N-(4-氧代-2-硫代噻唑并噁唑烷-3-基)苯磺酰胺 | 301343-38-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-氧代-2-硫代噻唑并噁唑烷-3-基)苯磺酰胺
• 英文名称: 3-(benzenesulfonylamino)-4-oxo-2-thionothiazolidine
• 英文别名: N-(4-oxo-2-thioxothiazolidin-3-yl)benzenesulfonamide；3-(benzenesulfonylamino)rhodanine；N-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)benzenesulfonamide
• CAS: 301343-38-4
• 化学式: C₉H₈N₂O₃S₃
• 分子量: 288.372
• InChiKey: JLAFUTNZTWXZJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-氧代-2-硫代噻唑并噁唑烷-3-基)苯磺酰胺 在 CoCl₂ 2,2'-联吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium acetate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5-(3,4-Dichlorobenzyl)-3-(benzenesulfonylamino)-4-hydroxy-2-thionothiazolidine
  参考文献：
  名称：

  SAR and Mode of Action of Novel Non-Nucleoside Inhibitors of Hepatitis C NS5b RNA Polymerase

  摘要：

  Novel non-nucleoside inhibitors of the HCV RNA polymerase (NS5b) with sub-micromolar biochemical potency have been identified which are selective for the inhibition of HCV NS5b over other polymerases. The structures of the complexes formed between several of these inhibitors and HCV NS5b were determined by X-ray crystallography, and the inhibitors were found to bind in an allosteric binding site separate from the active site. Structure-activity relationships and structural studies have identified the mechanism of action for compounds in this series, several of which possess drug-like properties, as unique, reversible, covalent inhibitors of HCV NS5b.

  DOI：

  10.1021/jm050859x
• 作为产物：
  描述：

  双(羧甲基)三硫代碳酸盐 、 苯磺酰肼 以 水 为溶剂， 反应 6.0h， 生成 N-(4-氧代-2-硫代噻唑并噁唑烷-3-基)苯磺酰胺
  参考文献：
  名称：

  Thermodynamics of Substituted Rhodanine III: Potentiometric and Spectrophotometric Studies of Complexes of Some Transition Metals with 3-Phenylsulfonamidorhodanine

  摘要：

  The dissociation constants of 3-phenylsulfonamidorhodanine (PSR) were determined potentiometrically in 0.1 M KCI and 20% (v/v) ethanol-water. The stepwise stability constants of the complexes of Mn2+, Co2+, Ni2+, Cu2+, Zn2+, La3+, Ce3+, Gd3+, UO22+ and Th4+ with PSR were determined. The stabilities of the complexes were found as follows: Th4+ > UO22+ > Gd3+ > Ce3+ > La3+ > Mn2+ < Co2+ < Ni2+ < Cu2+ > Zn2+. The thermodynamic parameters for PSR and its complexes were evaluated and discussed. The dissociation process is non-spontaneous, endothermic, and entropically unfavourable. The formation of the complexes was found to be spontaneous, exothermic or endothermic (depending on the metal), and entropically favourable. The stoichiometries of the complexes were determined spectrophotometrically and indicate the formation of 1:1 and 1:2 (metal:ligand) complexes.

  DOI：

  10.1007/pl00010137

文献信息

• Design and Microwave Synthesis of New (5Z) 5-Arylidene-2-thioxo-1,3-thiazolinidin-4-one and (5Z) 2-Amino-5-arylidene-1,3-thiazol-4(5H)-one as New Inhibitors of Protein Kinase DYRK1A
  作者：Khadidja Bourahla、Solène Guihéneuf、Emmanuelle Limanton、Ludovic Paquin、Rémy Le Guével、Thierry Charlier、Mustapha Rahmouni、Emilie Durieu、Olivier Lozach、François Carreaux、Laurent Meijer、Jean-Pierre Bazureau

  DOI：10.3390/ph14111086

  日期：——

  Here, we report on the synthesis of libraries of new 5-arylidene-2-thioxo-1,3-thiazolidin-4-ones 3 (twenty-two compounds) and new 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones 5 (twenty-four compounds) with stereo controlled Z-geometry under microwave irradiation. The 46 designed final compounds were tested in order to determine their activity against four representative protein kinases (DYR1A, CK1, CDK5/p25, and GSK3α/β). Among these 1,3-thiazolidin-4-ones, the molecules (5Z) 5-(4-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one 3e (IC50 0.028 μM) and (5Z)-5-benzo[1,3]dioxol-5-ylmethylene-2-(pyridin-2-yl)amino-1,3-thiazol-4(5H)-one 5s (IC50 0.033 μM) were identified as lead compounds and as new nanomolar DYRK1A inhibitors. Some of these compounds in the two libraries have been also evaluated for their in vitro inhibition of cell proliferation (Huh7 D12, Caco2, MDA-MB 231, HCT 116, PC3, and NCI-H2 tumor cell lines). These results will enable us to use the 1,3-thiazolidin-4-one core as pharmacophores to develop potent treatment for neurological or oncological disorders in which DYRK1A is fully involved.

  在这里，我们报道了在微波辐射下合成了新的5-芳基亚基-2-硫代-1,3-噻唑啉-4-酮3类（二十二个化合物）和新的2-氨基-5-芳基亚基-1,3-噻唑-4（5H）-酮5类（二十四个化合物），具有立体控制的Z-几何构型。设计的46个最终化合物被测试，以确定它们对四种代表性蛋白激酶（DYR1A、CK1、CDK5/p25和GSK3α/β）的活性。在这些1,3-噻唑啉-4-酮中，分子（5Z）5-（4-羟基苯基亚基）-2-硫代-1,3-噻唑啉-4-酮3e（IC50为0.028μM）和（5Z）-5-苯并[1,3]二氧杂环-5-基亚甲基-2-（吡啶-2-基）氨基-1,3-噻唑-4（5H）-酮5s（IC50为0.033μM）被确定为引物化合物和新的纳摩尔级DYRK1A抑制剂。这两个库中的一些化合物也已评估其对细胞增殖的体外抑制作用（Huh7 D12、Caco2、MDA-MB 231、HCT 116、PC3和NCI-H2肿瘤细胞系）。这些结果将使我们能够利用1,3-噻唑啉-4-酮核作为药效团，开发用于治疗DYRK1A完全参与的神经或肿瘤疾病的有效治疗方法。
• NS5B HCV polymerase inhibitors
  申请人：Tularik Inc.

  公开号：US20020142290A1

  公开（公告）日：2002-10-03

  Compounds, compositions and methods are provided that are useful in the treatment and prevention of certain viral infections and associated diseases. In particular, the compounds of the invention inhibit the activity of a viral RNA polymerase. The subject methods are particularly useful in the treatment of diseases causes by hepatitis C virus infection.

  提供了一些在治疗和预防特定病毒感染和相关疾病中有用的化合物、组合物和方法。具体来说，本发明的化合物抑制了病毒RNA聚合酶的活性。这些方法特别适用于治疗由丙型肝炎病毒感染引起的疾病。
• NS5B HVC polymerase inhibitors
  申请人：Tularik Inc.

  公开号：US06727267B2

  公开（公告）日：2004-04-27

  Compounds, compositions and methods are provided that are useful in the treatment and prevention of certain viral infections and associated diseases. In particular, the compounds of the invention inhibit the activity of a viral RNA polymerase. The subject methods are particularly useful in the treatment of diseases causes by hepatitis C virus infection.

  本发明提供了在治疗和预防某些病毒感染和相关疾病方面有用的化合物、组合物和方法。特别是，本发明的化合物抑制病毒RNA聚合酶的活性。本方法在治疗由丙型肝炎病毒感染引起的疾病方面特别有用。
• Thermodynamics of Substituted Rhodanine III: Potentiometric and Spectrophotometric Studies of Complexes of Some Transition Metals with 3-Phenylsulfonamidorhodanine
  作者：Ashraf A. El-Bindary、Mohammed M. Ghoneim、Adel Z. El-Sonbati、Sahar A. Barakat

  DOI：10.1007/pl00010137

  日期：1998.12

  The dissociation constants of 3-phenylsulfonamidorhodanine (PSR) were determined potentiometrically in 0.1 M KCI and 20% (v/v) ethanol-water. The stepwise stability constants of the complexes of Mn2+, Co2+, Ni2+, Cu2+, Zn2+, La3+, Ce3+, Gd3+, UO22+ and Th4+ with PSR were determined. The stabilities of the complexes were found as follows: Th4+ > UO22+ > Gd3+ > Ce3+ > La3+ > Mn2+ < Co2+ < Ni2+ < Cu2+ > Zn2+. The thermodynamic parameters for PSR and its complexes were evaluated and discussed. The dissociation process is non-spontaneous, endothermic, and entropically unfavourable. The formation of the complexes was found to be spontaneous, exothermic or endothermic (depending on the metal), and entropically favourable. The stoichiometries of the complexes were determined spectrophotometrically and indicate the formation of 1:1 and 1:2 (metal:ligand) complexes.
• US6727267B2
  申请人：——

  公开号：US6727267B2

  公开（公告）日：2004-04-27