N-(2-azidoethyl)-4-pentylbenzamide | 1192358-22-7

• 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: N-(2-azidoethyl)-4-pentylbenzamide
• CAS: 1192358-22-7
• 化学式: C₁₄H₂₀N₄O
• 分子量: 260.339
• InChiKey: DJZQVSOAKVAXND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  N-(2-azidoethyl)-4-pentylbenzamide 在 盐酸 、 Jones reagent 、 草酰氯 、 氰胺 、 氢溴酸 、 copper(II) sulfate 、 sodium ascorbate 、 N,N-二甲基甲酰胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 22.58h， 生成 N-(2-(4-(5-(2-amino-1-phenyl-1H-imidazol-4-yl)pentyl)-1H-1,2,3-triazol-1-yl)ethyl)-4-pentylbenzamide
  参考文献：
  名称：

  A flexible approach to 1,4-di-substituted 2-aminoimidazoles that inhibit and disperse biofilms and potentiate the effects of β-lactams against multi-drug resistant bacteria

  摘要：

  The pyrrole-imidazole alkaloids are a 2-aminoimidazoles containing family of natural products that possess anti-biofilm activity. A library of 1,4-di-substituted 2-aminoimidazole/triazoles (2-AITs) was synthesized, and its anti-biofilm activity as well as oxacillin resensitization efficacy toward methicillin resistant Staphylococcus aureus (MRSA) was investigated. These 2-AITs were found to inhibit biofilm formation by MRSA with low micromolar IC50 values. Additionally, the most active compound acted synergistically with oxacillin against MRSA lowering the minimum inhibitory concentration (MIC) 4-fold. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.005
• 作为产物：
  描述：

  2-叠氮基乙胺 、 4-戊基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到N-(2-azidoethyl)-4-pentylbenzamide
  参考文献：
  名称：

  INHIBITION AND DISPERSION OF BACTERIAL BIOFILMS WITH IMIDAZOLE-TRIAZOLE DERIVATIVES

  摘要：

  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。

  公开号：

  US20090263438A1

文献信息

• Chemical Synthesis and Biological Screening of 2-Aminoimidazole-Based Bacterial and Fungal Antibiofilm Agents
  作者：Steven A. Rogers、Joseph D. Bero、Christian Melander

  DOI：10.1002/cbic.200900617

  日期：2010.2.15

  Film breaker: A collection of aminoimidazole/triazole amides has been synthesized and screened for antibiofilm activity. These small molecules were found to modulate the biofilm activity of fungi and bacteria, including some drug‐resistant strains. Moreover, lead compounds were found to not lyse red blood cells at active concentrations.

  破膜剂：合成了一组氨基咪唑/三唑酰胺，并针对其抗生物膜活性进行了筛选。发现这些小分子可调节真菌和细菌（包括某些耐药菌株）的生物膜活性。此外，发现铅化合物不能以有效浓度裂解红细胞。
• Structural Studies on 4,5-Disubstituted 2-Aminoimidazole-Based Biofilm Modulators that Suppress Bacterial Resistance to β-Lactams
  作者：Zhaoming Su、Andrew A. Yeagley、Rui Su、Lingling Peng、Christian Melander

  DOI：10.1002/cmdc.201200350

  日期：2012.11

  synergism and resensitization studies with β‐lactam antibiotics against MRSA. Lead compounds were identified that suppress the antibiotic resistance of MRSA by working synergistically with oxacillin, a β‐lactam antibiotic resistant to penicillinase. A further structure–activity relationship (SAR) study on the parent 2‐AITA compound delivered a 2‐aminoimidazole diamide (2‐AIDA) conjugate with significantly

  已成功组装了4,5-二取代的2-氨基咪唑三唑酰胺（2-AITA）共轭物的文库。经过生物筛选后，此类小分子被发现是通过抗微生物的抗甲氧西林金黄色葡萄球菌（MRSA）和耐多药鲍曼不动杆菌的增强的生物膜调节剂。（MDRAB），其活性浓度在低微摩尔范围内。该文库还接受了针对MRSA的β-内酰胺类抗生素的协同作用和重新敏化研究。通过与奥沙西林（一种对青霉素酶有抗药性的β-内酰胺抗生素）协同作用，可以抑制MRSA的抗生素抗药性。对母体2-AITA化合物进行的进一步的结构-活性关系（SAR）研究提供了2-氨基咪唑二酰胺（2-AIDA）结合物，与奥沙西林对MRSA的协同活性显着增强，从而降低了β-内酰胺抗生素的MIC值。 64倍。抗生物膜活性的提高并不一定会导致对抗生素耐药性的抑制作用增强，这表明生物膜抑制和再敏化很可能是通过不同的机制发生的。
• N-Substituted 2-aminoimidazoleinhibitors of MRSA biofilm formation accessed through direct 1,3-bis(tert-butoxycarbonyl)guanidine cyclization
  作者：Andrew A. Yeagley、Zhaoming Su、Kára D. McCullough、Roberta J. Worthington、Christian Melander

  DOI：10.1039/c2ob26469b

  日期：——

  Antibiotic resistance is a significant problem and is compounded by the ability of many pathogenic bacteria to form biofilms. A library of N-substituted derivatives of a previously reported 2-aminoimidazole/triazole (2-AIT) biofilm modulator was constructed via α-bromoketone cyclization with 1,3-bis(tert-butoxycarbonyl)guanidine, followed by selective substitution. Several compounds exhibited the ability to inhibit biofilm formation by three strong biofilm forming strains of methicillin resistant Staphylococcus aureus (MRSA). Additionally, a number of members of this library exhibited synergistic activity with oxacillin against planktonic MRSA. Compounds with this type of dual activity have the potential to be used as adjuvants with conventional antibiotics.

  抗生素耐药性是一个严重的问题，而许多致病细菌形成生物膜的能力更是加剧了这一问题。通过α-溴酮的环化反应与1,3-双(叔丁氧羰基)胍的反应，构建了一组之前报道的2-氨基咪唑/三唑（2-AIT）生物膜调节剂的N-取代衍生物库，随后进行选择性取代。其中几个化合物表现出抑制三种强生物膜形成菌株的耐甲氧西林金黄色葡萄球菌（MRSA）形成生物膜的能力。此外，该化合物库中的多个成员与苯唑西林联合使用，对浮游状态的MRSA显示出协同活性。具有这种双重活性的化合物有可能作为辅助剂与常规抗生素联用。
• [EN] INHIBITION AND DISPERSION OF BIOFILMS IN PLANTS WITH IMIDAZOLE-TRIAZOLE DERIVATIVES<br/>[FR] INHIBITION ET DISPERSION DE BIOFILMS DANS DES PLANTES AVEC DÉRIVÉS D'IMIDAZOLE-TRIAZOLE
  申请人：UNIV NORTH CAROLINA STATE

  公开号：WO2010077603A1

  公开（公告）日：2010-07-08

  Disclosure is provided for methods of preventing, removing or inhibiting microbial biofilm formation or microbial infection in a plant or plant part thereof, including applying thereto a treatment effective amount of an active compound as described herein, or an agriculturally acceptable salt thereof. Methods of enhancing a microbicide (e.g., including a copper, antibiotic, bacteriophage, etc.) and/or plant defense activator are also provided, including applying an active compound as described herein. Compositions comprising an active compound as described herein in an agriculturally acceptable carrier are also provided, and in some embodiments the compositions further include a microbicide (e.g., including copper, antibiotic, bacteriophage, etc.) and/or plant defense activator.

  本公开提供了一种防止、去除或抑制植物或植物部分中微生物生物膜形成或微生物感染的方法，包括向其施加根据本文所述的有效化合物或其农业可接受的盐的治疗有效量。还提供了增强微生物杀灭剂（例如，包括铜、抗生素、细菌噬菌体等）和/或植物防御激活剂的方法，包括施加本文所述的有效化合物。还提供了包含本文所述的有效化合物在农业可接受载体中的组合物，有些实施例中，这些组合物进一步包括微生物杀灭剂（例如，包括铜、抗生素、细菌噬菌体等）和/或植物防御激活剂。
• Potent Small-Molecule Suppression of Oxacillin Resistance in Methicillin-Resistant<i>Staphylococcus aureus</i>
  作者：Tyler L. Harris、Roberta J. Worthington、Christian Melander

  DOI：10.1002/anie.201206911

  日期：2012.11.5

  the ability to restore the susceptibility of multi‐drug‐resistant bacteria, such as MRSA, to clinically available antibiotics are a promising alternative to the development of novel antimicrobials. Pictured is a potent small molecule (1) that, at sub‐minimum inhibitory concentration (sub‐MIC) levels, lowers the MIC of oxacillin (2) against a number of MRSA strains by up to 512‐fold.

  盾牌落下！能够恢复多重耐药细菌（例如 MRSA）对临床可用抗生素的敏感性的佐剂分子是开发新型抗菌药物的有前途的替代方案。图中是一种有效的小分子 ( 1 )，在亚最低抑制浓度 (亚 MIC) 水平下，可将苯唑西林 ( 2 ) 对多种 MRSA 菌株的 MIC 降低高达 512 倍。