3-[5-(2,4-Dioxothiazolidin-5-ylidenemethyl)furan-2-yl]benzoic acid

• 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: 3-[5-(2,4-Dioxothiazolidin-5-ylidenemethyl)furan-2-yl]benzoic acid
• 英文别名: 3-[5-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]furan-2-yl]benzoic acid
• 化学式: C₁₅H₉NO₅S
• 分子量: 315.306
• InChiKey: QBZLYEDJIWHIEF-GHXNOFRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 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：
  122
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  间溴苯甲酸 在 四(三苯基膦)钯 、 potassium carbonate 、 溶剂黄146 、 β-丙氨酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 13.0h， 生成 3-[5-(2,4-Dioxothiazolidin-5-ylidenemethyl)furan-2-yl]benzoic acid
  参考文献：
  名称：

  Furan-2-ylmethylene Thiazolidinediones as Novel, Potent, and Selective Inhibitors of Phosphoinositide 3-Kinase γ

  摘要：

  Class I phosphoinositide 3-kinases (PI3Ks), in particular PI3K gamma, have become attractive drug targets for inflammatory and autoimmune diseases. Here, we disclose a novel series of furan-2-ylmethylene thiazolidinediones as selective, ATP-competitive PI3K gamma inhibitors. Structure-based design and X-ray crystallography of complexes formed by inhibitors bound to PI3K gamma identified key pharmacophore features for potency and selectivity. An acidic NH group on the thiazolidinedione moiety and a hydroxy group on the furan-2-yl-phenyl part of the molecule play crucial roles in binding to PI3K and contribute to class IB PI3K selectivity. Compound 26 (AS-252424), a potent and selective small-molecule PI3K gamma inhibitor emerging from these efforts, was further profiled in three different cellular PI3K assays and shown to be selective for class IB PI3K-mediated cellular effects. Oral administration of 26 in a mouse model of acute peritonitis led to a significant reduction of leukocyte recruitment.

  DOI：

  10.1021/jm0601598

文献信息

• Inhibitors of 15-hydroxyprostaglandin dehydrogenase for stimulating pigmentation of the skin or skin appendages
  申请人：Michelet Jean-Francois

  公开号：US20060034786A1

  公开（公告）日：2006-02-16

  Inhibitors of 15-hydroxyprostaglandin dehydrogenase (15-PGDH), for example tetrazole, styrylpyrazole, phenylfuran, phenylthiophene, phenylpyrrazole, pyrazolecarboxamide, 2-thioacetamide and azo compounds, are useful for promoting or stimulating pigmentation of the skin and/or skin appendages and/or for preventing and/or for limiting depigmentation and/or whitening of the skin and/or skin appendages, notably for preventing and/or limiting canities.

  15-羟基前列腺素脱氢酶（15-PGDH）的抑制剂，例如四唑、苯基吡唑、苯基呋喃、苯基噻吩、苯基吡唑、吡唑羧酰胺、2-硫代乙酰胺和偶氮化合物，可用于促进或刺激皮肤和/或皮肤附属物的色素沉淀和/或预防和/或限制皮肤和/或皮肤附属物的脱色和/或变白，特别是用于预防和/或限制白发。
• Heterocyclic compound for stimulating or inducing the growth of the hair or eyelashes and/or slowing down their loss, composition comprising it and its uses
  申请人：Boulle Christophe

  公开号：US20060008436A1

  公开（公告）日：2006-01-12

  Heterocyclic compounds useful for stimulating/inducing the growth of keratinous fibers, notably human hair/eyelashes, and/or slowing the loss of same, have the following structural formula (I) or salt thereof: in which Hy is a heterocycle of 4 to 7 atoms, optionally comprising carbonyl/thiocarbonyl functional groups, and G is O, S or NH.

  杂环化合物对于刺激/诱导角质纤维生长，特别是人类头发/睫毛的生长和/或减缓它们的脱落很有用，其结构式(I)或其盐如下：其中Hy是由4至7个原子组成的杂环，可选包括羰基/硫代羰基官能团，而G是O，S或NH。
• RHODANINES AND RELATED HETEROCYCLES AS KINASE INHIBITORS
  申请人：HADDACH Mustapha

  公开号：US20100331315A1

  公开（公告）日：2010-12-30

  The invention provides compounds that inhibit PIM kinases and/or CK2, and compositions containing such compounds. These compounds and compositions are useful for treating proliferative disorders such as cancer, as well as other kinase-associated conditions including inflammation, pain, vascular disorders, pathogenic infections and certain immunological disorders.

  该发明提供了能够抑制PIM激酶和/或CK2的化合物以及含有这些化合物的组合物。这些化合物和组合物可用于治疗增殖性疾病如癌症，以及其他与激酶相关的疾病，包括炎症、疼痛、血管疾病、病原体感染和某些免疫性疾病。
• INHIBITORS OF 15-HYDROXYPROSTAGLANDIN DEHYDROGENASE FOR STIMULATING PIGMENTATION OF THE SKIN OR SKIN APPENDAGES
  申请人：MICHELET JEAN-FRANCOIS

  公开号：US20110014250A1

  公开（公告）日：2011-01-20

  Inhibitors of 15-hydroxyprostaglandin dehydrogenase (15-PGDH), for example tetrazole, styrylpyrazole, phenylfuran, phenylthiophene, phenylpyrrazole, pyrazolecarboxamide, 2-thioacetamide and azo compounds, are useful for promoting or stimulating pigmentation of the skin and/or skin appendages and/or for preventing and/or for limiting depigmentation and/or whitening of the skin and/or skin appendages, notably for preventing and/or limiting canities.

  15-羟基前列腺素脱氢酶（15-PGDH）的抑制剂，例如四唑、苯乙烯吡唑、苯并呋喃、苯并硫吩、苯并吡唑、吡唑羧酰胺、2-硫代乙酰胺和偶氮化合物，可用于促进或刺激皮肤和/或皮肤附属物的色素沉着，或预防和/或限制皮肤和/或皮肤附属物的脱色和/或变白，特别是预防和/或限制白发。
• Utilisation d'un inhibiteur de 15-hydroxy prostaglandine déshydrogénase pour favoriser la pigmentation de la peau ou des phanères
  申请人：L'Oréal

  公开号：EP1594438B1

  公开（公告）日：2013-07-17