2-chloro-5-{[(4,6-dimethyl-2-pyrimidinyl)sulfanyl]acetyl}benzenesulfonamide | 1376685-43-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloro-5-{[(4,6-dimethyl-2-pyrimidinyl)sulfanyl]acetyl}benzenesulfonamide
• 英文别名: 2-Chloro-5-{[(4,6-Dimethylpyrimidin-2-Yl)sulfanyl]acetyl}benzenesulfonamide；2-chloro-5-[2-(4,6-dimethylpyrimidin-2-yl)sulfanylacetyl]benzenesulfonamide
• CAS: 1376685-43-6
• 化学式: C₁₄H₁₄ClN₃O₃S₂
• 分子量: 371.868
• InChiKey: GMUOUKSISIODEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-(2-bromoacetyl)-2-chloro-benzenesulfonamide 、 4,6-二甲基-2-巯基嘧啶 在 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以93%的产率得到2-chloro-5-{[(4,6-dimethyl-2-pyrimidinyl)sulfanyl]acetyl}benzenesulfonamide
  参考文献：
  名称：

  Design of [(2-pyrimidinylthio)acetyl]benzenesulfonamides as inhibitors of human carbonic anhydrases

  摘要：

  A series of [(2-pyrimidinylthio)acetyl]benzenesulfonamides were designed and synthesized. Their binding affinities as inhibitors of several recombinant human carbonic anhydrase (CA) isozymes were determined by isothermal titration calorimetry (ITC) and thermal shift assay (TSA). A group of compounds containing a chlorine atom in the benzenesulfonamide ring were found to exhibit higher selectivity but lower binding affinity toward tested CAs. The crystal structures of selected compounds in complex with CA II were determined to atomic resolution. Docking studies were performed to compare the binding modes of experimentally determined crystallographic structures with computational prediction of the pyrimidine derivative binding to CA II. Several compounds bound to select CAs with single-digit nanomolar affinities and could be used as leads for inhibitor development toward a select CA isozyme. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.050

文献信息

• [EN] SELECTIVE INHIBITORS OF CARBONIC ANHYDRASE<br/>[FR] INHIBITEURS SÉLECTIFS D'ANHYDRASE CARBONIQUE
  申请人：UNIV VILNIUS

  公开号：WO2017017505A1

  公开（公告）日：2017-02-02

  Invention is related to novel compounds – benzenesulfonamides of general formulas (I) and (II). The compounds can be used in biomedicine as active ingredients in pharmaceutical formulations, because they inhibit enzymes which participate in disease progression. Acknowledgements: This research was funded by the European Social Fund under the Global Grant measure (no. VP1-3.1.-SMM-07-K-02-009).

  发明涉及新化合物 - 通式（I）和（II）的苯磺酰胺。这些化合物可以作为药物配方中的活性成分在生物医学中使用，因为它们抑制参与疾病进展的酶。致谢：本研究得到欧洲社会基金在全球拨款措施（编号VP1-3.1.-SMM-07-K-02-009）下的资助。
• Selective inhibitors of carbonic anhydrase
  申请人：VILNIUS UNIVERSITY

  公开号：US11312682B2

  公开（公告）日：2022-04-26

  Disclosed are novel compounds—benzenesulfonamides of general formulas (I) and (II) The compounds can be used in biomedicine as active ingredients in pharmaceutical formulations, because they inhibit enzymes which participate in disease progression. Also disclosed are method of treatment using such compounds.

  公开了通式 (I) 和 (II) 的新型化合物-苯磺酰胺 这些化合物可用于生物医学，作为药物制剂的活性成分，因为它们能抑制参与疾病进展的酶。此外，还公开了使用此类化合物进行治疗的方法。
• SELECTIVE INHIBITORS OF CARBONIC ANHYDRASE
  申请人：Vilnius University

  公开号：EP3328833A1

  公开（公告）日：2018-06-06
• Design of [(2-pyrimidinylthio)acetyl]benzenesulfonamides as inhibitors of human carbonic anhydrases
  作者：Edita Čapkauskaitė、Asta Zubrienė、Lina Baranauskienė、Giedrė Tamulaitienė、Elena Manakova、Visvaldas Kairys、Saulius Gražulis、Sigitas Tumkevičius、Daumantas Matulis

  DOI：10.1016/j.ejmech.2012.02.050

  日期：2012.5

  A series of [(2-pyrimidinylthio)acetyl]benzenesulfonamides were designed and synthesized. Their binding affinities as inhibitors of several recombinant human carbonic anhydrase (CA) isozymes were determined by isothermal titration calorimetry (ITC) and thermal shift assay (TSA). A group of compounds containing a chlorine atom in the benzenesulfonamide ring were found to exhibit higher selectivity but lower binding affinity toward tested CAs. The crystal structures of selected compounds in complex with CA II were determined to atomic resolution. Docking studies were performed to compare the binding modes of experimentally determined crystallographic structures with computational prediction of the pyrimidine derivative binding to CA II. Several compounds bound to select CAs with single-digit nanomolar affinities and could be used as leads for inhibitor development toward a select CA isozyme. (C) 2012 Elsevier Masson SAS. All rights reserved.