2-(carboxy{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}methyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

• 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: 2-(carboxy{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}methyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• 英文别名: (2r,4s)-2-[(R)-Carboxy{[(5-Methyl-3-Phenyl-1,2-Oxazol-4-Yl)carbonyl]amino}methyl]-5,5-Dimethyl-1,3-Thiazolidine-4-Carboxylic Acid；(2R,4S)-2-[(R)-carboxy-[(5-methyl-3-phenyl-1,2-oxazole-4-carbonyl)amino]methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• 化学式: C₁₉H₂₁N₃O₆S
• 分子量: 419.458
• InChiKey: JCHZLBSPYSDECZ-OFQRWUPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  167
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  Bristopen 在 C₁₉H₃₆N₂O₈Zn₂ 作用下， 以 二甲基亚砜 为溶剂， 生成 2-(carboxy{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}methyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Metallo-β-lactamase and phosphotriesterase activities of some zinc(II) complexes

  摘要：

  Metallo-beta-lactamases (m beta l) and phosphotriesterase (PTE) are zinc(II) enzymes, which hydrolyze the beta-lactam antibiotics and toxic organophosphotriesters, respectively. In the present work, we have synthesized a few asymmetric phenolate-based ligands by sequential Mannich reaction and their corresponding zinc(II) complexes. These zinc(II) complexes were studied for their m beta l and PTE activities. It is shown that the zinc(II) complexes can hydrolyze oxacillin, the beta-lactam antibiotic, at much higher rates as compared to the hydrolysis of p-nitrophenyl diphenylphosphate (PNPDPP), the phosphotriester. Among the complexes studied, the binuclear asymmetric complex 1 having a water molecule coordinated to one of the zinc(II) ions exhibits much better mbl activity than the mononuclear complexes. However, the mononuclear zinc(II) complexes having labile chloride ions exhibit significant PTE activity, which can be ascribed to the replacement of chloride ions by hydroxide ions during hydrolysis reactions. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.03.064

文献信息

• Antibiotic Resistance: Mono- and Dinuclear Zinc Complexes as Metallo-β-Lactamase Mimics
  作者：A. Tamilselvi、Munirathinam Nethaji、G. Mugesh

  DOI：10.1002/chem.200600629

  日期：2006.10.16

  which has no water molecules, but labile chloride ligands, shows a much lower activity. The high beta-lactamase activity of complex 1 can be ascribed to the presence of a zinc-bound water molecule that is activated by being hydrogen bonded to acetate substituents. The kinetics of the hydrolysis of oxacillin by complex 1 and the effect of pH on the reaction rates are reported in detail. In addition

  作为金属β-内酰胺酶的功能模拟物，开发了包含一个或两个由酚盐配体支撑的锌（II）离子的仿生系统。这些配合物显示出催化水解β-内酰胺底物的作用，例如奥沙西林和青霉素G。双核锌配合物1具有协调的水分子，显示出高的β-内酰胺酶活性，而双核锌配合物2没有水。分子，但不稳定的氯化物配体，表现出低得多的活性。配合物1的高β-内酰胺酶活性可以归因于锌结合的水分子的存在，该锌分子通过氢键合至乙酸酯取代基而被活化。详细报道了配合物1水解奥沙西林的动力学以及pH对反应速率的影响。此外，将合成类似物获得的动力学参数与蜡状芽孢杆菌（Bcillus）的天然金属β-内酰胺酶的动力学参数进行了比较。为了理解第二金属离子在水解中的作用，描述了包括配位水分子的两个单核络合物（3和4）的合成和催化活性。有趣的是，单核锌配合物3和4也表现出高活性，支持了第二个锌离子对β-内酰胺酶活性不是至关重要的假设。
• High frequency ultrasound as a selective advanced oxidation process to remove penicillinic antibiotics and eliminate its antimicrobial activity from water
  作者：Efraim A. Serna-Galvis、Javier Silva-Agredo、Ana L. Giraldo-Aguirre、Oscar A. Flórez-Acosta、Ricardo A. Torres-Palma

  DOI：10.1016/j.ultsonch.2016.01.007

  日期：2016.7

  This work studies the sonochemical degradation of a penicillinic antibiotic (oxacillin) in simulated pharmaceutical wastewater. High frequency ultrasound was applied to water containing the antibiotic combined with mannitol or calcium carbonate. In the presence of additives, oxacillin was efficiently removed through sonochemical action. For comparative purposes, the photo-Fenton, TiO2 photocatalysis

  这项工作研究了在模拟制药废水中青霉素抗生素（奥沙西林）的声化学降解。高频超声应用于含有抗生素与甘露醇或碳酸钙结合的水中。在存在添加剂的情况下，通过声化学作用有效地除去了奥沙西林。为了进行比较，还测试了光芬顿，TiO2光催化和电化学氧化过程。因此，监测了抗生素的演变及其相关的抗菌活性（AA）。在消除添加剂引起的抗菌活性方面，发现对其他三个氧化过程的抑制作用很高。而对于超声波处理，观察到的影响可忽略不计。声化学过程能够完全降解抗生素，生成没有AA的解决方案。实际上，抗菌活性的消除显示了根据指数动力学型衰减进行调节的优异性能。通过HPLC-MS测定主要的声产生的有机副产物。确定了四个中间物，它们已经修饰了青霉素结构，该结构是负责抗菌活性的部分。此外，根据副产物的演变及其化学结构，提出了可能的奥沙西林钠离子沉缓机理。此外，在120分钟内进行的高频超声作用可轻松清除奥沙西林并消除其抗菌活性。但是，即
• Metallo-β-lactamase and phosphotriesterase activities of some zinc(II) complexes
  作者：Muthaiah Umayal、Govindasamy Mugesh

  DOI：10.1016/j.ica.2011.03.064

  日期：2011.6

  Metallo-beta-lactamases (m beta l) and phosphotriesterase (PTE) are zinc(II) enzymes, which hydrolyze the beta-lactam antibiotics and toxic organophosphotriesters, respectively. In the present work, we have synthesized a few asymmetric phenolate-based ligands by sequential Mannich reaction and their corresponding zinc(II) complexes. These zinc(II) complexes were studied for their m beta l and PTE activities. It is shown that the zinc(II) complexes can hydrolyze oxacillin, the beta-lactam antibiotic, at much higher rates as compared to the hydrolysis of p-nitrophenyl diphenylphosphate (PNPDPP), the phosphotriester. Among the complexes studied, the binuclear asymmetric complex 1 having a water molecule coordinated to one of the zinc(II) ions exhibits much better mbl activity than the mononuclear complexes. However, the mononuclear zinc(II) complexes having labile chloride ions exhibit significant PTE activity, which can be ascribed to the replacement of chloride ions by hydroxide ions during hydrolysis reactions. (C) 2011 Elsevier B.V. All rights reserved.