1,4-diphenyl-2-hydroxy-3-aminobutane | 151830-80-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 1,4-diphenyl-2-hydroxy-3-aminobutane
• 英文别名: 3-amino-1,4-diphenyl-2-butanol；3-Amino-1,4-diphenylbutan-2-ol
• CAS: 151830-80-7
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: YASZJQILMBBZMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-diphenyl-2-hydroxy-3-aminobutane 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 3-Amino-1,4-diphenylbutan-2-one
  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：

  Β-硝基苯乙烷 在 platinum(IV) oxide 、 potassium fluoride on basic alumina 、 氢气 作用下， 以 乙醇 为溶剂， 23.0 ℃ 、344.73 kPa 条件下， 反应 8.0h， 生成 1,4-diphenyl-2-hydroxy-3-aminobutane
  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

文献信息

• A Convenient One-Pot Synthesis of 1,2-Aminoalcohols
  作者：J. Howarth、D. G. Lloyd、P. McCormac

  DOI：10.1080/00397919808004848

  日期：1998.8

  We have developed a rapid facile synthesis of 1,2-aminoalcohols from a variety of aldehyde starting materials. This one pot synthesis proceeds via the in situ formation of cyanohydrin trimethylsilyl ethers and the subsequent addition of Grignard reagents. This method is of particular use where the initial aldehyde exhibits water solubility.
• Synthesis and LTB4 receptor antagonist activities of the naturally occurring LTB4 receptor antagonist leucettamine A and related analogs
  作者：Jeffrey C. Boehm、John G. Gleason、Israil Pendrak、Henry M. Sarau、Dulcie B. Schmidt、James J. Foley、William D. Kingsbury

  DOI：10.1021/jm00074a014

  日期：1993.10

  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).