2-(4-乙酰基氨基苯氧基)乙酸甲酯 | 220299-99-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4-乙酰基氨基苯氧基)乙酸甲酯
• 英文名称: methyl 2-(4-acetylaminophenoxy)acetate
• 英文别名: methyl 2-(4-acetamidophenoxy)acetate；(4-acetylamino-phenoxy)-acetic acid methyl ester；(4-Acetylamino-phenoxy)-essigsaeure-methylester；4-Acetamino-phenoxyessigsaeure-methylester；methyl (4-acetaminophenoxy)acetate；Methyl [4-(acetylamino)phenoxy]acetate
• CAS: 220299-99-0
• 化学式: C₁₁H₁₃NO₄
• mdl: MFCD03899149
• 分子量: 223.229
• InChiKey: DPOLBUJUVCUNQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-乙酰基氨基苯氧基)乙酸甲酯 在 一水合肼 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 19.0h， 生成 N-(4-[(5-sulfanyl-1,3,4-oxadiazol-2yl)methoxy]phenyl)acetamide
  参考文献：
  名称：

  具有抗惊厥活性的1,3,4-恶二唑衍生物的合成及其与GABAA受体的结合。

  摘要：

  在这项研究中，设计了一系列1,3,4-恶二唑衍生物（5a-s，10a-s和16a-d），并使用最大电击（MES）模型和皮下戊四氮（sc PTZ）模型进行了合成，以进行测试目标化合物在体内的抗惊厥活性。使用旋转棒（ROT）方法测量目标化合物的神经毒性（NT）。选择了具有潜在活性的七种化合物来测试50％有效剂量（ED 50）和50％有毒剂量（TD 50）。药理实验表明，6-（（5-（戊硫基）-1,3,4-恶二唑-2-基）甲氧基）-3,4-二氢喹啉-2（1 H）-一（5b）表现出最佳的抗惊厥活性（MES，ED 50  = 8.9 mg / kg; sc PTZ，ED 50  = 10.2 mg / kg），大于卡马西平和乙磺酰亚胺的活性。在体外结合实验中，化合物5b对GABA A受体表现出最强的结合亲和力（IC 50  = 0.11μM）。在高架迷宫（EPM）测试中，化合物5b在低剂量（1 mg

  DOI：

  10.1016/j.ejmech.2020.112672
• 作为产物：
  描述：

  对乙酰氨基酚 、 氯乙酸甲酯 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 18.0h， 以81.1%的产率得到2-(4-乙酰基氨基苯氧基)乙酸甲酯
  参考文献：
  名称：

  Design and synthesis of newer potential 4-(N-acetylamino)phenol derived piperazine derivatives as potential cognition enhancers

  摘要：

  A series of novel hybrids has been designed, synthesized and evaluated for cognition enhancing activities through the inhibition of acetylcholinesterase (AChE) and by passive avoidance mouse model. All the compounds showed excellent AChE inhibition activities and potentially reversed the scopolamine induced memory deficit. Enzyme kinetic and molecular docking studies have confirmed their dual binding affinity and mixed type inhibition. Among them, compounds 1b and 2d displayed excellent IC50 values of 1.66 mu M and 0.49 mu M and competitive inhibitor constant K-i 43.66 mu M and 4.10 mu M respectively. Ex vivo study confirmed their CNS penetration and brain AChE inhibition abilities. Furthermore, 1b and 2d showed significant antiamnesic activity at a dose of 1.0 mg/kg as compared to the reference compounds piracetam and rivastigmine. The results indicate that these two compounds emerged to be developed as cognition enhancers worthy of future pursuit. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.04.004

文献信息

• Substituted piperidine compounds useful as modulators of chemokine receptor activity
  申请人：Thom Stephen

  公开号：US06903085B1

  公开（公告）日：2005-06-07

  The invention provides compounds of formula (I) wherein R 1 , R 2 , R 3 , R 6 , Z, Q, m, n, X 1 , X 2 , X 3 , X 4 and T are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them, and their use in therapy, especially for the treatment of chemokine receptor related diseases and conditions

  这项发明提供了式（I）中R1、R2、R3、R6、Z、Q、m、n、X1、X2、X3、X4和T的化合物，其制备方法，含有它们的药物组合物，以及它们在治疗中的应用，特别是用于治疗与趋化因子受体相关的疾病和症状。
• Jindal, Dharam Paul; Coumar, Mohane S.; Singh, Babita, Arzneimittel-Forschung/Drug Research, 2003, vol. 53, # 1, p. 34 - 39
  作者：Jindal, Dharam Paul、Coumar, Mohane S.、Singh, Babita、Mohammed Ismail, Mohammed Muhiyiden、Zambare, Girish Nilkanth、Bodhankar, Subhash Laxmanrao

  DOI：——

  日期：——
• DE96492
  申请人：——

  公开号：——

  公开（公告）日：——
• Design and synthesis of newer potential 4-(N-acetylamino)phenol derived piperazine derivatives as potential cognition enhancers
  作者：Poonam Piplani、Chhanda Charan Danta

  DOI：10.1016/j.bioorg.2015.04.004

  日期：2015.6

  A series of novel hybrids has been designed, synthesized and evaluated for cognition enhancing activities through the inhibition of acetylcholinesterase (AChE) and by passive avoidance mouse model. All the compounds showed excellent AChE inhibition activities and potentially reversed the scopolamine induced memory deficit. Enzyme kinetic and molecular docking studies have confirmed their dual binding affinity and mixed type inhibition. Among them, compounds 1b and 2d displayed excellent IC50 values of 1.66 mu M and 0.49 mu M and competitive inhibitor constant K-i 43.66 mu M and 4.10 mu M respectively. Ex vivo study confirmed their CNS penetration and brain AChE inhibition abilities. Furthermore, 1b and 2d showed significant antiamnesic activity at a dose of 1.0 mg/kg as compared to the reference compounds piracetam and rivastigmine. The results indicate that these two compounds emerged to be developed as cognition enhancers worthy of future pursuit. (C) 2015 Elsevier Inc. All rights reserved.
• Synthesis of 1,3,4-oxadiazole derivatives with anticonvulsant activity and their binding to the GABAA receptor
  作者：Shiben Wang、Hui Liu、Xuekun Wang、Kang Lei、Guangyong Li、Jun Li、Renmin Liu、Zheshan Quan

  DOI：10.1016/j.ejmech.2020.112672

  日期：2020.11

  4-dihydroquinolin-2(1H)-one (5b) showed the best anticonvulsant activity (MES, ED50 = 8.9 mg/kg; scPTZ, ED50 = 10.2 mg/kg), which was greater than the activities of carbamazepine and ethosuximide. Compound 5b exhibited the most potent binding affinity toward the GABAA receptor (IC50 = 0.11 μM) in the in vitro binding experiments. Compound 5b displayed significant anxiolytic activity at a low dose (1 mg/kg) in the elevated

  在这项研究中，设计了一系列1,3,4-恶二唑衍生物（5a-s，10a-s和16a-d），并使用最大电击（MES）模型和皮下戊四氮（sc PTZ）模型进行了合成，以进行测试目标化合物在体内的抗惊厥活性。使用旋转棒（ROT）方法测量目标化合物的神经毒性（NT）。选择了具有潜在活性的七种化合物来测试50％有效剂量（ED 50）和50％有毒剂量（TD 50）。药理实验表明，6-（（5-（戊硫基）-1,3,4-恶二唑-2-基）甲氧基）-3,4-二氢喹啉-2（1 H）-一（5b）表现出最佳的抗惊厥活性（MES，ED 50  = 8.9 mg / kg; sc PTZ，ED 50  = 10.2 mg / kg），大于卡马西平和乙磺酰亚胺的活性。在体外结合实验中，化合物5b对GABA A受体表现出最强的结合亲和力（IC 50  = 0.11μM）。在高架迷宫（EPM）测试中，化合物5b在低剂量（1 mg