(E)-2-[(3-cyclopentyloxy-4-methoxyphenyl)methylene]hydrazinecarboximidamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-2-[(3-cyclopentyloxy-4-methoxyphenyl)methylene]hydrazinecarboximidamide
• 英文别名: 2-[(E)-(3-cyclopentyloxy-4-methoxyphenyl)methylideneamino]guanidine
• 化学式: C₁₄H₂₀N₄O₂
• 分子量: 276.338
• InChiKey: YKAJIJIRGVGKAB-RQZCQDPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  溴代环戊烷 在 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-2-[(3-cyclopentyloxy-4-methoxyphenyl)methylene]hydrazinecarboximidamide
  参考文献：
  名称：

  Improvement of therapeutic index of phosphodiesterase type IV inhibitors as anti-Asthmatics

  摘要：

  A new series of catechol hydrazines was synthesized and their structure-activity relationship (SAR) was analyzed for developing an effective phosphodiesterase 4 (PDE4) inhibitor as an anti-asthmatic drug candidate. Among the (E)-Analogues tested using in vitro assays, 5CC showed a strong PDE4 inhibitory activity and a significantly improved rolipram binding profile compared with rolipram, a prototype PDE4 inhibitor. Moreover, from in-vivo asthma model, we observed that (E)-Analogue 5CC had a good efficacy against guinea-pig respiratory tract inflammation and bronchoconstriction, along with a remarkably reduced emetic side effect, compared with rolipram. Conclusively, (E)-Analogue 5CC seems to be a promising candidate for the development of anti-asthmatic PDE4 inhibitors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00405-0

文献信息

• CATHECOL HYDRAZONE DERIVATIVES, PROCESS FOR PREPARING THE SAME AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME
  申请人：Cheil Jedang Corporation

  公开号：EP1187817A1

  公开（公告）日：2002-03-20
• US6610715B1
  申请人：——

  公开号：US6610715B1

  公开（公告）日：2003-08-26
• [EN] CATHECOL HYDRAZONE DERIVATIVES, PROCESS FOR PREPARING THE SAME AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME<br/>[FR] DERIVES DE CATHECOL-HYDRAZONE, PROCEDE DE PREPARATION CORRESPONDANT, ET COMPOSITION PHARMACEUTIQUE RENFERMANT LESDITS DERIVES
  申请人：CHEIL JEDANG CORP

  公开号：WO2000073280A1

  公开（公告）日：2000-12-07

  The present invention provides novel cathecol hydrazone derivatives of formula (I) or pharmaceutically acceptable salts thereof, wherein R1 is C¿1-7? alkyl or C3-7 cycloalkyl; R?2¿ is hydrogen, hydroxy, C¿1-5? alkyl or -CH2CH2C(=O)NH2; R?3 and R4¿ are independently hydrogen, C¿1-7? alkyl, -C(=X)-R?5¿, or 2-, 3- or 4-pyridyl, prymidyl or phenyl substituted with one or two selected from a group consisting of halogen, C¿1-6? alkoxy, nitro, trifluoromethyl, C1-6 alkyl and carboxyl, or R?3 and R4¿ are directly bonded by C¿3-4? containing oxygen, sulfur or nitrogen to form a heterocyclic ring, X is oxygen, sulfur or NH and R?5¿ is C¿1-7? alkyl, -NHR?6¿, CONH¿2? or 2-, 3- or 4-pyridyl, prymidyl or phenyl substituted with one selected from a group consisting of halogen, C1-6 alkoxy, nitrile, trifluoromethyl, C1-6 alkyl and carboxyl, and R?6¿ is hydrogen, hydroxy, NH¿2?, C1-5 alkoxy, C1-5 alkyl, pyridyl or phenyl.
• Improvement of therapeutic index of phosphodiesterase type IV inhibitors as anti-Asthmatics
  作者：Euikyung Kim、Hyung-Ok Chun、Sung-Hak Jung、Jong Hoon Kim、Jae-Mok Lee、Byung-Chul Suh、Myung Xik Xiang、Chung K Rhee

  DOI：10.1016/s0960-894x(03)00405-0

  日期：2003.7

  A new series of catechol hydrazines was synthesized and their structure-activity relationship (SAR) was analyzed for developing an effective phosphodiesterase 4 (PDE4) inhibitor as an anti-asthmatic drug candidate. Among the (E)-Analogues tested using in vitro assays, 5CC showed a strong PDE4 inhibitory activity and a significantly improved rolipram binding profile compared with rolipram, a prototype PDE4 inhibitor. Moreover, from in-vivo asthma model, we observed that (E)-Analogue 5CC had a good efficacy against guinea-pig respiratory tract inflammation and bronchoconstriction, along with a remarkably reduced emetic side effect, compared with rolipram. Conclusively, (E)-Analogue 5CC seems to be a promising candidate for the development of anti-asthmatic PDE4 inhibitors. (C) 2003 Elsevier Science Ltd. All rights reserved.