(20S,24R)-epoxy-3β,12β-diacetyldammarane-25-ol | 145644-03-7

• 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: (20S,24R)-epoxy-3β,12β-diacetyldammarane-25-ol
• 英文别名: [(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 145644-03-7
• 化学式: C₃₄H₅₆O₆
• 分子量: 560.815
• InChiKey: MRCMHQPBXBYCBW-HFNVXUDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (20S,24R)-epoxy-3β,12β-diacetyldammarane-25-ol 在 甲醇 、 potassium hydroxide 作用下， 反应 6.0h， 以65%的产率得到(20S,24R)-epoxy-12β-O-acetyl-dammarane-3β, 25-diol
  参考文献：
  名称：

  Synthesis and biological evaluation of novel ocotillol-type triterpenoid derivatives as antibacterial agents

  摘要：

  A novel class of ocotillol-type triterpenoid derivatives have been synthesized and evaluated for their in vitro antibacterial activity against several representative pathogenic bacterial strains. Compounds 20(S)-protopanaxadiol (PPD), 3, 5,16 and 24 exhibited potent antibacterial activity against Gram-positive bacteria. Compounds 3 and 5 also displayed promising antibacterial activity against a community-associated methicillin-resistant Staphylococcus aureus (CA-MRSA; strain USA300). Furthermore, compounds PPD, 3 and 16 combined with two commercially available antibiotics kanamycin and chloramphenicol showed strong synergistic inhibitory effects at their sub-MIC concentrations against S. aureus USA300 and Bacillus subtilis 168. Additionally, cytotoxic activity assay showed that the compounds tested did not affect cell viability of the human epithelial kidney (HEK-293) and human cervical (HeLa) cells at their MICs. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.041
• 作为产物：
  描述：

  原人参二醇 在 4-二甲氨基吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (20S,24R)-epoxy-3β,12β-diacetyldammarane-25-ol
  参考文献：
  名称：

  新型抗炎药—邻苯二酚衍生物的合成及其构效关系

  摘要：

  吡xin醇是人肝脏中20 S-庚二醇的主要代谢物，被选作开发抗炎药的新型骨架。设计，制备并研究了在C-3，C-12或C-25处修饰的Pyxinol衍生物和选定的立体异构体的体外抗炎活性。基于骨架抑制脂多糖（LPS）诱导的一氧化氮（NO）合成的能力，分析了骨架之间的构效关系（SAR）。初步的SAR结果表明，pyxinol衍生物的生物学活性在很大程度上取决于pyxinol骨架的R / S立体化学，C-3处的羟基是可修饰的。在测试的化合物中，3-oximinopyxinol（4a）显示出最有效的NO抑制活性，甚至与类固醇药物相当。此外，化合物4a还通过NF-κB途径显着降低了LPS诱导的TNF-α和IL-6合成以及iNOS和COX-2的表达。这项研究证明了pyxinol是消炎药发现的有趣骨架。

  DOI：

  10.1021/acsmedchemlett.9b00562

文献信息

• Synthesis and biological evaluation of (20S,24R)-epoxy-dammarane-3β,12β,25-triol derivatives as α-glucosidase and PTP1B inhibitors
  作者：Xiao-Tong Yang、Tian-Ze Li、Chang-An Geng、Pei Liu、Ji-Jun Chen

  DOI：10.1007/s00044-021-02836-0

  日期：2022.2

  activity against α-glucosidase, and four compounds (8, 15, 26, 42) significantly inhibited PTP1B. It was noted that compounds 8 and 26 could inhibit both α-glucosidase and PTP1B as dual-target inhibitors with IC50 values of 489.8, 467.7 μM (α-glucosidase) and 319.7, 269.1 μM (PTP1B). Compound 26 was revealed to be a mix-type inhibitor on α-glucosidase and a noncompetitive-type inhibitor on PTP1B based

  我们之前的研究中从青钱柳中获得的达玛烷三萜(20 S ,24 R )-epoxy-dammarane-3 β ,12 β ,25- triol 在体外对α-葡萄糖苷酶有抑制活性，抑制率为32.2%。浓度为 200 μM。为了揭示构效关系（SARs）并获得更多活性化合物，对羟基进行化学修饰合成了(20 S ,24 R )-epoxy-dammarane-3 β ,12 β ,25-triol 的42个衍生物。 （C-3 和 C-12），环 A 和 E，并测定它们的α-葡萄糖苷酶和PTP1B抑制活性。两种化合物 ( 8 , 26 ) 增加了对α-葡萄糖苷酶的活性，四种化合物 ( 8 , 15 , 26 , 42 ) 显着抑制了 PTP1B。值得注意的是，化合物8和26作为双靶点抑制剂可同时抑制α-葡萄糖苷酶和 PTP1B，其 IC 50值为 489.8、467.7 μM（α-葡萄糖苷酶）和 319
• Synthesis and Structure–Activity Relationship of Pyxinol Derivatives as Novel Anti-Inflammatory Agents
  作者：Yixiao Sun、Xiaojuan Fang、Meng Gao、Conghui Wang、Hongyan Gao、Wenjing Bi、Hanhan Tang、Yetong Cui、Leiming Zhang、Huaying Fan、Hui Yu、Gangqiang Yang

  DOI：10.1021/acsmedchemlett.9b00562

  日期：2020.4.9

  development of anti-inflammatory agents. Pyxinol derivatives modified at C-3, C-12, or C-25 and selected stereoisomers were designed, prepared, and investigated for in vitro anti-inflammatory activities. Structure–activity relationship (SAR), focused on skeleton, was analyzed based on their ability to inhibit lipopolysaccharide (LPS)-induced nitric oxide (NO) synthesis. The preliminary SAR results signified

  吡xin醇是人肝脏中20 S-庚二醇的主要代谢物，被选作开发抗炎药的新型骨架。设计，制备并研究了在C-3，C-12或C-25处修饰的Pyxinol衍生物和选定的立体异构体的体外抗炎活性。基于骨架抑制脂多糖（LPS）诱导的一氧化氮（NO）合成的能力，分析了骨架之间的构效关系（SAR）。初步的SAR结果表明，pyxinol衍生物的生物学活性在很大程度上取决于pyxinol骨架的R / S立体化学，C-3处的羟基是可修饰的。在测试的化合物中，3-oximinopyxinol（4a）显示出最有效的NO抑制活性，甚至与类固醇药物相当。此外，化合物4a还通过NF-κB途径显着降低了LPS诱导的TNF-α和IL-6合成以及iNOS和COX-2的表达。这项研究证明了pyxinol是消炎药发现的有趣骨架。
• Synthesis and biological evaluation of novel ocotillol-type triterpenoid derivatives as antibacterial agents
  作者：Zhiwen Zhou、Cong Ma、Hengyuan Zhang、Yi Bi、Xia Chen、Hua Tian、Xiaoni Xie、Qingguo Meng、Peter John Lewis、Jinyi Xu

  DOI：10.1016/j.ejmech.2013.07.041

  日期：2013.10

  A novel class of ocotillol-type triterpenoid derivatives have been synthesized and evaluated for their in vitro antibacterial activity against several representative pathogenic bacterial strains. Compounds 20(S)-protopanaxadiol (PPD), 3, 5,16 and 24 exhibited potent antibacterial activity against Gram-positive bacteria. Compounds 3 and 5 also displayed promising antibacterial activity against a community-associated methicillin-resistant Staphylococcus aureus (CA-MRSA; strain USA300). Furthermore, compounds PPD, 3 and 16 combined with two commercially available antibiotics kanamycin and chloramphenicol showed strong synergistic inhibitory effects at their sub-MIC concentrations against S. aureus USA300 and Bacillus subtilis 168. Additionally, cytotoxic activity assay showed that the compounds tested did not affect cell viability of the human epithelial kidney (HEK-293) and human cervical (HeLa) cells at their MICs. (C) 2013 Elsevier Masson SAS. All rights reserved.