demonstrate that a non-toxic hydrophilic lysinated derivative of betulonic acid and its solubility in a biocompatible aqueous medium has enhanced the bioavailability of the drug and has thus unleashed its full anti-prostate cancer activity. (c) 2006 Elsevier Ltd. All rights reserved.