3,4-di(tert-butyldiphenylsilyloxy)phenylacetic acid | 182414-76-2

• 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: 3,4-di(tert-butyldiphenylsilyloxy)phenylacetic acid
• 英文别名: 2-[3,4-Bis[[tert-butyl(diphenyl)silyl]oxy]phenyl]acetic acid
• CAS: 182414-76-2
• 化学式: C₄₀H₄₄O₄Si₂
• 分子量: 644.958
• InChiKey: NUMNHPSRUWCSLE-UHFFFAOYSA-N

物化性质

• 沸点：
  656.7±55.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-di(tert-butyldiphenylsilyloxy)phenylacetic acid 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 、 间甲酚 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.5h， 生成
  参考文献：
  名称：

  6-Arylmethylidene Penicillin-Based Sulfone Inhibitors for Repurposing Antibiotic Efficiency in Priority Pathogens

  摘要：

  The ability of 6-(aryl)methylidene penicillin-based sulfones 1-7 to repurpose beta-lactam antibiotics activity with bacterial species that carry carbapenem-hydrolyzing class D beta-lactamases (OXA-23, OXA-24/40 and OXA-48), as well as with class A (TEM-1, CTX-M-2) and class C (CMY-2, DHA-1) enzymes, is reported. The combinations imipenem/3 and imipenem/4 restored almost completely the antibiotic efficacy in OXA-23 and OXA-24/40 carbapenemase-producing A. baumannii strains (1 mu g mL(-1)) and also provided good results for OXA-48 carbapenemase-producing K. pneumoniae strains (4 mu g mL(-1)). Compounds 2-6 in combinations with ceftazidime and ampicillin were also efficient in restoring antibiotic efficacy in E. coli strains carrying class C (CMY-2 and DHA-1) and class A (TEM-1 and CTX-M-2) beta-lactamase enzymes, respectively. Kinetic and inhibition studies with the OXA-24/40 enzyme, protein mass spectrometry analysis and docking studies allowed us to gain an insight into the inhibition mechanism and the experimentally observed differences between the ligands.

  DOI：

  10.1021/acs.jmedchem.0c00127
• 作为产物：
  描述：

  3,4-二羟基苯乙酸 在 咪唑 、 potassium fluoride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.0h， 生成 3,4-di(tert-butyldiphenylsilyloxy)phenylacetic acid
  参考文献：
  名称：

  Inhibitors of Bacterial Signal Peptidase: A Series of 6-(Substituted oxyethyl)penems.

  摘要：

  介绍了一系列具有 (5S) 立体化学结构的 6-（取代氧乙基）青柠酯，它们是大肠杆菌头肽酶的强效抑制剂。讨论了结构-活性关系。

  DOI：

  10.7164/antibiotics.49.921

文献信息

• Inhibitors of Bacterial Signal Peptidase: A Series of 6-(Substituted oxyethyl)penems.
  作者：AILEEN ALLSOP、GERALD BROOKS、PETER D. EDWARDS、ARUN C. KAURA、ROBERT SOUTHGATE

  DOI：10.7164/antibiotics.49.921

  日期：——

  A series of 6-(substituted oxyethyl)penem esters having the (5S) stereochemistry which are potent inhibitors of Escherichia coli leader peptidase is described. Structure-activity relationships are discussed.

  介绍了一系列具有 (5S) 立体化学结构的 6-（取代氧乙基）青柠酯，它们是大肠杆菌头肽酶的强效抑制剂。讨论了结构-活性关系。
• 6-Arylmethylidene Penicillin-Based Sulfone Inhibitors for Repurposing Antibiotic Efficiency in Priority Pathogens
  作者：Diana Rodríguez、María Maneiro、Juan C. Vázquez-Ucha、Alejandro Beceiro、Concepción González-Bello

  DOI：10.1021/acs.jmedchem.0c00127

  日期：2020.4.9

  The ability of 6-(aryl)methylidene penicillin-based sulfones 1-7 to repurpose beta-lactam antibiotics activity with bacterial species that carry carbapenem-hydrolyzing class D beta-lactamases (OXA-23, OXA-24/40 and OXA-48), as well as with class A (TEM-1, CTX-M-2) and class C (CMY-2, DHA-1) enzymes, is reported. The combinations imipenem/3 and imipenem/4 restored almost completely the antibiotic efficacy in OXA-23 and OXA-24/40 carbapenemase-producing A. baumannii strains (1 mu g mL(-1)) and also provided good results for OXA-48 carbapenemase-producing K. pneumoniae strains (4 mu g mL(-1)). Compounds 2-6 in combinations with ceftazidime and ampicillin were also efficient in restoring antibiotic efficacy in E. coli strains carrying class C (CMY-2 and DHA-1) and class A (TEM-1 and CTX-M-2) beta-lactamase enzymes, respectively. Kinetic and inhibition studies with the OXA-24/40 enzyme, protein mass spectrometry analysis and docking studies allowed us to gain an insight into the inhibition mechanism and the experimentally observed differences between the ligands.