2-(2-phenoxyphenyl)acetic acid hydrazide | 159731-09-6

• 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: 2-(2-phenoxyphenyl)acetic acid hydrazide
• 英文别名: (2-phenoxyphenyl)acetohydrazide；2-(2-phenoxyphenyl)acetohydrazide
• CAS: 159731-09-6
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: OTJXSOJLVNHHDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-phenoxyphenyl)acetic acid hydrazide 在 碳酸氢钠 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 6.58h， 生成 5-ethoxy-3-(2-phenoxybenzyl)-4H-1,2,4-triazole
  参考文献：
  名称：

  Synthesis, receptor affinity and effect on pentylenetetrazole-induced seizure threshold of novel benzodiazepine analogues: 3-Substituted 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles and 2-amino-5-(phenoxybenzyl)-1,3,4-oxadiazoles

  摘要：

  The new series of 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles, possessing C-3 thio, alkylthio and ethoxy substituents, and 2-amino-5-(2-phenoxybenzyl)-1,3,4-oxadiazoles were designed and synthesized as novel benzodiazepine analogues. Most of them revealed similar to superior binding affinity to the GABA(A)/benzodiazepine receptor complex, relative to diazepam as the reference drug. Among them, 5-(4-chloro-2-(2-fluorophenoxy) benzyl)-3-benzylthio-4H-1,2,4-triazole (8l) showed the highest affinity (IC50 = 0.892 nM) relative to diazepam (IC50 = 2.857 nM) and also showed the most increase in pentylen-etetrazole-induced seizure threshold relative to diazepam as the reference drug. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.041
• 作为产物：
  描述：

  苯氧苯甲酸 在 吡啶 、 lithium aluminium tetrahydride 、 氯化亚砜 、 一水合肼 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 、 正丁醇 、 苯 为溶剂， 反应 86.0h， 生成 2-(2-phenoxyphenyl)acetic acid hydrazide
  参考文献：
  名称：

  Synthesis, receptor affinity and effect on pentylenetetrazole-induced seizure threshold of novel benzodiazepine analogues: 3-Substituted 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles and 2-amino-5-(phenoxybenzyl)-1,3,4-oxadiazoles

  摘要：

  The new series of 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles, possessing C-3 thio, alkylthio and ethoxy substituents, and 2-amino-5-(2-phenoxybenzyl)-1,3,4-oxadiazoles were designed and synthesized as novel benzodiazepine analogues. Most of them revealed similar to superior binding affinity to the GABA(A)/benzodiazepine receptor complex, relative to diazepam as the reference drug. Among them, 5-(4-chloro-2-(2-fluorophenoxy) benzyl)-3-benzylthio-4H-1,2,4-triazole (8l) showed the highest affinity (IC50 = 0.892 nM) relative to diazepam (IC50 = 2.857 nM) and also showed the most increase in pentylen-etetrazole-induced seizure threshold relative to diazepam as the reference drug. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.041

文献信息

• Fungicidal oxazolyl and oxadiazolyl derivatives
  申请人：Zeneca Limited

  公开号：US05668160A1

  公开（公告）日：1997-09-16

  A compound of formula (I) wherein Q is oxazol-2-yl, 1,3,4-oxadiazol-2-yl, C.sub.1-4 -oxadiazol-3-yl or 1,2,4-oxadiazol-5-yl; Z is CH or N; A is hydrogen, halogen, C.sub.1-4 alkyl, 1,2,4 alkoxy, cyano, nitro or trifluoromethyl; X is halogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, OR.sup.1, SR.sup.1, SOR.sup.1, SO.sub.2 R.sup.1, COR.sup.1, CO.sub.2 R.sup.1, NR.sup.1 R.sup.2 or CONR.sup.1 R.sup.2 ; and R.sup.1 and R.sup.2 are, independently, hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heteroaryl. ##STR1##

  式(I)的化合物，其中Q为噁唑-2-基，1,3,4-噻二唑-2-基，C.sub.1-4-噻二唑-3-基或1,2,4-噻二唑-5-基；Z为CH或N；A为氢，卤素，C.sub.1-4烷基，1,2,4-烷氧基，氰基，硝基或三氟甲基；X为卤素，可选取代的烷基，可选取代的烯基，可选取代的炔基，可选取代的芳基，可选取代的杂芳基，可选取代的环烷基，OR.sup.1，SR.sup.1，SOR.sup.1，SO.sub.2R.sup.1，COR.sup.1，CO.sub.2R.sup.1，NR.sup.1R.sup.2或CONR.sup.1R.sup.2；R.sup.1和R.sup.2独立地为氢，可选取代的烷基，可选取代的烯基，可选取代的炔基，可选取代的环烷基，可选取代的芳基或可选取代的杂芳基。 ##STR1##
• FUNGICIDAL OXAZOLYL AND OXADIAZOLYL DERIVATIVES
  申请人：ZENECA LIMITED

  公开号：EP0693061B1

  公开（公告）日：2000-11-22
• US5668160A
  申请人：——

  公开号：US5668160A

  公开（公告）日：1997-09-16
• [EN] FUNGICIDAL OXAZOLYL AND OXADIAZOLYL DERIVATIVES<br/>[FR] DERIVES FONGICIDES D'OXAZOLYLE ET D'OXADIAZOLYLE
  申请人：ZENECA LIMITED

  公开号：WO1994022844A1

  公开（公告）日：1994-10-13

  (EN) A compound of formula (I) wherein Q is oxazol-2-yl, 1,3,4-oxadiazol-2-yl, 1,2,4-oxadiazol-3-yl or 1,2,4-oxadiazol-5-yl; Z is CH or N; A is hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, cyano, nitro or trifluoromethyl; X is halogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, OR1, SR1, SOR1, SO2R1, COR1, CO2R1, NR1R2 or CONR1R2; and R1 and R2 are, independently, hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heteroaryl.(FR) Composé représenté par la formule (I) dans laquelle Q représente oxazol-2-yle, 1,3,4-oxadiazol-2-yle, 1,2,4-oxadiazol-3-yle ou 1,2,4-oxadiazol-5-yle; Z représente CH ou N; A représente hydrogène, halogène, alkyle C1-4; alcoxy C1-4, cyano, nitro ou trifluorométhyle; X représente halogène, alkyle éventuellement substitué, alcényle éventuellement substitué, alcynyle éventuellement substitué, aryle éventuellement substitué, hétéroaryle éventuellement substitué, cycloalkyle éventuellement substitué, OR1, SR1, SOR1, SO2R1, COR1, CO2R1, NR1R2 ou CONR1R2; R1 et R2 représentent indépendamment hydrogène, alkyle éventuellement substitué, alcényle éventuellement substitué, alcynyle éventuellement substitué, cycloalkyle éventuellement substitué, aryle éventuellement substitué ou hétéroaryle éventuellement substitué.
• Synthesis, receptor affinity and effect on pentylenetetrazole-induced seizure threshold of novel benzodiazepine analogues: 3-Substituted 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles and 2-amino-5-(phenoxybenzyl)-1,3,4-oxadiazoles
  作者：Siavash Mashayekh、Narges Rahmanipour、Behnaz Mahmoodi、Fatemeh Ahmadi、Dina Motaharian、Soraya Shahhosseini、Hamed Shafaroodi、Hamid R. Banafshe、Abbas Shafiee、Latifeh Navidpour

  DOI：10.1016/j.bmc.2014.01.041

  日期：2014.3

  The new series of 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles, possessing C-3 thio, alkylthio and ethoxy substituents, and 2-amino-5-(2-phenoxybenzyl)-1,3,4-oxadiazoles were designed and synthesized as novel benzodiazepine analogues. Most of them revealed similar to superior binding affinity to the GABA(A)/benzodiazepine receptor complex, relative to diazepam as the reference drug. Among them, 5-(4-chloro-2-(2-fluorophenoxy) benzyl)-3-benzylthio-4H-1,2,4-triazole (8l) showed the highest affinity (IC50 = 0.892 nM) relative to diazepam (IC50 = 2.857 nM) and also showed the most increase in pentylen-etetrazole-induced seizure threshold relative to diazepam as the reference drug. (C) 2014 Elsevier Ltd. All rights reserved.