甘氨酸,N-(2-硝基苯甲酰)-,苯基甲基酯 | 150374-96-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 甘氨酸,N-(2-硝基苯甲酰)-,苯基甲基酯
• 英文名称: N-(2-nitrobenzoyl)glycine benzyl ester
• 英文别名: Benzyl 2-[(2-nitrophenyl)formamido]acetate；benzyl 2-[(2-nitrobenzoyl)amino]acetate
• CAS: 150374-96-2
• 化学式: C₁₆H₁₄N₂O₅
• mdl: MFCD11655971
• 分子量: 314.298
• InChiKey: PEMMBVCTNHEWLV-UHFFFAOYSA-N

物化性质

• 沸点：
  519.8±40.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甘氨酸,N-(2-硝基苯甲酰)-,苯基甲基酯 在 palladium on activated charcoal ammonium hydroxide 、 氢气 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 26.0h， 生成 N-(2-aminobenzoyl)glycinamide
  参考文献：
  名称：

  Neutral, acidic, and basic derivatives of anthranilamide that confer different formal charge to reducing oligosaccharides

  摘要：

  To facilitate the use of oligosaccharides as analytical tools in biological studies, we have designed, synthesized, and conjugated to maltosaccharides a novel series of homologous small fluorescent moieties that differ in formal charge. These moieties are amide derivatives of anthranilic acid: uncharged N-(2-aminobenzoyl)glycinamide (ABGlyAmide; 2), acidic N,N-dimethyl-N'-(2-aminobenzoyl)ethylenediamine (ABGlyDIMED; 3), and basic N-(2-aminobenzoyl)glycine (ABGly; 1). Routes for synthesis and optimal reaction conditions for glycoconjugation by conventional reductive amination are presented, as is the compatibility of these adducts with common analytical and preparative chromatographic methods, including RP-HPLC and HPAEC-PAD. These novel anthranilic acid derivatives confer both fluorescence and defined charge to oligosaccharides, and so enhance the repertoire of chromatographic and analytical methods for which anthranilic acid can be used. Furthermore, because glucosaccharides have rigid solution structure, these small fluorescent adducts with different formal charge are ideal tools for molecular sizing studies of membrane pores. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.10.020
• 作为产物：
  描述：

  邻硝基苯甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 甘氨酸,N-(2-硝基苯甲酰)-,苯基甲基酯
  参考文献：
  名称：

  Neutral, acidic, and basic derivatives of anthranilamide that confer different formal charge to reducing oligosaccharides

  摘要：

  To facilitate the use of oligosaccharides as analytical tools in biological studies, we have designed, synthesized, and conjugated to maltosaccharides a novel series of homologous small fluorescent moieties that differ in formal charge. These moieties are amide derivatives of anthranilic acid: uncharged N-(2-aminobenzoyl)glycinamide (ABGlyAmide; 2), acidic N,N-dimethyl-N'-(2-aminobenzoyl)ethylenediamine (ABGlyDIMED; 3), and basic N-(2-aminobenzoyl)glycine (ABGly; 1). Routes for synthesis and optimal reaction conditions for glycoconjugation by conventional reductive amination are presented, as is the compatibility of these adducts with common analytical and preparative chromatographic methods, including RP-HPLC and HPAEC-PAD. These novel anthranilic acid derivatives confer both fluorescence and defined charge to oligosaccharides, and so enhance the repertoire of chromatographic and analytical methods for which anthranilic acid can be used. Furthermore, because glucosaccharides have rigid solution structure, these small fluorescent adducts with different formal charge are ideal tools for molecular sizing studies of membrane pores. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.10.020

文献信息

• Glycine derivative monosodium salt tetrahydrate
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：US05359121A1

  公开（公告）日：1994-10-25

  N-[o-(p-pivaloyloxybenzenesulfonylamino)benzoyl]glycine monosodium salt tetrahydrate of the formula (I): ##STR1## is non-hygroscopic, homogeneous and stable compound, and has an inhibitory effect on elastase. Accordingly, the compound may be useful for the treatment and/or prevention of diseases induced by the abnormal enhancing of degradation of elastin, collagen fiber and/or proteoglican by the action of elastase, e.g., pulmonary emphysema, atherosclerosis, rheumatoid arthritis, etc.

  N-[o-(p-pivaloyloxybenzenesulfonylamino)benzoyl]glycine单钠盐四水合物的化学式（I）：##STR1##是一种不吸湿、均匀且稳定的化合物，并具有对弹性蛋白酶的抑制作用。因此，该化合物可能对由于弹性蛋白酶作用导致弹性蛋白、胶原纤维和/或蛋白聚糖异常降解而引起的疾病的治疗和/或预防具有益。例如，肺气肿、动脉粥样硬化、类风湿性关节炎等。
• Glycine derivative monosodium salt tetrahydrate having an inhibitory effect on elastase
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP0539223A1

  公开（公告）日：1993-04-28

  N-[o-(p-pivaloyloxybenzenesulfonylamino)benzoyl] glycine monosodium salt tetrahydrate of the formula (I) : is a non-hygroscopic, homogeneous and stable compound, and has an inhibitory effect on elastase.

  化合物N-[o-(p-戊二酰氧基苯磺酰氨基)苯甲酰]甘氨酸单钠盐四水合物，化学式为(I)：是一种非吸湿性、均匀且稳定的化合物，并具有对弹性蛋白酶的抑制作用。
• Derivatives of p-substituted phenyl ester of pivalic acid
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：US05017610A1

  公开（公告）日：1991-05-21

  A derivative of general formula: ##STR1## wherein Y is --SO.sub.2 -- or ##STR2## (i) R.sup.1 and R.sup.2, which may be the same or different, each represent, (1) --H, (2) C1-16 alkyl or (3) the formula: --X-- .circle.A --(R.sup.4).sub.n wherein X is a single-bond, --SO.sub.2 --, C1-4 alkylene, C1-4 alkylene substituted by ##STR3## -- .circle.A -- is carbocyclic or heterocyclic ring, n is 1.about.5, R.sup.4 is (1) --H or C1-8 alkyl, (2) C1-14 alkoxy, (3) C1-6 alkylthio, (4) --OH, halogen, --NO.sub.2 or trihalomethyl, (5) the formula: --NR.sup.41 R.sup.42 wherein R.sup.41 and R.sup.42 each represents halogen or C1-4 alkyl, (6) tetrazole, (7) --SO.sub.3 H or --CH.sub.2 OH, (8) the formula: --SO.sub.2 NR.sup.41 R.sup.42 (9) the formula: --Z.sup.41 --COOR.sup.43 wherein Z.sup.41 is single-bond, C1-4 alkylene or C2-4 alkenylene, R.sup.43 is --H, C1-4 alkyl or benzyl, (10) the formula: --CONR.sup.41 R.sup.42 (11) the formula: --COO--Z.sup.42 --COOR.sup.43 wherein Z.sup.42 is C1-4 alkylene, R.sup.43 is --H, C1-4 alkyl or benzyl, (12) the formula: --COO--Z.sup.42 --CONR.sup.41 R.sup.42 (13) the formula: --OCO--R.sup.45 wherein R.sup.45 is C1-8 alkyl or p-guanidinophenyl, (14) the formula: --CO--R.sup.46 wherein R.sup.46 is C1-4 alkyl, (15) the formula: --O--Z.sup.43 --COOR.sup.450 wherein Z.sup.43 is C1-6 alkylene, R.sup.450 represents a hydrogen, C1-8 alkyl or p-guanidinophenyl, (16) the formula: ##STR4## wherein ##STR5## is an amino acid residue, R.sup.47 is bond, C1-4 alkyl, R.sup.48 is --H or C1-4 alkyl, R.sup.49 is --OH, C1-4 alkoxy, --NH.sub.2, amino substituted by one or two C1-4 alkyl, carbamoylmethoxy or carbamoylmethoxy substituted by one or two C1-4 alkyl at N atom of carbamoyl, wherein ##STR6## is C3-6 heterocyclic ring, (ii) R.sup.1, R.sup.2 and N atom bonded to R.sup.1 and R.sup.2 together represents heterocyclic ring containing at least a N atom(s) and substituted by --COOH or unsubstituted heterocyclic ring containing at least a N atom(s), R.sup.3 is (1) --H, (2) --OH, (3) C1-6 alkyl, (4) halogen, (5) C1-4 alkoxy or (6) C2-5 acyloxy, m is 1-4. or non-toxic salt or an acid addition salt thereof possess inhibitory activity on elastase, and therefore is useful for treating and/or preventing agent for pulmonary emphysema, atherosclerosis and rheumatoid arthritis and the like.

  通用公式的衍生物：##STR1## 其中Y为--SO.sub.2--或##STR2## (i) R.sup.1和R.sup.2，可以相同或不同，分别表示(1)--H，(2)C1-16烷基或(3)公式：--X-- .circle.A --(R.sup.4).sub.n其中X为单键，--SO.sub.2--，C1-4烷基，C1-4烷基被##STR3##取代，.circle.A为碳环或杂环，n为1-5，R.sup.4为(1)--H或C1-8烷基，(2)C1-14烷氧基，(3)C1-6烷基硫，(4)--OH，卤素，--NO.sub.2或三卤甲基，(5)公式：--NR.sup.41 R.sup.42其中R.sup.41和R.sup.42分别表示卤素或C1-4烷基，(6)四唑，(7)--SO.sub.3 H或--CH.sub.2 OH，(8)公式：--SO.sub.2 NR.sup.41 R.sup.42 (9)公式：--Z.sup.41 --COOR.sup.43其中Z.sup.41为单键，C1-4烷基或C2-4烯基，R.sup.43为--H，C1-4烷基或苄基，(10)公式：--CONR.sup.41 R.sup.42 (11)公式：--COO--Z.sup.42 --COOR.sup.43其中Z.sup.42为C1-4烷基，R.sup.43为--H，C1-4烷基或苄基，(12)公式：--COO--Z.sup.42 --CONR.sup.41 R.sup.42 (13)公式：--OCO--R.sup.45其中R.sup.45为C1-8烷基或p-鸟氨酸苯基，(14)公式：--CO--R.sup.46其中R.sup.46为C1-4烷基，(15)公式：--O--Z.sup.43 --COOR.sup.450其中Z.sup.43为C1-6烷基，R.sup.450代表氢，C1-8烷基或p-鸟氨酸苯基，(16)公式：##STR4##其中##STR5##为氨基酸残基，R.sup.47为键，C1-4烷基，R.sup.48为--H或C1-4烷基，R.sup.49为--OH，C1-4烷氧基，--NH.sub.2，被一或两个C1-4烷基取代的氨基，羰酰甲氧基或在羰酰基N原子处被一或两个C1-4烷基取代的羰酰甲氧基，其中##STR6##为C3-6杂环，(ii)R.sup.1，R.sup.2和与R.sup.1和R.sup.2结合的N原子共同表示含有至少一个N原子的杂环，被--COOH或至少一个未取代的含有至少一个N原子的杂环取代，R.sup.3为(1)--H，(2)--OH，(3)C1-6烷基，(4)卤素，(5)C1-4烷氧基或(6)C2-5酰氧基，m为1-4。或其无毒盐或其酸加成盐具有弹性蛋白酶抑制活性，因此可用于治疗和/或预防肺气肿、动脉粥样硬化和类风湿性关节炎等疾病。
• 10.1039/d4gc02602k
  作者：Zhuang, Xiaohui、Song, Haijing、Wang, Jiayin、Zhang, Zhaokang、Wang, Jiayang、Sun, Bin、Su, Weike、Jin, Can

  DOI：10.1039/d4gc02602k

  日期：——

  The photochemistry of EDA complexes is initiated from a ground-state associate with a biomolecule capable of intermolecular electron transfer by channelling chemical synthesis via a specific radical-based mechanistic pathway. Herein, we activate the innovative cascade mode of EDA complex photoexcitation for nitro-reduction in aqueous media using charge transfer interactions between a sole donor and

  EDA 复合物的光化学是从与生物分子的基态缔合开始的，该生物分子能够通过特定的基于自由基的机械途径引导化学合成来进行分子间电子转移。在此，我们利用单一供体和多个受体（ArNO 2 、ArNO 和 ArNHOH·甘氨酸加合物）之间的电荷转移相互作用，激活了 EDA 复合物光激发的创新级联模式，用于水介质中的硝基还原。三重态猝灭实验、紫外可见分光光度分析、核磁共振滴定和初步动力学研究验证了该机理的合理性和可行性。随着该级联系统在芳胺化合物和商业药物合成（61 个实例）中的成功应用，这些成就凸显了该方案的吸引力、有用性和有效性。
• US5359121A
  申请人：——

  公开号：US5359121A

  公开（公告）日：1994-10-25