4-(2-oxoimidazolidin-1-yl)benzenesulfonyl chloride | 827579-44-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-(2-oxoimidazolidin-1-yl)benzenesulfonyl chloride
• 英文别名: 4-(2-oxoimidazolidin-1-yl)benzene-1-sulfonyl chloride；1-(p-chlorosulfonyl)-phenyl-2-oxo-imidazolidin
• CAS: 827579-44-2
• 化学式: C₉H₉ClN₂O₃S
• 分子量: 260.701
• InChiKey: RMEQLFLQQGVWBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-oxoimidazolidin-1-yl)benzenesulfonyl chloride 、 3,4-二甲氧基苯胺 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 以59%的产率得到N-(3,4-dimethoxyphenyl)-4-(2-oxoimidazolidin-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonamides as antimitotics. Antiproliferative, antiangiogenic and antitumoral activity, and quantitative structure-activity relationships

  摘要：

  The importance of the bridge linking the two phenyl moieties of substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates (PIB-SOs) was assessed using a sulfonamide group, which is a bioisostere of sulfonate and ethenyl groups. Forty one phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonamide (PIB-SA) derivatives were prepared and biologically evaluated. PIB-SAs exhibit antiproliferative activities at the nanomolar level against sixteen cancer cell lines, block the cell cycle progression in G(2)/M phase, leading to cytoskeleton disruption and anoikis. These results were subjected to CoMFA and CoMSIA analyses to establish quantitative structure-activity relationships. These results evidence that the sulfonate and sulfonamide moieties are reciprocal bioisosteres and that phenylimidazolidin-2-one could mimic the trimethoxyphenyl moiety found in the structure of numerous potent antimicrotubule agents. Finally, compounds 16 and 17 exhibited potent antitumor and antiangiogenic activities on HT-1080 fibrosarcoma cells grafted onto chick chorioallantoic membrane similar to CA-4 without significant toxicity for the chick embryos, making this class of compounds a promising class of anticancer agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.034
• 作为产物：
  描述：

  1-(2-氯乙基)-3-苯基脲 在 氯磺酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 32.0h， 生成 4-(2-oxoimidazolidin-1-yl)benzenesulfonyl chloride
  参考文献：
  名称：

  吡啶基部分对 4-(2-氧代咪唑啉-1-基)苯磺酸苯酯的苯环 B 进行修饰，产生针对秋水仙碱结合位点的新型抗有丝分裂剂

  摘要：

  设计、制备了一系列 8 种新型吡啶基 4-(2-氧代咪唑烷-1-基)苯磺酸盐 (PYRIB-SO) 并评估了其作用机制。研究发现 PYRIB-SO 对几种乳腺癌细胞系具有纳摩尔至亚微摩尔范围的抗增殖活性。此外，随后的生物功能测定表明，最有效的 PYRIB-SO 作为抗有丝分裂剂与 α、β-微管蛋白的秋水仙碱结合位点 (C-BS) 结合，并将细胞周期进程阻止在 G2/M 期。微管免疫荧光和微管蛋白聚合测定证实，它们通过抑制微管蛋白聚合来破坏细胞骨架，正如用微管去稳定剂观察到的那样。它们还表现出良好的整体理论理化、药代动力学和药物样特性。总的来说，这些结果表明 PYRIB-SOs 是一个新的有前途的抗有丝分裂药物家族，有待进一步研究以进行生物制药和药效学评估。

  DOI：

  10.1016/j.bmcl.2024.129745

文献信息

• [EN] SUBSTITUTED 2-IMIDAZOLIDONES AND ANALOGS<br/>[FR] 2-IMIDAZOLIDONES SUBSTITUES ET ANALOGUES
  申请人：UNIV LAVAL

  公开号：WO2011100840A1

  公开（公告）日：2011-08-25

  Compounds of formula (I): wherein R1, R2, R3, R4, R7, R6, R7, R8, R9, A, X and Y as defined herein are provided as useful for the treatment of cancer or for the manufacture of anti-cancer agents.

  式（I）的化合物：其中所述的R1、R2、R3、R4、R7、R6、R7、R8、R9、A、X和Y如本文所定义的那样，被提供为用于治疗癌症或用于制造抗癌药物。
• Arylsulfonamide derivatives
  申请人：Anthony J. Neville

  公开号：US20060142612A1

  公开（公告）日：2006-06-29

  N-aryl arylsulfonamide derivatives are bradykinin B1 antagonists or inverse agonists useful in the treatment or prevention of symptoms such as pain and inflammation associated with the bradykinin B1 pathway.

  N-芳基磺酰胺衍生物是布雷金肽B1拮抗剂或逆激动剂，可用于治疗或预防与布雷金肽B1通路相关的疼痛和炎症等症状。
• Design, Synthesis, Biological Evaluation, and Structure–Activity Relationships of Substituted Phenyl 4-(2-Oxoimidazolidin-1-yl)benzenesulfonates as New Tubulin Inhibitors Mimicking Combretastatin A-4
  作者：Sébastien Fortin、Lianhu Wei、Emmanuel Moreau、Jacques Lacroix、Marie-France Côté、Éric Petitclerc、Lakshmi P. Kotra、René C.-Gaudreault

  DOI：10.1021/jm200488a

  日期：2011.7.14

  Sixty-one phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates (PIB-SOs) and 13 of their tetrahydro-2-oxopyrimidin-1(2H)-yl analogues (PPB-SOs) were prepared and biologically evaluated. The antiproliferative activities of PIB-SOs on 16 cancer cell lines are in the nanomolar range and unaffected in cancer cells resistant to colchicine, paclitaxel, and vinblastine or overexpressing the P-glycoprotein. None of the PPB-SOs exhibit significant antiproliferative activity. PIB-SOs block the cell cycle progression in the G(2)/M phase and bind to the colchicine-binding site on beta-tubulin leading to cytoskeleton disruption and cell death. Chick chorioallantoic membrane tumor assays show that compounds 36, 44, and 45 efficiently block angiogenesis and tumor growth at least at similar levels as combretastatin A-4 (CA-4) and exhibit low to very low toxicity on the chick embryos. PIB-SOs were subjected to CoMFA and CoMSIA analyses to establish quantitative structure-activity relationships.
• ARYLSULFONAMIDE DERIVATIVES
  申请人：Merck & Co., Inc.

  公开号：EP1643960A2

  公开（公告）日：2006-04-12
• SUBSTITUTED 2-IMIDAZOLIDONES AND ANALOGS
  申请人：Université Laval

  公开号：EP2536693A1

  公开（公告）日：2012-12-26