P,P'-methanediyl-bis-phosphonic acid tetraallyl ester | 25091-05-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: P,P'-methanediyl-bis-phosphonic acid tetraallyl ester
• 英文别名: methanediyl-bis-phosphonic acid tetraallyl ester；Methandiyl-bis-phosphonsaeure-tetraallylester；Bis-diallyloxyphosphoryl-methan；tetraallyl methylene-1,1-bisphosphonate；Tetraallyl methylenebisphosphonate；Tetraallyl-methylendiphosphonat；3-[bis(prop-2-enoxy)phosphorylmethyl-prop-2-enoxyphosphoryl]oxyprop-1-ene
• CAS: 25091-05-8
• 化学式: C₁₃H₂₂O₆P₂
• 分子量: 336.262
• InChiKey: RSUSEISKYLWKSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  P,P'-methanediyl-bis-phosphonic acid tetraallyl ester 在 sodium hydride 、 二苯基膦酰羟胺 作用下， 以 N,N-二甲基甲酰胺 、 四氢呋喃 为溶剂， 以59%的产率得到tetrallyl 1-aminomethylenebisphosphonate
  参考文献：
  名称：

  Synthesis and in vitro evaluation of bisphosphonated glycopeptide prodrugs for the treatment of osteomyelitis

  摘要：

  As therapeutic agents of choice in the treatment of complicated infections, glycopeptide antibiotics are often preferentially used in cases of osteomyelitis, an infection located in bone and notoriously difficult to successfully manage. Yet frequent and heavy doses of these systemically administered antibiotics are conventionally prescribed to obtain higher antibiotic levels in the bone and reduce the high recurrence rates. Targeting antibiotics to the bone after systemic administration would present at least three potential advantages: (i) greater efficacy, by concentrating the therapeutic agent in bone; (ii) greater convenience, through a reduction in the frequency of administration; and (iii) greater safety, by reducing the levels of systemic drug exposure. We present here the design, synthesis and in vitro evaluation of eight prodrugs of the glycopeptide antibacterial agents vancomycin and oritavancin taking advantage of the affinity of the bisphosphonate group for bone for delivery to osseous tissues. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.006
• 作为产物：
  描述：

  亚甲基二磷酸 、 烯丙基原甲酸酯 生成 P,P'-methanediyl-bis-phosphonic acid tetraallyl ester
  参考文献：
  名称：

  Convenient method of esterification of polyphosphonic acids

  摘要：

  DOI：

  10.1021/jo00834a066

文献信息

• Synthesis of Symmetrical Methylenebis(Alkyl Hydrogen Phosphonates) by Selective Cleavage of Methylenebis(Dialkyl Phosphonates) with Morpholine
  作者：Gantla Vidyasagar Reddy、Hollie K. Jacobs、Aravamudan S. Gopalan、Richard E. Barrans、Mark L. Dietz、Dominique C. Stepinski、Albert W. Herlinger

  DOI：10.1081/scc-120027271

  日期：2004.1

  c acids has been of recent interest due to their potential therapeutic applications. This paper describes a convenient method to prepare symmetrical methylenebis(alkyl hydrogen phosphonates) by the selective cleavage of the corresponding methylenebis(dialkyl phosphonate) with refluxing morpholine. The effects of structural variations on the amine as well as the substrate have been investigated to understand

  摘要 由于其潜在的治疗应用，亚甲基双膦酸偏酯的制备最近引起了人们的兴趣。本文描述了一种通过用回流的吗啉选择性裂解相应的亚甲基双（二烷基膦酸）来制备对称亚甲基双（烷基氢膦酸）的简便方法。已经研究了结构变化对胺和底物的影响，以了解该反应的范围和局限性。受阻双膦酸酯的一种更好的方法是使用吗啉裂解它们的二甲酯 4。该方法也可用于获取许多 C-烷基二烷基亚甲基双膦酸，例如 6。该研究清楚地表明，用吗啉裂解方便、便宜、
• PHOSPHONATED GLYCOPEPTIDE AND LIPOGLYCOPEPTIDE ANTIBIOTICS AND USES THEREOF FOR THE PREVENTION AND TREATMENT OF BONE AND JOINT INFECTIONS
  申请人：Tanaka Kelly

  公开号：US20100113333A1

  公开（公告）日：2010-05-06

  The present invention is directed to antimicrobial compounds which have an affinity for binding bones. More particularly, the invention is directed to phosphonated derivatives of glycopeptide or lipoglycopeptide antibiotics. These compounds are useful as antibiotics for the prevention or treatment of bone and joint infections, especially for the prevention and treatment of osteomyelitis.

  本发明涉及具有结合骨头亲和力的抗微生物化合物。更具体地说，本发明涉及糖肽或脂肽糖肽抗生素的膦酸衍生物。这些化合物可用作抗生素，用于预防或治疗骨和关节感染，特别是用于预防和治疗骨髓炎。
• PHOSPHONATED RIFAMYCINS AND USES THEREOF FOR THE PREVENTION AND TREATMENT OF BONE AND JOINT INFECTIONS
  申请人：Dietrich Evelyne

  公开号：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 glycopeptide and lipoglycopeptide antibiotics and uses thereof for the prevention and treatment of bone and joint infections
  申请人：Tanaka Kelly

  公开号：US08946144B2

  公开（公告）日：2015-02-03

  The present invention is directed to antimicrobial compounds which have an affinity for binding bones. More particularly, the invention is directed to phosphonated derivatives of glycopeptide or lipoglycopeptide antibiotics. These compounds are useful as antibiotics for the prevention or treatment of bone and joint infections, especially for the prevention and treatment of osteomyelitis.

  本发明涉及具有结合骨头亲和力的抗微生物化合物。更具体地说，本发明涉及糖肽或脂肽糖肽抗生素的膦酸衍生物。这些化合物可用作预防或治疗骨和关节感染的抗生素，尤其是预防和治疗骨髓炎。
• Use of methanebisphosphonic acid derivatives for the manufacture of a medicament for fracture healing
  申请人：CIBA-GEIGY AG

  公开号：EP0600834A1

  公开（公告）日：1994-06-08

  The invention relates to the use of certain methanebisphosphonic acid derivatives (for the manufacture of a pharmaceutical composition) for the treatment of fractures. These compounds have surprisingly been found to promote a more rapid and stronger fracture healing in mammals including man.

  本发明涉及使用某些甲烷二膦酸衍生物（用于制造药物组合物）治疗骨折。令人惊奇的是，这些化合物能促进包括人类在内的哺乳动物更快、更牢固地愈合骨折。