2-{[N-(2-dimethylaminoethyl)-N-methyl]-aminomethyl}-4-bromo-6-[[N'-2-(2'-pyridyl)-ethyl]-aminomethyl]phenol | 289040-21-7

• 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: 2-{[N-(2-dimethylaminoethyl)-N-methyl]-aminomethyl}-4-bromo-6-[[N'-2-(2'-pyridyl)-ethyl]-aminomethyl]phenol
• 英文别名: 4-Bromo-2-[[2-(dimethylamino)ethyl-methylamino]methyl]-6-[(2-pyridin-2-ylethylamino)methyl]phenol；4-bromo-2-[[2-(dimethylamino)ethyl-methylamino]methyl]-6-[(2-pyridin-2-ylethylamino)methyl]phenol
• CAS: 289040-21-7
• 化学式: C₂₀H₂₉BrN₄O
• 分子量: 421.38
• InChiKey: CXTYNZYHKONQFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  51.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-{[N-(2-dimethylaminoethyl)-N-methyl]-aminomethyl}-4-bromo-6-[[N'-2-(2'-pyridyl)-ethyl]-aminomethyl]phenol 、 zinc(II) nitrate hexahydrate 在 LiOH*H₂O 作用下， 以 乙醇 、 水 为溶剂， 以40%的产率得到[Zn2(2-[(N-(2-dimethylaminoethyl)-N-methyl)aminomethyl]-4-bromo-6-[(N'-2-(2'-pyridyl)ethyl)aminomethyl]phenolate)(NO3)3]
  参考文献：
  名称：

  Hydrolysis of β-Lactam Antibiotics Catalyzed by Dinuclear Zinc(II) Complexes:  Functional Mimics of Metallo-β-lactamases

  摘要：

  Three stable dinuclear zinc(II) complexes, [Zn2L1(mu-NO3)(NO3)(2)] and [Zn2L1(mu-OMe)(NO3)(2)], where L-1 is 2,6-bis {{N-(2-dimethylaminoethyl)-N-methyl]aminomethyl}-4-methylphenolate, and [Zn2L2(NO3)(3)], where L-2 is 2-{[N-(2-dimethylaminoethyl)-N-methyl]aminomethyl}-4-bromo-6-{[N'-2-(2'-pyridyl)ethyl]aminomethyl}phenolate, were synthesized and characterized in the solid stare and in aqueous solution. These complexes catalyze the hydrolysis of penicillin G and nitrocefin, serving as functional synthetic analogues of the metallo-beta-lactamases, bacterial enzymes responsible for antibiotic resistance. The mechanism of the hydrolysis was studied in detail for the catalyst precursor [Zn2L1(mu-NO3)(NO3)(2)], which converts into [Zn2L1(mu-OH)(NO3), (sol)(2-n)]((2-n)+) in the presence of water. The complex [Zn2L1(mu-OH)(No-3)(2)] (n = 2) was characterized in the solid state. Initial coordination of the substrate carboxylate group is followed by the rate-limiting nucleophilic attack of the bridging hydroxide at the beta-lactam carbonyl group in aqueous solution. The product is formed upon fast protonation of the intermediate. Mononuclear complexes Zn(cyclen)(NO3)(2) and Zn(bpta)(NO3)(2) are as reactive in the beta-lactam hydrolysis as the dinuclear complexes. Consequently, the second zinc ion is not required for catalytic activity.

  DOI：

  10.1021/ja993704l
• 作为产物：
  描述：

  3-trimethylethylenediaminomethyl-5-bromosalicyldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 2-{[N-(2-dimethylaminoethyl)-N-methyl]-aminomethyl}-4-bromo-6-[[N'-2-(2'-pyridyl)-ethyl]-aminomethyl]phenol
  参考文献：
  名称：

  Hydrolysis of β-Lactam Antibiotics Catalyzed by Dinuclear Zinc(II) Complexes:  Functional Mimics of Metallo-β-lactamases

  摘要：

  Three stable dinuclear zinc(II) complexes, [Zn2L1(mu-NO3)(NO3)(2)] and [Zn2L1(mu-OMe)(NO3)(2)], where L-1 is 2,6-bis {{N-(2-dimethylaminoethyl)-N-methyl]aminomethyl}-4-methylphenolate, and [Zn2L2(NO3)(3)], where L-2 is 2-{[N-(2-dimethylaminoethyl)-N-methyl]aminomethyl}-4-bromo-6-{[N'-2-(2'-pyridyl)ethyl]aminomethyl}phenolate, were synthesized and characterized in the solid stare and in aqueous solution. These complexes catalyze the hydrolysis of penicillin G and nitrocefin, serving as functional synthetic analogues of the metallo-beta-lactamases, bacterial enzymes responsible for antibiotic resistance. The mechanism of the hydrolysis was studied in detail for the catalyst precursor [Zn2L1(mu-NO3)(NO3)(2)], which converts into [Zn2L1(mu-OH)(NO3), (sol)(2-n)]((2-n)+) in the presence of water. The complex [Zn2L1(mu-OH)(No-3)(2)] (n = 2) was characterized in the solid state. Initial coordination of the substrate carboxylate group is followed by the rate-limiting nucleophilic attack of the bridging hydroxide at the beta-lactam carbonyl group in aqueous solution. The product is formed upon fast protonation of the intermediate. Mononuclear complexes Zn(cyclen)(NO3)(2) and Zn(bpta)(NO3)(2) are as reactive in the beta-lactam hydrolysis as the dinuclear complexes. Consequently, the second zinc ion is not required for catalytic activity.

  DOI：

  10.1021/ja993704l

文献信息

• Hydrolysis of β-Lactam Antibiotics Catalyzed by Dinuclear Zinc(II) Complexes:  Functional Mimics of Metallo-β-lactamases
  作者：Natalia V. Kaminskaia、Bernhard Spingler、Stephen J. Lippard

  DOI：10.1021/ja993704l

  日期：2000.7.1

  Three stable dinuclear zinc(II) complexes, [Zn2L1(mu-NO3)(NO3)(2)] and [Zn2L1(mu-OMe)(NO3)(2)], where L-1 is 2,6-bis N-(2-dimethylaminoethyl)-N-methyl]aminomethyl}-4-methylphenolate, and [Zn2L2(NO3)(3)], where L-2 is 2-[N-(2-dimethylaminoethyl)-N-methyl]aminomethyl}-4-bromo-6-[N'-2-(2'-pyridyl)ethyl]aminomethyl}phenolate, were synthesized and characterized in the solid stare and in aqueous solution. These complexes catalyze the hydrolysis of penicillin G and nitrocefin, serving as functional synthetic analogues of the metallo-beta-lactamases, bacterial enzymes responsible for antibiotic resistance. The mechanism of the hydrolysis was studied in detail for the catalyst precursor [Zn2L1(mu-NO3)(NO3)(2)], which converts into [Zn2L1(mu-OH)(NO3), (sol)(2-n)]((2-n)+) in the presence of water. The complex [Zn2L1(mu-OH)(No-3)(2)] (n = 2) was characterized in the solid state. Initial coordination of the substrate carboxylate group is followed by the rate-limiting nucleophilic attack of the bridging hydroxide at the beta-lactam carbonyl group in aqueous solution. The product is formed upon fast protonation of the intermediate. Mononuclear complexes Zn(cyclen)(NO3)(2) and Zn(bpta)(NO3)(2) are as reactive in the beta-lactam hydrolysis as the dinuclear complexes. Consequently, the second zinc ion is not required for catalytic activity.