N-(3-hydroxypropyl) desloratadine | 1239701-59-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并环庚烷吡啶
• 英文名称: N-(3-hydroxypropyl) desloratadine
• 英文别名: 8-chloro-11-1-(1-(3-hydroxypropyl)piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2b]pyridine；3-[4-(13-Chloro-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene)piperidin-1-yl]propan-1-ol
• CAS: 1239701-59-7
• 化学式: C₂₂H₂₅ClN₂O
• 分子量: 368.906
• InChiKey: PUHYGVFHSNFDET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-hydroxypropyl) desloratadine 在 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 2-[3-[4-(13-Chloro-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene)piperidin-1-yl]propyl]isoindole-1,3-dione
  参考文献：
  名称：

  Design, synthesis and biological activity evaluation of desloratadine analogues as H1 receptor antagonists

  摘要：

  A series of N-substituted desloratadine analogues were designed and synthesized. They were tested for H-1 antihistamine activity by inhibiting histamine-induced contraction of isolated ileum muscles of guinea-pigs in vitro and inhibiting histamine-induced asthmatic reaction in guinea-pigs in vivo. All the evaluated compounds exhibited significant antihistamine activity compared with desloratadine. Five active compounds induced no sedative effects on mouse and four of them exhibited lower anticholinergic side effects than desloratadine. Among these analogues, compound 10, (1S,4S)-4-chlorocyclohexyl desloratadine displayed the highest activity and best safety profile. And it was believed to be a potential candidate as the 3rd generation antihistamine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.004
• 作为产物：
  描述：

  methyl 3-[(2-methoxycarbonylethyl)(3-hydroxypropyl)amino]propionate 在 盐酸 、 水 、 sodium methylate 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 24.0h， 生成 N-(3-hydroxypropyl) desloratadine
  参考文献：
  名称：

  Synthesis and antihistamine evaluations of novel loratadine analogues

  摘要：

  A series of loratadine analogues containing hydroxyl group and chiral center were synthesized. The effect of the synthesized compounds on the histamine-induced contractions of guinea-pig ileum muscles was studied. In addition, the in vivo asthma-relieving effect of the analogues in the histamine induced asthmatic reaction in guinea-pigs was determined. Most of the compounds exhibited definite H-1 antihistamine activity. The S-enantiomers, compounds 2, 4 and 8, are more potent than the R-enantiomers, compounds 1, 3 and 7. Compound 6 was the most active one among the eight synthesized compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.012

文献信息

• CN115141229
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and antihistamine evaluations of novel loratadine analogues
  作者：Yue Wang、Juan Wang、Yan Lin、Li-Feng Si-Ma、Dong-hua Wang、Li-Gong Chen、Deng-Ke Liu

  DOI：10.1016/j.bmcl.2011.06.012

  日期：2011.8

  A series of loratadine analogues containing hydroxyl group and chiral center were synthesized. The effect of the synthesized compounds on the histamine-induced contractions of guinea-pig ileum muscles was studied. In addition, the in vivo asthma-relieving effect of the analogues in the histamine induced asthmatic reaction in guinea-pigs was determined. Most of the compounds exhibited definite H-1 antihistamine activity. The S-enantiomers, compounds 2, 4 and 8, are more potent than the R-enantiomers, compounds 1, 3 and 7. Compound 6 was the most active one among the eight synthesized compounds. (C) 2011 Elsevier Ltd. All rights reserved.
• Design, synthesis and biological activity evaluation of desloratadine analogues as H1 receptor antagonists
  作者：Yan Lin、Yue Wang、Li-Feng Sima、Dong-Hua Wang、Xiao-Hui Cao、Li-Gong Chen、Bo Chen

  DOI：10.1016/j.bmc.2013.05.004

  日期：2013.7

  A series of N-substituted desloratadine analogues were designed and synthesized. They were tested for H-1 antihistamine activity by inhibiting histamine-induced contraction of isolated ileum muscles of guinea-pigs in vitro and inhibiting histamine-induced asthmatic reaction in guinea-pigs in vivo. All the evaluated compounds exhibited significant antihistamine activity compared with desloratadine. Five active compounds induced no sedative effects on mouse and four of them exhibited lower anticholinergic side effects than desloratadine. Among these analogues, compound 10, (1S,4S)-4-chlorocyclohexyl desloratadine displayed the highest activity and best safety profile. And it was believed to be a potential candidate as the 3rd generation antihistamine. (C) 2013 Elsevier Ltd. All rights reserved.