(2-Benzotriazol-1-yl-1-methyl-2-oxo-ethyl)-carbamic acid tert-butyl ester | 478358-11-1

• 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-Benzotriazol-1-yl-1-methyl-2-oxo-ethyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[1-(benzotriazol-1-yl)-1-oxopropan-2-yl]carbamate
• CAS: 478358-11-1
• 化学式: C₁₄H₁₈N₄O₃
• 分子量: 290.322
• InChiKey: NOGPAJUWHWZNGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  86.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  环丙沙星 、 (2-Benzotriazol-1-yl-1-methyl-2-oxo-ethyl)-carbamic acid tert-butyl ester 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Fluoroquinolone-3-carboxamide Amino Acid Conjugates: Synthesis, Antibacterial Properties And Molecular Modeling Studies

  摘要：

  背景：细菌感染被认为是全球主要的健康威胁之一，因此设计和开发新的抗菌剂以克服现有抗菌剂的缺点非常重要。 方法：本研究的目的是通过分子杂交合成一系列新的氟喹诺酮-3-羧酰胺氨基酸共轭物。我们利用苯并三唑化学来合成所需的混合共轭物。 结果：所有的共轭物均以良好的产率合成，经过表征，并评估其抗菌活性。这些化合物通过临床和实验室标准协会的方法进行了抗菌活性筛选。合成的共轭物被测试对医学相关的病原体的活性；大肠杆菌（ATCC 25922）、铜绿假单胞菌（ATCC 27856）、金黄色葡萄球菌（ATCC 25923）和肠球菌（ATCC 19433）。 结论：观察到的抗菌实验数据表明我们合成的共轭物对大肠杆菌具有选择性。氨基酸上的保护基降低了抗菌活性。合成的共轭物对正常细胞系非毒性。实验数据得到了计算研究的支持。

  DOI：

  10.2174/1573406415666190904143852
• 作为产物：
  描述：

  T406石油添加剂 在 TEA 作用下， 生成 (2-Benzotriazol-1-yl-1-methyl-2-oxo-ethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Solid-phase preparation of amides using N-acylbenzotriazoles

  摘要：

  Wang resin linked amines were efficiently converted into amides using acylbenzotriazoles. Cleavage of resins gave the desired amides 7Aa-Gf in 30-99% yields with good to excellent purities. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00278-0

文献信息

• Design, synthesis, antimicrobial, and DNA gyrase inhibitory properties of fluoroquinolone–dichloroacetic acid hybrids
  作者：Israa A. Seliem、Siva S. Panda、Adel S. Girgis、Yosra I. Nagy、Riham F. George、Walid Fayad、Nehmedo G. Fawzy、Tarek S. Ibrahim、Amany M. M. Al‐Mahmoudy、Rajeev Sakhuja、Zakaria K. M. Abdel‐samii

  DOI：10.1111/cbdd.13638

  日期：2020.2

  AbstractA series of new fluoroquinolone conjugates 8a–g and 9a–f were synthesized via benzotriazole‐mediated synthetic approach with good yield and purity. Some of the synthesized analogs exhibited significant antibacterial properties against Escherichia coli and Staphylococcus aureus with potency higher than that of the parent drugs through in vitro standard bioassay procedure (conjugates 8c and 8d reveal antimicrobial properties with potency 1.9, 61.9, 20.7 and 2.4, 37.1, 8.3 folds relative to the parent antibiotic 6 against E. coli, S. aureus, and Enterococcus faecalis, respectively). The observed experimental data were supported by enzymatic DNA gyrase inhibitory property. Developed BMLR‐QSAR model validates the observed experimental data and recognizes the parameters responsible for the enhanced antibacterial properties.
• Fluoroquinolone-3-carboxamide Amino Acid Conjugates: Synthesis, Antibacterial Properties And Molecular Modeling Studies
  作者：Riham M. Bokhtia、Siva S. Panda、Adel S. Girgis、Hitesh H. Honkanadavar、Tarek S. Ibrahim、Riham F. George、Mona T. Kashef、Walid Fayad、Rajeev Sakhuja、Eatedal H. Abdel-Aal、Amany M. M. Al-Mahmoudy

  DOI：10.2174/1573406415666190904143852

  日期：2020.12.29

  Bacterial infections are considered as one of the major global health threats, so it is very essential to design and develop new antibacterial agents to overcome the drawbacks of existing antibacterial agents.

  The aim of this work is to synthesize a series of new fluoroquinolone-3-carboxamide amino acid conjugates by molecular hybridization. We utilized benzotriazole chemistry to synthesize the desired hybrid conjugates.

  All the conjugates were synthesized in good yields, characterized, evaluated for their antibacterial activity. The compounds were screened for their antibacterial activity using methods adapted from the Clinical and Laboratory Standards Institute. Synthesized conjugates were tested for activity against medically relevant pathogens; Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27856) Staphylococcus aureus (ATCC 25923) and Enterococcus faecalis (ATCC 19433).

  The observed antibacterial experimental data indicates the selectivity of our synthesized conjugates against E.Coli. The protecting group on amino acids decreases the antibacterial activity. The synthesized conjugates are non-toxic to the normal cell lines. The experimental data were supported by computational studies.

  背景：细菌感染被认为是全球主要的健康威胁之一，因此设计和开发新的抗菌剂以克服现有抗菌剂的缺点非常重要。 方法：本研究的目的是通过分子杂交合成一系列新的氟喹诺酮-3-羧酰胺氨基酸共轭物。我们利用苯并三唑化学来合成所需的混合共轭物。 结果：所有的共轭物均以良好的产率合成，经过表征，并评估其抗菌活性。这些化合物通过临床和实验室标准协会的方法进行了抗菌活性筛选。合成的共轭物被测试对医学相关的病原体的活性；大肠杆菌（ATCC 25922）、铜绿假单胞菌（ATCC 27856）、金黄色葡萄球菌（ATCC 25923）和肠球菌（ATCC 19433）。 结论：观察到的抗菌实验数据表明我们合成的共轭物对大肠杆菌具有选择性。氨基酸上的保护基降低了抗菌活性。合成的共轭物对正常细胞系非毒性。实验数据得到了计算研究的支持。
• Solid-phase preparation of amides using N-acylbenzotriazoles
  作者：Alan R Katritzky、Boris V Rogovoy、Nataliya Kirichenko、Vladimir Vvedensky

  DOI：10.1016/s0960-894x(02)00278-0

  日期：2002.7

  Wang resin linked amines were efficiently converted into amides using acylbenzotriazoles. Cleavage of resins gave the desired amides 7Aa-Gf in 30-99% yields with good to excellent purities. (C) 2002 Elsevier Science Ltd. All rights reserved.