2-(4-nitrophenyl)-2-hydroxy-1-cyclohexyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide | 1040373-92-9

• 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: 2-(4-nitrophenyl)-2-hydroxy-1-cyclohexyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide
• 英文别名: 1-cyclododecyl-2-(4-nitrophenyl)-3H-imidazo[1,2-a]pyrimidin-4-ium-2-ol;bromide
• CAS: 1040373-92-9
• 化学式: Br*C₂₄H₃₃N₄O₃
• 分子量: 505.455
• InChiKey: IIBOSUVSEDMLBA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  86.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-nitrophenyl)-2-hydroxy-1-cyclohexyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide 在 PPA 作用下， 反应 0.25h， 以44%的产率得到2-(4-nitrophenyl)-1-cyclododecylimidazo[1,2-a]pyrimidin-1-ium perchlorate
  参考文献：
  名称：

  A Divergent Synthesis of Substituted 2-Aminoimidazoles from 2-Aminopyrimidines

  摘要：

  A new divergent and efficient synthesis of substituted 2-aminoimidazoles 5 and 6 has been developed starting from the readily available 2-aminopyrimidines 1 and alpha-broinocarbonyl compounds 2, Using conventional heating or microwave irradiation. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1 -iumsalts 4 with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles 5, when the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts 3, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles 6. The relevant pathway of transformations was identified by characterization of the intermediates.

  DOI：

  10.1021/jo8008758
• 作为产物：
  描述：

  环十二烷基(嘧啶-2-基)胺 、 2-溴-4'-硝基苯乙酮 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 2-(4-nitrophenyl)-2-hydroxy-1-cyclohexyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide
  参考文献：
  名称：

  2-羟基-2-芳基-2,3-二氢咪唑并[1,2- a ]嘧啶盐和2 N-取代的4（5）-芳基-2-氨基-1 H-咪唑的结构-活性关系鼠伤寒沙门氏菌和铜绿假单胞菌生物膜形成的抑制剂

  摘要：

  80个1取代的2-羟基-2-芳基-2,3-二氢咪唑并[1,2- a ]嘧啶盐和54 2 N取代的4（5）-芳基-2-氨基-1 H的文库合成了咪唑并测试了鼠伤寒沙门氏菌和铜绿假单胞菌对生物膜形成的拮抗作用。发现在盐的1-位上的取代基的性质对其生物膜抑制活性具有重大影响。一般而言，在1位取代的具有中等长度正烷基或环烷基链（C7–C10）的盐通常会阻止两种物种在低摩尔浓度下的生物膜形成，而具有较短n-烷基或环烷基链（C1-C5）或更长的正烷基链（C11-C14）效力较弱。然而，发现具有长环烷基链的盐是强生物膜抑制剂。此外，我们证明了在1位具有某些芳族取代基的盐（例如胡椒基或3-甲氧基苯乙炔基）的生物膜抑制潜力。发现2-氨基咪唑的活性取决于2 N-取代基的性质。与未取代的对应物相比，在2 N位具有正丁基，异丁基，正戊基，环戊基或正己基链的化合物具有更高的活性，而具有2 N较短的化合物-烷基链确实具有降低的活性，而具有更长的2

  DOI：

  10.1016/j.bmc.2011.04.026

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.
• A Divergent Synthesis of Substituted 2-Aminoimidazoles from 2-Aminopyrimidines
  作者：Denis S. Ermolat’ev、Erik V. Van der Eycken

  DOI：10.1021/jo8008758

  日期：2008.9.1

  A new divergent and efficient synthesis of substituted 2-aminoimidazoles 5 and 6 has been developed starting from the readily available 2-aminopyrimidines 1 and alpha-broinocarbonyl compounds 2, Using conventional heating or microwave irradiation. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1 -iumsalts 4 with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles 5, when the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts 3, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles 6. The relevant pathway of transformations was identified by characterization of the intermediates.