cyclopentylcarbamic acid 4-(4,5-dihydrooxazol-2-yl)phenyl ester | 1165760-89-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cyclopentylcarbamic acid 4-(4,5-dihydrooxazol-2-yl)phenyl ester
• 英文别名: Cyclopentylcarbamic acid 4-(4,5-dihydrooxazol-2-yl)phenylester；[4-(4,5-dihydro-1,3-oxazol-2-yl)phenyl] N-cyclopentylcarbamate
• CAS: 1165760-89-3
• 化学式: C₁₅H₁₈N₂O₃
• 分子量: 274.32
• InChiKey: SAYBKFABPXLSRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(4,5-二氢-2-噁唑)苯酚 、 环戊基异氰酸酯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以90%的产率得到cyclopentylcarbamic acid 4-(4,5-dihydrooxazol-2-yl)phenyl ester
  参考文献：
  名称：

  The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors

  摘要：

  A series of para-substituted phenolic N-alkyl carbamates were evaluated for their FAAH and MGL inhibitory activities. The compounds were generally selective for FAAH, with IC50 values in the nM range, whereas inhibition of MGL required concentrations three orders of magnitude higher. The most potent compounds, dodecylcarbamic acid 4-(4,5-dihydrothiazol-2-yl)phenyl (12) and 4-(1,2,3-thiadiazol-4-yl)phenyl (26) esters, inhibited FAAH and MGL with IC50 values at the low-nanomolar (IC(50)s: 0.0063 and 0.012 mu M) and the low-micromolar ranges (IC(50)s; 2.1 and 1.0 mu M), respectively. Compound 26 also inhibited both FAAH-dependent AEA uptake and AEA hydrolysis (IC50; 0.082 mu M) by intact RBL2H3 cells, and could also reduce 2-AG hydrolysis by these cells at concentrations >= 0.030 mu M. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.01.007

文献信息

• The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors
  作者：Anna Minkkilä、Mikko J. Myllymäki、Susanna M. Saario、Joel A. Castillo-Melendez、Ari M.P. Koskinen、Christopher J. Fowler、Jukka Leppänen、Tapio Nevalainen

  DOI：10.1016/j.ejmech.2009.01.007

  日期：2009.7

  A series of para-substituted phenolic N-alkyl carbamates were evaluated for their FAAH and MGL inhibitory activities. The compounds were generally selective for FAAH, with IC50 values in the nM range, whereas inhibition of MGL required concentrations three orders of magnitude higher. The most potent compounds, dodecylcarbamic acid 4-(4,5-dihydrothiazol-2-yl)phenyl (12) and 4-(1,2,3-thiadiazol-4-yl)phenyl (26) esters, inhibited FAAH and MGL with IC50 values at the low-nanomolar (IC(50)s: 0.0063 and 0.012 mu M) and the low-micromolar ranges (IC(50)s; 2.1 and 1.0 mu M), respectively. Compound 26 also inhibited both FAAH-dependent AEA uptake and AEA hydrolysis (IC50; 0.082 mu M) by intact RBL2H3 cells, and could also reduce 2-AG hydrolysis by these cells at concentrations >= 0.030 mu M. (C) 2009 Elsevier Masson SAS. All rights reserved.