2-(4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yloxy)carbonylbenzoic acid | 1011714-98-9

• 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: 2-(4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yloxy)carbonylbenzoic acid
• 英文别名: α-amyrin 3-O-(2-carboxybenzoate)；urs-12-ene-3β-o-carboxibenzoate；α-amyrin o-carboxibenzoate；2-[[(3S,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-yl]oxycarbonyl]benzoic acid
• CAS: 1011714-98-9
• 化学式: C₃₈H₅₄O₄
• 分子量: 574.844
• InChiKey: JCAWAUOAMXNNAV-DHEXBYIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  42
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯酐 、 α-香树精 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以42%的产率得到2-(4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yloxy)carbonylbenzoic acid
  参考文献：
  名称：

  α-amyrin衍生物的合成及其体内降血糖活性

  摘要：

  榕榕属榕科（Moraceae）家族，在印度北部通常被称为“ Gular”。上的水果生物活性引导隔离工作F.总状导致的抗糖尿病活性成分，α香树脂醇乙酸酯的识别7。在浓度为100 mg / kg体重的蔗糖激发的链脲佐菌素诱导的糖尿病大鼠（STZ-S）模型中，化合物7在5和24 h分别将血糖水平降低了18.4和17.0％。十五新型衍生物即，9 - 21，24，25的α-香树脂8的制备和它们的抗高血糖活性谱进行了评估。该p在100mg / kg体重下，-氯苯甲酸衍生物9和烟酸衍生物14显示出有效的降血糖活性。

  DOI：

  10.1016/j.ejmech.2008.09.011

文献信息

• Amyrin esters induce cell death by apoptosis in HL-60 leukemia cells
  作者：Francisco W.A. Barros、Paulo N. Bandeira、Daisy J.B. Lima、Assuero S. Meira、Silvana S. de Farias、Maria Rose J.R. Albuquerque、Hélcio S. dos Santos、Telma L.G. Lemos、Manoel Odorico de Morais、Letícia Veras Costa-Lotufo、Claudia do Ó Pessoa

  DOI：10.1016/j.bmc.2010.12.016

  日期：2011.2

  Four derivatives of an alpha,beta-amyrin mixture were synthesized by acylation with appropriate anhydrides. The structures of the compounds were confirmed by means of IR and H-1 and C-13 NMR. The compounds were screened for cytotoxic activity using four human tumor cell lines (HL-60, MDAMB-435, SF-295 and HCT-8) and normal peripheral blood mononuclear cells (PBMC). 3-O-Carboxymaleinate of alpha,beta-amyrin (3a/3b) were found to be the only active compounds of the series (high cytotoxicity), showing IC50 values ranging from 1.8 to 3 mu M. In PBMC, 3a/3b were not toxic, suggesting selectivity for tumor cells. To better understand the mechanism of action involved in the cytotoxicity of 3a/3b, HL-60 cells treated with 3a/3b were examined for morphological changes, DNA fragmentation, cell cycle perturbation, externalization of phosphatidylserine and activation of caspases 3/7, with doxorubicin serving as the positive control. The results indicate that the cytotoxicity of 3a/3b involves the induction of cell death by apoptosis. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of α-amyrin derivatives and their in vivo antihyperglycemic activity☆
  作者：T. Narender、T. Khaliq、A.B. Singh、M.D. Joshi、P. Mishra、J.P. Chaturvedi、A.K. Srivastava、R. Maurya、S.C. Agarwal

  DOI：10.1016/j.ejmech.2008.09.011

  日期：2009.3

  principle, α-amyrin acetate 7. Compound 7 lowered the blood glucose levels by 18.4 and 17.0% at 5 and 24 h, respectively, in sucrose challenged streptozotocin induced diabetic rat (STZ-S) model at the dose of 100 mg/kg body weight. Fifteen novel derivatives viz, 9–21, 24, 25 of α-amyrin 8 were prepared and their antihyperglycemic activity profile was assessed. The p-chlorobenzoic acid derivative 9 and nicotinic

  榕榕属榕科（Moraceae）家族，在印度北部通常被称为“ Gular”。上的水果生物活性引导隔离工作F.总状导致的抗糖尿病活性成分，α香树脂醇乙酸酯的识别7。在浓度为100 mg / kg体重的蔗糖激发的链脲佐菌素诱导的糖尿病大鼠（STZ-S）模型中，化合物7在5和24 h分别将血糖水平降低了18.4和17.0％。十五新型衍生物即，9 - 21，24，25的α-香树脂8的制备和它们的抗高血糖活性谱进行了评估。该p在100mg / kg体重下，-氯苯甲酸衍生物9和烟酸衍生物14显示出有效的降血糖活性。