3'-methyl-2'-butenyl 3β-hydroxyurs-12-en-28-oate | 1198208-27-3

• 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: 3'-methyl-2'-butenyl 3β-hydroxyurs-12-en-28-oate
• 英文别名: 3β-hydroxy-urs-12-en-28-prenylate；3-methylbut-2-enyl (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
• CAS: 1198208-27-3
• 化学式: C₃₅H₅₆O₃
• 分子量: 524.828
• InChiKey: JPTCBBAZOADPAH-ZUCJICFVSA-N

物化性质

• 沸点：
  581.6±50.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3'-methyl-2'-butenyl 3β-hydroxyurs-12-en-28-oate 在 三氟化硼乙醚 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 熊果酸
  参考文献：
  名称：

  使用三氟化硼醚酯对异戊二烯、香叶基和植基醚和酯进行高效和选择性脱保护的方法

  摘要：

  摘要 开发了一种高效、简单、实用的方法，用于在室温下使用三氟化硼醚合物 (BF3 · OEt2) 对异戊二烯、香叶基和植基醚以及芳香族和脂肪族化合物的酯进行脱保护，首次获得良好的收率。时间。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要

  DOI：

  10.1080/00397911.2011.589561
• 作为产物：
  描述：

  熊果酸 、 1-溴-3-甲基-2-丁烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以30%的产率得到3'-methyl-2'-butenyl 3β-hydroxyurs-12-en-28-oate
  参考文献：
  名称：

  使用三氟化硼醚酯对异戊二烯、香叶基和植基醚和酯进行高效和选择性脱保护的方法

  摘要：

  摘要 开发了一种高效、简单、实用的方法，用于在室温下使用三氟化硼醚合物 (BF3 · OEt2) 对异戊二烯、香叶基和植基醚以及芳香族和脂肪族化合物的酯进行脱保护，首次获得良好的收率。时间。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要

  DOI：

  10.1080/00397911.2011.589561

文献信息

• Synthesis and anti-cancer activity of some novel C-17 analogs of ursolic and oleanolic acids
  作者：Uppuluri V. Mallavadhani、Anita Mahapatra、Banita Pattnaik、Nagireddy Vanga、Nitasha Suri、Ajit K. Saxena

  DOI：10.1007/s00044-012-0106-y

  日期：2013.3

  A series of seventeen novel analogs of ursolic and oleanolic acid were synthesized (60–98 %), and evaluated for their anti-cancer potential against a panel of eight human cancer cell lines. Compounds (3–10) showed comparable or better activities than their respective parent compounds against SiHa and HeLa (Cervix), A-549 (Lung), and IMR-32 (Neuroblastoma) cancer cell lines. Significantly, among the

  合成了一系列17种新颖的熊果酸和齐墩果酸类似物（60-98％），并评估了它们对八种人类癌细胞系的抗癌潜力。化合物（3–10）对SiHa和HeLa（宫颈），A-549（肺）和IMR-32（神经母细胞瘤）癌细胞的活性比其各自的母体化合物更好或更高。值得注意的是，在溴代烷基酯中（11-19），化合物13在10μM浓度下对白血病THP-1细胞系显示出有希望的抗癌活性。在这个系列中，有趣的是，链长的增加对活性有不利影响。
• Ursolic acid derivatives induce cell cycle arrest and apoptosis in NTUB1 cells associated with reactive oxygen species
  作者：Huang-Yao Tu、A-Mei Huang、Bai-Luh Wei、Kim-Hong Gan、Tzyh-Chyuan Hour、Shyh-Chyun Yang、Yeong-Shiau Pu、Chun-Nan Lin

  DOI：10.1016/j.bmc.2009.08.046

  日期：2009.10

  Twenty-three ursolic acid (1) derivatives 2-24 including nine new 1 derivatives 5, 7-11, 20-22 were synthesized and evaluated for cytotoxicities against NTUB1 cells (human bladder cancer cell line). Compounds 5 and 17 with an isopropyl ester moiety at C-17-COOH and a succinyl moiety at C-3-OH showed potent inhibitory effect on growth of NTUB1 cells. Compounds 23 and 24 with seco-structures prepared from 1 also showed the increase of the cytotoxicity against NTUB1 cells. Exposure of NTUB1 to 5 (40 mu M) and 23 (20 and 50 mu M) for 24 h significantly increased the production of reactive oxygen species (ROS) while exposure of NTUB1 to 5 (20 and 40 mu M) and 23 (20 and 50 mu M) for 48 h also significantly increased the production of ROS while exposure of cells to 17 did not increase the amount of ROS. Flow cytometric analysis exhibited that treatment of NTUB1 with 5 or 17 or 23 led to the cell cycle arrest accompanied by an increase in apoptotic cell death after 24 or 48 h. These data suggest that the presentation of G1 phase arrest and apoptosis in 5- and 23-treated NTUB1 for 24 h mediated through increased amount of ROS in cells exposed with 5 and 23, respectively, while the presence of G2/M arrest before accumulation of cells in sub-G1 phase in 5-treated cells for 48 h also due to increased amount of ROS in cells exposed with 5. The inhibition of tubulin polymerization and cell cycle arrest at G2/M following by apoptosis presented in the cell cycle of 23 also mediates through the increase amount of ROS induced by treating NTUB1 with 23 for 48 h. (C) 2009 Elsevier Ltd. All rights reserved.
• Highly Efficient and Selective Deprotection Method for Prenyl, Geranyl, and Phytyl Ethers and Esters Using Borontrifluoride–Etherate
  作者：T. Narender、K. Venkateswarlu、G. Madhur、K. Papi Reddy

  DOI：10.1080/00397911.2011.589561

  日期：2013.1.1

  Abstract An efficient, simple, and practical method has been developed for the deprotection of prenyl, geranyl, and phytyl ethers and esters of aromatic and aliphatic compounds using borontrifluoride–etherate (BF3 · OEt2) at room temperature in good to excellent yields for the first time. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications®

  摘要 开发了一种高效、简单、实用的方法，用于在室温下使用三氟化硼醚合物 (BF3 · OEt2) 对异戊二烯、香叶基和植基醚以及芳香族和脂肪族化合物的酯进行脱保护，首次获得良好的收率。时间。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要