2-azido-N-cyclopentylacetamide | 1192358-61-4

• 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-azido-N-cyclopentylacetamide
• CAS: 1192358-61-4
• 化学式: C₇H₁₂N₄O
• 分子量: 168.198
• InChiKey: XPBLNJSKJHSIFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-azido-N-cyclopentylacetamide 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 生成 2-[4-(aminomethyl)triazol-1-yl]-N-cyclopentylacetamide
  参考文献：
  名称：

  In vitro antimalarial activity, β-haematin inhibition and structure–activity relationships in a series of quinoline triazoles

  摘要：

  A novel series of quinoline triazole amide analogues (38-51) has been synthesized. Analogues 38-44 had a Cl substituent at the 7-position of the quinoline ring, while 45-51 had a CN substituent at this position. Compounds 40,45 and 49 were found to be the most active in the series against the Plasmodium falciparum chloroquine-sensitive D10 strain, with IC50 values in the range of 349-1247 nM, with 40 and 45, but not 49 also exhibiting similar activity against the chloroquine-resistant 1(1 strain of parasite. Quinoline triazoles 40 and 44 were the most active beta-haematin inhibitors, with 50% inhibitory concentrations of 14.7 and 8.9 1tM respectively. In vitro antimalarial activity of the 7-C1 bearing analogues 38 -44 exhibited a strong linear dependence of log(1/IC50) on log P. Thus, the more lipophilic, the more active it was found be. The 7-CN series 45-51 showed no such dependence. The resistance index (IC50 K1 /IC50 D10) also exhibited a linear dependence on log P, with a substantially steeper slope in the case of the 7-CI series. The findings demonstrate the feasibility of producing hydrophilic analogues with strong activity and low cross-resistance with chloroquine. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.046
• 作为产物：
  描述：

  2-氯-n-环戊基乙酰胺 在 sodium azide 、 potassium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-azido-N-cyclopentylacetamide
  参考文献：
  名称：

  基于 1,2,3-三唑的 2-氨基苯并咪唑作为铜绿假单胞菌中 LasR 依赖性群体感应的新型抑制剂的设计、合成和生物学评价†

  摘要：

  细菌通过称为群体感应的信号通路调节其表型、生长和种群。在此过程中，细菌产生信号分子（自诱导剂）来识别其种群密度。抑制这种群体感应信号通路是治疗细菌感染的潜在方法之一。据报道，2-氨基苯并咪唑是野生型铜绿假单胞菌群体感应最强的抑制剂。 1,2,3-三唑基酰基高丝氨酸内酯被发现是群体感应 LasR 受体的良好抑制剂。因此，在我们目前的研究中，合成了 40 种 1,2,3-三唑基 2-氨基苯并咪唑，并使用 IR、NMR、MS 和元素分析进行​​了表征。开发了N- (1 H-苯并[ d ]咪唑-2-基)-2-(4-壬基-1 H -1,2,3-三唑-1-基)乙酰胺( 6d )的单晶。筛选所有最终化合物对铜绿假单胞菌的体外群体感应抑制活性。通过测量绿色荧光蛋白的产生来确定表达 LasR 的铜绿假单胞菌MH602 报告菌株的群体感应抑制活性。标题化合物中， N- ( 1H-苯并[ d ]咪唑-2-基)-2-(4-(4-氯苯基)-1H

  DOI：

  10.1039/c9ra05059k

文献信息

• INHIBITION AND DISPERSION OF BACTERIAL BIOFILMS WITH IMIDAZOLE-TRIAZOLE DERIVATIVES
  申请人：Melander Christian

  公开号：US20090263438A1

  公开（公告）日：2009-10-22

  Disclosure is provided for imidazole-triazole derivative compounds that prevent, remove and/or inhibit the formation of biofilms, compositions comprising these compounds, devices comprising these compounds, and methods of using the same.

  披露了咪唑-三唑衍生物化合物，用于防止、移除和/或抑制生物膜的形成，包含这些化合物的组合物，包含这些化合物的设备，以及使用这些化合物的 methods。
• Flustramine inspired synthesis and biological evaluation of pyrroloindoline triazole amides as novel inhibitors of bacterial biofilms
  作者：Cynthia Bunders、John Cavanagh、Christian Melander

  DOI：10.1039/c1ob05605k

  日期：——

  Anti-biofilm agents have been developed based upon the flustramine family of alkaloids isolated from Flustra foliacea. A Garg interrupted Fischer indolization reaction was employed to access a core pyrroloindoline scaffold that was subsequently employed to create a pyrroloindoline triazole amide library. Screening for the ability to modulate biofilm formation against strains of Gram-positive and Gram-negative

  抗生物膜剂是基于从Flustra foliacea中分离出的 Flustraamine 生物碱家族而开发的。采用 Garg 中断的 Fischer 吲哚化反应来获得核心吡咯并吲哚啉支架，随后将其用于创建吡咯并吲哚啉三唑酰胺文库。筛选针对革兰氏阳性和革兰氏阴性细菌菌株调节生物膜形成的能力，鉴定出几种具有低微摩尔、无毒IC 50值的化合物。
• Modulating the development of E. coli biofilms with 2-aminoimidazoles
  作者：Catherine S. Reed、Robert W. Huigens、Steven A. Rogers、Christian Melander

  DOI：10.1016/j.bmcl.2010.08.075

  日期：2010.11

  The synthesis of a 20 member 2-aminoimidazole/triazole pilot library is reported. Each member of the library was screened for its ability to inhibit or promote biofilm development of either Escherichia coli and Acinetobacter baumannii. From this screen, E. coli-selective 2-aminoimidazoles were discovered, with the best inhibitor inhibiting biofilm development with an IC(50) of 13 mu M. The most potent promoter of E. coli biofilm formation promoted biofilm development by 321% at 400 mu M. (C) 2010 Elsevier Ltd. All rights reserved.
• US7897631B2
  申请人：——

  公开号：US7897631B2

  公开（公告）日：2011-03-01
• US8367713B2
  申请人：——

  公开号：US8367713B2

  公开（公告）日：2013-02-05