匹西狄醇 A | 100198-09-2

• 物质功能分类: 天然产物 - 萜类
• 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
• 中文名称: 匹西狄醇 A
• 中文别名: 匹西狄醇A
• 英文名称: 3-oxothreo-23,24,25-trihydroxytirucall-7-ene
• 英文别名: piscidinal A；piscidinol A；(5R,9R,10R,13S,14S,17S)-4,4,10,13,14-pentamethyl-17-[(2S,4R,5S)-4,5,6-trihydroxy-6-methylheptan-2-yl]-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 100198-09-2
• 化学式: C₃₀H₅₀O₄
• 分子量: 474.725
• InChiKey: DCGUKHULKAAOPB-QBLSGNHRSA-N

物化性质

• 熔点：
  195 °C(Solv: methanol (67-56-1))
• 沸点：
  599.4±50.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  匹西狄醇 A 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以75.3%的产率得到(13α,14β,17α,20S)-tirucall-7-ene-3β,23,24,25-tetrol
  参考文献：
  名称：

  Synthesis of piscidinol A derivatives and their ability to inhibit HIV-1 protease

  摘要：

  Four types of piscidinol A derivatives were synthesized and evaluated their ability to inhibit HIV-1 protease to understand their structure-activity relationships. Of these tirucallane-type triterpene derivatives, an A-seco derivative (1b) moderately inhibited human immunodeficiency virus (HIV) protease (IC50 38.2M). The 2,2-dimethyl succinic acid (DMS) acylated tirucallane derivatives (4b, 6a, and 7b, 50100M). These findings indicated that the 2,3-seco-2,3-dioic acid (1b) and DMS-acylated tirucallane-type derivatives preferably inhibited HIV viral protease.

  DOI：

  10.1080/10286020.2015.1084505

文献信息

• Synthesis and antiproliferative activities of novel piscidinol a derivatives as potential anticancer agents
  作者：Swarna Kumari Gaja、Siva Bandi、Pavan Kumar Pavuluri、Shainy Sambyal、Vinod Kumar Jaina、H. M. Sampath Kumar、Sai Balaji Andugulapati、Ramalingam V、K. Suresh Babu

  DOI：10.1080/14786419.2022.2056889

  日期：——

  a series of analogues were synthesised by modification of the key structural functionalities of this high yield natural product and assessed for their anticancer potential against various cancer cell lines. Among the tested derivatives, the compounds 6e and 6i are significantly reduced the cell viability at 5.38 and 5.02 µM against DU145 prostate cancer cells, respectively. Additionally, both the

  摘要 Piscidinol A ( 1 ) 是从Aphanamixis polystachya中分离出来的主要化合物，对癌细胞系表现出适度的抗癌活性。随后，通过修饰这种高产天然产物的关键结构功能合成了一系列类似物，并评估了它们对各种癌细胞系的抗癌潜力。在测试的衍生物中，化合物6e和6i分别在 5.38 和 5.02 µM 浓度下显着降低对 DU145 前列腺癌细胞的细胞活力。此外，这两种化合物均将细胞周期阻滞在 S 期，并诱导 DU145 细胞晚期凋亡。总之，结果表明化合物6e和6i可能是开发针对 DU145 的抗癌药物的有希望的先导，并且非常值得进一步研究，旨在产生潜在的抗癌药物。
• Synthesis of piscidinol A derivatives and their ability to inhibit HIV-1 protease
  作者：Ying Wei、Chao-Mei Ma、Tai-Bai Jiang、Jiang Du、Xing Zhou、Guo-Qing Liu、Masao Hattori

  DOI：10.1080/10286020.2015.1084505

  日期：2015.11.2

  Four types of piscidinol A derivatives were synthesized and evaluated their ability to inhibit HIV-1 protease to understand their structure-activity relationships. Of these tirucallane-type triterpene derivatives, an A-seco derivative (1b) moderately inhibited human immunodeficiency virus (HIV) protease (IC50 38.2M). The 2,2-dimethyl succinic acid (DMS) acylated tirucallane derivatives (4b, 6a, and 7b, 50100M). These findings indicated that the 2,3-seco-2,3-dioic acid (1b) and DMS-acylated tirucallane-type derivatives preferably inhibited HIV viral protease.