[2-(3-Aminopropylamino)-1,3-thiazol-4-yl]-(2-methylphenyl)methanone | 749846-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-(3-Aminopropylamino)-1,3-thiazol-4-yl]-(2-methylphenyl)methanone
• CAS: 749846-46-6
• 化学式: C₁₄H₁₇N₃OS
• 分子量: 275.374
• InChiKey: NTMQRZKPLYIFMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  96.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2-(3-Aminopropylamino)-1,3-thiazol-4-yl]-(2-methylphenyl)methanone 、 2-氯-5-（三氟甲基）苯-1-磺酰氯 生成 2-Chloro-N-{3-[4-(2-methyl-benzoyl)-thiazol-2-ylamino]-propyl}-5-trifluoromethyl-benzenesulfonamide
  参考文献：
  名称：

  Isomeric thiazole derivatives as ligands for the neuropeptide Y5 receptor

  摘要：

  Sets of isomeric thiazole derivatives I and 2 have been synthesised in a parallel iterative solution-phase synthesis approach guided by the SAR analysis derived from biological results and computer-aided design and analysis. This synergistic and streamlined working procedure led to highly active isomeric NPY5 receptor ligands. However, a 10-fold difference at least in their respective binding affinities was consistently found for all isomeric pairs 1 and 2. The analysis of conformational differences due to heteroatom interactions in I and 2 revealed a favourable C=(OS)-S-... interaction in 1, whereas thiazoles 2 showed a repulsive C=(ON)-N-... interaction. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.009
• 作为产物：
  描述：

  3-bromo-1-o-methylphenylpropane-1,2-dione 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 2.0h， 生成 [2-(3-Aminopropylamino)-1,3-thiazol-4-yl]-(2-methylphenyl)methanone
  参考文献：
  名称：

  Isomeric thiazole derivatives as ligands for the neuropeptide Y5 receptor

  摘要：

  Sets of isomeric thiazole derivatives I and 2 have been synthesised in a parallel iterative solution-phase synthesis approach guided by the SAR analysis derived from biological results and computer-aided design and analysis. This synergistic and streamlined working procedure led to highly active isomeric NPY5 receptor ligands. However, a 10-fold difference at least in their respective binding affinities was consistently found for all isomeric pairs 1 and 2. The analysis of conformational differences due to heteroatom interactions in I and 2 revealed a favourable C=(OS)-S-... interaction in 1, whereas thiazoles 2 showed a repulsive C=(ON)-N-... interaction. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.009

文献信息

• THIAZOLE DERIVATIVES
  申请人：——

  公开号：US20030225141A1

  公开（公告）日：2003-12-04

  Compounds of formula I are provided 1 as well as pharmaceutically acceptable salts and esters thereof, wherein R 1 to R 5 , n, m and A have the significance disclosed in the specification, and can be used for the treatment or prevention of arthritis, cardiovascular diseases, diabetes, renal failure, eating disorders and obesity.

  提供了式I的化合物，以及其药学上可接受的盐和酯，其中R1至R5，n，m和A的含义如规范中所披露的那样，并可用于治疗或预防关节炎、心血管疾病、糖尿病、肾衰竭、进食障碍和肥胖症。
• [EN] THIAZOLE DERIVATIVES AS NPY RECEPTOR ANTAGONISTS<br/>[FR] DERIVES THIAZOLES UTILISES COMME ANTAGONISTES DU RECEPTEUR NPY
  申请人：HOFFMANN LA ROCHE

  公开号：WO2003072577A1

  公开（公告）日：2003-09-04

  Compounds of formula (I) as well as pharmaceutically acceptable salts and esters thereof, wherein R1 to R5, n, m and A have the significance given in claim 1, can be used in the form of pharmaceutical preparations for the treatment or prevention of arthritis, cardiovascular diseases, diabetes, renal failure, eating disorders and obesity.

  公式（I）的化合物，以及其药学上可接受的盐和酯，其中R1到R5，n，m和A的含义如权利要求书1所述，可以用作制备药物治疗或预防关节炎，心血管疾病，糖尿病，肾衰竭，进食障碍和肥胖症。
• THIAZOLE DERIVATIVES AS NPY RECEPTOR ANTAGONISTS
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1480976A1

  公开（公告）日：2004-12-01
• US6686381B2
  申请人：——

  公开号：US6686381B2

  公开（公告）日：2004-02-03
• Isomeric thiazole derivatives as ligands for the neuropeptide Y5 receptor
  作者：Matthias Nettekoven、Wolfgang Guba、Werner Neidhart、Patrizio Mattei、Philippe Pflieger、Olivier Roche、Sven Taylor

  DOI：10.1016/j.bmcl.2005.05.009

  日期：2005.7

  Sets of isomeric thiazole derivatives I and 2 have been synthesised in a parallel iterative solution-phase synthesis approach guided by the SAR analysis derived from biological results and computer-aided design and analysis. This synergistic and streamlined working procedure led to highly active isomeric NPY5 receptor ligands. However, a 10-fold difference at least in their respective binding affinities was consistently found for all isomeric pairs 1 and 2. The analysis of conformational differences due to heteroatom interactions in I and 2 revealed a favourable C=(OS)-S-... interaction in 1, whereas thiazoles 2 showed a repulsive C=(ON)-N-... interaction. (c) 2005 Elsevier Ltd. All rights reserved.