methyl 3-[1-(6-chloropyridazin-3-yl)-2-oxo-4-(trimethylsilyl)but-3-yn-1-yl]-4-methoxybenzoate | 940891-77-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-[1-(6-chloropyridazin-3-yl)-2-oxo-4-(trimethylsilyl)but-3-yn-1-yl]-4-methoxybenzoate
• 英文别名: methyl 3-[1-(6-chloropyridazin-3-yl)-2-oxo-4-trimethylsilylbut-3-ynyl]-4-methoxybenzoate
• CAS: 940891-77-0
• 化学式: C₂₀H₂₁ClN₂O₄Si
• 分子量: 416.936
• InChiKey: IFJSJSXOGQYKRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-[1-(6-chloropyridazin-3-yl)-2-oxo-4-(trimethylsilyl)but-3-yn-1-yl]-4-methoxybenzoate 在 N-甲基吡咯烷酮 、 四丁基氟化铵 、 caesium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N-甲基吡咯烷酮 为溶剂， 反应 4.67h， 生成 3-(2-(2,4-二氟苯氧基)-6-氧代-6H-吡啶并[1,2-b]吡嗪-5-基)-4-甲氧基苯甲酸
  参考文献：
  名称：

  Synthesis, antimycobacterial and antibacterial activity of ciprofloxacin derivatives containing a N-substituted benzyl moiety

  摘要：

  We report herein the design and synthesis of a series of novel ciprofloxacin (CPFX) derivatives with remarkable improvement in lipophilicity by introducing a substituted benzyl moiety to the N atom on the C-7 piperazine ring of CPFX. Antimycobacterial and antibacterial activity of the newly synthesized compounds was evaluated. Results reveal that compound 4f has good in vitro activity against all of the tested Gram-positive strains including MRSA and MRSE (MICs: 0.06-32 mu g/mL) which is two to eightfold more potent than or comparable to the parent drug CPFX (MICs: 0.25-128 mu g/mL), Gram-negative bacteria P. aeruginosa (MICs: 0.5-4 mu g/mL) and M. tuberculosis H37Rv ATCC 27294 (MIC: 1 mu g/mL). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.040
• 作为产物：
  描述：

  4-甲氧基-3-甲基苯甲酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 lithium hexamethyldisilazane 、 锌 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 3.0h， 生成 methyl 3-[1-(6-chloropyridazin-3-yl)-2-oxo-4-(trimethylsilyl)but-3-yn-1-yl]-4-methoxybenzoate
  参考文献：
  名称：

  Synthesis, antimycobacterial and antibacterial activity of ciprofloxacin derivatives containing a N-substituted benzyl moiety

  摘要：

  We report herein the design and synthesis of a series of novel ciprofloxacin (CPFX) derivatives with remarkable improvement in lipophilicity by introducing a substituted benzyl moiety to the N atom on the C-7 piperazine ring of CPFX. Antimycobacterial and antibacterial activity of the newly synthesized compounds was evaluated. Results reveal that compound 4f has good in vitro activity against all of the tested Gram-positive strains including MRSA and MRSE (MICs: 0.06-32 mu g/mL) which is two to eightfold more potent than or comparable to the parent drug CPFX (MICs: 0.25-128 mu g/mL), Gram-negative bacteria P. aeruginosa (MICs: 0.5-4 mu g/mL) and M. tuberculosis H37Rv ATCC 27294 (MIC: 1 mu g/mL). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.040

文献信息

• P38 kinase inhibiting agents
  申请人：Chen Meng-Hsin

  公开号：US20070129372A1

  公开（公告）日：2007-06-07

  Compounds described by the chemical formula (I) or pharmaceutically acceptable salts thereof: are inhibitors of p38 and are useful in the treatment of inflammation such as in the treatment of rheumatoid arthritis, rheumatoid spondylitis, osteoarthritis, gouty arthritis and other arthritic conditions; inflamed joints, eczema, psoriasis or other inflammatory skin conditions such as sunburn; inflammatory eye conditions including conjunctivitis; pyresis, pain and other conditions associated with inflammation.

  化学式（I）描述的化合物或其药用盐：是p38的抑制剂，可用于治疗炎症，如治疗类风湿关节炎、类风湿脊柱炎、骨关节炎、痛风性关节炎和其他关节炎症状；发炎关节、湿疹、牛皮癣或其他炎症性皮肤病症，如晒伤；包括结膜炎在内的炎症性眼部疾病；发热、疼痛和其他与炎症相关的病症。
• P38 Kinase Inhibiting Agents
  申请人：Chen Meng-Hsin

  公开号：US20090088436A1

  公开（公告）日：2009-04-02

  Compounds described by the chemical formula (I) or pharmaceutically acceptable salts thereof: are inhibitors of p38 and are useful in the treatment of inflammation such as in the treatment of rheumatoid arthritis, rheumatoid spondylitis, osteoarthritis, gouty arthritis and other arthritic conditions; inflamed joints, eczema, psoriasis or other inflammatory skin conditions such as sunburn; inflammatory eye conditions including conjunctivitis; pyresis, pain and other conditions associated with inflammation.

  化学式(I)或其药学上可接受的盐所描述的化合物：是p38的抑制剂，可用于治疗炎症，如类风湿性关节炎、类风湿性脊柱炎、骨关节炎、痛风性关节炎和其他关节炎症状；发炎的关节、湿疹、牛皮癣或其他炎症性皮肤病，如晒伤；炎症性眼部疾病，包括结膜炎；与炎症相关的发热、疼痛和其他症状。
• Synthesis, antimycobacterial and antibacterial activity of ciprofloxacin derivatives containing a N-substituted benzyl moiety
  作者：Shuo Wang、Xue-Dong Jia、Ming-Liang Liu、Yu Lu、Hui-Yuan Guo

  DOI：10.1016/j.bmcl.2012.07.040

  日期：2012.9

  We report herein the design and synthesis of a series of novel ciprofloxacin (CPFX) derivatives with remarkable improvement in lipophilicity by introducing a substituted benzyl moiety to the N atom on the C-7 piperazine ring of CPFX. Antimycobacterial and antibacterial activity of the newly synthesized compounds was evaluated. Results reveal that compound 4f has good in vitro activity against all of the tested Gram-positive strains including MRSA and MRSE (MICs: 0.06-32 mu g/mL) which is two to eightfold more potent than or comparable to the parent drug CPFX (MICs: 0.25-128 mu g/mL), Gram-negative bacteria P. aeruginosa (MICs: 0.5-4 mu g/mL) and M. tuberculosis H37Rv ATCC 27294 (MIC: 1 mu g/mL). (C) 2012 Elsevier Ltd. All rights reserved.