tert-butyl 4-methyl-1H-benzimidazole-1-carboxylate | 139525-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: tert-butyl 4-methyl-1H-benzimidazole-1-carboxylate
• 英文别名: 4-methylbenzimidazole-1-carboxylic acid,1,1-dimethylethyl ester；t-butyl 4-methylbenzimidazole-1-carboxylate；1,1-dimethylethyl 4-methyl-1H-benzimidazole-1-carboxylate；t-butyl 4-methyl-1H-benzimidazole-1-carboxylate；tert-butyl 4-methylbenzimidazole-1-carboxylate
• CAS: 139525-24-9
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: WNPRBPBRPPUZSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-methyl-1H-benzimidazole-1-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 sodium ethanolate 、 potassium hydride 作用下， 以 四氯化碳 、 乙醇 、 水 为溶剂， 反应 13.08h， 生成 ethyl α-(dipropylamino)-1H-benzimidazole-4-propanoate
  参考文献：
  名称：

  Dopaminergic and serotonergic activities of imidazoquinolinones and related compounds

  摘要：

  The synthesis of 5-(dipropylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (5), a potent dopamine D2 agonist showing high dopamine/serotonin (5HT1A) selectivity, is described. Dopaminergic activity is associated with the (R)-enantiomer of 5; the (S)-enantiomer shows no dopaminergic activity. A series of analogues where the imidazolone ring was modified to various 5- or 6-membered heterocyclic rings were prepared. Some of these compounds showed a combination of dopaminergic and serotonergic activity, while one compound, 6-(dipropylamino)-1,2,6,7-tetrahydro-3H,5H-pyrido[3,2,1-ij]quinazolin-3-one (24), was a selective serotonergic agonist. Various analogues of 5 where the dipropylamine substituent was modified were prepared. Most of these showed reduced dopaminergic activity, while several were as potent as 5 at the serotonin 5HT1A receptor. Orientations for the new compounds at dopamine and serotonin receptors are proposed and compared with those of other tricyclic ligands known to have high affinity at these receptors.

  DOI：

  10.1021/jm00084a013
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 7 - 甲基-1H -苯并[D]咪唑 在 oil 、 silica gel 、 正己烷 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以hexane as the eluant to give 18.7 g (92%) of t-butyl 4-methyl-1H-benzimidazole-1-carboxylate as an oil的产率得到tert-butyl 4-methyl-1H-benzimidazole-1-carboxylate
  参考文献：
  名称：

  Heterocyclic amines having central nervous system activity

  摘要：

  三环氮含化合物，具有下列结构式的中枢神经系统活性：##STR1##及其药学上可接受的盐，其中R.sub.1、R.sub.2和R.sub.3独立地为氢、C.sub.1-6烷基、烯基或炔基、C.sub.3-10环烷基，或R.sub.1和R.sub.2结合形成可含有额外杂原子的C.sub.3-7环胺；X为氢、C.sub.1-6烷基卤素、羟基、烷氧基、氰基、羧酰胺、羧基或羧基烷氧基；A为SO.sub.2、N、CH、CH.sub.2、CHCH.sub.3、C.dbd.O、C.dbd.S、C-SCH.sub.3、C.dbd.NH、C-NH.sub.2、C-NHCH.sub.3、C--NHCOOCH.sub.3或C--NHCN。B为CH.sub.2、CH、C.dbd.O、N、NH或N--CH.sub.3；n为0或1；D为CH、CH.sub.2、C.dbd.O、O、N、NH或N--CH.sub.3。这些新化合物适用于治疗精神分裂症、帕金森病、焦虑症、抑郁症，或作为降低动物或人体内血压的化合物。

  公开号：

  US05273975A1

文献信息

• [EN] BENZOXAZINONE DERIVATIVES FOR THE TREATMENT OF GLYTL MEDIATED DISORDERS<br/>[FR] DÉRIVÉS DE BENZOXAZINONE POUR TRAITER DES TROUBLES INDUITS PAR GLYTL
  申请人：GLAXO GROUP LTD

  公开号：WO2011012622A1

  公开（公告）日：2011-02-03

  The present invention relates to benzoxazinone derivatives, processes for their preparation, pharmaceutical compositions and medicaments containing them and to their use in treating disorders mediated by GlyT1, including neurological and neuropsychiatric disorders, in particular psychoses, dementia or attention deficit disorder.

  本发明涉及苯并噁唑酮衍生物，其制备方法，含有它们的药物组合物和药物，以及它们在治疗由GlyT1介导的疾病中的应用，包括神经系统和神经精神疾病，特别是精神病、痴呆或注意力缺陷障碍。
• Diaminopropionic acid derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US06331640B1

  公开（公告）日：2001-12-18

  A compound of formula 1a which is useful for treating reperfusion injury, and salts, prodrugs, and related compounds.

  一种用于治疗再灌注损伤的化合物1a及其盐、前药和相关化合物。
• Chemokine receptor binding heterocyclic compounds
  申请人：——

  公开号：US20030028022A1

  公开（公告）日：2003-02-06

  Compounds which modulate chemokine receptor activities are disclosed. These compounds are preferably tertiary amines comprising tetrahydroquinoline and benzimidazole.

  本发明揭示了调节趋化因子受体活性的化合物。这些化合物通常为包含四氢喹啉和苯并咪唑的三级胺。
• HETEROCYCLIC AMINES HAVING CENTRAL NERVOUS SYSTEM ACTIVITY
  申请人：THE UPJOHN COMPANY

  公开号：EP0480939B1

  公开（公告）日：1995-01-25
• GUANIDINYLAMINO HETEROCYCLE COMPOUNDS USEFUL AS ALPHA-2 ADRENOCEPTOR AGONISTS
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0944601B1

  公开（公告）日：2003-02-12