1-O-acetylbritannilactone

• 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-acetylbritannilactone
• 英文别名: 1-O-acetylbritannilatone；[(4S)-4-[(3aS,4R,7aR)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3a,4,7,7a-tetrahydro-1-benzofuran-5-yl]pentyl] acetate
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: QKUFZFLZBUSEHN-CIGJXOAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-O-acetylbritannilactone 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-O-acetyl-6-oxobritannilactone
  参考文献：
  名称：

  1-O-ACETYLBRITANNILATONE SPIRO ARYL ISOXAZOLINE COMPOUNDS AND A METHOD OF USING THE SAME

  摘要：

  公开了化学式I的化合物或其药用可接受的盐。R1为OH或OAc；X为C或N；R2为H、烷基、烷氧基、苄氧基、卤代烷基、OH、CN、NO2或卤素，条件是当X为N时，R2为零。

  公开号：

  US20190185488A1

文献信息

• Design, Synthesis, and Antitumor Activity of Novel Acylate of 6-OH at 1- O-acetylbritannilactone
  作者：Shouxin Liu、Jun Feng、He Liu、Junzhang Li、Xia Tian

  DOI：10.2174/1573406410666140815123216

  日期：2015.1.30

  N-(α-Alkyloxime-3-phenylpropionyl) proline was designed and synthesized as an acylating agent to modify the 6-OH of 1-O-acetylbritannilactone. Eight intermediates and eight target compounds were obtained. The structures of sixteen novel compounds were characterized by 1HNMR, IR and HRMS. The activities against HL-60 and Bel-7402 cell lines were tested, the IC50 values of compound IVg were 2.7 μM and 4.3 μM, respectively.

  设计并合成了 N-(α-烷氧基肟-3-苯基丙酰基)脯氨酸作为酰化剂，用于修饰 1-O-acetylbritannilactone 的 6-OH。共得到 8 个中间体和 8 个目标化合物。通过 1HNMR、IR 和 HRMS 对 16 种新型化合物的结构进行了表征。测试了化合物 IVg 对 HL-60 和 Bel-7402 细胞株的活性，其 IC50 值分别为 2.7 μM 和 4.3 μM。
• 1-O-acetylbritannilatone spiro aryl isoxazoline compounds
  申请人：Li Han

  公开号：US10618911B2

  公开（公告）日：2020-04-14

  A compound of chemical formula I: or formula II: or a pharmaceutical acceptable salt thereof is disclosed. R1 is OH or OAc; X is C or N; and R2 is H, alkyl, alkoxy, benzyloxy, haloalkyl, OH, CN, NO2, or halogen, provided that when X is N, R2 is nil.

  化学式 I 的化合物： 或式 II： 或其可接受的药物盐。R1 是 OH 或 OAc；X 是 C 或 N；R2 是 H、烷基、烷氧基、苄氧基、卤代烷基、OH、CN、NO2 或卤素，但当 X 是 N 时，R2 为零。
• Methods of using 1-O-acetylbritannilatone spiro aryl isoxazoline compounds
  申请人：XI'AN TAIKOMED PHARMACEUTICAL TECHNOLOGY CO., LTD.

  公开号：US11028102B2

  公开（公告）日：2021-06-08

  A method of inhibiting leukotriene include: administrating a therapeutically effective amount of a compound of chemical formula I or II or a pharmaceutical acceptable salt thereof to a subject, R1 is OH or OAc; X is C or N; and R2 is H, alkyl, alkoxy, benzyloxy, haloalkyl, OH, CN, NO2, or halogen, provided that when X is N, R2 is nil.

  一种抑制白三烯的方法包括：向受试者施用治疗有效量的化学式 I 或 II 的化合物或其药物可接受盐、 R1是OH或OAc；X是C或N；R2是H、烷基、烷氧基、苄氧基、卤代烷基、OH、CN、NO2或卤素，但当X是N时，R2为零。
• Studies on 1- O -acetylbritannilactone and its derivative, (2- O -butyloxime-3-phenyl)-propionyl-1- O -acetylbritannilactone ester
  作者：Shouxin Liu、He Liu、Weiying Yan、Li Zhang、Naisheng Bai、Chi-Tang Ho

  DOI：10.1016/j.bmcl.2003.12.078

  日期：2004.3

  The crystal structures of 1-O-acetylbritannilactone 6 isolated from Inula britannica, and its derivative (2-O-butyloxime-3-phenyl) propionyl 1-O-acetylbritannilactone ester 7 are reported. The structure of synthesized derivative 7 was established by spectroscopic methods. Both compounds inhibited the growth of human HL-60, Bel-7402 cell lines and compound 7 had the stronger cytotoxic activity. (C) 2004 Elsevier Ltd. All rights reserved.
• METHODS OF USING 1-O-ACETYLBRITANNILATONE SPIRO ARYL ISOXAZOLINE COMPOUNDS
  申请人：XI'AN TAIKOMED PHARMACEUTICAL TECHNOLOGY CO., LTD.

  公开号：US20200199152A1

  公开（公告）日：2020-06-25

  A method of inhibiting leukotriene include: administrating a therapeutically effective amount of a compound of chemical formula I or II or a pharmaceutical acceptable salt thereof to a subject, R 1 is OH or OAc; X is C or N; and R 2 is H, alkyl, alkoxy, benzyloxy, haloalkyl, OH, CN, NO 2 , or halogen, provided that when X is N, R 2 is nil.