(E)-3-(1-(thiophen-2-yl)-9H-pyrido[3,4-b]indol-3-yl)-acrylic acid | 1536469-88-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (E)-3-(1-(thiophen-2-yl)-9H-pyrido[3,4-b]indol-3-yl)-acrylic acid
• 英文别名: (E)-3-(1-thiophen-2-yl-9H-pyrido[3,4-b]indol-3-yl)prop-2-enoic acid
• CAS: 1536469-88-1
• 化学式: C₁₈H₁₂N₂O₂S
• 分子量: 320.371
• InChiKey: LJHJPJUATZANJA-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙二酸 、 1-(1,3-benzodioxol-5-yl)-9H-β-carboline-3-carbaldehyde 在 哌啶 、 吡啶 作用下， 反应 4.0h， 以85%的产率得到(E)-3-(1-(thiophen-2-yl)-9H-pyrido[3,4-b]indol-3-yl)-acrylic acid
  参考文献：
  名称：

  Synthesis and Antiviral and Fungicidal Activity Evaluation of β-Carboline, Dihydro-β-carboline, Tetrahydro-β-carboline Alkaloids, and Their Derivatives

  摘要：

  Six known beta-carboline, dihydro-beta-carboline, and tetrahydro-beta-carboline alkaloids and a series of their derivatives were designed, synthesized, and evaluated for their anti-tobacco mosaic virus (TMV) and fungicidal activities for the first time. All of the alkaloids and some of their derivatives (compounds 3, 4, 14, and 19) exhibited higher anti-TMV activity than the commercial antiviral agent Ribavirin both in vitro and in vivo. Especially, the inactivation, curative, and protection activities of alkaloids Harmalan (62.3, 55.1, and 60.3% at 500 mu g/mL) and tetrahydroharmane (64.2, 57.2, and 59.5% at 500 mu g/mL) in vivo were much higher than those of Ribavirin (37.4, 36.2, and 38.5% at 500 mu g/mL). A new derivative, 14, with optimized physicochemical properties, obviously exhibited higher activities in vivo (50.4, 43.9, and 47.9% at 500 mu g/mL) than Ribavirin and other derivatives; therefore, 14 can be used as a new lead structure for the development of anti-TMV drugs. Moreover, most of these compounds exhibited good fungicidal activity against 14 kinds of fungi, especially compounds 4, 7, and 11.

  DOI：

  10.1021/jf404840x