(R)-4-((5S,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-3,7,12-trioxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester | 204705-14-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (R)-4-((5S,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-3,7,12-trioxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester
• 英文别名: (2,5-dioxopyrrolidin-1-yl) (4R)-4-[(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 204705-14-6
• 化学式: C₂₈H₃₇NO₇
• 分子量: 499.604
• InChiKey: RLSWSPJXRFHPRW-RFLWYZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-4-((5S,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-3,7,12-trioxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester 在 potassium carbonate 、 三乙胺 、 聚甘氨酸 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3-bromopropyl ((R)-4-((5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyl)glycinate
  参考文献：
  名称：

  Synthesis, Anticancer Activities, Antimicrobial Activities and Bioavailability of Berberine-Bile Acid Analogues

  摘要：

  合成了十五种小檗碱–胆酸类似物。与小檗碱（BBR）相比，这些类似物的抗癌活性在体外进行了评估；在这些类似物中，A4、B4 和 B5 的细胞毒性高于 BBR。大多数类似物对金黄色葡萄球菌 ATCC 25923 和白色念珠菌 ATCC 8799 具有较高的抗菌活性，而对枯草芽孢杆菌 AS 1.398 和大肠杆菌 ATCC 31343 则无敏感性。A4 和 B4 在血清稳定性实验中表现出稳定性。B4 在小鼠中显示出良好的口服生物利用度。

  DOI：

  10.2174/157018012800673010
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 去氢胆酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (R)-4-((5S,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-3,7,12-trioxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester
  参考文献：
  名称：

  Synthesis, Anticancer Activities, Antimicrobial Activities and Bioavailability of Berberine-Bile Acid Analogues

  摘要：

  合成了十五种小檗碱–胆酸类似物。与小檗碱（BBR）相比，这些类似物的抗癌活性在体外进行了评估；在这些类似物中，A4、B4 和 B5 的细胞毒性高于 BBR。大多数类似物对金黄色葡萄球菌 ATCC 25923 和白色念珠菌 ATCC 8799 具有较高的抗菌活性，而对枯草芽孢杆菌 AS 1.398 和大肠杆菌 ATCC 31343 则无敏感性。A4 和 B4 在血清稳定性实验中表现出稳定性。B4 在小鼠中显示出良好的口服生物利用度。

  DOI：

  10.2174/157018012800673010

文献信息

• Li; Gao; Qiu, Letters in drug design and discovery, 2011, vol. 8, # 9, p. 698 - 703
  作者：Li、Gao、Qiu、Zu、Su、He、Deng

  DOI：——

  日期：——
• Syntheses and structural study of bile acid amidoalcohols
  作者：Arto Valkonen、Manu Lahtinen、Erkki Kolehmainen

  DOI：10.1016/j.steroids.2008.06.006

  日期：2008.11

  Preparation, structural and thermoanalytical characterization of fourteen N-hydroxyalkyl 5 beta-cholan-24-amides have been performed in this study. The utilized techniques include liquid state and CP-MAS C-13 NMR spectroscopy, thermogravimetry, differential scanning calorimetry, and also powder and single crystal X-ray crystallography. The results were discussed and compared to each other and also to previous findings on similar compounds. One pure hydrate form was obtained. Six new single crystal structures were determined, including one hydrated chloroform solvate. Decomposition temperatures were found to correlate with the side chain length, and the number of the hydroxyl groups. The spatial direction of the groups in the steroid skeleton was also found to be relevant in predicting the thermal properties of bile acid amidoalcohols studied. (C) 2008 Elsevier Inc. All rights reserved.
• Synthesis of N-hydroxysuccinimide esters using polymer bound HOBT
  作者：Kleanthis G. Dendrinos、Aristotle G. Kalivretenos

  DOI：10.1016/s0040-4039(98)00002-1

  日期：1998.3

  The preparation of the N-hydroxysuccinimide esters via reactions mediated by polymer bound 1-hydroxybenzotriazole (HOBT) is reported. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Design, synthesis, and antitumor activity of bile acid–polyamine–nucleoside conjugates
  作者：Dimao Wu、Sanhao Ji、Yan Wu、Yong Ju、Yufen Zhao

  DOI：10.1016/j.bmcl.2007.03.067

  日期：2007.6

  A series of bile acid-polyamine amides conjugated with 3 '-azido-3 '-deoxythymidine (AZT) as potential antitumor prodrugs in the form of phosphoramidates were synthesized in good yields and their antitumor activities were assayed against two human cancer cells in vitro: cervix cancer HeLa cells and renal cancer 7860 cells. The improved antitumor activity probably derived from the enhanced delivery efficiency of AZT due to bile acid-polyamine conjugates. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis, Anticancer Activities, Antimicrobial Activities and Bioavailability of Berberine-Bile Acid Analogues
  作者：Qingyong Li、Wuna He、Li Zhang、Yuangang Zu、Qiaochu Zhu、Xiaoqiu Deng、Tengfei Zhao、Wenqing Gao、Baoyou Zhang

  DOI：10.2174/157018012800673010

  日期：2012.5.1

  Fifteen berberine–bile acid analogues were synthesized. Anticancer activities of these analogues compared with berberine (BBR) were evaluated in vitro; among the analogues, A4, B4, and B5 had higher cytotoxicity than that of BBR. Most of the analogues showed higher antimicrobial activity against Staphylococcus aureus ATCC 25923 and Staphylococcus albus ATCC 8799 than that of BBR, but Bacillus subtilis AS 1.398 and Escherichia coli ATCC 31343 were not sensitive to all of the analogues. A4 and B4 were stable in the serum stability assay. B4 showed promising oral bioavailability in mice.

  合成了十五种小檗碱–胆酸类似物。与小檗碱（BBR）相比，这些类似物的抗癌活性在体外进行了评估；在这些类似物中，A4、B4 和 B5 的细胞毒性高于 BBR。大多数类似物对金黄色葡萄球菌 ATCC 25923 和白色念珠菌 ATCC 8799 具有较高的抗菌活性，而对枯草芽孢杆菌 AS 1.398 和大肠杆菌 ATCC 31343 则无敏感性。A4 和 B4 在血清稳定性实验中表现出稳定性。B4 在小鼠中显示出良好的口服生物利用度。