methyl (2R)-<(tert-butyloxycarbonyl)amino>-4-bromobutyrate | 177472-33-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2R)-<(tert-butyloxycarbonyl)amino>-4-bromobutyrate
• 英文别名: methyl (R)-4-bromo-2-[(tert-butoxycarbonyl)amino]butanoate；(R)-2-(Boc-amino)-4-bromobutyric acid methyl ester；methyl (2R)-4-bromo-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 177472-33-2
• 化学式: C₁₀H₁₈BrNO₄
• 分子量: 296.161
• InChiKey: MBWPBNACYMMIKZ-SSDOTTSWSA-N

物化性质

• 沸点：
  358.7±37.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2R)-<(tert-butyloxycarbonyl)amino>-4-bromobutyrate 在 水 、 四丁基碘化铵 、 potassium carbonate 、 1-羟基苯并三唑 、 caesium carbonate 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 (R)-tert-butyl {4-[bis(benzyloxy)phosphoryl]}-1-(((3-(6-hydroxyhexyl)phenyl)amino)-1-oxobutan-2-yl)carbamate
  参考文献：
  名称：

  Synthesis of fluorinated analogues of sphingosine-1-phosphate antagonists as potential radiotracers for molecular imaging using positron emission tomography

  摘要：

  Sphingosine-1-phosphate (S1P) receptors play major roles in cardiovascular, immunological and neurological diseases. The recent approval of the sphingolipid drug Fingolimod (Gilenya®), a sphingosine-1-phosphate agonist for relapsing multiple sclerosis, in 2010 exemplifies the potential for targeting sphingolipids for the treatment of human disorders. Moreover, non-invasive in vivo imaging of S1P receptors that are not available till now would contribute to the understanding of their role in specific pathologies and is therefore of preclinical interest. Based on fluorinated analogues of the S1P1 receptor antagonist W146 showing practically equal in vitro potency as the lead structure, the first S1P receptor antagonist [18F]-radiotracer has been synthesized and tested for in vivo imaging of the S1P1 receptor using positron emission tomography (PET). Though the tracer is serum stable, initial in vivo images show fast metabolism and subsequent accumulation of free [18F]fluoride in the bones.

  DOI：

  10.1016/j.bmc.2014.08.009
• 作为产物：
  描述：

  N-{[(2-甲基-2-丙基)氧基]羰基}-D-高丝氨酸 在 甲基磺酰氯 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 55.5h， 生成 methyl (2R)-<(tert-butyloxycarbonyl)amino>-4-bromobutyrate
  参考文献：
  名称：

  Synthesis of fluorinated analogues of sphingosine-1-phosphate antagonists as potential radiotracers for molecular imaging using positron emission tomography

  摘要：

  Sphingosine-1-phosphate (S1P) receptors play major roles in cardiovascular, immunological and neurological diseases. The recent approval of the sphingolipid drug Fingolimod (Gilenya®), a sphingosine-1-phosphate agonist for relapsing multiple sclerosis, in 2010 exemplifies the potential for targeting sphingolipids for the treatment of human disorders. Moreover, non-invasive in vivo imaging of S1P receptors that are not available till now would contribute to the understanding of their role in specific pathologies and is therefore of preclinical interest. Based on fluorinated analogues of the S1P1 receptor antagonist W146 showing practically equal in vitro potency as the lead structure, the first S1P receptor antagonist [18F]-radiotracer has been synthesized and tested for in vivo imaging of the S1P1 receptor using positron emission tomography (PET). Though the tracer is serum stable, initial in vivo images show fast metabolism and subsequent accumulation of free [18F]fluoride in the bones.

  DOI：

  10.1016/j.bmc.2014.08.009

文献信息

• MONOBACTAM ORGANIC COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS
  申请人：AULAKH Virender Singh

  公开号：US20150266867A1

  公开（公告）日：2015-09-24

  This invention pertains generally to antibacterial compounds of Formula I, as further described herein, and pharmaceutically acceptable salts and formulations thereof. In certain aspects, the invention pertains to methods of using such compounds to treat infections such as those caused by Gram-negative bacteria.

  这项发明通常涉及公式I的抗菌化合物，如本文进一步描述，并其药用盐和制剂。在某些方面，该发明涉及使用这些化合物治疗由革兰氏阴性细菌引起的感染的方法。
• Monobactam organic compounds for the treatment of bacterial infections
  申请人：Novartis AG

  公开号：US10369138B2

  公开（公告）日：2019-08-06

  This invention pertains generally to antibacterial compounds of Formula I, as further described herein, and pharmaceutically acceptable salts and formulations thereof. In certain aspects, the invention pertains to methods of using such compounds to treat infections such as those caused by Gram-negative bacteria.

  本发明一般涉及式 I 的抗菌化合物、 及其药学上可接受的盐类和制剂。在某些方面，本发明涉及使用此类化合物治疗感染（如革兰氏阴性细菌引起的感染）的方法。
• A Phosphinate Inhibitor of the <i>meso</i>-Diaminopimelic Acid-Adding Enzyme (MurE) of Peptidoglycan Biosynthesis
  作者：Binqi Zeng、Kenny K. Wong、David L. Pompliano、Sreelatha Reddy、Martin E. Tanner

  DOI：10.1021/jo981895p

  日期：1998.12.1
• US9174978B2
  申请人：——

  公开号：US9174978B2

  公开（公告）日：2015-11-03
• Synthesis of fluorinated analogues of sphingosine-1-phosphate antagonists as potential radiotracers for molecular imaging using positron emission tomography
  作者：Vysakh Pushpa Prasad、Stefan Wagner、Petra Keul、Sven Hermann、Bodo Levkau、Michael Schäfers、Günter Haufe

  DOI：10.1016/j.bmc.2014.08.009

  日期：2014.10

  Sphingosine-1-phosphate (S1P) receptors play major roles in cardiovascular, immunological and neurological diseases. The recent approval of the sphingolipid drug Fingolimod (Gilenya®), a sphingosine-1-phosphate agonist for relapsing multiple sclerosis, in 2010 exemplifies the potential for targeting sphingolipids for the treatment of human disorders. Moreover, non-invasive in vivo imaging of S1P receptors that are not available till now would contribute to the understanding of their role in specific pathologies and is therefore of preclinical interest. Based on fluorinated analogues of the S1P1 receptor antagonist W146 showing practically equal in vitro potency as the lead structure, the first S1P receptor antagonist [18F]-radiotracer has been synthesized and tested for in vivo imaging of the S1P1 receptor using positron emission tomography (PET). Though the tracer is serum stable, initial in vivo images show fast metabolism and subsequent accumulation of free [18F]fluoride in the bones.