3--1,4-bis<3,4-(methylenedioxy)phenyl>-2-butanone | 151830-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3--1,4-bis<3,4-(methylenedioxy)phenyl>-2-butanone
• CAS: 151830-66-9
• 化学式: C₂₄H₂₇NO₇
• 分子量: 441.481
• InChiKey: RWOPHCNJHMMAQD-UHFFFAOYSA-N

物化性质

• 沸点：
  560.9±39.0 °C(predicted)
• 密度：
  1.277±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  83.53
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3--1,4-bis<3,4-(methylenedioxy)phenyl>-2-butanone 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis and LTB4 receptor antagonist activities of the naturally occurring LTB4 receptor antagonist leucettamine A and related analogs

  摘要：

  The isolation and structure determination of the naturally occurring LTB4 receptor antagonist Leucettamine A (1) was recently reported.1 Herein we describe the synthesis of this natural product, the preparation of several analogues, and their effectiveness as antagonists of [H-3]LTB4 binding to intact human U-937 cells. Total synthesis of Leucettamine A 1) is achieved by a convergent route which takes advantage of the elements of symmetry within the molecule. Syntheses of analogues of 1, which lacked the same degree of symmetry, are achieved by a different approach starting from alpha-amino acids. The natural product 1 inhibits [H-3]LTB4 binding to its receptors on intact human U-937 cells with a K(i) = 3.5 +/- 0. 8 muM and is devoid of measurable agonist activity at the concentrations tested. 2-Amino imidazole analogues of 1 lacking the dioxolane groups were prepared. Generally these are significantly less potent than 1. However, one (26), designed on the basis of a putative structural overlay with LTB4, demonstrated potency comparable to that of the natural product (K(i) = 2.4 +/- 0.2 muM).

  DOI：

  10.1021/jm00074a014
• 作为产物：
  描述：

  3--1,4-bis<3,4-(methylenedioxy)phenyl>-2-butanol 在 重铬酸吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以56%的产率得到3--1,4-bis<3,4-(methylenedioxy)phenyl>-2-butanone
  参考文献：
  名称：

  Synthesis and LTB4 receptor antagonist activities of the naturally occurring LTB4 receptor antagonist leucettamine A and related analogs

  摘要：

  The isolation and structure determination of the naturally occurring LTB4 receptor antagonist Leucettamine A (1) was recently reported.1 Herein we describe the synthesis of this natural product, the preparation of several analogues, and their effectiveness as antagonists of [H-3]LTB4 binding to intact human U-937 cells. Total synthesis of Leucettamine A 1) is achieved by a convergent route which takes advantage of the elements of symmetry within the molecule. Syntheses of analogues of 1, which lacked the same degree of symmetry, are achieved by a different approach starting from alpha-amino acids. The natural product 1 inhibits [H-3]LTB4 binding to its receptors on intact human U-937 cells with a K(i) = 3.5 +/- 0. 8 muM and is devoid of measurable agonist activity at the concentrations tested. 2-Amino imidazole analogues of 1 lacking the dioxolane groups were prepared. Generally these are significantly less potent than 1. However, one (26), designed on the basis of a putative structural overlay with LTB4, demonstrated potency comparable to that of the natural product (K(i) = 2.4 +/- 0.2 muM).

  DOI：

  10.1021/jm00074a014