4-(3,4,5-trimethoxy-benzoylamino)-butyric acid ethyl ester | 58345-09-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(3,4,5-trimethoxy-benzoylamino)-butyric acid ethyl ester
• 英文别名: ethyl 4-((3,4,5-trimethoxybenzoyl)amino)butanoate；Ethyl-N-(3,4,5-trimethoxybenzoyl)-γ-aminobutyrat；Ethyl 4-[(3,4,5-trimethoxybenzoyl)amino]butanoate
• CAS: 58345-09-8
• 化学式: C₁₆H₂₃NO₆
• 分子量: 325.362
• InChiKey: YWRHQMWTHHOYCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  73-76 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  423.8±45.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(3,4,5-trimethoxy-benzoylamino)-butyric acid ethyl ester 在 lithium hydroxide 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以99%的产率得到4-(3,4,5-trimethoxy-benzoylamino)-butyric acid
  参考文献：
  名称：

  Rational Design of Novel, Potent Small Molecule Pan-Selectin Antagonists

  摘要：

  This report describes the first results of a rational hit-finding strategy to design novel small molecule antiinflammatory drugs targeting selectins, a family of three cellular adhesion molecules. Based on recent progress in understanding of molecular interaction between selectins and their natural ligands as well as progress in clinical development of synthetic antagonists like 1 (bimosiamose, TBC1269), this study was initiated to discover small molecule selectin antagonists with improved pharmacological properties. Considering 1 as template structure, a ligand-based approach followed by focused chemical synthesis has been applied to yield novel synthetic small molecules (MWr < 500) with a trihydroxybenzene motif, bearing neither peptidic nor glycosidic components, with nanomolar in vitro activity. Biological evaluation involves two kinds of in vitro assays, a static molecular binding assay, and a dynamic HL-60 cell attachment assay. As compared to controls, the novel compounds showed improved biological in vitro activity both under static and dynamic conditions.

  DOI：

  10.1021/jm060536g
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸 在 N,N-二甲基甲酰胺 草酰氯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-(3,4,5-trimethoxy-benzoylamino)-butyric acid ethyl ester
  参考文献：
  名称：

  Novel Heterobivalent Tacrine Derivatives as Cholinesterase Inhibitors with Notable Selectivity Toward Butyrylcholinesterase

  摘要：

  Two series of novel heterobivalent tacrine derivatives were synthesized. A trimethoxy substituted benzene was linked to the tacrine moiety by a hydrazide-based linker. The compounds were evaluated as cholinesterase inhibitors, and trimethoxybenzoic acid derivatives with 11- or 12-atom spacers were the most potent inhibitors of human acetylcholinesterase. The inhibitors showed a surprising selectivity toward human butyrylcholinesterase, where several trimethoxyphenylpropionic acid derivatives had IC50 values less than 250 mu M.

  DOI：

  10.1021/jm060742o

文献信息

• Non-glycosylated/-glycosidic/-peptidic small molecule selectin inhibitors for the treament of inflammatory disorders
  申请人：Revotar Biopharmaceuticals AG

  公开号：EP1577289A1

  公开（公告）日：2005-09-21

  The compounds having the general structure of formula (I) wherein the symbols, indices and substituents have the following meaning if R2=OH and R3=H then R1=H, CN, NO2, CF3, F, Cl, Br, I, CH3 or if R3=OH and R2=H then R1=H, CN, NO2, CF3, F, Cl, Br, I, CH3, Et, n-Pr, i-Pr, n-Bu, i-Bu, t-Bu, phenyl, thienyl, furyl, thiazolyl or if R3=OH and R1=H then R2=H, CN, NO2, CF3, F, Cl, Br, I, CH3, Et, n-Pr, i-Pr, n-Bu, t-Bu, phenyl, thienyl, furyl, thiazolyl then X is e.g.    with R4 being H, CH3, CH2CH3 or or    and Y being or and the pharmaceutically acceptable salts, esters or amides and prodrugs of the above identified compounds of formula (I). The compounds are applied to modulate the in-vitro and in-vivo binding processes mediated by E-, P- or L-selectin binding.

  具有通式（I）的化合物中，符号、指数和取代基的含义如下： 如果R2=OH且R3=H，则R1=H、CN、NO2、CF3、F、Cl、Br、I、CH3或 如果R3=OH且R2=H，则R1=H、CN、 、 、F、Cl、Br、I、 、Et、n-Pr、i-Pr、n-Bu、i-Bu、t-Bu、苯基、噻吩基、呋喃基、噻唑基或 如果R3=OH且R1=H，则R2=H、CN、 、 、F、Cl、Br、I、 、Et、n-Pr、i-Pr、n-Bu、t-Bu、苯基、噻吩基、呋喃基、噻唑基 然后，X为例如，其中R4为H、 、CH2 或 或 而Y为 上述通式（I）的药物可接受的盐、酯或酰胺以及前药。这些化合物可用于调节E、P或L选择素结合介导的体外和体内结合过程。
• Fominova,O.S. et al., Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, # 9, p. 1783 - 1786
  作者：Fominova,O.S. et al.

  DOI：——

  日期：——
• FOMINOVA O. S.; SKACHILOVA S. YA.; ERMAKOV A. I.; PLESHAKOV M. G., ZH. ORG. XIMII, 1977, 13, HO 9, 1922-1926
  作者：FOMINOVA O. S.、 SKACHILOVA S. YA.、 ERMAKOV A. I.、 PLESHAKOV M. G.

  DOI：——

  日期：——