7-(3-biphenyl-4-yl-5-ethyl-4H-1,2,4-triazol-4-yl)-1H-indole | 1348013-18-2

• 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: 7-(3-biphenyl-4-yl-5-ethyl-4H-1,2,4-triazol-4-yl)-1H-indole
• 英文别名: 7-[3-ethyl-5-(4-phenylphenyl)-1,2,4-triazol-4-yl]-1H-indole
• CAS: 1348013-18-2
• 化学式: C₂₄H₂₀N₄
• 分子量: 364.45
• InChiKey: JABAGHPAKORHJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-(3-biphenyl-4-yl-5-ethyl-4H-1,2,4-triazol-4-yl)-1H-indole 、 碘甲烷 在 potassium carbonate 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到7-(3-biphenyl-4-yl-5-ethyl-4H-1,2,4-triazol-4-yl)-1-methyl-1H-indole
  参考文献：
  名称：

  Synthesis and biological evaluation of (4H-1,2,4-triazol-4-yl)isoquinoline derivatives as selective glycine transporter 1 inhibitors

  摘要：

  To identify novel glycine transporter 1(GlyT1) inhibitors with greater selectivity relative to GlyT2 and improved aqueous solubility, we synthesized a series of 4H-1,2,4-triazole derivatives with heteroaromatic rings at the 4-position and investigated their structure-activity relationships. Replacement of the 2-fluorophenyl group of lead compound 5 with various aromatic groups led to the identification of 5-(3-biphenyl-4-yl-5-ethyl-4H-1,2,4-triazol-4-yl)isoquinoline (15) with 38-fold selectivity between GlyT1 and GlyT2. 15 also showed improved aqueous solubility and in vivo efficacy on (+)-HA966-induced hyperlocomotion in mice over the lead compound. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.038
• 作为产物：
  描述：

  4-联苯基羧酸肼 在 对甲苯磺酸 、 三乙胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 7-(3-biphenyl-4-yl-5-ethyl-4H-1,2,4-triazol-4-yl)-1H-indole
  参考文献：
  名称：

  Synthesis and biological evaluation of (4H-1,2,4-triazol-4-yl)isoquinoline derivatives as selective glycine transporter 1 inhibitors

  摘要：

  To identify novel glycine transporter 1(GlyT1) inhibitors with greater selectivity relative to GlyT2 and improved aqueous solubility, we synthesized a series of 4H-1,2,4-triazole derivatives with heteroaromatic rings at the 4-position and investigated their structure-activity relationships. Replacement of the 2-fluorophenyl group of lead compound 5 with various aromatic groups led to the identification of 5-(3-biphenyl-4-yl-5-ethyl-4H-1,2,4-triazol-4-yl)isoquinoline (15) with 38-fold selectivity between GlyT1 and GlyT2. 15 also showed improved aqueous solubility and in vivo efficacy on (+)-HA966-induced hyperlocomotion in mice over the lead compound. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.038

文献信息

• Synthesis and biological evaluation of (4H-1,2,4-triazol-4-yl)isoquinoline derivatives as selective glycine transporter 1 inhibitors
  作者：Takashi Sugane、Takahiko Tobe、Wataru Hamaguchi、Itsuro Shimada、Kyoichi Maeno、Junji Miyata、Takeshi Suzuki、Tetsuya Kimizuka、Takuma Morita、Shuichi Sakamoto、Shin-ichi Tsukamoto

  DOI：10.1016/j.bmc.2011.11.038

  日期：2012.1

  To identify novel glycine transporter 1(GlyT1) inhibitors with greater selectivity relative to GlyT2 and improved aqueous solubility, we synthesized a series of 4H-1,2,4-triazole derivatives with heteroaromatic rings at the 4-position and investigated their structure-activity relationships. Replacement of the 2-fluorophenyl group of lead compound 5 with various aromatic groups led to the identification of 5-(3-biphenyl-4-yl-5-ethyl-4H-1,2,4-triazol-4-yl)isoquinoline (15) with 38-fold selectivity between GlyT1 and GlyT2. 15 also showed improved aqueous solubility and in vivo efficacy on (+)-HA966-induced hyperlocomotion in mice over the lead compound. (C) 2011 Elsevier Ltd. All rights reserved.