4-(2-phenoxyethyl)-morpholine hydrochloride | 29488-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(2-phenoxyethyl)-morpholine hydrochloride
• 英文别名: N-(2-phenoxyethyl)morpholine HCl salt；4-(2-phenoxyethyl)morpholine;hydrochloride
• CAS: 29488-54-8
• 化学式: C₁₂H₁₇NO₂*ClH
• 分子量: 243.733
• InChiKey: BUFDKUZHXRBYBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-苯氧基乙基)吗啉 、 4-(2-phenoxyethyl)-morpholine hydrochloride 在 氯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 [2-(morpholin-4-yl)ethoxy]benzene-4-sulfonyl chloride 、 4-(3-morpholinopropoxy)benzene-1-sulfonyl chloride
  参考文献：
  名称：

  Prodrugs of proton pump inhibitors

  摘要：

  该类型的吡啶甲基亚砜基苯并咪唑类质子泵抑制剂药物的前药，其将可水解的芳基磺酰基或杂环芳基磺酰基连接到咪唑类氮原子上。本发明的前药在生理条件下水解，提供半衰期可在小时内测量的质子泵抑制剂，并能够提供比目前使用的药物更长时间的持续血浆浓度。在生理条件下从本发明的前药生成质子泵抑制剂药物，可更有效地治疗由胃酸分泌引起的多种疾病和症状。

  公开号：

  US06559167B1
• 作为产物：
  描述：

  4-(2-氯乙基)吗啉 、 苯酚 在 potassium carbonate 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 乙醚 为溶剂， 反应 18.0h， 以75%的产率得到4-(2-phenoxyethyl)-morpholine hydrochloride
  参考文献：
  名称：

  Synthesis, binding and structure–affinity studies of new ligands for the microsomal anti-estrogen binding site (AEBS)

  摘要：

  New compounds have been synthesized based on the structure of the anti-tumoral drug tamoxifen and its diphenylmethane derivative, N,N-diethyl-2-[(4-phenyl-methyl)-phenoxy]-ethanamine HCl (DPPE). These new compounds have no affinity for the estrogen receptor (ER) and bind with various affinity to the anti-estrogen binding site (AEBS). Compounds 2, 10, 12, 13, 20a, 20b, 23a, 23b, 29 exhibited 1.1- 69.5 higher affinity than DPPE, and compounds 23a and 23b have 1.2 and 3.5 higher affinity than tamoxifen. Three-dimensional structure analysis, performed using the intersection of the van der Waals volume occupied by tamoxifen in its crystallographic state and the van der Waals volume of these new compounds in their calculated minimal energy conformation, correlated well with their pki for AEBS (r = 0.84, P < 0.0001, n = 18). This is the first structure-affinity relationship (SAR) ever reported for AEBS ligands. Moreover in this study we have reported the synthesis of new compounds of higher affinity than the lead compounds and that are highly specific for AEBS. Since these compounds do not bind ER they will be helpful to study AEBS mediated cytotoxicity. Moreover our study shows that our strategy is a new useful guide to design high affinity and selective ligands for AEBS. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00119-x

文献信息

• PRODRUGS OF PROTON PUMP INHIBITORS
  申请人：Winston Pharmateuticals LLC

  公开号：EP1105387B1

  公开（公告）日：2003-01-29
• US6559167B1
  申请人：——

  公开号：US6559167B1

  公开（公告）日：2003-05-06
• Synthesis, binding and structure–affinity studies of new ligands for the microsomal anti-estrogen binding site (AEBS)
  作者：Marc Poirot、Philippe De Medina、Frederic Delarue、Jean-Jacques Perie、Alain Klaebe、Jean-Charles Faye

  DOI：10.1016/s0968-0896(00)00119-x

  日期：2000.8

  New compounds have been synthesized based on the structure of the anti-tumoral drug tamoxifen and its diphenylmethane derivative, N,N-diethyl-2-[(4-phenyl-methyl)-phenoxy]-ethanamine HCl (DPPE). These new compounds have no affinity for the estrogen receptor (ER) and bind with various affinity to the anti-estrogen binding site (AEBS). Compounds 2, 10, 12, 13, 20a, 20b, 23a, 23b, 29 exhibited 1.1- 69.5 higher affinity than DPPE, and compounds 23a and 23b have 1.2 and 3.5 higher affinity than tamoxifen. Three-dimensional structure analysis, performed using the intersection of the van der Waals volume occupied by tamoxifen in its crystallographic state and the van der Waals volume of these new compounds in their calculated minimal energy conformation, correlated well with their pki for AEBS (r = 0.84, P < 0.0001, n = 18). This is the first structure-affinity relationship (SAR) ever reported for AEBS ligands. Moreover in this study we have reported the synthesis of new compounds of higher affinity than the lead compounds and that are highly specific for AEBS. Since these compounds do not bind ER they will be helpful to study AEBS mediated cytotoxicity. Moreover our study shows that our strategy is a new useful guide to design high affinity and selective ligands for AEBS. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Prodrugs of proton pump inhibitors
  申请人：Regents of the University of California

  公开号：US06559167B1

  公开（公告）日：2003-05-06

  Prodrugs of the pyridyl methyl sulfinyl benzimidazole type proton pump inhibitor drugs have a hydrolyzable arylsulfonyl or heteroarylsulfonyl group attached to the benzimidazole nitrogen. The prodrugs of the invention hydrolyze under physiological conditions to provide the proton pump inhibitors with a half life measurable in hours, and are capable of providing sustained plasma concentrations of the proton pump inhibitor drugs for longer time than presently used drugs. The generation of the proton pump inhibitor drugs from the prodrugs of the invention under physiological conditions allows for more effective treatment of several diseases and conditions caused by gastric acid secretion.

  该类型的吡啶甲基亚砜基苯并咪唑类质子泵抑制剂药物的前药，其将可水解的芳基磺酰基或杂环芳基磺酰基连接到咪唑类氮原子上。本发明的前药在生理条件下水解，提供半衰期可在小时内测量的质子泵抑制剂，并能够提供比目前使用的药物更长时间的持续血浆浓度。在生理条件下从本发明的前药生成质子泵抑制剂药物，可更有效地治疗由胃酸分泌引起的多种疾病和症状。