2-(3-nitrophenyl)thiazole-4-carboxylic acid ethyl ester | 121262-07-5

• 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-(3-nitrophenyl)thiazole-4-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-(3-nitrophenyl)-1,3-thiazole-4-carboxylate
• CAS: 121262-07-5
• 化学式: C₁₂H₁₀N₂O₄S
• mdl: MFCD23148893
• 分子量: 278.288
• InChiKey: LWGLXPDMTJTNNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3-nitrophenyl)thiazole-4-carboxylic acid ethyl ester 在 氢氧化钾 、 ammonium hydroxide 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.83h， 生成 2-(3-nitrophenyl)thiazole-4-carboxylic acid amide
  参考文献：
  名称：

  Anilinoquinazoline Inhibitors of Fructose 1,6-Bisphosphatase Bind at a Novel Allosteric Site:  Synthesis, In Vitro Characterization, and X-ray Crystallography

  摘要：

  The synthesis and in vitro structure-activity relationships (SAR) of a novel series of anilinoquinazolines as allosteric inhibitors of fructose-1,6-bisphosphatase (F16Bpase) are reported. The compounds have a different SAR as inhibitors of F16Bpase than anilinoquinazolines previously reported. Selective inhibition of F16Bpase can be attained through the addition of appropriate polar functional groups at the quinazoline 2-position, thus separating the F16Bpase inhibitory activity from the epidermal growth factor receptor tyrosine kinase inhibitory activity previously observed with similar structures. The compounds have been found to bind at a symmetry-repeated novel allosteric site at the subunit interface of the enzyme. Inhibition is brought about by binding to a loop comprised of residues 52-72, preventing the necessary participation of these residues in the assembly of the catalytic site. Mutagenesis studies have identified the key amino acid residues in the loop that are required for inhibitor recognition and binding.

  DOI：

  10.1021/jm010496a
• 作为产物：
  描述：

  ethyl (4R)-2-(3-nitrophenyl)-4,5-dihydro-1,3-thiazole-4-carboxylate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以82%的产率得到2-(3-nitrophenyl)thiazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Oxidation of 4-carboxylate thiazolines to 4-carboxylate thiazoles by molecular oxygen

  摘要：

  A facile and environment-benign oxidation by molecular oxygen was applied for the conversion of 4-carboxylate thiazolines to 4-carboxylate thiazoles. The substituent effect on thiazoline ring was investigated. it was found that electron-poor group on the thiazoline ring could facilitate the oxidation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.091

文献信息

• Fructose 1,6-bisphosphatase inhibitors
  申请人：——

  公开号：US20030144308A1

  公开（公告）日：2003-07-31

  The present invention relates to certain quinazoline compounds which have utility in the treatment of diabetes mellitus, hypercholesterolemia, hyperlipidemia, diabetic complications and cancer. The invention also relates to pharmaceutical compositions and kits comprising such quinazoline compounds and to methods of using such compounds in the treatment of diabetes mellitus, hypercholesterolemia, hyperlipidemia, diabetic complications and cancer.

  本发明涉及某些喹唑啉化合物，其在糖尿病、高胆固醇血症、高脂血症、糖尿病并发症和癌症治疗中具有用途。该发明还涉及含有这种喹唑啉化合物的药物组合物和配套工具，以及使用这些化合物治疗糖尿病、高胆固醇血症、高脂血症、糖尿病并发症和癌症的方法。
• Nitric ester derivative
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04923886A1

  公开（公告）日：1990-05-08

  Nitric acid esters of Thiazole carboxamides exhibiting vasodilating activities have been prepared.

  已制备出具有扩血管作用的噻唑羧酰胺的硝酸酯。
• Nitric acid ester derivative
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0300400B1

  公开（公告）日：1994-03-16
• US4923886A
  申请人：——

  公开号：US4923886A

  公开（公告）日：1990-05-08
• US5010093A
  申请人：——

  公开号：US5010093A

  公开（公告）日：1991-04-23