20(R)-20,25-epoxy-2,3-seco-12β-hydroxydammaran-2,3-dioicacid | 1160164-62-4

• 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: 20(R)-20,25-epoxy-2,3-seco-12β-hydroxydammaran-2,3-dioicacid
• 英文别名: 2-[(3S,3aR,4R,5aR,6R,7R,9aR,9bR)-6-(carboxymethyl)-4-hydroxy-6,9a,9b-trimethyl-3-[(2R)-2,6,6-trimethyloxan-2-yl]-1,2,3,3a,4,5,5a,7,8,9-decahydrocyclopenta[a]naphthalen-7-yl]-2-methylpropanoic acid
• CAS: 1160164-62-4
• 化学式: C₃₀H₅₀O₆
• 分子量: 506.723
• InChiKey: YDGLWSROGMMRPN-KQLLEDISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  20(R)-20,25-epoxy-2,3-seco-12β-hydroxydammaran-2,3-dioicacid 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以10%的产率得到(20R)-20,25-epoxy-12-oxo-2,3-seco-dammaran-2,3-dioic acid
  参考文献：
  名称：

  Synthesis of dammarane-type triterpene derivatives and their ability to inhibit HIV and HCV proteases

  摘要：

  We synthesized dammarane-type triterpene derivatives and evaluated their ability to inhibit HIV-1 and HCV proteases to understand their structure-activity relationships. All of the mono- and di-succinyl derivatives (5a-5f) were powerful inhibitors of HIV-1 protease (IC50 < 10 mu M). However, only di-succinyl (5e) and 2,3-seco-2,3-dioic acid (3b) derivatives similarly inhibited HCV protease (IC50 < 10 mu M). A-nor dammarane- type triterpenes (4a and 4b, IC50 10.0 and 29.9 mu M, respectively) inhibited HIV-1 protease moderately or strongly, but were inactive against HCV protease. All compounds that powerfully inhibited HIV-1 or HCV protease did not appreciably inhibit the general human proteases, renin and trypsin (IC50 > 1000 mu M). These findings indicated that the mono-succinyl dammarane type derivatives (5a-5d) selectively inhibited HIV-1 protease and that the di-succinyl (5e, 5f) as well as 2,3-seco-2,3-dioic acid (3b) derivatives preferably inhibited both viral proteases. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.019
• 作为产物：
  描述：

  3-oxo-20(R)-panaxadiol 在 potassium tert-butylate 、 双氧水 、 氧气 、 potassium hydroxide 作用下， 以 甲醇 、 叔丁醇 为溶剂， 反应 3.67h， 生成 20(R)-20,25-epoxy-2,3-seco-12β-hydroxydammaran-2,3-dioicacid
  参考文献：
  名称：

  人参二醇氧化和氮杂化衍生物的合成、表征和细胞毒活性评价†

  摘要：

  Panaxadiol (PD) 是一种二醇型人参皂甙，具有达玛烷骨架，在肿瘤细胞凋亡中发挥潜在作用。本研究合成了 28 种 PD 的氧化氮杂化衍生物，其中 20 种为新型化合物。在六种细胞系中筛选所有获得的化合物的细胞毒活性。与阳性对照相比，一些化合物表现出更好的抗增殖活性，但对正常细胞生长的作用却要弱得多。其中，环 A 融合的 PD ( 1j ) 显示出令人印象深刻的细胞毒活性，对 A549、HeLa 和 8901 细胞系的 IC 50分别为 9.62 ± 1.34、11.65 ± 1.71 和 13.45 ± 1.60 μM。此外，化合物2f表现出最强的活性，具有 IC对细胞系 A549 的50值为 8.93 ± 1.11 μM。因此，我们的结果表明， 1j和2f可以成为进一步研究的有希望的主要候选者。

  DOI：

  10.1039/c8md00387d

文献信息

• Synthesis, characterization and cytotoxic activity evaluation of ginsengdiol oxidation and nitrogen hybrid derivatives
  作者：Yumeng Zhang、Weihui Yuan、Xude Wang、Hongyu Zhang、Yuanyuan Sun、Xiaoshu Zhang、Yuqing Zhao

  DOI：10.1039/c8md00387d

  日期：——

  Panaxadiol (PD), a diol-type ginseng saponin, with a dammarane skeleton plays a potential role in the apoptosis of tumor cells. In this study, 28 oxidation and nitrogen hybrid derivatives of PD were synthesized, of which 20 were novel compounds. All the obtained compounds were screened for their cytotoxic activity in six cell lines. As compared with the positive control, some compounds showed better

  Panaxadiol (PD) 是一种二醇型人参皂甙，具有达玛烷骨架，在肿瘤细胞凋亡中发挥潜在作用。本研究合成了 28 种 PD 的氧化氮杂化衍生物，其中 20 种为新型化合物。在六种细胞系中筛选所有获得的化合物的细胞毒活性。与阳性对照相比，一些化合物表现出更好的抗增殖活性，但对正常细胞生长的作用却要弱得多。其中，环 A 融合的 PD ( 1j ) 显示出令人印象深刻的细胞毒活性，对 A549、HeLa 和 8901 细胞系的 IC 50分别为 9.62 ± 1.34、11.65 ± 1.71 和 13.45 ± 1.60 μM。此外，化合物2f表现出最强的活性，具有 IC对细胞系 A549 的50值为 8.93 ± 1.11 μM。因此，我们的结果表明， 1j和2f可以成为进一步研究的有希望的主要候选者。
• Synthesis of dammarane-type triterpene derivatives and their ability to inhibit HIV and HCV proteases
  作者：Ying Wei、Chao-Mei Ma、Masao Hattori

  DOI：10.1016/j.bmc.2009.03.019

  日期：2009.4

  We synthesized dammarane-type triterpene derivatives and evaluated their ability to inhibit HIV-1 and HCV proteases to understand their structure-activity relationships. All of the mono- and di-succinyl derivatives (5a-5f) were powerful inhibitors of HIV-1 protease (IC50 < 10 mu M). However, only di-succinyl (5e) and 2,3-seco-2,3-dioic acid (3b) derivatives similarly inhibited HCV protease (IC50 < 10 mu M). A-nor dammarane- type triterpenes (4a and 4b, IC50 10.0 and 29.9 mu M, respectively) inhibited HIV-1 protease moderately or strongly, but were inactive against HCV protease. All compounds that powerfully inhibited HIV-1 or HCV protease did not appreciably inhibit the general human proteases, renin and trypsin (IC50 > 1000 mu M). These findings indicated that the mono-succinyl dammarane type derivatives (5a-5d) selectively inhibited HIV-1 protease and that the di-succinyl (5e, 5f) as well as 2,3-seco-2,3-dioic acid (3b) derivatives preferably inhibited both viral proteases. (C) 2009 Elsevier Ltd. All rights reserved.