methyl N-(2,6-dimethoxybenzoyl)glycine ester | 51579-20-5

• 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: methyl N-(2,6-dimethoxybenzoyl)glycine ester
• 英文别名: N-(2,6-Dimethoxybenzoyl)-glycin-methylester；Methyl 2-[(2,6-dimethoxybenzoyl)amino]acetate
• CAS: 51579-20-5
• 化学式: C₁₂H₁₅NO₅
• mdl: MFCD01213474
• 分子量: 253.255
• InChiKey: UCXGJZUPCCTRBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 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：

  methyl N-(2,6-dimethoxybenzoyl)glycine ester 在 一水合肼 作用下， 以 乙醇 为溶剂， 以90%的产率得到N-(2-hydrazinyl-2-oxoethyl)-2,6-dimethoxybenzamide
  参考文献：
  名称：

  L-氨基酸酯研究：第二部分：N-(二甲氧基/3,5-二乙酰氧基苯甲酰基)-L-氨基酸酰肼的合成及其与醛和酮的反应

  摘要：

  摘要 描述了N-(二甲氧基和3,5-二乙酰氧基苯甲酰基)-L-氨基酸酰肼的合成及其与一些醛和酮的反应。

  DOI：

  10.1080/00397919908086107
• 作为产物：
  描述：

  2,6-二甲氧基苯甲酸 、 甘氨酸甲酯盐酸盐 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 29.0h， 以89%的产率得到methyl N-(2,6-dimethoxybenzoyl)glycine ester
  参考文献：
  名称：

  L-氨基酸酯研究：第一部分：新甲基 N-(二甲氧基/3,5-二乙酰氧基苯甲酰基)-L-氨基酸酯衍生物的合成

  摘要：

  摘要 通过两种方法合成了一系列新的甲基N-(二甲氧基/3,5-二乙酰氧基苯甲酰基)-L-氨基酸酯。

  DOI：

  10.1080/00397919908086185

文献信息

• L-Amino Acid Esters Studies: Part I: Synthesis Of New Methyl N -(Dimethoxy / 3,5 -Diacetoxybenzoyl) -L- Amino Acid Ester Derivatives
  作者：Eljazi I. Al-afaleq、Samar A. Abubshait

  DOI：10.1080/00397919908086185

  日期：1999.6

  Abstract A series of new methyl N-(dimedioxy / 3,5-diacetoxybenzoyl)-L-amino acid esters have been synthesized by two methods.

  摘要 通过两种方法合成了一系列新的甲基N-(二甲氧基/3,5-二乙酰氧基苯甲酰基)-L-氨基酸酯。
• 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。
• Synthesis and evaluation of boronic acids as inhibitors of Penicillin Binding Proteins of classes A, B and C
  作者：Astrid Zervosen、André Bouillez、Alexandre Herman、Ana Amoroso、Bernard Joris、Eric Sauvage、Paulette Charlier、André Luxen

  DOI：10.1016/j.bmc.2012.04.018

  日期：2012.6

  In response to the widespread use of beta-lactam antibiotics bacteria have evolved drug resistance mechanisms that include the production of resistant Penicillin Binding Proteins (PBPs). Boronic acids are potent beta-lactamase inhibitors and have been shown to display some specificity for soluble transpeptidases and PBPs, but their potential as inhibitors of the latter enzymes is yet to be widely explored. Recently, a (2,6-dimethoxybenzamido) methylboronic acid was identified as being a potent inhibitor of Actinomadura sp. R39 transpeptidase (IC50: 1.3 mu M). In this work, we synthesized and studied the potential of a number of acylaminomethylboronic acids as inhibitors of PBPs from different classes. Several derivatives inhibited PBPs of classes A, B and C from penicillin sensitive strains. The (2-nitrobenzamido) methylboronic acid was identified as a good inhibitor of a class A PBP (PBP1b from Streptococcus pneumoniae, IC50 = 26 mu M), a class B PBP (PBP2xR6 from Streptococcus pneumoniae, IC50 = 138 mu M) and a class C PBP (R39 from Actinomadura sp., IC50 = 0.6 mu M). This work opens new avenues towards the development of molecules that inhibit PBPs, and eventually display bactericidal effects, on distinct bacterial species. (C) 2012 Elsevier Ltd. All rights reserved.
• L-Amino Acid Esters Studies: Part II: Synthesis of N-(Dimethoxy/3,5-Diacetoxybenzoyl)-L-Amino Acid Hydrazides and their Reactions with Aldehydes and Ketones
  作者：Eljazi I. Al-afaleq、Samar A. Abubshait

  DOI：10.1080/00397919908086107

  日期：1999.4

  Abstract The synthesis of N-(dimethoxy and 3, 5-diacetoxybenzoyl) -L- amino acid hydrazides, and their reactions with some aldehydes and ketones are described.

  摘要 描述了N-(二甲氧基和3,5-二乙酰氧基苯甲酰基)-L-氨基酸酰肼的合成及其与一些醛和酮的反应。