7-(4-((1-chloroethoxy)carbonyl)-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinlone-3-carboxylic acid | 925684-53-3

• 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-((1-chloroethoxy)carbonyl)-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinlone-3-carboxylic acid
• 英文别名: 7-(4-((1-chloroethoxy)carbonyl)-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid；7-[4-(1-chloroethoxycarbonyl)-3-methylpiperazin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid
• CAS: 925684-53-3
• 化学式: C₂₂H₂₅ClFN₃O₆
• 分子量: 481.908
• InChiKey: XLXXZSDSXZKGIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  661.0±55.0 °C(Predicted)
• 密度：
  1.452±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.6
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  7-(4-((1-chloroethoxy)carbonyl)-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinlone-3-carboxylic acid 、 4-[(tetraethylbisphosphonomethyl)carbamoyl]butanoic acid sodium salt 在 三甲基溴硅烷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成 1-Cyclopropyl-7-[4-[1-[5-(diphosphonomethylamino)-5-oxopentanoyl]oxyethoxycarbonyl]-3-methylpiperazin-1-yl]-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Phosphonated Fluoroquinolones, Antibacterial Analogs Thereof, and Methods for the Prevention and Treatment of Bone and Joint Infections

  摘要：

  本发明涉及磷酸化氟喹诺酮及其抗菌类似物，以及使用这些化合物的方法。这些化合物可用作抗生素，用于预防和/或治疗骨骼和关节感染，特别是用于预防和/或治疗骨髓炎。

  公开号：

  US20080287396A1
• 作为产物：
  描述：

  1-氯乙基氯甲酸酯 、 加替沙星 在 1,8-双二甲氨基萘 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以98%的产率得到7-(4-((1-chloroethoxy)carbonyl)-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinlone-3-carboxylic acid
  参考文献：
  名称：

  Phosphonated Fluoroquinolones, Antibacterial Analogs Thereof, and Methods for the Prevention and Treatment of Bone and Joint Infections

  摘要：

  本发明涉及磷酸化氟喹诺酮及其抗菌类似物，以及使用这些化合物的方法。这些化合物可用作抗生素，用于预防和/或治疗骨骼和关节感染，特别是用于预防和/或治疗骨髓炎。

  公开号：

  US20080287396A1

文献信息

• Linking Bisphosphonates to the Free Amino Groups in Fluoroquinolones: Preparation of Osteotropic Prodrugs for the Prevention of Osteomyelitis
  作者：Tom J. Houghton、Kelly S. E. Tanaka、Ting Kang、Evelyne Dietrich、Yanick Lafontaine、Daniel Delorme、Sandra S. Ferreira、Frederic Viens、Francis F. Arhin、Ingrid Sarmiento、Dario Lehoux、Ibtihal Fadhil、Karine Laquerre、Jing Liu、Valérie Ostiguy、Hugo Poirier、Gregory Moeck、Thomas R. Parr、Adel Rafai Far

  DOI：10.1021/jm801007z

  日期：2008.11.13

  Osteomyelitis is an infection located in bone and a notoriously difficult disease to manage, requiring frequent and heavy doses of systemically administered antibiotics. Targeting antibiotics to the bone after systemic administration may provide both greater efficacy of treatment and less frequent administration. By taking advantage, of the affinity of the bisphosphonate group for bone mineral, we have prepared a set of 13 bisphosphonated antibacterial prodrugs based on eight different linkers tethered to the free amino functionality on fluoroquinolone antibiotics. While all but one of the prodrugs were shown in vitro to be effective and rapid bone binders (over 90% in 1 h), only eight of them demonstrated the capacity to significantly regenerate the parent drug. In a rat model of the disease, a selected group of agents demonstrated their ability to prevent osteomyelitis when used in circumstances under which the parent drug had already been cleared and is thus inactive.
• [EN] PHOSPHONATED FLUOROQUINOLONES, ANTIBACTERIAL ANALOGS THEREOF, AND METHODS FOR THE PREVENTION AND TREATMENT OF BONE AND JOINT INFECTIONS<br/>[FR] FLUOROQUINOLONES PHOSPHONEES, LEURS ANALOGUES ANTIBACTERIENS, ET METHODES PERMETTANT DE PREVENIR ET DE TRAITER DES INFECTIONS OSSEUSES ET ARTICULAIRES
  申请人：TARGANTA THERAPEUTICS INC

  公开号：WO2007017762A2

  公开（公告）日：2007-02-15

  [EN] The present invention relates to phosphonated fluoroquinolones, antibacterial analogs thereof, and methods of using such compounds. These compounds are useful as antibotics for prevention and/or the treatment of bone and joint infections, especially for the prevention and/or treatment of osteomyelitis.
  [FR] La présente invention se rapporte à des fluoroquinolones phosphonées, à des analogues antibactériens de celles-ci, et à des procédés d'utilisation de tels composés. Lesdits composés sont utiles en tant qu'antibiotiques destinés à prévenir et/ou à traiter des infections osseuses et articulaires, en particulier l'ostéomyélite.