5-[5-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]furan-2-yl]-2-hydroxybenzoic acid | 313394-27-3

• 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: 5-[5-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]furan-2-yl]-2-hydroxybenzoic acid
• CAS: 313394-27-3
• 化学式: C₁₅H₉NO₆S
• 分子量: 331.3
• InChiKey: SXAUTKUIIXFACR-SDQBBNPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 5-(5-formylfuran-2-yl)-2-hydroxybenzoic acid 在 哌啶 作用下， 以 乙醇 为溶剂， 以56 %的产率得到5-[5-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]furan-2-yl]-2-hydroxybenzoic acid
  参考文献：
  名称：

  抗乙二醛酶-I 的有效噻唑烷二酮水杨酸抑制剂作为潜在抗癌药物的设计、合成和生物学评价

  摘要：

  全球癌症发病率和死亡率的上升促使人们寻找与癌症发生和进展有关的新途径。其中一个靶标是乙二醛酶 1 (GLO-I)，它是甲基乙二醛解毒的关键参与者，也是多种癌症增殖和预后的一个因素。 Al-Shar'i 等人最近领导的研究。利用计算机辅助药物设计来识别 GLO-I 的潜在抑制剂。第二个最有效的命中是 ( Z )-5-(5-((2,4-二氧噻唑烷-5-亚基)甲基)呋喃-2-基)-2-羟基苯甲酸，(IC 50 = 4.24 µM) 是被选为进一步优化的先导。通过分子对接，设计了 27 种类似物并评估了结合亲和力，合成了得分最高的 14 种类似物并测试了它们对 GLO-I 的抑制活性。相对于先导化合物，这些类似物中的大多数显示出增强的活性，其中最有效的 IC 50为 150 nM。这些发现为持续开发高效的 GLO-I 抑制剂铺平了道路。

  DOI：

  10.1007/s00044-024-03247-7

文献信息

• COMPOSITIONS AND METHODS FOR TREATMENT OF DISEASE CAUSED BY YERSINIA SPP INFECTION
  申请人：Mustelin Tomas Mikael

  公开号：US20090312352A1

  公开（公告）日：2009-12-17

  The invention generally relates to compositions and methods for treatment of disease caused by Yersinia spp. infection. More specifically, the invention relates to protein tyrosine phosphatase inhibitors and derivatives and analogs thereof, pharmaceutical compositions containing the protein tyrosine phosphatase inhibitors and analogs, methods of making the protein tyrosine phosphatase inhibitors and analogs and methods of use thereof.

  本发明通常涉及用于治疗由耶尔森氏菌感染引起的疾病的组合物和方法。更具体地，本发明涉及蛋白酪氨酸磷酸酶抑制剂及其衍生物和类似物，含有蛋白酪氨酸磷酸酶抑制剂和类似物的制药组合物，制造蛋白酪氨酸磷酸酶抑制剂和类似物的方法以及使用它们的方法。
• NOVEL ANTAGONISTS OF THE HUMAN FATTY ACID SYNTHASE THIOESTERASE
  申请人：Smith W. Jeffrey

  公开号：US20070203236A1

  公开（公告）日：2007-08-30

  The present invention provides for compounds of formula (I)-(XIII), as well as pharmaceutically acceptable salts thereof, metabolites thereof, pro-drugs thereof, and pharmaceutical kits that include such compounds. The present invention also provides for the compounds of formula (I)-(XIII) for use in medical therapy or diagnosis. The present invention also provides for the use of the compounds of formula (I)-(XIII) in treating cancer in mammals (e.g., humans), as well inhibiting tumor cell growth in such mammals. The present invention also provides for methods of inhibiting FAS. The methods include contacting FAS with an effective amount of a compound of formula (I)-(XIII). The present invention also provides for methods of inhibiting the TE domain of the FAS. The methods include contacting the thioesterase TE domain of the FAS with an effective amount of a compound of formula (I)-(XIII). The present invention also provides for methods of treating cancer in mammals, as well as methods of inhibiting tumor cell growth in such mammals. The methods include administering a compound of formula (I)-(XIII) to a mammal in need of such treatment.
• 10.1007/s00044-024-03247-7
  作者：Alomari, Banan O.、Fakhouri, Lara I.、Al‑Shar’i, Nizar A.、Albalas, Qosay

  DOI：10.1007/s00044-024-03247-7

  日期：——

  One such target is glyoxalase 1 (GLO-I), a key player in methylglyoxal detoxification and a factor in the proliferation and prognosis of numerous cancers. Recent studies led by Al-Shar’i et al. utilized computer-aided drug design to identify potential inhibitors of GLO-I. The second most potent hit, (Z)-5-(5-((2,4-dioxothiazolidin-5-ylidene)methyl)furan-2-yl)-2-hydroxybenzoic acid, (IC50 = 4.24 µM)

  全球癌症发病率和死亡率的上升促使人们寻找与癌症发生和进展有关的新途径。其中一个靶标是乙二醛酶 1 (GLO-I)，它是甲基乙二醛解毒的关键参与者，也是多种癌症增殖和预后的一个因素。 Al-Shar'i 等人最近领导的研究。利用计算机辅助药物设计来识别 GLO-I 的潜在抑制剂。第二个最有效的命中是 ( Z )-5-(5-((2,4-二氧噻唑烷-5-亚基)甲基)呋喃-2-基)-2-羟基苯甲酸，(IC 50 = 4.24 µM) 是被选为进一步优化的先导。通过分子对接，设计了 27 种类似物并评估了结合亲和力，合成了得分最高的 14 种类似物并测试了它们对 GLO-I 的抑制活性。相对于先导化合物，这些类似物中的大多数显示出增强的活性，其中最有效的 IC 50为 150 nM。这些发现为持续开发高效的 GLO-I 抑制剂铺平了道路。