2-<4-(chloropropoxy)phenyl>imidazo<1,2-a>pyrimidine | 115407-31-3

• 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-<4-(chloropropoxy)phenyl>imidazo<1,2-a>pyrimidine
• 英文别名: 2-[4-(chloropropoxy)phenyl]imidazo[1,2-a]pyrimidine；2-[4-(3-Chloropropoxy)phenyl]imidazo[1,2-a]pyrimidine
• CAS: 115407-31-3
• 化学式: C₁₅H₁₄ClN₃O
• 分子量: 287.749
• InChiKey: GSEZHQBHGMMKBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-methoxyphenyl)piperazine hydrochloride 、 2-<4-(chloropropoxy)phenyl>imidazo<1,2-a>pyrimidine 在 potassium carbonate 、 5-甲基-2-己酮 作用下， 反应 10.0h， 生成 2-[4-[3-[4-(2-Methoxyphenyl)piperazin-1-yl]propoxy]phenyl]imidazo[1,2-a]pyrimidine
  参考文献：
  名称：

  Laszlovszky; Acs; Kiss, Pharmazie, 2001, vol. 56, # 4, p. 287 - 289

  摘要：

  DOI：
• 作为产物：
  描述：

  1-[4-(3-chloropropoxy)phenyl]ethanone 在 溴 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 24.0h， 生成 2-<4-(chloropropoxy)phenyl>imidazo<1,2-a>pyrimidine
  参考文献：
  名称：

  Synthesis of (aryloxy)alkylamines. 2. Novel imidazo-fused heterocycles with calcium channel blocking and local anesthetic activity

  摘要：

  A series of imidazo-fused heterocycles substituted with an aryloxy)alkylamine side chain were prepared as modifications to butoprozine (I) and found to possess calcium channel blocking activity similar in potency to that of bepridil in trachea smooth muscle and similar to that of verapamil in nitrendipine binding affinity in rabbit cardiac muscle. Of the various imidazo-fused heterocycles prepared, the imidazo[1,2-a]pyridines were also found to be potent local anesthetic agents. While most compounds in this series were equipotent to lidocaine in our initial screen, compounds 2 and 35 showed local anesthetic activity approximately 100 times more potent than lidocaine in our preliminary assays. These compounds represent a novel structural class of local anesthetic agents, and compound 2 is under further investigation.

  DOI：

  10.1021/jm00119a026

文献信息

• [EN] 2-METHOXYPHENYLPIPERAZINE DERIVATIVES<br/>[FR] DERIVES DE LA 2-METHOXYPHENYLPIPERAZINE
  申请人：RICHTER GEDEON VEGYÉSZETI GYÁR RT.

  公开号：WO1998018797A1

  公开（公告）日：1998-05-07

  (EN) The invention relates to novel fused heterocyclic compounds with ring junction nitrogen atom of formula (I), wherein Q stands for 2-indolizinyl, 2-imidazo[1,2-a]pyridinyl, 2-imidazo[1,2-a]pyrimidinyl, 6-(2,3-dihydroimidazo[2,1-b]thiazol)-yl or 6-imidazo[2,1-b]thiazolyl group; and n is an integer from 2 to 4, as well as their therapeutically useful salts thereof. The invention further relates to pharmaceutical compositions containing these compounds as well as a process for the preparation of the above compounds and compositions. The novel compounds of formula (I) exhibit mainly antipsychotic effects so the invention relates also to a method of treatment of schizophrenia, organic mental disorders, affective disorders, anxiety and personality disorders.(FR) L'invention concerne de nouveaux composés hétérocycliques condensés avec un atome d'azote à la jonction du cycle, de formule (I), dans laquelle Q représente les groupes 2-indolizinyle, 2-imidazo[1,2-a]pyridinyle, 2-imidazo[1,2-a]pyrimidinyle, 6-(2,3-dihydroimidazo[2,1-b]thiazol)-yle ou 6-imidazo[2,1-b]thiazolyle, et n est un entier compris entre 2 et 4, ainsi que leurs sels utiles sur le plan thérapeutique. L'invention concerne également des compositions pharmaceutiques contenant lesdits composés, ainsi qu'un procédé permettant de préparer lesdits composés et compositions. Les nouveaux composés de formule (I) présentent une activité principalement antipsychotique, si bien que l'invention concerne également une méthode permettant de traiter la schizophrénie, les troubles mentaux organiques, les troubles affectifs, l'angoisse et les troubles de la personnalité.

  本发明涉及具有公式（I）中环节氮原子的新型融合杂环化合物，其中Q代表2-吲哚啉基，2-咪唑[1,2-a]吡啶基，2-咪唑[1,2-a]嘧啶基，6-(2,3-二氢咪唑[2,1-b]噻唑)-基或6-咪唑[2,1-b]噻唑基；n为2至4的整数，以及它们的治疗有用的盐。本发明还涉及含有这些化合物的制药组合物以及上述化合物和组合物的制备方法。公式（I）的新型化合物主要表现为抗精神病作用，因此本发明还涉及一种治疗精神分裂症、器质性心理障碍、情感障碍、焦虑和人格障碍的方法。
• SANFILIPPO, PAULINE J.;URBANSKI, MAUD;PRESS, JEFFERY B.;DUBINSKY, BARRY;M+, J. MED. CHEM., 31,(1988) N 11, C. 2201-2227
  作者：SANFILIPPO, PAULINE J.、URBANSKI, MAUD、PRESS, JEFFERY B.、DUBINSKY, BARRY、M+

  DOI：——

  日期：——
• 2-METHOXYPHENYLPIPERAZINE DERIVATIVES
  申请人：RICHTER GEDEON VEGYESZETI GYAR R.T.

  公开号：EP0935599A1

  公开（公告）日：1999-08-18
• US6103724A
  申请人：——

  公开号：US6103724A

  公开（公告）日：2000-08-15
• Synthesis of (aryloxy)alkylamines. 2. Novel imidazo-fused heterocycles with calcium channel blocking and local anesthetic activity
  作者：Pauline J. Sanfilippo、Maud Urbanski、Jeffery B. Press、Barry Dubinsky、John B. Moore

  DOI：10.1021/jm00119a026

  日期：1988.11

  A series of imidazo-fused heterocycles substituted with an aryloxy)alkylamine side chain were prepared as modifications to butoprozine (I) and found to possess calcium channel blocking activity similar in potency to that of bepridil in trachea smooth muscle and similar to that of verapamil in nitrendipine binding affinity in rabbit cardiac muscle. Of the various imidazo-fused heterocycles prepared, the imidazo[1,2-a]pyridines were also found to be potent local anesthetic agents. While most compounds in this series were equipotent to lidocaine in our initial screen, compounds 2 and 35 showed local anesthetic activity approximately 100 times more potent than lidocaine in our preliminary assays. These compounds represent a novel structural class of local anesthetic agents, and compound 2 is under further investigation.