3-β-hydroxy-11-keto-β-boswellic acid | 810684-51-6

• 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-β-hydroxy-11-keto-β-boswellic acid
• 英文别名: 3β-hydroxy-11-keto-β-boswellic acid；3-epi-11-keto-β-boswellic acid；11-keto-3β-hydroxyurs-12-ene-24-oic acid；3beta-11-Keto-beta-boswellic acid；(3S,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4a,5,6,7,8,9,10,11,12,12a,14a-tetradecahydropicene-4-carboxylic acid
• CAS: 810684-51-6
• 化学式: C₃₀H₄₆O₄
• 分子量: 470.693
• InChiKey: YIMHGPSYDOGBPI-SCAHIRPMSA-N

物化性质

• 熔点：
  289 °C(Solv: methanol (67-56-1))
• 沸点：
  591.8±50.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丁酸酐 、 3-β-hydroxy-11-keto-β-boswellic acid 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 3-O-β-butyryl-11-keto-β-boswellic acid
  参考文献：
  名称：

  Acyl derivatives of boswellic acids as inhibitors of NF-κB and STATs

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2011.10.112
• 作为产物：
  描述：

  methyl 3,11-dioxours-12-en-24-oate 在 sodium tetrahydroborate 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 3-β-hydroxy-11-keto-β-boswellic acid
  参考文献：
  名称：

  Acyl derivatives of boswellic acids as inhibitors of NF-κB and STATs

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2011.10.112

文献信息

• 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.
• USE OF SEMI SYNTHETIC ANALOGUES OF BOSWELLIC ACIDS FOR ANTICANCER ACTIVITY
  申请人：Qazi Ghulam Nabi

  公开号：US20090298938A1

  公开（公告）日：2009-12-03

  The present invention relates to use of compounds of general formula 1 for anticancerous activity, wherein the said compound being derived semi-synthetically from natural triterpenoic acids known as boswellic acids by the induction of apoptosis thereof cytotoxicity and anti-cancer activity displayed by semi-synthetic analogues of natural triterpenes, known as Boswellic acids. These compounds may be used for the treatment of cancer, alone or in combination with pharmaceutically acceptable or other carriers, displaying cytotoxicity and anti-cancer activity for colon, prostrate, liver, breast, central nervous system (CNS), leukemia and malignancy of other tissues, including ascites and solid tumors. The cancer cell death is mediated by induction of apoptosis and inhibition of cell proliferation at specific doses.
• Analogues of boswellic acids as inhibitors of pro-inflammatory cytokines TNF-α and IL-6
  作者：Simmi Sharma、Shilpa Gupta、Vidushi Khajuria、Asha Bhagat、Zabeer Ahmed、Bhahwal Ali Shah

  DOI：10.1016/j.bmcl.2015.11.035

  日期：2016.1

  A library of boswellic acid analogues were synthesized and tested for their anti-inflammatory potential on key inflammatory mediators, TNF-alpha and IL-6. The study led to the identification of lead compounds showing significant inhibition of the cytokines, TNF-alpha and IL-6 both in vitro and in vivo. (C) 2015 Elsevier Ltd. All rights reserved.
• 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.