1-(5-ethyl-5H-[1,3]dioxolo[4,5-f]indol-6-yl)ethanone | 790239-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(5-ethyl-5H-[1,3]dioxolo[4,5-f]indol-6-yl)ethanone
• 英文别名: 1-(5-Ethyl-[1,3]dioxolo[4,5-f]indol-6-yl)ethanone
• CAS: 790239-12-2
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: JSSWCUHUPAULKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(5-ethyl-5H-[1,3]dioxolo[4,5-f]indol-6-yl)ethanone 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 (Z)-4-(5-ethyl-5H-[1,3]dioxolo[4,5-f]indol-6-yl)-2-hydroxy-4-oxobut-2-enoic acid
  参考文献：
  名称：

  Design and Synthesis of Novel Indole β-Diketo Acid Derivatives as HIV-1 Integrase Inhibitors

  摘要：

  Diketo acids such as S-1360 (1A) and L-731,988 (2) are potent and selective inhibitors of HIV-1 integrase (IN). A plethora of diketo acid-containing compounds have been claimed in patent literature without disclosing much biological activities and synthetic details (reviewed in Neamati, N. Exp. Opin. Ther. Pat. 2002, 12, 709-724). To establish a coherent structure-activity relationship among the substituted indole nucleus bearing a beta-diketo acid moiety, a series of substituted indole-beta-diketo acids (4a-f and 5a-e) were synthesized. All compounds tested showed anti-IN activity at low micromolar concentrations with varied selectivity against the strand transfer process. Three compounds, the indole-3-beta-diketo acids 5a and 5c, and the parent ester 9c, have shown an antiviral activity in cell-based assays. We further confirmed a keto-enolic structure in the 2,3-position of the diketo acid moiety of a representative compound (4c) using NMR and X-ray crystallographic analysis. Using this structure as a lead for all of our computational studies, we found that the title compounds extensively interact with the essential amino acids on the active site of IN.

  DOI：

  10.1021/jm049944f
• 作为产物：
  描述：

  5H-[1,3]1,3-二氧杂环戊基[4,5-F]吲哚-6-甲酸甲酯 在 氢氧化钾 作用下， 以 乙醚 、 水 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 1-(5-ethyl-5H-[1,3]dioxolo[4,5-f]indol-6-yl)ethanone
  参考文献：
  名称：

  Design and Synthesis of Novel Indole β-Diketo Acid Derivatives as HIV-1 Integrase Inhibitors

  摘要：

  Diketo acids such as S-1360 (1A) and L-731,988 (2) are potent and selective inhibitors of HIV-1 integrase (IN). A plethora of diketo acid-containing compounds have been claimed in patent literature without disclosing much biological activities and synthetic details (reviewed in Neamati, N. Exp. Opin. Ther. Pat. 2002, 12, 709-724). To establish a coherent structure-activity relationship among the substituted indole nucleus bearing a beta-diketo acid moiety, a series of substituted indole-beta-diketo acids (4a-f and 5a-e) were synthesized. All compounds tested showed anti-IN activity at low micromolar concentrations with varied selectivity against the strand transfer process. Three compounds, the indole-3-beta-diketo acids 5a and 5c, and the parent ester 9c, have shown an antiviral activity in cell-based assays. We further confirmed a keto-enolic structure in the 2,3-position of the diketo acid moiety of a representative compound (4c) using NMR and X-ray crystallographic analysis. Using this structure as a lead for all of our computational studies, we found that the title compounds extensively interact with the essential amino acids on the active site of IN.

  DOI：

  10.1021/jm049944f