2-溴-1-[4-(1-吡咯烷基磺酰基)苯基]乙酮 | 58722-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-溴-1-[4-(1-吡咯烷基磺酰基)苯基]乙酮
• 英文名称: 2-bromo-1-(4-(pyrrolidin-1-ylsulfonyl)phenyl)ethanone
• 英文别名: 2-Bromo-1-[4-(pyrrolidine-1-sulfonyl)phenyl]ethan-1-one；2-bromo-1-(4-pyrrolidin-1-ylsulfonylphenyl)ethanone
• CAS: 58722-38-6
• 化学式: C₁₂H₁₄BrNO₃S
• mdl: MFCD06356470
• 分子量: 332.218
• InChiKey: DNFXLQROGLQKEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  2-溴-1-[4-(1-吡咯烷基磺酰基)苯基]乙酮 在 哌啶 、 硫化氢 、 sodium acetate 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 5-(4-fluorobenzylidene)-2-((4-(4-(pyrrolidin-1-ylsulfonyl)phenyl)thiazol-2-yl)methyl)thiazol-4(5H)-one
  参考文献：
  名称：

  Synthesis, Molecular Docking and Anti-Human Breast Cancer Activities of Novel Thiazolylacetonitriles and Thiazolylacrylonitriles and Their Derivatives Containing Benzenesulfonylpyrrolidine Moiety

  摘要：

  This article describes the synthesis of some novel sulfonamides having the biologically active, thiazole 3, 8-10, 13, 19, 20, 24, 30, 31, 35-41, pyrazolo [5,1-c] [1,2,4]triazine 5, 1H-1,2,4-triazole 6, thiazolo[3,2-a]pyridine 14, chromen-2-one 16, benzo[f]chromen-3-imine 17, benzoNchromen-3-one 18, triazolo[4,3-a]pyrimidine 22, pyrazolo[1,5-c]pyrimidine 23, isoxazole 26, 2,4-diaminopyrimidine 27, benzo[4,5]imidazo[1,2-a]pyridine 28, imidazolidine 32 and 1H-benzo[d]imidazolidene 33 moieties, starting with 2-(4-(4-(pyrrolidinl-ylsulfonyl)phenyl)thiazol-2-yl)acetonitrile (2), which was prepared from cyclocondensation of phenacyl bromide derivative 1 with 2-cyanoethanethio-amide. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, H-1 NMR, C-13 NMR and Ms spectral data. All the compounds were tested in-vitro antihuman breast cancer cell line (MCF7). Compounds 18, 8, 41 and 28 with IC50 values of 48.01, 49.11, 49.27 and 49.78 mu M, respectively, exhibited better activity than doxorubicin (DOX) as a reference drug with 1050 value of 68.6 mu M. Molecular Operating Environment (MOE) performed virtual screening using molecular docking studies of the synthesized compounds. The results indicated that some synthesized compounds suitable inhibitor against dihydrofolate reductase (DHFR) enzyme (PDB ID: 4DFR) with further modification.

  DOI：

  10.3987/com-15-13384
• 作为产物：
  描述：

  1-[4-(吡咯烷-1-磺酰基)苯基]乙酮 生成 2-溴-1-[4-(1-吡咯烷基磺酰基)苯基]乙酮
  参考文献：
  名称：

  VEJDELEK Z. J.; METYS J.; NEMEC J.; PROTIVA M., COLLECT. CZECH. CHEM. COMMUNS. , 1975, 40, NO 12, 3895-3903

  摘要：

  DOI：

文献信息

• Synthesis, Molecular Docking and Anti-Human Breast Cancer Activities of Novel Thiazolylacetonitriles and Thiazolylacrylonitriles and Their Derivatives Containing Benzenesulfonylpyrrolidine Moiety
  作者：Mahmoud S. Bashandy、Shimaa M. Abd El-Gilil

  DOI：10.3987/com-15-13384

  日期：——

  This article describes the synthesis of some novel sulfonamides having the biologically active, thiazole 3, 8-10, 13, 19, 20, 24, 30, 31, 35-41, pyrazolo [5,1-c] [1,2,4]triazine 5, 1H-1,2,4-triazole 6, thiazolo[3,2-a]pyridine 14, chromen-2-one 16, benzo[f]chromen-3-imine 17, benzoNchromen-3-one 18, triazolo[4,3-a]pyrimidine 22, pyrazolo[1,5-c]pyrimidine 23, isoxazole 26, 2,4-diaminopyrimidine 27, benzo[4,5]imidazo[1,2-a]pyridine 28, imidazolidine 32 and 1H-benzo[d]imidazolidene 33 moieties, starting with 2-(4-(4-(pyrrolidinl-ylsulfonyl)phenyl)thiazol-2-yl)acetonitrile (2), which was prepared from cyclocondensation of phenacyl bromide derivative 1 with 2-cyanoethanethio-amide. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, H-1 NMR, C-13 NMR and Ms spectral data. All the compounds were tested in-vitro antihuman breast cancer cell line (MCF7). Compounds 18, 8, 41 and 28 with IC50 values of 48.01, 49.11, 49.27 and 49.78 mu M, respectively, exhibited better activity than doxorubicin (DOX) as a reference drug with 1050 value of 68.6 mu M. Molecular Operating Environment (MOE) performed virtual screening using molecular docking studies of the synthesized compounds. The results indicated that some synthesized compounds suitable inhibitor against dihydrofolate reductase (DHFR) enzyme (PDB ID: 4DFR) with further modification.
• VEJDELEK Z. J.; METYS J.; NEMEC J.; PROTIVA M., COLLECT. CZECH. CHEM. COMMUNS. <CCCC-AK>, 1975, 40, NO 12, 3895-3903
  作者：VEJDELEK Z. J.、 METYS J.、 NEMEC J.、 PROTIVA M.

  DOI：——

  日期：——