tetraethyl 4-iodobutylene-1,1-bisphosphonate | 925684-41-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: tetraethyl 4-iodobutylene-1,1-bisphosphonate
• 英文别名: 1,1-bis(diethoxyphosphoryl)-4-iodobutane
• CAS: 925684-41-9
• 化学式: C₁₂H₂₇IO₆P₂
• 分子量: 456.195
• InChiKey: QFPDNWWKFSOMCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tetraethyl 4-iodobutylene-1,1-bisphosphonate 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 6.5h， 生成
  参考文献：
  名称：

  PHOSPHONATED RIFAMYCINS AND USES THEREOF FOR THE PREVENTION AND TREATMENT OF BONE AND JOINT INFECTIONS

  摘要：

  本发明涉及磷酸化利福霉素以及制备和使用这类化合物的方法。这些化合物可用作预防和/或治疗骨骼和关节感染的抗生素，特别是用于预防和/或治疗骨髓炎。

  公开号：

  US20110263534A1
• 作为产物：
  描述：

  tetraethyl 4-hydroxybutylene-1,1-bisphosphonate 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到tetraethyl 4-iodobutylene-1,1-bisphosphonate
  参考文献：
  名称：

  PHOSPHONATED RIFAMYCINS AND USES THEREOF FOR THE PREVENTION AND TREATMENT OF BONE AND JOINT INFECTIONS

  摘要：

  本发明涉及磷酸化利福霉素以及制备和使用这类化合物的方法。这些化合物可用作预防和/或治疗骨骼和关节感染的抗生素，特别是用于预防和/或治疗骨髓炎。

  公开号：

  US20110263534A1

文献信息

• Phosphonated Fluoroquinolones, Antibacterial Analogs Thereof, and Methods for the Prevention and Treatment of Bone and Joint Infections
  申请人：Delorme Daniel

  公开号：US20080287396A1

  公开（公告）日：2008-11-20

  The present invention relates to phosphonated fluoroquinolones, antibacterial analogs thereof, and methods of using such compounds. These compounds are useful as antibiotics for prevention and/or the treatment of bone and joint infections, especially for the prevention and/or treatment of osteomyelitis.

  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。
• Phosphonated Rifamycins and uses thereof for the prevention and treatment of bone and joint infections
  申请人：Rose Yannick Stephane

  公开号：US08404664B2

  公开（公告）日：2013-03-26

  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。
• 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