11,13-dihydroparthenolide | 241165-54-8

• 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: 11,13-dihydroparthenolide
• 英文别名: (1S,2S,4R,7E,11S,12S)-4,8,12-trimethyl-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one
• CAS: 241165-54-8
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: GSVWPONNFJXHJL-KPZOZZDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11,13-dihydroparthenolide 以 苯 为溶剂， 反应 20.0h， 以100%的产率得到(-)-(1aR,4Z,7aS,8S,10aS,10bS)-2,3,6,7,7a,8,10a,10b-octahydro-1a,5,8-trmethyloxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one
  参考文献：
  名称：

  苯乙内酯及其光化学合成的1（10）Z异构体：人类白细胞趋化性中的化学反应性和构效关系研究。

  摘要：

  目前的研究已经实现了杀菌剂金葡糖胺的光化学转化为聚丙烯酰胺。对它们的化学性质的研究使我们能够评估杀菌棒中C（10）环跨环桥接所需的最小原子间距离，并解释了亲电环化的区域化学选择性。通过对人嗜中性白细胞的体外趋化性分析评估了小白菊内酯及其半合成衍生物的抗炎活性。这些结构-活性关系研究导致了一种新的药效团的假设，并为计算设计的药物提供了有用的信息。

  DOI：

  10.1016/s0968-0896(02)00553-9
• 作为产物：
  描述：

  parthenolide 在 氢气 作用下， 生成 11,13-dihydroparthenolide
  参考文献：
  名称：

  苯乙内酯及其光化学合成的1（10）Z异构体：人类白细胞趋化性中的化学反应性和构效关系研究。

  摘要：

  目前的研究已经实现了杀菌剂金葡糖胺的光化学转化为聚丙烯酰胺。对它们的化学性质的研究使我们能够评估杀菌棒中C（10）环跨环桥接所需的最小原子间距离，并解释了亲电环化的区域化学选择性。通过对人嗜中性白细胞的体外趋化性分析评估了小白菊内酯及其半合成衍生物的抗炎活性。这些结构-活性关系研究导致了一种新的药效团的假设，并为计算设计的药物提供了有用的信息。

  DOI：

  10.1016/s0968-0896(02)00553-9

文献信息

• Transformations of Some Sesquiterpene Lactones by Filamentous Fungi and Cytotoxic Evaluations
  作者：Arturo Cano-Flores、Guillermo Delgado

  DOI：10.1002/cbdv.201700211

  日期：2017.10

  be useful for the biotransformation of sesquiterpene lactones (SLs), leading to unusual structural changes that modify their biological activities, and other transformations mimic their biosynthetic pathways, generating evidences for the proposed biogenesis. Eight filamentous fungi were screened for their ability to transform different SLs (1 - 9), and microbial reactions yielded compounds 10 - 17, which

  生物转化是一种经济上和生态上可行的技术，已被用于修饰许多类生物活性产品的结构。一些真菌可能对倍半萜内酯（SLs）的生物转化有用，导致异常结构改变，从而改变其生物活性，而其他转化则模仿其生物合成途径，从而为拟议的生物发生提供证据。筛选了八种丝状真菌转化不同SL的能力（1-9），微生物反应产生的化合物10-17反过来又被分离为天然产物，从而模拟了它们的生物合成。根据NMR和MS光谱分析鉴定了它们的结构。SL 1、4、6、7和9及其生物转化产物的细胞毒性（10、14，
• Synthesis and anti-viral activity of a series of sesquiterpene lactones and analogues in the subgenomic HCV replicon system
  作者：Der-Ren Hwang、Yu-Shan Wu、Chun-Wei Chang、Tzu-Wen Lien、Wei-Cheng Chen、Uan-Kang Tan、John T.A. Hsu、Hsing-Pang Hsieh

  DOI：10.1016/j.bmc.2005.07.055

  日期：2006.1

  fever and migraine, as a lead compound with an EC50 value of 2.21 microM against HCV replication in a subgenomic RNA replicon assay system. Parthenolide is able to potentiate the interferon alpha-exerted anti-HCV effect. Several commercially available sesquiterpene lactones (2-5) structurally analogous to parthenolide and a series of synthesized Michael-type adducts of parthenolide (12-18) also exhibit

  丙型肝炎病毒（HCV）感染是一种严重的肝脏疾病，通常会导致肝硬化和肝细胞癌（HCC）。当前的疗法不足以克服这种病毒性疾病。在这项研究中，我们确定了亚群（1），一种在小白菊中的有效成分，这是一种用于治疗发烧和偏头痛的常用药物，是在亚基因组RNA复制子检测系统中对抗HCV复制的EC50值为2.21 microM的先导化合物。帕特诺尔能够增强干扰素α-抗-HCV的作用。在结构上类似于小白菊内酯的几种市售倍半萜内酯（2-5）和一系列合成的小白菊内酯的迈克尔型加合物（12-18）也具有抗HCV活性的微摩尔浓度。阐明了结构活性关系，以揭示与α-亚甲基-γ-内酯部分融合的萜类骨架的空间排列产生最大的抗HCV活性。另外，强的抗HCV效力表明仲氨基加合物（12-18）可能转化回小白菊内酯或被细胞内蛋白质的亲核残基取代。这项工作表明，天然产物的筛选是鉴定新型分子多样性作为潜在药物线索的可行且快速的方法。
• Sesquiterpene Lactones with Potential Use as Natural Herbicide Models (I):  <i>trans,trans-</i>Germacranolides
  作者：Francisco A. Macías、Juan C. G. Galindo、Diego Castellano、Raúl F. Velasco

  DOI：10.1021/jf9903612

  日期：1999.10.1

  A structure-activity study to evaluate the effect of the trans,trans-germacranolide sesquiterpene lactones costunolide, parthenolide, and their 1,10-epoxy and 11,13-dihydro derivatives (in a range of 100-0.001 mu M) on the growth and germination of several mono and dicotyledon target species is accomplished. Results are compared with those obtained in the same bioassay with an internal standard, the commercial herbicide Logran, to validate the results with a known active formulation and to compare the results with a commercial product to test their potential use as natural herbicide models. These compounds appear to have a more selective effects on the radicle growth of monocotyledons. Certain factors such as the presence of nucleophile-acceptor groups and their accessibility enhance the inhibitory activity. The levels of radicle inhibition obtained with some compounds on wheat are totally comparable to those of Logran and allow to propose them as lead compounds.
• Syntheses and Biological Evaluation of Costunolide, Parthenolide, and Their Fluorinated Analogues
  作者：Zhong-Jin Yang、Wei-Zhi Ge、Qiu-Ying Li、Yaxin Lu、Jian-Miao Gong、Bei-Jia Kuang、Xiaonan Xi、Haiting Wu、Quan Zhang、Yue Chen

  DOI：10.1021/acs.jmedchem.5b00915

  日期：2015.9.10

  Inspired by the biosynthesis of sesquiterpene lactones (SLs), herein we report the asymmetric total synthesis of the germacrane ring (24). The synthetic strategy features a selective aldol reaction between beta,gamma-unsaturated chiral sulfonylamide 15a and aldehyde 13, as well as the intramolecular alpha-alkylation of sulfone 21 to construct a 10-membered carbocylic ring. The key intermediate 24 can be used to prepare the natural products costunolide and parthenolide (PTL), which are the key precursors for transformation into other SLs. Furthermore, the described synthetic sequences are amenable to the total synthesis of SL analogues, such as trifluoro-methylated analogues 32 and 45. Analogues 32 and 45 maintained high activities against a series of cancer cell lines compared to their parent PTL and costunolide, respectively. In addition, 32 showed enhanced tolerance to acidic media compared with PTL. To our surprise, PTL and 32 showed comparable half-lives in rat plasma and in the presence of human liver microsomes.
• Parthenolide and its photochemically synthesized 1(10) Z isomer: chemical reactivity and structure–activity relationship studies in human leucocyte chemotaxis
  作者：Hannes Neukirch、Nicole C Kaneider、Christian J Wiedermann、Antonio Guerriero、Michele D'Ambrosio

  DOI：10.1016/s0968-0896(02)00553-9

  日期：2003.4

  germacrolide into a melampolide. The investigation on their chemical properties allowed us to evaluate the minimum interatomic distance needed for transannular bridging of C(10) ring in germacrolides and to explain the regiochemical selectivity of electrophilic cyclizations. The antiinflammatory activity of parthenolide and its semisynthetic derivatives was evaluated by in vitro chemotaxis assay with human neutrophiles

  目前的研究已经实现了杀菌剂金葡糖胺的光化学转化为聚丙烯酰胺。对它们的化学性质的研究使我们能够评估杀菌棒中C（10）环跨环桥接所需的最小原子间距离，并解释了亲电环化的区域化学选择性。通过对人嗜中性白细胞的体外趋化性分析评估了小白菊内酯及其半合成衍生物的抗炎活性。这些结构-活性关系研究导致了一种新的药效团的假设，并为计算设计的药物提供了有用的信息。