1-([1,1'-biphenyl]-4-yloxy)-3-(isopropylamino)propan-2-ol | 5741-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-([1,1'-biphenyl]-4-yloxy)-3-(isopropylamino)propan-2-ol
• 英文别名: N-<3-p-Biphenylyloxy-2-hydroxy-propyl>-isopropylamin；1-(Biphenyl-4-yloxy)-3-isopropylamino-propan-2-ol；1-(4-phenylphenoxy)-3-(propan-2-ylamino)propan-2-ol
• CAS: 5741-13-9
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: YBTGLLRMGKEQCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-([1,1'-biphenyl]-4-yloxy)-3-(isopropylamino)propan-2-ol 以40%的产率得到
  参考文献：
  名称：

  GREEMWOOD D. T.; MALLION K. B.; TODD A. H.; TURNER R. W., J. MED. CHEM. , 1975, 18, NO 6, 573-577

  摘要：

  DOI：
• 作为产物：
  描述：

  对羟基联苯 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 、 异丙醇 为溶剂， 反应 7.33h， 生成 1-([1,1'-biphenyl]-4-yloxy)-3-(isopropylamino)propan-2-ol
  参考文献：
  名称：

  Drug repurposing and rediscovery: Design, synthesis and preliminary biological evaluation of 1-arylamino-3-aryloxypropan-2-ols as anti-melanoma agents

  摘要：

  Malignant melanoma (MM) presents as the highest morbidity and mortality type in skin cancer. Herein, inspired by the previously reported anti-melanoma effect of propranolol, a widely applied beta adrenergic receptor antagonist as cardiovascular drug, we set out to exploit its potential as anti-melanoma therapy based on the drug repurposing strategy. Structural optimization of propranolol yielded 5m, which exhibits dramatically improved potency on human melanoma cell growth (1.98-3.70 mu M), compared to propranolol (59.5-75.8 mu M). Further investigation demonstrated that 5m could inhibit colony formation of melanoma cell line (completely abolished at 2 mu M for 5m, partially inhibited at 50 mu M for propranolol), induce cell apoptosis and cell cycle arrest in the G(2)/M phase (both observed at 1 mu M). Preliminary mechanism study indicated that 5m could disrupt the cellular microtubule network, which suggested tubulin as a potential target. Docking study provided a structural insight into the interaction between 5m and tubulin. In summary, our study presents a drug repurposing case that redirects a cardiovascular agent to an anti-melanoma agent.

  DOI：

  10.1016/j.bmc.2020.115404

文献信息

• Linked aryl aryloxypropanolamines as a new class of lipid catabolic agents
  作者：Michael T. Cox、Stuart E. Jaggers、Geraint Jones

  DOI：10.1021/jm00200a008

  日期：1978.2

  The synthesis of a series of stilbene, biaryl, tolane, diaryl ether, sulfide, sulfoxide, and sulfone oxypropanolamines as potential antiobesity agents is described. These compounds were evaluated in a mouse lipid catabolism screen, and the more active members of the series, 4, 57, and 58, were further investigated in rats and dogs. 1-(2,6-Ditert-butyl-4-trans-styrylphenoxy)-3-isopropylamino-2-propanol (4) possessed considerable lipid catabolic activity in mice and caused a significant reduction in the body weight of rats after 5 weeks and of dogs after 6 weeks. Only hematological irregularities in a chronic toxicity study precluded further development of this compound as an alternative antiobesity treatment.
• Adlerova,E. et al., Collection of Czechoslovak Chemical Communications, 1969, vol. 34, p. 479 - 484
  作者：Adlerova,E. et al.

  DOI：——

  日期：——