tert-butyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxopropan-2-yl)carbamate

• 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: tert-butyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxopropan-2-yl)carbamate
• 英文别名: tert-butyl N-[(2R)-1-(benzotriazol-1-yl)-1-oxopropan-2-yl]carbamate
• 化学式: C₁₄H₁₈N₄O₃
• 分子量: 290.322
• InChiKey: NOGPAJUWHWZNGH-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  86.11
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxopropan-2-yl)carbamate 、 mafenide hydrochloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以85%的产率得到tert-butyl (R)-(1-oxo-1-((4-sulphamoylbenzyl)amino)propan-2-yl)carbamate
  参考文献：
  名称：

  新型氨基酸-磺酰胺偶联物的合成和人碳酸酐酶I，II，VA和XII抑制作用。

  摘要：

  通过苯并三唑介导的偶联反应制备了一系列氨基酸-磺酰胺偶联物，并通过1H-NMR，13C-NMR，MS和FTIR光谱技术以及元素分析进行​​了表征。确定了新化合物的碳酸酐酶（CA，EC 4.2.1.1）对四种人（h）亚型hCA I，hCA II，hCA VA和hCA XII的抑制活性。大多数合成的化合物显示出有效的体外CA抑制特性。新的氨基酸-磺酰胺结合物显示出对hCA II的有效抑制活性，其中一些处于亚纳摩尔水平，与标准药物乙酰唑胺相比，具有更有效的抑制活性。还发现这些磺酰胺中的一些是hCA I，hCA VA和hCA XII的有效抑制剂，其活性范围从低至高纳摩尔范围。

  DOI：

  10.1080/14756366.2019.1710503
• 作为产物：
  描述：

  BOC-D-丙氨酸 、 1-(甲磺酰基)-1H-苯并三唑 在 三乙胺 作用下， 反应 1.03h， 生成 tert-butyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxopropan-2-yl)carbamate
  参考文献：
  名称：

  Design, synthesis, antimicrobial, and DNA gyrase inhibitory properties of fluoroquinolone–dichloroacetic acid hybrids

  摘要：

  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.

  DOI：

  10.1111/cbdd.13638

文献信息

• 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。
• Preparation, carbonic anhydrase enzyme inhibition and antioxidant activity of novel 7-amino-3,4-dihydroquinolin-2(1H)-one derivatives incorporating mono or dipeptide moiety
  作者：Hasan Küçükbay、Zeynep Gönül、F. Zehra Küçükbay、Andrea Angeli、Gianluca Bartolucci、Claudiu T. Supuran

  DOI：10.1080/14756366.2020.1751620

  日期：2020.1.1

  mediated nucleophilic acyl substitution reaction and their structures were elucidated by spectroscopic and analytic techniques. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was determined against four human (h) isoforms, hCA I, hCA II, hCA IX and hCA XII. While all compounds showed moderate to good in vitro CA inhibitory properties against hCA IX and hCA XII with inhibition

  通过苯并三唑介导的亲核酰基取代反应成功合成了新的二肽-二氢喹啉酮衍生物，并通过光谱和分析技术阐明了它们的结构。确定了新化合物的碳酸酐酶（CA，EC 4.2.1.1）对四种人（h）同工型hCA I，hCA II，hCA IX和hCA XII的抑制活性。尽管所有化合物在体外均显示出对hCA IX和hCA XII的中度至良好的CA抑制特性，且微摩尔水平的抑制常数（分别为37.7-86.8和2.0-8.6 µM），但它们均未显示对hCA I和hCA II的抑制活性最高浓度为100 µM。肽-二氢喹啉酮缀合物的抗氧化能力是通过1,1-二苯基-2-吡啶并肼基（DPPH）自由基清除方法确定的。
• Synthesis carbonic anhydrase enzyme inhibition and antioxidant activity of novel benzothiazole derivatives incorporating glycine, methionine, alanine, and phenylalanine moieties
  作者：Deniz Üzeroğlu Payaz、F. Zehra Küçükbay、Hasan Küçükbay、Andrea Angeli、Claudiu T. Supuran

  DOI：10.1080/14756366.2018.1553040

  日期：2019.1.1

  Abstract Thirteen novel benzothiazole derivatives incorporating glycine, methionine, alanine, and phenylalanine were synthesised by facile acylation reactions through benzotriazole or DCC mediated reactions and their structures were identified by 1H-NMR, 13C-NMR, and FT-IR spectroscopic techniques and elemental analysis. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds

  抽象的 通过苯并三唑或DCC介导的轻度酰化反应合成了13种新的结合有甘氨酸，蛋氨酸，丙氨酸和苯丙氨酸的苯并噻唑衍生物，并通过1 H-NMR，13C-NMR和FT-IR光谱技术及元素分析鉴定了它们的结构。评估了新化合物的碳酸酐酶（CA，EC 4.2.1.1）对四种人（h）同工型hCA I，hCA II，hCA V和hCA XIII的抑制活性。一些合成的化合物显示出良好的体外碳酸酐酶抑制特性，且抑制常数在微摩尔水平上。发现新的氨基酸苯并噻唑缀合物对hCA V和hCA II抑制更有效。体外用DPPH法测定了新化合物的抗氧化活性。与对照抗氧化剂化合物（BHA和α-生育酚）相比，大多数合成的化合物显示出中等至低的抗氧化剂活性。
• 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.
• Synthesis and human carbonic anhydrase I, II, VA, and XII inhibition with novel amino acid–sulphonamide conjugates
  作者：Hasan Küçükbay、Nesrin Buğday、F. Zehra Küçükbay、Andrea Ageli、Gianluca Bartolucci、Claudiu T. Supuran

  DOI：10.1080/14756366.2019.1710503

  日期：2020.1.1

  inhibitory activity of the new compounds was determined against four human (h) isoforms, hCA I, hCA II, hCA VA, and hCA XII. Most of the synthesised compounds showed effective in vitro CA inhibitory properties. The new amino acid-sulphonamide conjugates showed potent inhibitory activity against hCA II, some of them at subnanomolar levels, exhibiting more effective inhibitory activity compared to the

  通过苯并三唑介导的偶联反应制备了一系列氨基酸-磺酰胺偶联物，并通过1H-NMR，13C-NMR，MS和FTIR光谱技术以及元素分析进行​​了表征。确定了新化合物的碳酸酐酶（CA，EC 4.2.1.1）对四种人（h）亚型hCA I，hCA II，hCA VA和hCA XII的抑制活性。大多数合成的化合物显示出有效的体外CA抑制特性。新的氨基酸-磺酰胺结合物显示出对hCA II的有效抑制活性，其中一些处于亚纳摩尔水平，与标准药物乙酰唑胺相比，具有更有效的抑制活性。还发现这些磺酰胺中的一些是hCA I，hCA VA和hCA XII的有效抑制剂，其活性范围从低至高纳摩尔范围。