2-(5-Bromo-2-methoxyphenyl)-5-hydroxymethyl-imidazole | 144650-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(5-Bromo-2-methoxyphenyl)-5-hydroxymethyl-imidazole
• 英文别名: [2-(5-bromo-2-methoxyphenyl)-1H-imidazol-5-yl]methanol
• CAS: 144650-02-2
• 化学式: C₁₁H₁₁BrN₂O₂
• 分子量: 283.125
• InChiKey: CCIKSUNOPRGBMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  526.7±50.0 °C(Predicted)
• 密度：
  1.570±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-Bromo-2-methoxyphenyl)-5-hydroxymethyl-imidazole 在 氯化亚砜 作用下， 反应 0.17h， 生成 2-(5-bromo-2-methoxyphenyl)-5-(chloromethyl)-1H-imidazole
  参考文献：
  名称：

  2-Phenyl-4-(aminomethyl)imidazoles as Potential Antipsychotic Agents. Synthesis and Dopamine D2 Receptor Binding

  摘要：

  A series of 2-phenyl-4-(aminomethyl)imidazoles were designed as conformationally restricted analogs of the dopamine D-2 selective benzamide antipsychotics. The title compounds were synthesized and tested for blockade of[H-3]YM-09151 binding in cloned African green monkey dopamine D-2 receptor preparations. The binding affinity data thus obtained were compared against that of the benzamides and a previously described series of 2-phenyl-5-(aminomethyl)-pyrroles.

  DOI：

  10.1021/jm00012a026
• 作为产物：
  描述：

  5-溴-2-甲氧基苯甲腈 在 ammonium hydroxide 、 氯化铵 、 lithium hexamethyldisilazane 作用下， 以 乙醚 为溶剂， 反应 2.5h， 生成 2-(5-Bromo-2-methoxyphenyl)-5-hydroxymethyl-imidazole
  参考文献：
  名称：

  2-Phenyl-4-(aminomethyl)imidazoles as Potential Antipsychotic Agents. Synthesis and Dopamine D2 Receptor Binding

  摘要：

  A series of 2-phenyl-4-(aminomethyl)imidazoles were designed as conformationally restricted analogs of the dopamine D-2 selective benzamide antipsychotics. The title compounds were synthesized and tested for blockade of[H-3]YM-09151 binding in cloned African green monkey dopamine D-2 receptor preparations. The binding affinity data thus obtained were compared against that of the benzamides and a previously described series of 2-phenyl-5-(aminomethyl)-pyrroles.

  DOI：

  10.1021/jm00012a026

文献信息

• Certain 4-aminomethyl-2-substituted imidazole derivatives and 2-aminomethyl-4-substituted imidazole derivatives: new classes of dopamine receptor subtype specific ligands
  申请人：Neurogen Corporation, Corporation of the State of Delaware

  公开号：US20030018025A1

  公开（公告）日：2003-01-23

  Disclosed are compounds of the formula: 1 wherein R 1 represents optionally substituted aryl, heteroaryl, arylalkyl, or cycloalkyl groups; X, Z, and Y are optionally substituted nitrogen or carbon atoms; R 3 and R 4 are organic or inorganic substitutents which may togther form ring structutes; m is zero, one or two; and R 5 and R 6 are are organic or inorganic substituents; and the pharmaceutically acceptable addition salts thereof, which compounds are highly selective partial agonists or antagonists at brain dopamine receptor subtypes or prodrugs thereof and are useful in the diagnosis and treatment of affective disorders such as schizophrenia and depression as well as certain movement disorders such as Parkinsonism.

  揭示了以下式的化合物： 其中R1代表可选择地取代的芳基、杂环芳基、芳基烷基或环烷基基团；X、Z和Y为可选择地取代的氮或碳原子；R3和R4为有机或无机取代基，可能共同形成环结构；m为零、一或二；R5和R6为有机或无机取代基； 以及其药学上可接受的盐， 这些化合物是高度选择性的部分激动剂或拮抗剂，作用于脑多巴胺受体亚型或其前药，并可用于诊断和治疗情感障碍，如精神分裂症和抑郁症，以及某些运动障碍，如帕金森病。
• Phenyloxazoles and phenylthiazoles as benzamide bioisosteres: synthesis and dopamine receptor binding profiles
  作者：Jürgen Einsiedel、Christoph Thomas、Harald Hübner、Peter Gmeiner

  DOI：10.1016/s0960-894x(00)00405-4

  日期：2000.9

  Conformationally restricted benzamide bioisosteres were investigated when the aminomethylpyrrolidine derivative 4o proved D3 as well as D4 binding properties which were comparable to those of the atypical neuroleptics sulpiride and clozapine, respectively.

  当氨基甲基吡咯烷衍生物4o证明了D3和D4的结合特性分别与非典型的抗精神病药舒必利和氯氮平相当时，研究了构象受限的苯甲酰胺生物异构体。
• Certain aminomethyl phenylimidazole derivatives; a class of dopamine
  申请人：Neurogen Corporation

  公开号：US05159083A1

  公开（公告）日：1992-10-27

  This invention encompasses compounds of the formula: ##STR1## where X, Y, Z, T, R.sub.1, R.sub.3, R.sub.4, and R.sub.5 are variables representing various organic and inorganic substituents; M is ##STR2## R.sub.2 and R.sub.6 represent hydrogen or alkyl substituents; or R.sub.1 and R.sub.2 together may represent --(CH.sub.2).sub.n1 where n.sub.1 is 1, 2, or 3; or NR.sub.4 R.sub.5 represents substituted or unsubstituted-tetrahydroisoquinolinyl; or ##STR3## where n is 1, 2, or 3; W is N or CH; and R.sub.7 represents hydrogen or aryl; or W--R.sub.7 is oxygen or sulfur. These compounds are highly selective partial agonists or antagonists at brain dopamine receptor subtypes or prodrugs thereof and are useful in the diagnosis and treatment of affective disorders such as schizophrenia and depression as well as certain movement disorders such as Parkinsonism. Futhermore compounds of this invention may be useful in treating the extraparamidyl side effects associated with the use of conventional neuroleptic agents.

  该发明涵盖了以下结构的化合物：##STR1## 其中X、Y、Z、T、R.sub.1、R.sub.3、R.sub.4和R.sub.5是代表各种有机和无机取代基的变量；M是##STR2## R.sub.2和R.sub.6代表氢或烷基取代基；或者R.sub.1和R.sub.2一起可以代表--(CH.sub.2).sub.n1，其中n.sub.1为1、2或3；或NR.sub.4 R.sub.5代表取代或未取代的四氢异喹啉基；或##STR3## 其中n为1、2或3；W为N或CH；R.sub.7代表氢或芳基；或W--R.sub.7为氧或硫。这些化合物在大脑多巴胺受体亚型上高度选择性地作为部分激动剂或拮抗剂或其前药，可用于诊断和治疗情感障碍，如精神分裂症和抑郁症，以及某些运动障碍，如帕金森病。此外，本发明化合物可能有用于治疗与传统神经精神药物使用相关的外围副作用。
• [EN] CERTAIN AMINOMETHYL PHENYLIMIDAZOLE DERIVATIVES; A NEW CLASS OF DOPAMINE RECEPTOR SUBTYPE SPECIFIC LIGANDS<br/>[FR] DERIVES DE L'AMINOMETHYLPHENYLIMIDAZOLE ET NOUVELLE CATEGORIE DE LIGANDS SPECIFIQUES DU SOUS-TYPE DU RECEPTEUR DE LA DOPAMINE
  申请人：NEUROGEN CORPORATION

  公开号：WO1996010018A1

  公开（公告）日：1996-04-04

  (EN) This invention encompasses compounds of formula (I) where R1, R3, R4, R6, X, Y, and Z and T are variables; and M is (a) or (b) where R2 is a variable; or R1 and R2 together may represent -(CH2)n1 where n1 is 1, 2 or 3. These compounds are highly selective partial agonists or antagonists at brain dopamine receptor subtypes or prodrugs thereof and are useful in the diagnosis and treatment of affective disorders such as schizophrenia and depression as well as certain movement disorders such as Parkinsonism. Furthermore, compounds of this invention may be useful in treating the extraparamidyl side effects associated with the use of conventional neuroleptic agents.(FR) L'invention porte sur des composés de formule (I) dans laquelle R1, R3 R4, R6, Z et T sont des variables et M est représenté par les formules (a) ou (b) dans lesquelles R2 est une variable; ou bien R1 et R2 peuvent représenter ensemble -(CH2)n1 où n1 vaut 1, 2 ou 3. Ces composés sont des agonistes ou antagonistes partiels hautement sélectifs des sous-types du récepteur de la dopamine du cerveau ou de leurs précurseurs, et s'avèrent utiles dans le diagnostic et le traitement de troubles affectifs tels que la schizophrénie et la dépression et de troubles moteurs tels que la maladie de Parkinson. Lesdits composés peuvent en outre s'avérer utiles dans le traitement des effets secondaires extraparamidyliques associés à l'utilisation de neuroleptiques usuels.

  该发明涉及公式（I）中的化合物，其中R1、R3、R4、R6、X、Y、Z和T是变量; M是（a）或（b），其中R2是变量; 或者R1和R2可以表示为-（CH2）n1，其中n1为1、2或3。这些化合物是高度选择性的部分激动剂或拮抗剂，作用于脑多巴胺受体亚型或其前药，并可用于诊断和治疗情感障碍，如精神分裂症和抑郁症，以及某些运动障碍，如帕金森病。此外，该发明的化合物可能有助于治疗与传统神经类药物使用相关的外围副作用。
• Certain 4-aryl substituted piperazinyl and piperidinylmethyl
  申请人：Neurogen Corporation

  公开号：US05428164A1

  公开（公告）日：1995-06-27

  This invention encompasses compounds of the formulas: ##STR1## where R.sub.1, R.sub.3, R.sub.4, R.sub.6, X, Y, and Z are T are variables; and M is ##STR2## where R.sub.2 is a variable; or R.sub.1 and R.sub.2 together may represent --(CH.sub.2).sub.n.sbsb.1 where n.sub.1 is 1, 2, or 3. These compounds are highly selective partial agonists or antagonists at brain dopamine receptor subtypes or prodrugs thereof and are useful in the diagnosis and treatment of affective disorders such as schizophrenia and depression as well as certain movement disorders such as Parkinsonism. Furthermore compounds of this invention may be useful in treating the extraparamidyl side effects associated with the use of conventional neuroleptic agents.

  本发明涵盖了以下结构的化合物：##STR1## 其中R.sub.1，R.sub.3，R.sub.4，R.sub.6，X，Y和Z是T变量；而M是##STR2## 其中R.sub.2是一个变量；或R.sub.1和R.sub.2可以代表--(CH.sub.2).sub.n.sbsb.1，其中n.sub.1为1、2或3。这些化合物是高度选择性的部分激动剂或拮抗剂，作用于脑多巴胺受体亚型或其前药，并且在诊断和治疗情感障碍，如精神分裂症和抑郁症，以及某些运动障碍，如帕金森氏症中非常有用。此外，本发明的化合物可能在治疗与使用传统神经精神药物相关的外围副作用方面有用。