N-acetyl-α-(2-furanyl)alanine methyl ester | 147495-01-0

• 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: N-acetyl-α-(2-furanyl)alanine methyl ester
• 英文别名: methyl α-acetamido-α-methyl-α-(furan-2-yl)acetate；Methyl 2-acetamido-2-(furan-2-yl)propanoate
• CAS: 147495-01-0
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: TTXJEGGHFVIEJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-acetyl-α-(2-furanyl)alanine methyl ester 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 以62%的产率得到α-acetamido-α-methyl-α-(furan-2-yl)acetic acid
  参考文献：
  名称：

  Synthesis and anticonvulsant activities of .alpha.-heterocyclic .alpha.-acetamido-N-benzylacetamide derivatives

  摘要：

  Earlier studies showed that (R,S)-alpha-acetamido-N-benzylacetamides (2) containing a five- and six-membered aromatic or heteroaromatic group appended at the C(alpha) site displayed outstanding activity in the maximal electroshock-induced seizure (MES) test in mice. An expanded set of C(alpha)-heteroaromatic analogues of 2 have been prepared and evaluated. The observed findings extended the structure-activity relationships previously discerned for this novel class of anti-convulsants and have validated previous trends. The alpha-furan-2-yl (4), alpha-oxazol-2-yl (18), and alpha-thiazol-2-yl (19) alpha-acetamido-N-benzylacetamides afforded excellent protection against MES-induced seizures in mice. The ED50 and PI values for these adducts rivaled those reported for phenytoin. The outstanding properties provided by 4 led to an in-depth examination of the effect of structural modification at key sites within this compound on biological activity. The pharmacological data in this series indicated that stringent steric and electronic requirements existed for maximal activity and revealed the outstanding activity of (R)-(-)-alpha-acetamido-N-(4-fluorobenzyl)-alpha-(furan-2-yl)acetamide [(R)-30].

  DOI：

  10.1021/jm00074a016
• 作为产物：
  描述：

  2-乙酰胺基丙烯酸甲酯 在 氢溴酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 氘代氯仿 为溶剂， 反应 3.5h， 生成 N-acetyl-α-(2-furanyl)alanine methyl ester
  参考文献：
  名称：

  Synthesis and anticonvulsant activities of .alpha.-heterocyclic .alpha.-acetamido-N-benzylacetamide derivatives

  摘要：

  Earlier studies showed that (R,S)-alpha-acetamido-N-benzylacetamides (2) containing a five- and six-membered aromatic or heteroaromatic group appended at the C(alpha) site displayed outstanding activity in the maximal electroshock-induced seizure (MES) test in mice. An expanded set of C(alpha)-heteroaromatic analogues of 2 have been prepared and evaluated. The observed findings extended the structure-activity relationships previously discerned for this novel class of anti-convulsants and have validated previous trends. The alpha-furan-2-yl (4), alpha-oxazol-2-yl (18), and alpha-thiazol-2-yl (19) alpha-acetamido-N-benzylacetamides afforded excellent protection against MES-induced seizures in mice. The ED50 and PI values for these adducts rivaled those reported for phenytoin. The outstanding properties provided by 4 led to an in-depth examination of the effect of structural modification at key sites within this compound on biological activity. The pharmacological data in this series indicated that stringent steric and electronic requirements existed for maximal activity and revealed the outstanding activity of (R)-(-)-alpha-acetamido-N-(4-fluorobenzyl)-alpha-(furan-2-yl)acetamide [(R)-30].

  DOI：

  10.1021/jm00074a016

文献信息

• Preparation of α- and β-substituted alanine derivatives by α-amidoalkylation or Michael addition reactions under heterogeneous catalysis assisted by microwave irradiation
  作者：Antonio de la Hoz、Angel Dı́az-Ortiz、Marı́a Victoria Gómez、José Antonio Mayoral、Andrés Moreno、Ana Marı́a Sánchez-Migallón、Ester Vázquez

  DOI：10.1016/s0040-4020(01)00461-6

  日期：2001.6

  Silica-supported Lewis acids are useful catalysts in conjunction with microwave irradiation for the synthesis of a range of alanine derivatives. Reaction of methyl α-acetamidoacrylate (1) with different heterocycles, such as furan (2), pyrrole (3), N-benzylpyrrole (4), indole (5) and pyrazole (6) and the carbocycle 1,3,5-trihydroxybenzene (7), led to several α-amino acid precursors.

  二氧化硅负载的路易斯酸与微波辐射一起用于合成一系列丙氨酸衍生物是有用的催化剂。α-乙酰氨基丙烯酸甲酯（1）与不同的杂环，例如呋喃（2），吡咯（3），N-苄基吡咯（4），吲哚（5）和吡唑（6）和1,3,5-碳环的反应三羟基苯（7）生成了几种α-氨基酸前体。
• Kotha, Sambasivarao; Ghosh, Arun Kumar; Behera, Manoranjan, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2002, vol. 41, # 11, p. 2330 - 2332
  作者：Kotha, Sambasivarao、Ghosh, Arun Kumar、Behera, Manoranjan

  DOI：——

  日期：——
• Synthesis and anticonvulsant activities of .alpha.-heterocyclic .alpha.-acetamido-N-benzylacetamide derivatives
  作者：Harold Kohn、Kailash N. Sawhney、Patrick Bardel、David W. Robertson、J. David Leander

  DOI：10.1021/jm00074a016

  日期：1993.10

  Earlier studies showed that (R,S)-alpha-acetamido-N-benzylacetamides (2) containing a five- and six-membered aromatic or heteroaromatic group appended at the C(alpha) site displayed outstanding activity in the maximal electroshock-induced seizure (MES) test in mice. An expanded set of C(alpha)-heteroaromatic analogues of 2 have been prepared and evaluated. The observed findings extended the structure-activity relationships previously discerned for this novel class of anti-convulsants and have validated previous trends. The alpha-furan-2-yl (4), alpha-oxazol-2-yl (18), and alpha-thiazol-2-yl (19) alpha-acetamido-N-benzylacetamides afforded excellent protection against MES-induced seizures in mice. The ED50 and PI values for these adducts rivaled those reported for phenytoin. The outstanding properties provided by 4 led to an in-depth examination of the effect of structural modification at key sites within this compound on biological activity. The pharmacological data in this series indicated that stringent steric and electronic requirements existed for maximal activity and revealed the outstanding activity of (R)-(-)-alpha-acetamido-N-(4-fluorobenzyl)-alpha-(furan-2-yl)acetamide [(R)-30].