1-(4-(piperidin-1-ylsulfonyl)phenyl)pyrrolidin-2-one | 293325-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-(4-(piperidin-1-ylsulfonyl)phenyl)pyrrolidin-2-one
• 英文别名: 1-[4-(Piperidine-1-sulfonyl)-phenyl]-pyrrolidin-2-one；1-(4-piperidin-1-ylsulfonylphenyl)pyrrolidin-2-one
• CAS: 293325-17-4
• 化学式: C₁₅H₂₀N₂O₃S
• 分子量: 308.401
• InChiKey: MHPNPLGXASZSRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-苯基-2-吡咯烷酮 在 氯磺酸 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 15.5h， 生成 1-(4-(piperidin-1-ylsulfonyl)phenyl)pyrrolidin-2-one
  参考文献：
  名称：

  新型叔磺酰胺类作为有效的抗癌药

  摘要：

  对于美国成年女性而言，乳腺癌是最普遍的癌症形式。靶向信号转导失调的化合物可以是有效的抗癌疗法。Wingless相关整合位点（Wnt）途径是乳腺癌细胞中经常失调的一个重要信号通路。这项工作的目的是优化筛选活动中的“成功”。在Wnt转录分析中测试了76,000种化合物，并揭示了有效且可重现的“命中”化合物1。的药物化学优化1导致更有效的和药物样分子，19，24和25（即，Wnt途径的IC 50值分别为11、18和7 nM）。主要结果表明化合物19，24和25分别为在乳腺癌细胞系中的有效的抗增殖剂，MCF-7（即，IC 50个值= 10，图7和4nM的，分别地）和MDA-MB 231（即，IC 50个值分别为13、13和16 nM）。化合物19在体外与化学治疗的阿霉素协同抗增殖。一个主要结论是，化合物19在体外和乳腺癌异种移植动物模型中增强了阿霉素的抗增殖能力。

  DOI：

  10.1016/j.bmc.2018.07.042

文献信息

• [EN] [4-(PHENYLSULFONYL)PIPERAZIN-1-YL](1H-1,2,3-TRIAZOL-4-YL)METHANONES<br/>[FR] [4-(PHÉNYLSULFONYL)PIPÉRAZIN-1-YL](1H-1,2,3-TRIAZOL-4-YL)MÉTHANONES
  申请人：BAYER PHARMA AG

  公开号：WO2018114670A1

  公开（公告）日：2018-06-28

  The present invention covers [4-(phenylsulfonyl)piperazin-1-yl](1H-1,2,3-triazol-4- yl)methanone compounds of general formula (I): (I), in which Q, R1, R2, R3, R4 and R5 are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of disorders, in particular of gynecological disorders, hyperproliferative disorders, metabolic disorders, or inflammatory disorders as a sole agent or in combination with other active ingredients.

  本发明涵盖了通式(I)的[4-(苯磺酰基)哌嗪-1-基](1H-1,2,3-三唑-4-基)甲酮化合物：(I)，其中Q、R1、R2、R3、R4和R5如本文所定义，制备该化合物的方法，用于制备该化合物的中间体化合物，包含该化合物的药物组合物和制造用于治疗或预防疾病的制药组合物的使用，特别是妇科疾病、高增殖性疾病、代谢性疾病或炎症性疾病，作为唯一的药剂或与其他活性成分组合使用。
• [8-(phenylsulfonyl)-3,8-diazabicyclo[3.2.1]oct-3-yl](1H-1,2,3-triazol-4-yl)methanones
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US10167293B2

  公开（公告）日：2019-01-01

  The present invention covers [8-(phenylsulfonyl)-3,8-diazabicyclo[3.2.1]oct-3-yl](1H-1,2,3-triazol-4-yl)methanone compounds of general formula (I): in which R1, R2, R3, R4 and R5 are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of disorders, in particular of gynecological disorders, hyperproliferative disorders, metabolic disorders, or inflammatory disorders as a sole agent or in combination with other active ingredients.

  本发明涉及通式(I)的[8-(苯磺酰基)-3,8-二氮杂双环[3.2.1]辛-3-基](1H-1,2,3-三唑-4-基)甲酮化合物： 其中 R1、R2、R3、R4 和 R5 如本文所定义；制备所述化合物的方法；用于制备所述化合物的中间体化合物；包含所述化合物的药物组合物和组合物；以及使用所述化合物制造药物组合物，用于治疗或预防疾病，特别是妇科疾病、过度增殖性疾病、代谢性疾病或炎症性疾病，作为单独制剂或与其他活性成分组合使用。
• Synthesis and structure–activity relationships for 1-(4-(piperidin-1-ylsulfonyl)phenyl)pyrrolidin-2-ones as novel non-carboxylate inhibitors of the aldo-keto reductase enzyme AKR1C3
  作者：Daniel M. Heinrich、Jack U. Flanagan、Stephen M.F. Jamieson、Shevan Silva、Laurent J.M. Rigoreau、Elisabeth Trivier、Tony Raynham、Andrew P. Turnbull、William A. Denny

  DOI：10.1016/j.ejmech.2013.01.047

  日期：2013.4

  High expression of the aldo-keto reductase enzyme AKR1C3 in the human prostate and breast has implicated it in the development and progression of leukemias and of prostate and breast cancers. Inhibitors are thus of interest as potential drugs. Most inhibitors of AKR1C3 are carboxylic acids, whose transport into cells is likely dominated by carrier-mediated processes. We describe here a series of (piperidinosulfonamidophenyl)pyrrolidin-2-ones as potent (<100 nM) and isoform-selective non-carboxylate inhibitors of AKR1C3. Structure-activity relationships identified the sulfonamide was critical, and a crystal structure showed the 2-pyrrolidinone does not interact directly with residues in the oxyanion hole. Variations in the position, co-planarity or electronic nature of the pyrrolidinone ring severely diminished activity, as did altering the size or polarity of the piperidino ring. There was a broad correlation between the enzyme potencies of the compounds and their effectiveness at inhibiting AKR1C3 activity in cells. (C) 2013 Elsevier Masson SAS. All rights reserved.
• [EN] [8-(PHENYLSULFONYL)-3,8-DIAZABICYCLO[3.2.1]OCT-3-YL] (1H-1,2,3-TRIAZOL-4-YL)METHANONES<br/>[FR] [8-(PHÉNYLSULFONYL)-3,8-DIAZABICYCLO[3.2.1]OCT-3-YL] (1H-1,2,3-TRIAZOL-4-YL)MÉTHANONES
  申请人：BAYER PHARMA AG

  公开号：WO2017202817A9

  公开（公告）日：2018-12-06
• [8-(PHENYLSULFONYL)-3,8-DIAZABICYCLO[3.2.1]OCT-3-YL](1H-1,2,3-TRIAZOL-4-YL)METHANONES
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：EP3464288A1

  公开（公告）日：2019-04-10