(20S,24R)-epoxy-12β-O-(2-carboxybenzoyl)dammarane-3β,25-diol | 1423042-85-6

• 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: (20S,24R)-epoxy-12β-O-(2-carboxybenzoyl)dammarane-3β,25-diol
• 英文别名: (20S,24R)-epoxy-12β-(2-carboxybenzoyl)dammarane-3β,25-diol；Dammarane-3,12,25-triol, 20,24-epoxy-, 12-(hydrogen 1,2-benzenedicarboxylate), (3I(2),12I(2),20S,24R)-；2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-3-hydroxy-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-12-yl]oxycarbonyl]benzoic acid
• CAS: 1423042-85-6
• 化学式: C₃₈H₅₆O₇
• 分子量: 624.858
• InChiKey: CRYHFAYVGUAMGK-PDCSQVAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  45
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  原人参二醇 在 吡啶 、 4-二甲氨基吡啶 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 83.0h， 生成 (20S,24R)-epoxy-12β-O-(2-carboxybenzoyl)dammarane-3β,25-diol
  参考文献：
  名称：

  具有抗菌活性的(20S，24R)-ocotillol型人参 皂苷类衍生物、其制备方法及用途

  摘要：

  本发明涉及有机合成和药物化学领域，具体涉及一类(20S，24R)‑ocotillol型人参皂苷类衍生物，结构如通式(I)。本发明还公开了这些(20S，24R)‑ocotillol型人参皂苷类衍生物的制备方法，含有它们的药物组合物及其抗细菌感染疾病用途。

  公开号：

  CN102924556B

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 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.
• Synthesis, Cytotoxic, and Antibacterial Evaluation of C-12 Substituted Ocotillol-type Derivatives
  作者：Jiangong Liu、Xiaoyu Zhang、Shuo Wang、Huili Zhang、Zhiwen Zhou

  DOI：10.1134/s1068162023060249

  日期：2023.11
• 具有抗菌活性的(20S，24R)-ocotillol型人参 皂苷类衍生物、其制备方法及用途
  申请人：烟台大学

  公开号：CN102924556B

  公开（公告）日：2017-08-22

  本发明涉及有机合成和药物化学领域，具体涉及一类(20S，24R)‑ocotillol型人参皂苷类衍生物，结构如通式(I)。本发明还公开了这些(20S，24R)‑ocotillol型人参皂苷类衍生物的制备方法，含有它们的药物组合物及其抗细菌感染疾病用途。