Methyl 4-(1-benzylindol-3-yl)-2,4-dioxobutanoate | 1027249-34-8

• 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: Methyl 4-(1-benzylindol-3-yl)-2,4-dioxobutanoate
• CAS: 1027249-34-8
• 化学式: C₂₀H₁₇NO₄
• 分子量: 335.359
• InChiKey: HKRJWXNGJNCUFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  65.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 4-(1-benzylindol-3-yl)-2,4-dioxobutanoate 在 hydrazine 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以57%的产率得到methyl 5-(1-benzyl-1H-indol-3-yl)-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Inhibition of α-class cytosolic human carbonic anhydrases I, II, IX and XII, and β-class fungal enzymes by carboxylic acids and their derivatives: New isoform-I selective nanomolar inhibitors

  摘要：

  The members of a focused series of carboxylic acids and of their derivatives (esters, amides and metal complexes) have been investigated as inhibitors of the main cytosolic/transmembrane carbonic anhydrase isoforms, CA I, II, IX and XII, belonging to the mammalian alpha-class of CAs. These enzymes are present in red blood cells in submillimolar concentration, and typical sulfonamide CA inhibitors do not selectively inhibit any of them. Among such isozymes, the isoform-I is an 'orphan' target that mediates hemorrhagic retinal and cerebral vascular permeability, involved in retinal and cerebral disease. In the present study, we identified the first selective CA I nanomolar inhibitors, that displayed activity against other isozymes in micromolar/millimolar concentration range. Selective CA II over CA I inhibition has also been observed with some diketo acids/metal complexes. Few diketo acid derivatives showed inhibition activities against the fungal beta-class enzymes from Candida albicans and Cryptococcus neoformans in low micromolar concentration range. Prediction of drug-like properties for the most interesting compounds suggests a favorable bioavailability. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.094
• 作为产物：
  描述：

  草酸二甲酯 、 1-(1-苄基-1H-吲哚-3-基)乙酮 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 Methyl 4-(1-benzylindol-3-yl)-2,4-dioxobutanoate
  参考文献：
  名称：

  Inhibition of α-class cytosolic human carbonic anhydrases I, II, IX and XII, and β-class fungal enzymes by carboxylic acids and their derivatives: New isoform-I selective nanomolar inhibitors

  摘要：

  The members of a focused series of carboxylic acids and of their derivatives (esters, amides and metal complexes) have been investigated as inhibitors of the main cytosolic/transmembrane carbonic anhydrase isoforms, CA I, II, IX and XII, belonging to the mammalian alpha-class of CAs. These enzymes are present in red blood cells in submillimolar concentration, and typical sulfonamide CA inhibitors do not selectively inhibit any of them. Among such isozymes, the isoform-I is an 'orphan' target that mediates hemorrhagic retinal and cerebral vascular permeability, involved in retinal and cerebral disease. In the present study, we identified the first selective CA I nanomolar inhibitors, that displayed activity against other isozymes in micromolar/millimolar concentration range. Selective CA II over CA I inhibition has also been observed with some diketo acids/metal complexes. Few diketo acid derivatives showed inhibition activities against the fungal beta-class enzymes from Candida albicans and Cryptococcus neoformans in low micromolar concentration range. Prediction of drug-like properties for the most interesting compounds suggests a favorable bioavailability. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.094

文献信息

• Organocatalytic Modified Guareschi–Thorpe Type Regioselective Synthesis: A Unified Direct Access to 5,6,7,8-Tetrahydroquinolines and Other Alicyclic[<i>b</i>]-Fused Pyridines
  作者：Pradeep K. Jaiswal、Vashundhra Sharma、Manas Mathur、Sandeep Chaudhary

  DOI：10.1021/acs.orglett.8b02132

  日期：2018.10.5

  An unprecedented organocatalytic, regioselective, modified Guareschi–Thorpe type protocol toward the modular synthesis of 5,6,7,8-tetrahydroquinolines 22a–g and other alicyclic[b]-fused pyridines 23–28 via the identification of Chitosan as a heterogeneous catalyst is reported. This novel strategy is operationally simple and showed a wide range of functional group tolerance and substrate compatibility

  前所未有的有机催化，区域选择性，改良的Guareschi-Thorpe型方案，通过鉴定壳聚糖作为多相催化剂，可模块化合成5,6,7,8-四氢喹啉22a – g和其他脂环式[ b ]稠合吡啶23 – 28。被报道。这种新颖的策略操作简单，并且具有广泛的官能团耐受性和底物相容性。拟议的机制途径涉及亚胺-烯胺级联方法，用于合成结构多样的脂环式[ b ]稠合吡啶杂环。新型抗真菌分子的克级合成和鉴定29 –图31强调了这种方法的实用性。