5-oxo-5-(4-phenylthiazol-2-ylamino)pentanoic acid | 306280-68-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-oxo-5-(4-phenylthiazol-2-ylamino)pentanoic acid
• 英文别名: 5-Oxo-5-[(4-phenyl-1,3-thiazol-2-yl)amino]pentanoic acid
• CAS: 306280-68-2
• 化学式: C₁₄H₁₄N₂O₃S
• 分子量: 290.343
• InChiKey: UXAHOAJABZHDSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-oxo-5-(4-phenylthiazol-2-ylamino)pentanoic acid 、 N-(1,2,3,4-tetrahydroacridin-9-yl)propane-1,3-diamine 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 以39%的产率得到N¹-(4-phenylthiazol-2-yl)-N⁵-(3-(1,2,3,4-tetrahydroacridin-9-ylamino)propyl)glutaramide
  参考文献：
  名称：

  Novel multipotent phenylthiazole–tacrine hybrids for the inhibition of cholinesterase activity, β-amyloid aggregation and Ca2+ overload

  摘要：

  In this study, a series of multipotent phenylthiazole-tacrine hybrids (7a-7e, 8, and 9a-9m) were synthesized and biologically evaluated. Screening results showed that phenylthiazole-tacrine hybrids were potent cholinesterase inhibitors with pIC(50) (-logIC(50)) value ranging from 5.78 +/- 0.05 to 7.14 +/- 0.01 for acetylcholinesterase (AChE), and from 5.75 +/- 0.03 to 10.35 +/- 0.15 for butyrylcholinesterase (BuChE). The second series of phenylthiazole-tacrine hybrids (9a-9m) could efficiently prevent A beta(1-42) self-aggregation. The structure-activity relationship revealed that their inhibitory potency relied on the type of middle linker and substitutions at 4'-position of 4-phenyl-2-aminothiazole. In addition, 7a and 7c also displayed the Ca2+ overload blockade effect in the primary cultured cortical neurons. Consequently, these compounds emerged as promising molecules for the therapy of Alzheimer's disease. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.040
• 作为产物：
  描述：

  戊二酸酐 、 2-氨基-4-苯基噻唑 以 四氢呋喃 为溶剂， 反应 7.0h， 以36%的产率得到5-oxo-5-(4-phenylthiazol-2-ylamino)pentanoic acid
  参考文献：
  名称：

  Novel multipotent phenylthiazole–tacrine hybrids for the inhibition of cholinesterase activity, β-amyloid aggregation and Ca2+ overload

  摘要：

  In this study, a series of multipotent phenylthiazole-tacrine hybrids (7a-7e, 8, and 9a-9m) were synthesized and biologically evaluated. Screening results showed that phenylthiazole-tacrine hybrids were potent cholinesterase inhibitors with pIC(50) (-logIC(50)) value ranging from 5.78 +/- 0.05 to 7.14 +/- 0.01 for acetylcholinesterase (AChE), and from 5.75 +/- 0.03 to 10.35 +/- 0.15 for butyrylcholinesterase (BuChE). The second series of phenylthiazole-tacrine hybrids (9a-9m) could efficiently prevent A beta(1-42) self-aggregation. The structure-activity relationship revealed that their inhibitory potency relied on the type of middle linker and substitutions at 4'-position of 4-phenyl-2-aminothiazole. In addition, 7a and 7c also displayed the Ca2+ overload blockade effect in the primary cultured cortical neurons. Consequently, these compounds emerged as promising molecules for the therapy of Alzheimer's disease. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.040

文献信息

• Piperazine and homopiperazine compounds
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US20030153556A1

  公开（公告）日：2003-08-14

  Compounds are provided having a piperazine or homopiperazine ring which are useful in the treatment of thrombosis.

  提供了具有哌嗪或同源哌嗪环的化合物，这些化合物在治疗血栓症方面很有用。
• US7115741B2
  申请人：——

  公开号：US7115741B2

  公开（公告）日：2006-10-03
• [EN] PIPERAZINE AND HOMOPIPERAZINE COMPOUNDS<br/>[FR] COMPOSES A BASE DE PIPERAZINE ET D'HOMOPIPERAZINE
  申请人：MILLENNIUM PHARM INC

  公开号：WO2003022214A2

  公开（公告）日：2003-03-20

  Compounds are provided having a piperazine or homopiperazine ring which are useful in the treatment of thrombosis.
• Novel multipotent phenylthiazole–tacrine hybrids for the inhibition of cholinesterase activity, β-amyloid aggregation and Ca2+ overload
  作者：Yue Wang、Fang Wang、Jun-Ping Yu、Feng-Chao Jiang、Xin-Lei Guan、Can-Ming Wang、Lei Li、Hui Cao、Ming-Xing Li、Jian-Guo Chen

  DOI：10.1016/j.bmc.2012.08.040

  日期：2012.11

  In this study, a series of multipotent phenylthiazole-tacrine hybrids (7a-7e, 8, and 9a-9m) were synthesized and biologically evaluated. Screening results showed that phenylthiazole-tacrine hybrids were potent cholinesterase inhibitors with pIC(50) (-logIC(50)) value ranging from 5.78 +/- 0.05 to 7.14 +/- 0.01 for acetylcholinesterase (AChE), and from 5.75 +/- 0.03 to 10.35 +/- 0.15 for butyrylcholinesterase (BuChE). The second series of phenylthiazole-tacrine hybrids (9a-9m) could efficiently prevent A beta(1-42) self-aggregation. The structure-activity relationship revealed that their inhibitory potency relied on the type of middle linker and substitutions at 4'-position of 4-phenyl-2-aminothiazole. In addition, 7a and 7c also displayed the Ca2+ overload blockade effect in the primary cultured cortical neurons. Consequently, these compounds emerged as promising molecules for the therapy of Alzheimer's disease. (C) 2012 Elsevier Ltd. All rights reserved.