(20S,24R)-epoxy-3β-O-acetyl-dammarane-12β,25-diol | 1423042-66-3

• 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-O-acetyl-dammarane-12β,25-diol
• 英文别名: (20S,24R)-epoxy-3β-acetyldammarane-12β,25-diol；[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-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-3-yl] acetate
• CAS: 1423042-66-3
• 化学式: C₃₂H₅₄O₅
• 分子量: 518.778
• InChiKey: NHBJTOHJGLCSIU-FFUXOBCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (20S,24R)-epoxy-3β-O-acetyl-dammarane-12β,25-diol 在 甲醇 、 pyridinium chlorochromate 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (20S,24R)-epoxy-12-oxodammarane-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 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 41.0h， 生成 (20S,24R)-epoxy-3β-O-acetyl-dammarane-12β,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

• Design, synthesis and biological evaluation of novel pyxinol derivatives with anti-heart failure activity
  作者：Junli Liu、Yunhe Liu、Hui Yu、Ying Zhang、Alan Chen-Yu Hsu、Mingming Zhang、Yawei Gou、Wei Sun、Fang Wang、Pingya Li、Jinping Liu

  DOI：10.1016/j.biopha.2020.111050

  日期：2021.1

  Natural products and its derivatives play a vital role in drug discovery and development owing to their efficacy and low toxicity. Pyxinol is a potent natural agent for cardiovascular disease. Thus we investigated the effect on ACE and HF of pyxinol derivatives. We designed and synthesized 32 novel fatty acid ester derivatives of pyxinol via esterification. Among them, compounds 2e (IC50=105 nM) and 3b

  心力衰竭（HF）是全球大量发病和死亡的重要原因。血管紧张素转换酶（ACE）是充血性心力衰竭的病因。天然产物及其衍生物由于其功效和低毒性而在药物开发中起着至关重要的作用。苯甲醇是治疗心血管疾病的有效天然药物。因此，我们研究了pyxinol衍生物对ACE和HF的影响。我们通过酯化反应设计并合成了32种新颖的pyxinol脂肪酸酯衍生物。其中，化合物2e（IC 50 = 105 nM）和3b（IC 50 = 114 nM）在体外显示出优异的ACE抑制活性，并且对H9c2细胞无毒。ACE与化合物之间的相互作用分别通过分子对接进行预测。在维拉帕米诱导的斑马鱼HF模型中，活性测定表明这两种衍生物可以剂量依赖性地改善心跳，静脉充血，心脏扩张，心输出量，射血分数和分数缩短的心血管生理指标。基于UPLC-QTOF-MS的血清代谢组学方法被用于探索潜在的机制。总共鉴定出25种分化的代谢产物和8种干扰的代谢途径
• 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
• Semisynthesis and bioactive evaluation of oxidized products from 20(S)-ginsenoside Rg3, Rh2, protopanaxadiol (PPD) and their 20(R)-epimers as cytotoxic agents
  作者：Jie Yang、Xuwen Li、Ting Sun、Yan Gao、Yanxin Chen、Yongri Jin、Yang Li

  DOI：10.1016/j.steroids.2015.12.005

  日期：2016.2

  eight compounds (3, 8, 9, 10, 15, 16, 19 and 22) with the cyclized side chain were firstly identified. Most of the tested compounds possessed cytotoxicity to a certain degree against the two types of cells which implied these oxidized products could play a certain role on anti-cancer functions of the raw materials in vivo. Meanwhile, the results proved that the configurations at C-20 or C-24 and the number

  已从20（S）-人参皂苷Rg3，Rh2、20（S）-原人参二醇（PPD）和它们的20（R）表观分子系统地合成了一系列氧化产物，并评估了其中大多数产物的抗细胞毒性活性首次通过MTT法检测HeLa细胞和HepG2细胞。根据全面的（1）H NMR，（13）C NMR，二维（2D）NMR和质谱数据，获得了22种产物并进行了阐明，其结果在以前的文献中已有报道。获得全部四种奥古洛尔型皂苷（20S，24R（delta86，delta85）; 20S，24S（delta87，delta88）; 20R，24R（delta86，delta86）; 20R，24S（delta86，delta87），此外，还得到了8种化合物首先鉴定了具有环化侧链的（3、8、9、10、15、16、19和22）。大多数测试化合物对两种类型的细胞都具有一定程度的细胞毒性，这暗示这些氧化产物可能对原料的体内抗癌功能起一定作用。同时，结
• Bi, Yi; Ma, Cong; Zhou, Zhiwen, Records of Natural Products, 2015, vol. 9, # 3, p. 356 - 368
  作者：Bi, Yi、Ma, Cong、Zhou, Zhiwen、Zhang, Tingting、Zhang, Hengyuan、Zhang, Xiaochen、Lu, Jing、Meng, Qingguo、Lewis, Peter J.、Xu, Jinyi

  DOI：——

  日期：——