3-(2-hydroxy-5-(ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoic acid | 925685-07-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(2-hydroxy-5-(ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoic acid
• 英文别名: 3-[5-[diethoxyphosphorylmethyl(ethoxy)phosphoryl]-2-hydroxyphenyl]-3-methylbutanoic acid
• CAS: 925685-07-0
• 化学式: C₁₈H₃₀O₈P₂
• 分子量: 436.379
• InChiKey: BCTDEFZHCJKIFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(2-hydroxy-5-(ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoic acid 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 吡啶 、 氢氧化钾 、 氢气 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 9.17h， 生成 3-(2-(2,2-dimethylacetoxy)-5-(ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoic 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：

  diethyl (ethoxyphosphinyl)methylphosphonate 在 四(三苯基膦)钯 氢氧化钾 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 20.0h， 生成 3-(2-hydroxy-5-(ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoic 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

• PHOSPHONATED RIFAMYCINS AND USES THEREOF FOR THE PREVENTION AND TREATMENT OF BONE AND JOINT INFECTIONS
  申请人：Dietrich Evelyne

  公开号：US20110178001A1

  公开（公告）日：2011-07-21

  The present invention relates to phosphonated Rifamycins, and methods of making and using such compounds. These compounds are useful as antibiotics for prophylaxis and/or the treatment of bone and joint infections, especially for the prophylaxis and/or treatment of osteomyelitis.

  本发明涉及磷酸化利福霉素，以及制备和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。
• Phosphonated rifamycins and uses thereof for the prevention and treatment of bone and joint infections
  申请人：Dietrich Evelyne

  公开号：US08524691B2

  公开（公告）日：2013-09-03

  The present invention relates to phosphonated Rifamycins, and methods of making and using such compounds. These compounds are useful as antibiotics for prophylaxis and/or the treatment of bone and joint infections, especially for the prophylaxis and/or treatment of osteomyelitis.

  本发明涉及磷酸化利福霉素及其制备和使用方法。这些化合物可用作抗生素，用于预防和/或治疗骨和关节感染，特别是用于预防和/或治疗骨髓炎。
• [EN] PHOSPHONATED RIFAMYCINS AND USES THEREOF FOR THE PREVENTION AND TREATMENT OF BONE AND JOINT INFECTIONS<br/>[FR] RIFAMYCINES PHOSPHONÉES ET LEURS UTILISATIONS POUR LA PRÉVENTION ET LE TRAITEMENT D'INFECTIONS DES OS ET DES ARTICULATIONS
  申请人：DIETRICH EVELYNE

  公开号：WO2010019511A3

  公开（公告）日：2010-06-24
• 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.
• 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