7-(4-(tert-butoxycarbonyl)-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid | 925684-44-2

• 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-(tert-butoxycarbonyl)-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid
• 英文别名: N-Boc Gatifloxacin；1-cyclopropyl-6-fluoro-8-methoxy-7-[3-methyl-4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
• CAS: 925684-44-2
• 化学式: C₂₄H₃₀FN₃O₆
• 分子量: 475.517
• InChiKey: IDCLIWMMICEQGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 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-(tert-butoxycarbonyl)-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 potassium carbonate 、 2-甲基苯亚磺酸钠 、 三乙胺 、 乙酰氯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.42h， 生成 7-(4-(3,3-bis(diethylphosphono)propionyl)-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-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：

  二碳酸二叔丁酯 、 加替沙星 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到7-(4-(tert-butoxycarbonyl)-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  转运蛋白靶向加替沙星前药：合成、渗透性和局部眼部给药

  摘要：

  在这项工作中，我们的目标是设计和合成靶向有机阳离子转运蛋白 (OCT)、单羧酸转运蛋白 (MCT) 和 ATB (0, +) 转运蛋白的加替沙星前药，并确定一种增强递送至眼后部的前药。设计并合成了加替沙星 (GFX)、DMAP-GFX、CP-GFX 和 APM-GFX 的二甲氨基-丙基、羧基-丙基和氨基-丙基（2-甲基）衍生物以靶向 OCT、MCT 和 ATB。 0, +) 转运蛋白。开发了一种 LC-MS 方法来分析各种研究中的药物和前药水平。溶解度和 log D测量前药和母体药物的 (pH 7.4)。在角膜、结膜和巩膜-脉络膜-视网膜色素上皮 (SCRPE) 中测定前药的渗透性，并使用 Ussing 室组件与加替沙星进行比较。通过在存在转运蛋白特异性抑制剂的情况下确定转运，阐明了渗透机制。1-甲基-4-苯基吡啶鎓碘化物（MPP +），烟酸钠盐，和α甲基dl的色氨酸被用来抑制OCT中，M

  DOI：

  10.1021/mp300245r

文献信息

• TOPICAL OCULAR DRUG DELIVERY
  申请人：The Regents of the University of Colorado, a body corporate

  公开号：US20130190324A1

  公开（公告）日：2013-07-25

  The present invention provides compositions and methods for increasing the delivery (i.e., bioavailability) of a compound to an ocular cell. Such compositions and methods can be used to treat an ocular clinical condition. Typically, increased bioavailability or delivery of the compound to ocular cells is achieved by utilizing a membrane transporter.

  本发明提供了增加化合物输送到眼细胞（即生物利用度）的组合物和方法。这些组合物和方法可用于治疗眼部临床疾病。通常，通过利用膜转运蛋白实现将化合物输送到眼细胞的生物利用度或输送量增加。
• 一种加替沙星衍生物、均相酶免疫检测试剂及其制备方法
  申请人：苏州博源医疗科技有限公司

  公开号：CN117820293A

  公开（公告）日：2024-04-05

  本发明公开了一种加替沙星衍生物、均相酶免疫检测试剂及其制备方法，涉及生物医学检测技术领域。使用所述加替沙星衍生物制备得到的加替沙星免疫原，并使用所述加替沙星免疫原免疫实验动物制备得到的抗加替沙星特异性抗体与108种常见其它药物无任何交叉反应。使用上述抗加替沙星特异性抗体与加替沙星酶标偶联物制备得到的加替沙星均相酶免疫检测试剂的检测灵敏度达到pg/mL级别，能准确检测生物样本中微量加替沙星的浓度，其检测的准确性、精密度、灵敏度与特异性都显著高于现有技术。
• 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.
• Bisphosphonated fluoroquinolone esters as osteotropic prodrugs for the prevention of osteomyelitis
  作者：Kelly S.E. Tanaka、Tom J. Houghton、Ting Kang、Evelyne Dietrich、Daniel Delorme、Sandra S. Ferreira、Laurence Caron、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：10.1016/j.bmc.2008.09.010

  日期：2008.10

  Osteomyelitis is a difficult to treat bacterial infection of the bone. Delivering antibacterial agents to the bone may overcome the difficulties in treating this illness by effectively concentrating the antibiotic at the site of infection and by limiting the toxicity that may result from systemic exposure to the large doses conventionally used. Using bisphosphonates as osteophilic functional groups, different forms of fluoroquinolone esters were synthesized and evaluated for their ability to bind bone and to release the parent antibacterial agent. Bisphosphonated glycolamide fluoroquinolone esters were found to present a profile consistent with effective and rapid bone binding and efficient release of the active drug moiety. They were assessed for their ability to prevent bone infection in vivo and were found to be effective when the free fluoroquinolones were not (C) 2008 Elsevier Ltd. All rights reserved.
• PHOSPHONATED FLUOROQUINOLONES, ANTIBACTERIAL ANALOGS THEREOF, AND METHODS FOR THE PREVENTION AND TREATMENT OF BONE AND JOINT INFECTIONS
  申请人：Targanta Therapeutics Inc.

  公开号：EP1881974A2

  公开（公告）日：2008-01-30