7-(4-acetyl-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 955283-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-(4-acetyl-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 7-(4-acetyl-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid
• CAS: 955283-66-6
• 化学式: C₂₁H₂₄FN₃O₅
• 分子量: 417.437
• InChiKey: CBEJXCSPOSIEGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-(4-acetyl-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 在 哌啶 、 水 、 三乙胺 、 sodium hydroxide 、 magnesium chloride 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 18.0h， 生成 1-cyclopropyl-6-fluoro-7-(3-methyl-4-acetylpiperazin-1-yl)-3-cinnamoylquinoline-4(1H)one
  参考文献：
  名称：

  一种N-乙酰基加替沙星的丙烯酮衍生物及其制备方法和应用

  摘要：

  本发明公开了一种N‑乙酰基加替沙星的丙烯酮衍生物及其制备方法和应用，采用如下式Ⅰ化学结构通式：式I中，芳香环Ar为苯环或取代苯环或呋喃环或吡啶环。本发明的一种N‑乙酰基加替沙星的丙烯酮衍生物，实现了氟喹诺酮骨架与丙烯酮骨架的有效拼合，进而构筑了新的氟喹诺酮“类查尔酮”化合物，从而增加了新化合物的抗肿瘤活性及抗耐药性，并降低对正常细胞的毒副作用，可以作为抗肿瘤活性物质开发全新结构的抗肿瘤药物。

  公开号：

  CN112824401B
• 作为产物：
  描述：

  乙酸酐 、 加替沙星 在 吡啶 作用下， 以74%的产率得到7-(4-acetyl-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis, characterization, antibacterial, antifungal, and immunomodulating activities of gatifloxacin derivatives

  摘要：

  Gatifloxacin is a synthetic broad-spectrum fluorquinolone antibacterial agent with a 3-methylpiperazinyl-side chain at position 7 and a methoxy group at position 8 of the quinolone ring. In the present study different analogues of gatifloxacin were prepared; the piperazinyl ring was chosen as the center of reaction for synthesizing this series of derivatives. The structures of these derivatives were established using spectroscopic techniques such as IR, H-1 NMR, and EIMS. In vitro antibacterial and antifungal activities were evaluated by disc diffusion method and these derivatives were compared with in-use fluoroquinolones like gatifloxacin, sparfloxacin, and gemifloxacin. Derivative A proved very potent against Gram-negative organisms, especially Pseudomonas aeruginosa, Shigella flexeneri, and Klebseilla pneumoniae, and derivatives A-C exhibited good antifungal activity compared to in-use quinolones. In addition, gatifloxacin and derivatives were investigated for immunomodulating activities. Derivative B has good anti-inflammatory activity, with IC50 < 12.5 mu g/ml.

  DOI：

  10.1007/s00044-009-9264-y

文献信息

• 加替沙星衍生物及其制备方法和用途
  申请人：西南大学

  公开号：CN107721924B

  公开（公告）日：2021-10-22

  本发明属于药物化学领域，具体涉及一种加替沙星衍生物及其制备方法和用途。本发明通过对加替沙星7位侧链进行结构修饰得到式I所示化合物，本发明的化合物不但能够对结核分支杆菌及普通细菌所致感染进行治疗，还对细菌持留菌、柑桔致病菌、烟酰胺N‑甲基转移酶(NNMT)、白细胞介素IL‑17 PPI及前蛋白转化酶枯草溶菌素9(PCSK9)具有抑制活性。本发明的化合物制备过程操作简便、条件温和，得到抗菌活性增强、水溶性提高、毒副作用降低的众多化合物，有望减少用药剂量、缩短治疗周期、提高患者依从性，为结核病药物和其他疾病研究提供新的分子类型与研究思路。
• Synthesis, characterization, antibacterial, antifungal, and immunomodulating activities of gatifloxacin derivatives
  作者：Najma Sultana、Asia Naz、Bushra Khan、M. Saeed Arayne、M. Ahmed Mesaik

  DOI：10.1007/s00044-009-9264-y

  日期：2010.12

  Gatifloxacin is a synthetic broad-spectrum fluorquinolone antibacterial agent with a 3-methylpiperazinyl-side chain at position 7 and a methoxy group at position 8 of the quinolone ring. In the present study different analogues of gatifloxacin were prepared; the piperazinyl ring was chosen as the center of reaction for synthesizing this series of derivatives. The structures of these derivatives were established using spectroscopic techniques such as IR, H-1 NMR, and EIMS. In vitro antibacterial and antifungal activities were evaluated by disc diffusion method and these derivatives were compared with in-use fluoroquinolones like gatifloxacin, sparfloxacin, and gemifloxacin. Derivative A proved very potent against Gram-negative organisms, especially Pseudomonas aeruginosa, Shigella flexeneri, and Klebseilla pneumoniae, and derivatives A-C exhibited good antifungal activity compared to in-use quinolones. In addition, gatifloxacin and derivatives were investigated for immunomodulating activities. Derivative B has good anti-inflammatory activity, with IC50 < 12.5 mu g/ml.
• 一种N-乙酰基加替沙星的丙烯酮衍生物及其制备方法和应用
  申请人：河南大学

  公开号：CN112824401B

  公开（公告）日：2023-08-11

  本发明公开了一种N‑乙酰基加替沙星的丙烯酮衍生物及其制备方法和应用，采用如下式Ⅰ化学结构通式：式I中，芳香环Ar为苯环或取代苯环或呋喃环或吡啶环。本发明的一种N‑乙酰基加替沙星的丙烯酮衍生物，实现了氟喹诺酮骨架与丙烯酮骨架的有效拼合，进而构筑了新的氟喹诺酮“类查尔酮”化合物，从而增加了新化合物的抗肿瘤活性及抗耐药性，并降低对正常细胞的毒副作用，可以作为抗肿瘤活性物质开发全新结构的抗肿瘤药物。