ethyl 4(5)-phenyl-1H-imidazole-2-carboxylate | 130493-12-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4(5)-phenyl-1H-imidazole-2-carboxylate
• 英文别名: 4-phenyl-1H-imidazole-2-carboxylic acid ethyl ester；ethyl 4-phenylimidazole-2-carboxylate；2-(ethoxycarbonyl)-4(5)-phenylimidazole；4-phenyl-1H-imidazol-2-carboxylic acid ethyl ester；ethyl 5-phenyl-1H-imidazole-2-carboxylate
• CAS: 130493-12-8
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: DNBIUWPIJOWUEU-UHFFFAOYSA-N

物化性质

• 沸点：
  405.4±38.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4(5)-phenyl-1H-imidazole-2-carboxylate 在 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到(4-phenyl-1H-imidazol-2-yl)methanol
  参考文献：
  名称：

  [DE] PHENYLTHIOESSIGSÄURE-DERIVATE UND IHRE VERWENDUNG
  [EN] PHENYLTHIOACETIC ACID DERIVATIVES AND USE THEREOF
  [FR] DERIVES D'ACIDE PHENYLTHIOACETIQUE ET LEUR UTILISATION

  摘要：

  本申请涉及新的Phenylthioessigsäure衍生物的化学式(I)，其制备方法，其用于治疗和/或预防疾病以及用于制造用于治疗和/或预防疾病的药物，特别是用于治疗和/或预防心血管疾病，特别是治疗和/或预防血脂异常和动脉粥样硬化。这些化合物作为PRAR-alpha受体的调节剂。

  公开号：

  WO2005097784A1
• 作为产物：
  描述：

  2′-氨基苯乙酮 盐酸盐 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 ethyl 4(5)-phenyl-1H-imidazole-2-carboxylate
  参考文献：
  名称：

  Certain 4-aminomethyl-2-substituted imidazole derivatives and 2-aminomethyl-4-substituted imidazole derivatives: new classes of dopamine receptor subtype specific ligands

  摘要：

  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。

  公开号：

  US20030018025A1

文献信息

• [EN] SUBSTITUTED TRICYCLIC 1,4-BENZODIAZEPINONE DERIVATIVES AS ALLOSTERIC MODULATORS OF GROUP II METABOTROPIC GLUTAMATE RECEPTORS<br/>[FR] DÉRIVÉS DE 1,4-BENZODIAZÉPINONE TRICYCLIQUES SUBSTITUÉS EN TANT QUE MODULATEURS ALLOSTÉRIQUES DES RÉCEPTEURS MÉTABOTROPIQUES DU GLUTAMATE DU GROUPE II
  申请人：MAVALON THERAPEUTICS LTD

  公开号：WO2017081483A1

  公开（公告）日：2017-05-18

  The present invention provides novel tricyclic 1,4-benzodiazepinone derivatives of the general formula (I) and pharmaceutical compositions containing them. Moreover, the compounds of formula (I) and the pharmaceutical compositions containing them are provided for use in the treatment and/or prophylaxis of conditions associated with altered glutamatergic signalling and/or functions, and/or conditions which can be affected by alteration of glutamate level or signalling in mammals. The tricyclic 1,4-benzodiazepinone derivatives of formula (I) can act as modulators of nervous system receptors sensitive to glutamate, in particular as modulators of metabotropic glutamate receptors (mGluRs), which makes them particularly suitable for the treatment and/or prophylaxis of acute and chronic neurological and/or psychiatric disorders. The present invention further provides tricyclic 1,4-benzodiazepinone derivatives of formula (I) that are modulators of metabotropic glutamate receptors (mGluRs), particularly positive allosteric modulators of mGluRs, and more specifically positive allosteric modulators of mGluR3. (I)

  本发明提供了一类新型的三环1,4-苯并二氮杂卓酮衍生物，其通式为(I)，以及含有这些化合物的药物组合物。此外，通式(I)的化合物及其药物组合物被提供用于治疗和/或预防与谷氨酸能信号传导和/或功能改变相关的病症，以及可以通过改变哺乳动物中谷氨酸水平或信号传导而受影响的病症。通式(I)的三环1,4-苯并二氮杂卓酮衍生物可以作为神经系统中对谷氨酸敏感的受体调节剂，特别是作为代谢型谷氨酸受体(mGluRs)的调节剂，这使得它们特别适合用于治疗和/或预防急性和慢性神经和/或精神障碍。本发明进一步提供通式(I)的三环1,4-苯并二氮杂卓酮衍生物，它们是代谢型谷氨酸受体(mGluRs)的调节剂，特别是mGluRs的正变构调节剂，更具体地说是mGluR3的正变构调节剂。(I)
• 4-aryl-thiazole derivatives
  申请人：AKZO N.V.

  公开号：US05254575A1

  公开（公告）日：1993-10-19

  The invention concerns a 4-aryl-thiazole or imidazole derivative having the formula I ##STR1## wherein X is 0 or NOH, Y is S or NR.sub.3, Ar is a group selected from phenyl, naphthyl, tetrahydronaphthyl, and biphenyl, R is one to four substituents independently selected from hydrogen, hydroxy, lower alkyl, lower alkoxy, lower thioalkyl, cycloalkyl, halogen, CF.sub.3, NO.sub.2, and O-ALK-NR.sub.1 R.sub.2, in which ALK is a saturated aliphatic hydrocarbon group having 2-6 carbon atoms, and R.sub.1 and R.sub.2 are independently hydrogen or lower alkyl, or form, together with the nitrogen atom to which they are bonded, a heterocyclic ring, and R.sub.3 is hydrogen or a lower alkyl; or a pharmaceutically acceptable salt thereof, with the proviso that 4-(4-chlorophenyl)-thiazole-2-carboxamide is excluded. The compounds according to the invention increase the sensitivity of cardiac myofibrils to calcium and possess phosphodiesterase inhibitory activity and bronchodilator activity, and are useful for the treatment of patients suffering from heart failure and asthma.

  该发明涉及具有以下式I的4-芳基噻唑或咪唑衍生物##STR1##其中X为0或NOH，Y为S或NR.sub.3，Ar为从苯基、萘基、四氢萘基和联苯基中选择的基团，R为独立选择的一个到四个取代基，选自氢、羟基、低烷基、低烷氧基、低硫代烷基、环烷基、卤素、CF.sub.3、NO.sub.2和O-ALK-NR.sub.1 R.sub.2，其中ALK为具有2-6个碳原子的饱和脂肪族碳氢基团，R.sub.1和R.sub.2独立地为氢或低烷基，或者与它们结合，与它们结合形成与氮原子共价的杂环，R.sub.3为氢或低烷基；或其药学上可接受的盐，但排除4-(4-氯苯基)-噻唑-2-甲酰胺。根据该发明的化合物增加心肌原纤维对钙的敏感性，并具有磷酸二酯酶抑制活性和支气管扩张活性，适用于治疗患有心力衰竭和哮喘的患者。
• 4-piperidino- and piperazinomethyl-2-cyclohexyl imidazole derivatives;
  申请人：Neurogen Corporation

  公开号：US05633377A1

  公开（公告）日：1997-05-27

  Disclosed are compounds of the formula: ##STR1## wherein R.sub.1 represents optionally substituted aryl, heteroaryl, arylalkyl, or cycloalkyl groups; X, Z, and Y are optionally substituted nitrogen or carbon atoms; R.sub.3 and R.sub.4 are organic or inorganic substitutents which may together form ring structures; m is zero, one or two; and R.sub.5 and R.sub.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.

  本发明涉及一种公式为：##STR1##的化合物，其中R.sub.1代表可选取代的芳基、杂环芳基、芳基烷基或环烷基基团；X、Z和Y是可选取代的氮或碳原子；R.sub.3和R.sub.4是有机或无机取代基，它们可以一起形成环结构；m为零、一或二；R.sub.5和R.sub.6是有机或无机取代基；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，可作为脑多巴胺受体亚型或其前药在情感障碍，如精神分裂症和抑郁症以及某些运动障碍，如帕金森症的诊断和治疗中使用。
• 4-aryl-imidazole derivatives
  申请人：Akzo N.V.

  公开号：US05462959A1

  公开（公告）日：1995-10-31

  The invention concerns a 4-aryl-imidazole derivative having the formula I ##STR1## wherein X is 0 or NOH, Y is NR.sub.3, Ar is a group selected from phenyl, naphthyl, tetrahydronaphthyl, and biphenyl, R is one to four substituents independently selected from hydrogen, hydroxy, lower alkyl, lower alkoxy, lower thioalkyl, cycloalkyl, halogen, CF.sub.3, NO.sub.2, and O--ALK--NR.sub.1 R.sub.2, in which ALK is a saturated aliphatic hydrocarbon group having 2-6 carbon atoms, and R.sub.1 and R.sub.2 are independently hydrogen or lower alkyl, or form, together with the nitrogen atom to which they are bonded, a heterocyclic ring, and R.sub.3 is hydrogen or a lower alkyl; or a pharmaceutically acceptable salt thereof, with the proviso that 4-(4-chlorophenyl)-thiazole-2-carboxamide is excluded. The compounds according to the invention increase the sensitivity of cardiac myofibrils to calcium and possess phosphodiesterase inhibitory activity and bronchodilator activity, and are useful for the treatment of patients suffering from heart failure and asthma.

  本发明涉及一种具有以下式I的4-芳基咪唑衍生物： ##STR1## 其中X为0或NOH，Y为NR.sub.3，Ar为从苯基、萘基、四氢萘基和联苯基中选择的基团，R为一个到四个取代基，独立地选择自氢、羟基、低碳基、低氧基、低硫代烷基、环烷基、卤素、CF.sub.3、NO.sub.2和O-ALK-NR.sub.1 R.sub.2，其中ALK是具有2-6个碳原子的饱和脂肪族碳氢基团，R.sub.1和R.sub.2独立地为氢或低碳基，或与它们所结合的氮原子一起形成杂环环，R.sub.3为氢或低碳基；或其药学上可接受的盐，但4-(4-氯苯基)-噻唑-2-羧酰胺被排除在外。该发明的化合物增加心脏肌纤维对钙的敏感性，并具有磷酸二酯酶抑制活性和支气管扩张活性，可用于治疗患有心力衰竭和哮喘的患者。
• Certain 4-piperidino- and piperazinomethyl-2-phenyl imidazole
  申请人：Neurogen Corporation

  公开号：US05646281A1

  公开（公告）日：1997-07-08

  Disclosed are compounds of the formula: ##STR1## wherein R.sub.1 represents optionally substituted aryl, heteroaryl, arylalkyl, or cycloalkyl groups; X, Z, and Y are optionally substituted nitrogen or carbon atoms; R.sub.3 and R.sub.4 are organic or inorganic substituents which may together form ring structures; m is zero, one or two; and R.sub.5 and R.sub.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.

  本发明涉及以下化合物：##STR1## 其中R.sub.1代表可选取代的芳基，杂环芳基，芳基烷基或环烷基基团；X，Z和Y是可选取代的氮或碳原子；R.sub.3和R.sub.4是有机或无机取代基，可以共同形成环结构；m为零、一或二；R.sub.5和R.sub.6是有机或无机取代基；以及其药学上可接受的加合盐。这些化合物是高度选择性的部分激动剂或拮抗剂，可作为脑多巴胺受体亚型的诊断和治疗工具，用于情感障碍，如精神分裂症和抑郁症，以及某些运动障碍，如帕金森病。