1-O-acetyl-6-O-chloracetylbritannilactone | 1613152-33-2

• 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: 1-O-acetyl-6-O-chloracetylbritannilactone
• 英文别名: Antifungal agent 66；[(3aR,4S,7aR)-5-[(2S)-5-acetyloxypentan-2-yl]-6-methyl-3-methylidene-2-oxo-3a,4,7,7a-tetrahydro-1-benzofuran-4-yl] 2-chloroacetate
• CAS: 1613152-33-2
• 化学式: C₁₉H₂₅ClO₆
• 分子量: 384.857
• InChiKey: RYKKXQWEYIZDNQ-VBJMPTANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-二硝基酚 、 1-O-acetyl-6-O-chloracetylbritannilactone 在 三乙醇胺 、 苄基三乙基氯化铵 、 sodium iodide 作用下， 以 丙酮 为溶剂， 以47%的产率得到1-O-acetyl-6-O-(2-(2,4-dinitrophenoxy)acetyl)britannilactone
  参考文献：
  名称：

  Synthesis of 1-O-acetylbritannilactone analogues from Inula britannica and in vitro evaluation of their anticancer potential

  摘要：

  一系列新颖的ABL类似物通过N/O原子的安装和芳香环酯化合成，其中4a显示出对HeLa细胞的显著体外抗癌活性，与诱导凋亡、激活caspase-3和G2/M细胞周期阻滞有关。

  DOI：

  10.1039/c4md00209a
• 作为产物：
  描述：

  旋复花内酯 、 氯乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以99%的产率得到1-O-acetyl-6-O-chloracetylbritannilactone
  参考文献：
  名称：

  Synthesis of 1-O-acetylbritannilactone analogues from Inula britannica and in vitro evaluation of their anticancer potential

  摘要：

  一系列新颖的ABL类似物通过N/O原子的安装和芳香环酯化合成，其中4a显示出对HeLa细胞的显著体外抗癌活性，与诱导凋亡、激活caspase-3和G2/M细胞周期阻滞有关。

  DOI：

  10.1039/c4md00209a

文献信息

• Discovery of Natural Sesquiterpene Lactone 1-<i>O</i>-Acetylbritannilactone Analogues Bearing Oxadiazole, Triazole, or Imidazole Scaffolds for the Development of New Fungicidal Candidates
  作者：Xiao-yan Zhi、Yuan Zhang、Yang-fan Li、Ying Liu、Wen-peng Niu、Yang Li、Cheng-ran Zhang、Hui Cao、Xiao-juan Hao、Chun Yang

  DOI：10.1021/acs.jafc.3c02497

  日期：2023.8.2

  control efficacy of compound 10 against B. cinerea was further studied using infected tomatoes (protective effect = 58.4%; therapeutic effect = 48.7%). The preliminary structure–activity relationship analysis suggested that the introduction of the 1,3,4-oxadiazole moiety (especially the 1,3,4-oxadiazole heterocycle containing the 4-chlorophenyl, 2-furyl, or 2-pyridinyl group) on the skeleton of ABL

  近几十年来，天然产物因其新颖的结构和多种生物活性而被认为是开发新型农用化学品的重要资源。因此，本文使用1- O-乙酰基不列颠尼内酯 (ABL)（一种来自不列颠旋覆花的天然倍半萜内酯）作为进一步修饰的先导物，以发现杀菌候选物。设计并合成了六系列含有恶二唑、三唑或咪唑部分的基于ABL的衍生物，并在体外和体内评估了它们的抗真菌活性。生物测定结果表明，化合物8d、8h和8j（EC 50分别为61.4、30.9和12.4 μg/mL）比其前体ABL（EC 50 > 500 μg/mL）表现出更显着的对尖孢镰刀菌的抑制活性，并且阳性对照海美唑 (EC 50 = 77.2 μg/mL)。衍生物8d和11j（EC 50分别为 19.6 和 41.5 μg/mL）比ABL（EC 50 = 68.3 μg/mL）表现出更有效的抗曼莎胞孢菌活性。化合物10对七种植物病原真菌菌丝体表现出优异的广谱抗真菌活性。特别
• Semisynthesis and in vitro cytotoxic evaluation of new analogues of 1-O-acetylbritannilactone, a sesquiterpene from Inula britannica
  作者：Shuai Dong、Jiang-Jiang Tang、Cheng-Chen Zhang、Jun-Mian Tian、Jun-Tao Guo、Qiang Zhang、He Li、Jin-Ming Gao

  DOI：10.1016/j.ejmech.2014.04.028

  日期：2014.6

  Semisynthetic analogues of the natural product 1-O-acetylbritannilactone (ABL), a sesquiterpene isolated from the medicinal plant Inula britannica, have been prepared and exhibited significant in vitro cytotoxic activities against four cell lines including three human cancer cell lines (HCT116, HEp-2 and HeLa) and one normal hamster cell line (CHO). Structure-activity relationships indicate that esterification of 6-OH (enhanced lipophilicity) and α-methylene-γ-lactone functionalities play important roles in conferring cytotoxicity. Among the tested compounds, 14 bearing a lauroyl group (12C) at the 6-OH position displayed most potent in vitro cytotoxic activity, with IC50 values between 2.91 and 6.78 μM, comparable to the positive control etoposide (VP-16, IC50 values between 2.13 and 4.79 μM). Moreover, the compound 14 triggered remarkable apoptosis at a low concentration, and induced cell cycle arrest in G2/M phase in HCT116 cells. The biological assays conducted with normal cells (CHO) revealed that all the synthetic compounds are no selective against cancer cell lines tested.
• CN116143736
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of 1-O-acetylbritannilactone analogues from Inula britannica and in vitro evaluation of their anticancer potential
  作者：Jiang-Jiang Tang、Shuai Dong、Yang-Yang Han、Ming Lei、Jin-Ming Gao

  DOI：10.1039/c4md00209a

  日期：——

  A series of novel ABL analogues was synthesized by N/O-atom installing and aromatic ring esterifying, and 4a showed in vitro markedly anticancer activities against HeLa cells associated with induction of apoptosis, activation of caspase-3 and G2/M cell arrest.

  一系列新颖的ABL类似物通过N/O原子的安装和芳香环酯化合成，其中4a显示出对HeLa细胞的显著体外抗癌活性，与诱导凋亡、激活caspase-3和G2/M细胞周期阻滞有关。