2-[2-(4-Methylphenyl)morpholin-4-yl]ethanol | 763912-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-[2-(4-Methylphenyl)morpholin-4-yl]ethanol
• CAS: 763912-54-5
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: ZFHLVXABFGPNCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[2-(4-Methylphenyl)morpholin-4-yl]ethanol 以 苯 为溶剂， 反应 12.0h， 生成 2-[2-(4-甲基苯基)吗啉-4-基]乙基吗啉-4-羧酸酯盐酸盐
  参考文献：
  名称：

  Synthesis, toxicological and pharmacological assessment of esters of carbonic and carbamic acids with 2-aryl-4-hydroxyethylmorpholines

  摘要：

  The synthesis of 15 original morpholine derivatives from 4-hydroxyethyl-2-arylmorpholines is described. The structures of the synthesized esters were proved by LR, H-1-NMR and C-13-NMR data. Acute toxicity studies of the compounds were performed on mice. A comparative pharmacological study of the in vivo effect on the central nervous system was realized by certain screening tests: hexobarbital-induced sleeping time, locomotor activity and behavior despair test for antidepressants. The results indicate that some of the compounds are less toxic than the reference drug Moclobemide (Aurorix). Compound 2d, 2-(4-bromphenyl)-4-(2-phenyloxycarbonyloxyethyl)morpholine, has a low toxicity and weak dose-dependent antidepressive activity. This compound does not influence hexobarbital-induced sleeping time or locomotor activity of mice.

  DOI：

  10.1016/s0223-5234(97)89855-8
• 作为产物：
  描述：

  2-溴-4'-甲基苯乙酮 在 甲酸 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 20.0h， 生成 2-[2-(4-Methylphenyl)morpholin-4-yl]ethanol
  参考文献：
  名称：

  吲哚美辛的2-（2-芳基吗啉代-4-基）乙基酯作为潜在的环氧合酶2（COX-2）抑制剂的设计，合成和生物学评估

  摘要：

  合成了许多新型的2-（2-芳基吗啉代-4-基）乙基1-（4-氯苯甲酰基）-5-甲氧基-2-甲基-1 H-吲哚-3-乙酸盐酸盐，并测试了其环氧合酶（COX ‐1和COX‐2）体外抑制特性。这些化合物中的许多化合物都表现出中等至良好的选择性COX-2抑制作用，并且酯部分侧链上取代基的细微结构变化显着改变了抑制性能。2- [2-（4-丁氧基苯基）吗啉代-4-基]乙基1-（4-氯苯甲酰基）-5-甲氧基-2-甲基-1 H-吲哚-3-乙酸盐酸盐（1f）具有良好的选择性COX-2抑制活性（选择性指数（SI）182），与二芳基吡唑的COX-2抑制剂塞来昔布（SI 214）比较。而2- [2-（2-（2,4-二氯-5-氟苯基）吗啉代-4-基]乙基1-（4-氯苯甲酰基）-5-甲氧基-2-甲基-1 H-吲哚-3-乙酸盐酸盐（1g）比塞来昔布具有更高的选择性COX-2抑制活性（SI 358）。两种化合物均被认为是

  DOI：

  10.1002/cjoc.201200196

文献信息

• Synthesis and Evaluation of 2-(2-Arylmorpholino)ethyl Esters of Ibuprofen Hydrochlorides as COX-2 and Serotonin Reuptake Inhibitors
  作者：Jie Dou、Lei Shi、Aixi Hu、Minyu Dong、Jiangping Xu、Ailin Liu、Yiping Jiang

  DOI：10.1002/ardp.201300279

  日期：2014.2

  COX‐2 inhibitors on depressive symptoms and the desirable physicochemical and biological properties of the morpholine group, a series of novel 2‐(2‐arylmorpholino)ethyl esters of ibuprofen hydrochlorides were designed, synthesized, and tested for their COX‐2 inhibitory and serotonin reuptake inhibitory activities in vitro. The structure–activity relationships of the 2‐(2‐arylmorpholino)ethyl esters

  基于 COX-2 抑制剂对抑郁症状的积极作用以及吗啉组的理想理化和生物学特性，设计、合成了一系列新型布洛芬盐酸盐的 2-(2-芳基吗啉)乙酯并测试了它们的作用。体外 COX-2 抑制和血清素再摄取抑制活性。确定并详细讨论了盐酸布洛芬的 2-（2-芳基吗啉代）乙酯作为 COX-2 和血清素再摄取双重抑制剂的构效关系。生物测定表明，其中五种化合物具有良好的 COX-2 选择性（选择性指数 COX-1/COX-2 42.8-158.1）。化合物2-[2-(4-苄氧基苯基)吗啉代]乙基2-(4-异丁基苯基)-丙酸酯盐酸盐(1k)显示出更好的COX-2抑制活性(IC50 = 0。
• Design, Synthesis and Biological Evaluation of 2-(2-Aryl-morpholino-4-yl)ethyl Esters of Indomethacin as Potential Cyclooxygenase-2 (COX-2) Inhibitors
  作者：Lei Shi、Aixi Hu、Jiangping Xu、Yiping Jiang

  DOI：10.1002/cjoc.201200196

  日期：2012.6

  significantly. 2‐[2‐(4‐Butoxyphenyl)morpholino‐4‐yl]ethyl 1‐(4‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1H‐indol‐3‐acetate hydrochloride (1f), showed good selective COX‐2 inhibitory activity (Selective index (SI) 182), which is comparative with celecoxib (SI 214), a COX‐2 inhibitor of diarylpyrazoles. While 2‐[2‐(2,4‐dichloro‐5‐fluorophenyl)morpholino‐4‐yl]ethyl 1‐(4‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1H‐indol‐3‐acetate

  合成了许多新型的2-（2-芳基吗啉代-4-基）乙基1-（4-氯苯甲酰基）-5-甲氧基-2-甲基-1 H-吲哚-3-乙酸盐酸盐，并测试了其环氧合酶（COX ‐1和COX‐2）体外抑制特性。这些化合物中的许多化合物都表现出中等至良好的选择性COX-2抑制作用，并且酯部分侧链上取代基的细微结构变化显着改变了抑制性能。2- [2-（4-丁氧基苯基）吗啉代-4-基]乙基1-（4-氯苯甲酰基）-5-甲氧基-2-甲基-1 H-吲哚-3-乙酸盐酸盐（1f）具有良好的选择性COX-2抑制活性（选择性指数（SI）182），与二芳基吡唑的COX-2抑制剂塞来昔布（SI 214）比较。而2- [2-（2-（2,4-二氯-5-氟苯基）吗啉代-4-基]乙基1-（4-氯苯甲酰基）-5-甲氧基-2-甲基-1 H-吲哚-3-乙酸盐酸盐（1g）比塞来昔布具有更高的选择性COX-2抑制活性（SI 358）。两种化合物均被认为是
• Synthesis, toxicological and pharmacological assessment of esters of carbonic and carbamic acids with 2-aryl-4-hydroxyethylmorpholines
  作者：PD Avramova、ND Danchev、RT Buyukliev

  DOI：10.1016/s0223-5234(97)89855-8

  日期：1996.1

  The synthesis of 15 original morpholine derivatives from 4-hydroxyethyl-2-arylmorpholines is described. The structures of the synthesized esters were proved by LR, H-1-NMR and C-13-NMR data. Acute toxicity studies of the compounds were performed on mice. A comparative pharmacological study of the in vivo effect on the central nervous system was realized by certain screening tests: hexobarbital-induced sleeping time, locomotor activity and behavior despair test for antidepressants. The results indicate that some of the compounds are less toxic than the reference drug Moclobemide (Aurorix). Compound 2d, 2-(4-bromphenyl)-4-(2-phenyloxycarbonyloxyethyl)morpholine, has a low toxicity and weak dose-dependent antidepressive activity. This compound does not influence hexobarbital-induced sleeping time or locomotor activity of mice.