(N-bromoacetyl)aminomethylbis(phosphonate) | 129557-33-1

• 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: (N-bromoacetyl)aminomethylbis(phosphonate)
• 英文别名: tetraethyl 1-(N-2-bromoacetylamino)methylenebisphosphonate；tetraethyl 1-(2-bromoacetamido)methylenebisphosphonate；N-[bis(diethoxyphosphoryl)methyl]-2-bromoacetamide
• CAS: 129557-33-1
• 化学式: C₁₁H₂₄BrNO₇P₂
• 分子量: 424.166
• InChiKey: KHSOHHYHGVPRAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  519.1±50.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (N-bromoacetyl)aminomethylbis(phosphonate) 、 sarcosyl-rifabutin 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以72%的产率得到
  参考文献：
  名称：

  [EN] PHOSPHONATED RIFAMYCINS AND USES THEREOF FOR THE PREVENTION AND TREATMENT OF BONE AND JOINT INFECTIONS
  [FR] RIFAMYCINES PHOSPHONÉES ET LEURS UTILISATIONS POUR LA PRÉVENTION ET LE TRAITEMENT D'INFECTIONS DES OS ET DES ARTICULATIONS

  摘要：

  公开号：

  WO2010019511A3
• 作为产物：
  描述：

  tetraethyl (N,N-dibenzyl)aminomethyl-bis(phosphonate) 在 palladium 10% on activated carbon 吡啶 、 环己烯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (N-bromoacetyl)aminomethylbis(phosphonate)
  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 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.

  本发明涉及具有与骨骼结合亲和力的抗微生物化合物。更具体地，该发明涉及磷酸酯化的糖肽类或脂质糖肽类抗生素的衍生物。这些化合物可用作抗生素，用于预防或治疗骨骼和关节感染，特别是用于预防和治疗骨髓炎。
• COMPOUND FOR BONE SCANNING AND USE THEREOF
  申请人：TAIWAN HOPAX CHEMS. MFG. CO., LTD.

  公开号：US20160304545A1

  公开（公告）日：2016-10-20

  The disclosure provides a compound comprising bisphosphonate functional group and chelating agent. The bisphosphonate functional group part has high affinity for bone tissue, and the chelating agent part has high affinity for metal tracer such as radioisotope. The disclosed compound could be rapidly adsorbed onto the bone surface, and could steady emit ionizing radiation. Therefore, the disclosed compound is suitable for bone scanning technology to find abnormalities in bone.

  该披露提供了一种包含双膦酸盐功能基团和螯合剂的化合物。双膦酸盐功能基团部分具有高亲和力与骨组织结合，而螯合剂部分具有高亲和力与金属示踪剂如放射性同位素结合。所披露的化合物可以迅速吸附到骨表面，并能稳定地发射电离辐射。因此，该披露的化合物适用于骨扫描技术，用于发现骨骼中的异常。
• 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。
• Synthesis and in vitro evaluation of bisphosphonated glycopeptide prodrugs for the treatment of osteomyelitis
  作者：Kelly S.E. Tanaka、Evelyne Dietrich、Stéphane Ciblat、Claude Métayer、Francis F. Arhin、Ingrid Sarmiento、Gregory Moeck、Thomas R. Parr、Adel Rafai Far

  DOI：10.1016/j.bmcl.2010.01.006

  日期：2010.2

  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.
• 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.