methyl 3-α-hydroxyurs-12-en-24-oate | 17019-94-2

• 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: methyl 3-α-hydroxyurs-12-en-24-oate
• 英文别名: 3α-hydoxy-urs-12-ene-24β-oic acid methyl ester；urs-12-en-23-oic acid, (R)-3-hydroxy-, methyl ester；Methyl-3α-hydroxyurs-12-en-24-oat；3α-hydroxy-ursen-(12)-oic acid-(24)-methyl ester；3α-Hydroxy-ursen-(12)-saeure-(24)-methylester；methyl (3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picene-4-carboxylate
• CAS: 17019-94-2
• 化学式: C₃₁H₅₀O₃
• 分子量: 470.736
• InChiKey: MTDJIWUMGYOEEV-WFKJPOIHSA-N

物化性质

• 熔点：
  187-190 °C
• 沸点：
  529.0±50.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  34
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-α-hydroxyurs-12-en-24-oate 在 吡啶 、 chromium(VI) oxide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 3β,24-dihydroxyurs-12-ene
  参考文献：
  名称：

  乳香酸的立体化学

  摘要：

  摘要 α-和β-乳香酸中 C(3)、C(4)、C(5)、C(8)、C(10)、C(13) 和 C(17) 处的取代基构型有熊烷-齐墩果烷相互转化表明它们是相同的。C(3) 差向异构醇的合成和脱水研究证实了乳香酸中羟基的轴向配置，并表明参与组的共面性不一定是环收缩的基本要求。乳香酸的 C(3) 和 C(24) 二羟基衍生物的环化反应表明，环 A 可以很容易地从椅子变成船形，以允许反式双轴羟基的循环缩醛化。

  DOI：

  10.1016/s0031-9422(00)82183-4
• 作为产物：
  描述：

  3α-acetyl-β-boswellic acid methyl ester 在 氢氧化钾 作用下， 生成 methyl 3-α-hydroxyurs-12-en-24-oate
  参考文献：
  名称：

  564.三萜和相关化合物的化学。第二十八部分。β-乳香酸

  摘要：

  DOI：

  10.1039/jr9560002904

文献信息

• Acyl derivatives of boswellic acids as inhibitors of NF-κB and STATs
  作者：Ajay Kumar、Bhahwal A. Shah、Samar Singh、Abid Hamid、Shashank K. Singh、Vijay K. Sethi、Ajit K. Saxena、Jaswant Singh、Subhash C. Taneja

  DOI：10.1016/j.bmcl.2011.10.112

  日期：2012.1

  Boswellic acid acylates including their epimers were synthesized and screened against a panel of human cancer cell lines. They exhibited a range of cytotoxicity against various human cancer cell lines thereby leading to the development of a possible SAR. One of the identified lead compounds was found to be an inhibitor of the NF-kappa B and STAT proteins, warranting further investigations to be developed into a potential anticancer lead. (C) 2011 Elsevier Ltd. All rights reserved.
• Cytotoxic and apoptotic activities of novel amino analogues of boswellic acids
  作者：Bhahwal A. Shah、Ajay Kumar、Pankaj Gupta、Madhunika Sharma、Vijay K. Sethi、Ajit K. Saxena、Jaswant Singh、Ghulam N. Qazi、Subhash C. Taneja

  DOI：10.1016/j.bmcl.2007.10.011

  日期：2007.12

  4-Amino analogues prepared from beta-boswellic acid and 11-keto-beta-boswellic acid, wherein the carboxyl group in ursane nucleus was replaced by an amino function via Curtius reaction, displayed improved cytotoxicity than the parent molecules. The same molecules also exhibited apoptotic activity by inducing DNA fragmentation. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of β-boswellic acid derivatives as cytotoxic and apoptotic agents
  作者：Arvind Kumar、Arem Qayum、Parduman Raj Sharma、Shashank Kumar Singh、Bhahwal Ali Shah

  DOI：10.1016/j.bmcl.2015.11.027

  日期：2016.1

  A series of beta-boswellic acid derivatives were synthesized and evaluated for anticancer activity. One of the lead analog 4f displayed significant anticancer activity against a panel of cancer cells as well as substantially inhibited colony formation in HCT-116 cells. Furthermore, 4f was found to be a potent inducer of apoptosis confirmed by loss of mitochondrial membrane potential, DAPI staining, Western blotting and ROS generation. (C) 2015 Elsevier Ltd. All rights reserved.
• 123. The triterpene group. Part I. β-Boswellic acid
  作者：James C. E. Simpson、Norman E. Williams

  DOI：10.1039/jr9380000686

  日期：——
• Winterstein; Stein, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1932, vol. 208, p. 10
  作者：Winterstein、Stein

  DOI：——

  日期：——