N'-[1-(4-hydroxy-phenyl)-ethylidene]-hydrazinecarboxylic acid ethyl ester | 59834-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N'-[1-(4-hydroxy-phenyl)-ethylidene]-hydrazinecarboxylic acid ethyl ester
• 英文别名: ethyl N-[1-(4-hydroxyphenyl)ethylideneamino]carbamate
• CAS: 59834-03-6
• 化学式: C₁₁H₁₄N₂O₃
• 分子量: 222.244
• InChiKey: CLJBVUUDSXMRPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N'-[1-(4-hydroxy-phenyl)-ethylidene]-hydrazinecarboxylic acid ethyl ester 在 氯化亚砜 作用下， 以85%的产率得到4-(1,2,3-噻重氮-4-基)苯酚
  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
• 作为产物：
  描述：

  对羟基苯乙酮 、 肼基甲酸乙酯 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以100%的产率得到N'-[1-(4-hydroxy-phenyl)-ethylidene]-hydrazinecarboxylic acid ethyl 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

• Crosslinking compositions and coatings formed therefrom
  申请人：PPG Industries Ohio, Inc.

  公开号：US11242430B2

  公开（公告）日：2022-02-08

  A crosslinking composition includes a compound having at least two functional groups that are each independently represented by Chemical Structure (I): X is an oxygen, sulfur, or nitrogen; R1 is an alkyl group, an aryl group, or an alkylaryl group; R2, R3, and R4 are each independently an alkyl group, an aryl group, an alkylaryl group, or a hydrogen; R5 is an alkyl group, an aryl group, an alkylaryl group, or a hydrogen; z is 0 when X is oxygen or sulfur and z is 1 when X is nitrogen; and when a double bond is formed between a carbon atom bonded to R3 and an adjacent nitrogen, m is 0, and when a single bond is formed between the carbon atom bonded to R3 and the adjacent nitrogen, m is 1.

  交联组合物包括一种化合物，该化合物至少具有两个各自独立由化学结构 (I) 表示的官能团： X是氧、硫或氮；R1是烷基、芳基或烷芳基；R2、R3和R4各自独立地是烷基、芳基、烷芳基或氢；R5是烷基、芳基、烷芳基或氢；当 X 为氧或硫时，z 为 0，当 X 为氮时，z 为 1；当与 R3 结合的碳原子与相邻的氮之间形成双键时，m 为 0，当与 R3 结合的碳原子与相邻的氮之间形成单键时，m 为 1。
• Crosslinking Compositions and Coatings Formed Therefrom
  申请人：PPG Industries Ohio, Inc.

  公开号：US20210115185A1

  公开（公告）日：2021-04-22

  A crosslinking composition includes a compound having at least two functional groups that are each independently represented by Chemical Structure (I): X is an oxygen, sulfur, or nitrogen; R 1 is an alkyl group, an aryl group, or an alkylaryl group; R 2 , R 3 , and R 4 are each independently an alkyl group, an aryl group, an alkylaryl group, or a hydrogen; R 5 is an alkyl group, an aryl group, an alkylaryl group, or a hydrogen; z is 0 when X is oxygen or sulfur and z is 1 when X is nitrogen; and when a double bond is formed between a carbon atom bonded to R 3 and an adjacent nitrogen, m is 0, and when a single bond is formed between the carbon atom bonded to R 3 and the adjacent nitrogen, m is 1.
• 架橋組成物およびそれから形成されたコーティング
  申请人：ピーピージー・インダストリーズ・オハイオ・インコーポレイテッド

  公开号：JP2022552376A

  公开（公告）日：2022-12-15

  架橋組成物は、各々独立して、請求項１に記載の化学構造（Ｉ）によって表される少なくとも２つの官能基を有する化合物を含み、式中、Ｘが、酸素、硫黄、または窒素であり、Ｒ１が、アルキル基、アリール基、またはアルキルアリール基であり、Ｒ２、Ｒ３、およびＲ４が、各々独立して、アルキル基、アリール基、アルキルアリール基、または水素であり、Ｒ５が、アルキル基、アリール基、アルキルアリール基、または水素であり、Ｘが酸素または硫黄である場合、ｚが０であり、Ｘが窒素である場合、ｚが１であり、Ｒ３に結合している炭素原子と隣接する窒素との間に二重結合が形成される場合、ｍが０であり、Ｒ３に結合している炭素原子と隣接する窒素との間に単結合が形成される場合、ｍが１である。
• 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.