N-(2,6-Dimethoxybenzoyl)-glycin-ethylester | 27532-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2,6-Dimethoxybenzoyl)-glycin-ethylester
• 英文别名: Ethyl 2-[(2,6-dimethoxybenzoyl)amino]acetate
• CAS: 27532-83-8
• 化学式: C₁₃H₁₇NO₅
• 分子量: 267.282
• InChiKey: XXZXOWXKAZZIMD-UHFFFAOYSA-N

物化性质

• 沸点：
  408.5±45.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2,6-Dimethoxybenzoyl)-glycin-ethylester 在 肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 N-(2-hydrazinyl-2-oxoethyl)-2,6-dimethoxybenzamide
  参考文献：
  名称：

  Inhibitors of Bacterial Cystathionine β-Lyase:  Leads for New Antimicrobial Agents and Probes of Enzyme Structure and Function

  摘要：

  The biosynthesis of methionine is an attractive antibiotic target given its importance in protein and DNA metabolism and its absence in mammals. We have performed a high-throughput screen of the methionine biosynthesis enzyme cystathionine beta-lyase (CBL) against a library of 50 000 small molecules and have identified several compounds that inhibit CBL enzyme activity in vitro. These hit molecules were of two classes: those that blocked CBL activity with mixed steady-state inhibition and those that covalently interacted with the enzyme at the active site pyridoxal phosphate cofactor with slow-binding inhibition kinetics. We determined the crystal structure of one of the slow-binding inhibitors in complex with CBL and used this structure as a guide in the synthesis of a small, focused library of analogues, some of which had improved enzyme inhibition properties. These studies provide the first lead molecules for antimicrobial agents that target cystathionine beta-lyase in methionine biosynthesis.

  DOI：

  10.1021/jm061132r
• 作为产物：
  描述：

  2,6-二甲氧基苯甲酰氯 在 sodium hydroxide 、 硫酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-(2,6-Dimethoxybenzoyl)-glycin-ethylester
  参考文献：
  名称：

  化学研究与青霉素超敏反应的潜在相关性。dl-2-苯氧基甲基青霉烯酸和dl-2-（2,6-二甲氧基苯基）青霉烯酸的合成

  摘要：

  DL-2-苯氧基melhylpenicillenic酸（的晶体样品14）和DL -2-（2，6-二甲氧基苯基）penicillenic酸（21）已经由反应合成DL青霉胺与2-苯氧基甲基-4-（甲氧基亚甲基）恶唑-5-酮和2-（2,6-二二甲氧基苯基）-4-（乙氧基亚甲基）恶唑-5-酮。这些关键的恶唑-5-酮中间体是通过适当取代的戊二酸二烷基乙缩醛的壬二酸化反应合成的。研究了氯化汞（II）与D-苯氧基甲基青霉素的反应，发现不适用于D-14的合成。结晶DL的比较-和分别通过“恶唑酮”和“氯化汞（11）”方法制备的无定形D-2-（2,6-二甲氧基苯基）青霉烯酸（21）表明，其纯度明显提高。DL-材料。

  DOI：

  10.1002/jhet.5570100609

文献信息

• Substituents Effect on the Erlenmeyer−Plöchl Reaction: Understanding an Observed Process Reaction Time
  作者：Flavio Chavez、Nicole Kennedy、Thimma Rawalpally、R. Thomas Williamson、Thomas Cleary

  DOI：10.1021/op100032s

  日期：2010.5.21

  A systematic study on hippuric acid substituents was performed in order to better understand the influence of stereoelectronic factors on the Erlenmeyer reaction rate. In addition, two reaction systems were evaluated: Hunig's base solvent free conditions and catalytic sodium acetate in 2-methyl-THF. The effect on reaction rate of electron withdrawing and electron donating groups are reported. Specifically, the study led to the conclusion that stereoelectronic factors have significant influence in one of our key Erlenmeyer reaction by affecting its reaction rate.
• Inhibitors of Bacterial Cystathionine β-Lyase:  Leads for New Antimicrobial Agents and Probes of Enzyme Structure and Function
  作者：Linda J. Ejim、Jan E. Blanchard、Kalinka P. Koteva、Rachael Sumerfield、Nadine H. Elowe、Jonathan D. Chechetto、Eric D. Brown、Murray S. Junop、Gerard D. Wright

  DOI：10.1021/jm061132r

  日期：2007.2.1

  The biosynthesis of methionine is an attractive antibiotic target given its importance in protein and DNA metabolism and its absence in mammals. We have performed a high-throughput screen of the methionine biosynthesis enzyme cystathionine beta-lyase (CBL) against a library of 50 000 small molecules and have identified several compounds that inhibit CBL enzyme activity in vitro. These hit molecules were of two classes: those that blocked CBL activity with mixed steady-state inhibition and those that covalently interacted with the enzyme at the active site pyridoxal phosphate cofactor with slow-binding inhibition kinetics. We determined the crystal structure of one of the slow-binding inhibitors in complex with CBL and used this structure as a guide in the synthesis of a small, focused library of analogues, some of which had improved enzyme inhibition properties. These studies provide the first lead molecules for antimicrobial agents that target cystathionine beta-lyase in methionine biosynthesis.
• Chemical studies of potential relevance to penicillin hypersensitivity. The synthesis of dl-2-phenoxymethylpenicillenic acid and of dl-2-(2,6-dimethoxyphenyl)penicillenic acid
  作者：Kenneth H. Dudley、Daniel L. Bius、Dorothy Johnson

  DOI：10.1002/jhet.5570100609

  日期：1973.12

  melhylpenicillenic acid (14) and of DL-2-(2, 6-dimethoxyphenyl)penicillenic acid (21) have been synthesized by the reaction of DL-penicillamine with 2 phenoxymethyl-4-(methoxymethylene)oxazol-5-one and 2-(2, 6-dimethoxyphenyl)-4-(ethoxymethylene)oxazol-5-one, respectively. These key oxazol-5-one intermediates were synthesized by azlactonization of the appropriately substituted penaldic acid dialkyl acetals

  DL-2-苯氧基melhylpenicillenic酸（的晶体样品14）和DL -2-（2，6-二甲氧基苯基）penicillenic酸（21）已经由反应合成DL青霉胺与2-苯氧基甲基-4-（甲氧基亚甲基）恶唑-5-酮和2-（2,6-二二甲氧基苯基）-4-（乙氧基亚甲基）恶唑-5-酮。这些关键的恶唑-5-酮中间体是通过适当取代的戊二酸二烷基乙缩醛的壬二酸化反应合成的。研究了氯化汞（II）与D-苯氧基甲基青霉素的反应，发现不适用于D-14的合成。结晶DL的比较-和分别通过“恶唑酮”和“氯化汞（11）”方法制备的无定形D-2-（2,6-二甲氧基苯基）青霉烯酸（21）表明，其纯度明显提高。DL-材料。