2-(4-chlorophenyl)-1-hexyl-2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide | 1313613-79-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(4-chlorophenyl)-1-hexyl-2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide
• 英文别名: 2-(4-chlorophenyl)-1-hexyl-3H-imidazo[1,2-a]pyrimidin-4-ium-2-ol;bromide
• CAS: 1313613-79-4
• 化学式: Br*C₁₈H₂₃ClN₃O
• 分子量: 412.757
• InChiKey: NWECKHCCGIWRPY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.27
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-1-hexyl-2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide 在 磷酸 、 高氯酸 作用下， 以 水 为溶剂， 反应 0.25h， 生成 2-(4-chlorophenyl)-1-hexylimidazo[1,2-a]pyrimidin-1-ium perchlorate
  参考文献：
  名称：

  Structure−Activity Relationship of 4(5)-Aryl-2-amino-1H-imidazoles, N1-Substituted 2-Aminoimidazoles and Imidazo[1,2-a]pyrimidinium Salts as Inhibitors of Biofilm Formation by Salmonella Typhimurium and Pseudomonas aeruginosa

  摘要：

  A library of 112 4(5)-aryl-2-amino-1H-imidazoles, 4,5-diphenyl-2-amino-1H-imidazoles, and N1-substituted 4(5)-phenyl-2-aminoimidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa. The substitution pattern of the 4(5)phenyl group and the nature of the N1-substituent were found to have a major effect on the biofilm inhibitory activity. The most active compounds of this series were shown to inhibit the biofilm formation at low micromolar concentrations. Furthermore, the influence of 6 imidazo[1,2-a]pyrimidines and 18 imidazo[1,2-a]pyrimidinium salts on the biofilm formation was tested. These compounds are the chemical precursors of the 2-aminoimidazoles in our synthesis pathway. A good correlation was found between the activity of the imidazo[1,2-a]pyrimidinium salts and their corresponding 2-aminoimidazoles, supporting the hypothesis that the imidazo[1,2-a]pyrimidinium salts are possibly cleaved by cellular nucleophiles to form the active 2-aminoimidazoles. However, the imidazo[1,2-a]pyrimidines did not show any biofilm inhibitory activity, indicating that these molecules are not susceptible to in situ degradation to 2-aminoimidazoles. Finally, we demonstrated the lack of biofilm inhibitory activity of an array of 37 2N-substituted 2-aminopyrimidines, which are the chemical precursors of the imidazo[1,2-a]pyrimidinium salts in our synthesis pathway.

  DOI：

  10.1021/jm1011148
• 作为产物：
  描述：

  正己胺 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 5.0h， 生成 2-(4-chlorophenyl)-1-hexyl-2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide
  参考文献：
  名称：

  Structure−Activity Relationship of 4(5)-Aryl-2-amino-1H-imidazoles, N1-Substituted 2-Aminoimidazoles and Imidazo[1,2-a]pyrimidinium Salts as Inhibitors of Biofilm Formation by Salmonella Typhimurium and Pseudomonas aeruginosa

  摘要：

  A library of 112 4(5)-aryl-2-amino-1H-imidazoles, 4,5-diphenyl-2-amino-1H-imidazoles, and N1-substituted 4(5)-phenyl-2-aminoimidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa. The substitution pattern of the 4(5)phenyl group and the nature of the N1-substituent were found to have a major effect on the biofilm inhibitory activity. The most active compounds of this series were shown to inhibit the biofilm formation at low micromolar concentrations. Furthermore, the influence of 6 imidazo[1,2-a]pyrimidines and 18 imidazo[1,2-a]pyrimidinium salts on the biofilm formation was tested. These compounds are the chemical precursors of the 2-aminoimidazoles in our synthesis pathway. A good correlation was found between the activity of the imidazo[1,2-a]pyrimidinium salts and their corresponding 2-aminoimidazoles, supporting the hypothesis that the imidazo[1,2-a]pyrimidinium salts are possibly cleaved by cellular nucleophiles to form the active 2-aminoimidazoles. However, the imidazo[1,2-a]pyrimidines did not show any biofilm inhibitory activity, indicating that these molecules are not susceptible to in situ degradation to 2-aminoimidazoles. Finally, we demonstrated the lack of biofilm inhibitory activity of an array of 37 2N-substituted 2-aminopyrimidines, which are the chemical precursors of the imidazo[1,2-a]pyrimidinium salts in our synthesis pathway.

  DOI：

  10.1021/jm1011148

文献信息

• COMPOUNDS, COMPOSITIONS AND METHODS FOR CONTROLLING BIOFILMS
  申请人：Katholieke Universiteit Leuven, K.U. Leuven R&D

  公开号：EP2513064A2

  公开（公告）日：2012-10-24
• COMPOUNDS, COMPOSITIONS, AND METHODS FOR CONTROLLING BIOFILMS
  申请人：De Keersmaecker Sigrid

  公开号：US20130029981A1

  公开（公告）日：2013-01-31

  The invention relates to substituted 2-aminoimidazoles and their imidazo[1,2- a ]pyrimidinium salts precursors being active against biofilm formation. The invention also relates to imidazo[1,2- a ]pyrimidinium salts bearing an azidoalkyl substituent, and to substituted 2-aminoimidazoles wherein the amino group bears a terminal heterocyclic group such as a triazolyl group which are formed through azide-alkyne Huisgen cycloaddition starting from said imidazo[1,2- a ]pyrimidinium salts bearing an azidoalkyl substituent. The invention also relates to a class of N-(azidoalkyl)pyrimidin-2-amines useful as starting materials for the synthesis of said imidazo[1,2- a ]pyrimidinium salts bearing an azidoalkyl substituent. The invention also relates to antimicrobial compositions that include a microbial biofilm formation inhibiting amount of such substituted 2-aminoimidazoles or imidazo[1,2- a ]pyrimidinium salts in combination with excipients. Methods for inhibiting or controlling microbial biofilm formation in a plant, a body part of a human or an animal, or a surface with which a human or an animal may come into contact are also disclosed.
• US8906915B2
  申请人：——

  公开号：US8906915B2

  公开（公告）日：2014-12-09
• [EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR CONTROLLING BIOFILMS<br/>[FR] COMPOSÉ, COMPOSITIONS ET PROCÉDÉS DE LUTTE CONTRE LES BIOFILMS
  申请人：UNIV LEUVEN KATH

  公开号：WO2011080132A2

  公开（公告）日：2011-07-07

  This invention relates to substituted 2-aminoimidazoles and their imidazo[1,2- a]pyrimidinium salts precursors being active against biofilm formation. The present invention also relates to antimicrobial compositions comprising a microbial biofilm formation inhibiting amount of such substituted 2-aminoimidazoles or imidazo[1,2- a]pyrimidinium salts in combination with excipients. The present invention also relates to methods for inhibiting or controlling microbial biofilm formation in a plant, a body part of a human or an animal, or a surface with which a human or an animal may come into contact.
• Structure−Activity Relationship of 4(5)-Aryl-2-amino-1<i>H</i>-imidazoles, <i>N</i>1-Substituted 2-Aminoimidazoles and Imidazo[1,2-<i>a</i>]pyrimidinium Salts as Inhibitors of Biofilm Formation by <i>Salmonella</i> Typhimurium and <i>Pseudomonas aeruginosa</i>
  作者：Hans P. L. Steenackers、Denis S. Ermolat’ev、Bharat Savaliya、Ami De Weerdt、David De Coster、Anamik Shah、Erik V. Van der Eycken、Dirk E. De Vos、Jozef Vanderleyden、Sigrid C. J. De Keersmaecker

  DOI：10.1021/jm1011148

  日期：2011.1.27

  A library of 112 4(5)-aryl-2-amino-1H-imidazoles, 4,5-diphenyl-2-amino-1H-imidazoles, and N1-substituted 4(5)-phenyl-2-aminoimidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa. The substitution pattern of the 4(5)phenyl group and the nature of the N1-substituent were found to have a major effect on the biofilm inhibitory activity. The most active compounds of this series were shown to inhibit the biofilm formation at low micromolar concentrations. Furthermore, the influence of 6 imidazo[1,2-a]pyrimidines and 18 imidazo[1,2-a]pyrimidinium salts on the biofilm formation was tested. These compounds are the chemical precursors of the 2-aminoimidazoles in our synthesis pathway. A good correlation was found between the activity of the imidazo[1,2-a]pyrimidinium salts and their corresponding 2-aminoimidazoles, supporting the hypothesis that the imidazo[1,2-a]pyrimidinium salts are possibly cleaved by cellular nucleophiles to form the active 2-aminoimidazoles. However, the imidazo[1,2-a]pyrimidines did not show any biofilm inhibitory activity, indicating that these molecules are not susceptible to in situ degradation to 2-aminoimidazoles. Finally, we demonstrated the lack of biofilm inhibitory activity of an array of 37 2N-substituted 2-aminopyrimidines, which are the chemical precursors of the imidazo[1,2-a]pyrimidinium salts in our synthesis pathway.