2-(3-Nitrophenyl)-1,3-thiazole-4-carboxylic acid | 92057-32-4

• 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)-1,3-thiazole-4-carboxylic acid
• CAS: 92057-32-4
• 化学式: C₁₀H₆N₂O₄S
• mdl: MFCD12114472
• 分子量: 250.235
• InChiKey: UBRRJFUWRWCSMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3-Nitrophenyl)-1,3-thiazole-4-carboxylic acid 在 ammonium hydroxide 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 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：

  2-(3-nitrophenyl)thiazole-4-carboxylic acid ethyl ester 在 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 生成 2-(3-Nitrophenyl)-1,3-thiazole-4-carboxylic acid
  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

文献信息

• Novel compounds and compositions as protease inhibitors
  申请人：AXYS PHARMACEUTICALS, INC.

  公开号：US20020086996A1

  公开（公告）日：2002-07-04

  The present invention relates to novel N-cyanomethyl amides which are cysteine protease inhibitors, the pharmaceutically acceptable salts and N-oxides thereof, their uses as therapeutic agents and the methods of their making.

  本发明涉及一种新颖的N-氰甲基酰胺，它们是半胱氨酸蛋白酶抑制剂，以及它们的药用盐和N-氧化物，它们作为治疗剂的用途以及它们的制备方法。
• 含苯基脒结构的硝基苯噻唑羧酸酰胺类化合物 及用途
  申请人：佛山市赛维斯医药科技有限公司

  公开号：CN104628671B

  公开（公告）日：2016-04-13

  本发明涉及与2型糖尿病相关的药物领域。具体而言，本发明涉及一种含苯基脒结构的硝基苯噻唑羧酸酰胺类非糖苷类SGLT2/SGLT1双靶点抑制剂、其制备方法及其在制备2型糖尿病药物中的应用。
• N-CYANOMETHYLAMIDES AS PROTEASE INHIBITORS
  申请人：AXYS PHARMACEUTICALS, INC.

  公开号：EP1161415B1

  公开（公告）日：2005-07-13
• US6476026B1
  申请人：——

  公开号：US6476026B1

  公开（公告）日：2002-11-05
• US6593327B2
  申请人：——

  公开号：US6593327B2

  公开（公告）日：2003-07-15