2-bromo-2-(4-azidophenyl)acetaldehyde | 851034-25-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-2-(4-azidophenyl)acetaldehyde
• CAS: 851034-25-8
• 化学式: C₈H₆BrN₃O
• 分子量: 240.059
• InChiKey: PKDXAWFDIANABS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65.83
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-bromo-2-(4-azidophenyl)acetaldehyde 在 三正丁胺 、 phenylphosphorochloridate 、 sodium acetate 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 28.0h， 生成 α-(4-azidophenyl)-1,N⁶-etheno-2'-deoxyadenosine 5'-triphosphate
  参考文献：
  名称：

  Side‐Chain Conformational Restriction in Template‐Competitive Inhibitors of E. coliDNA Polymerase I Klenow Fragment: Synthesis, Structural Characterization and Inhibition Activity

  摘要：

  Nucleotide triphosphate alpha-(4-azidophenyl)-1,N-6-etheno-dATP 3 and its monophosphate 3m were synthesized by condensation of 2-halo-2-(4-azidophenyl)acetaldehyes with dATP and dAMP, respectively. Structure analysis shows that the azidophenyl side chain is attached to the alpha-position of the etheno ring (i.e., the carbon attached to N1 of the purine), and conformation calculations show minima in the etheno-phenyl bond rotation at 50 and 130degrees where the bulk of the phenyl ring projects out from the plane of the etheno group. Like DNA Pol inhibitor 2-(4-azidophenacyl)thio-2'-deoxyadenosine 5'-triphosphate 1, nucleotide 3 is a template-competitive DNA polymerase inhibitor (TCPI), with a competitive Ki for Pol I KF of 3.41 muM, but has only weak activity as an HIV RT inhibitor relative to the template-competitive reverse transcriptase inhibitor 2-(4-azidophenacyl)thio-1,N-6-etheno-2'-deoxyadenosine 5'-triphosphate 2. Additionally, 3 photoinactivates KF in a time-dependent manner, confirming the kinetic data that 3 binds to the free form of KF. The TCPI activity of 3 provides evidence for an extended side chain conformational preference in the combined substrate polymerase inhibitors.

  DOI：

  10.1081/ncn-200034042
• 作为产物：
  描述：

  2-(4-azidophenyl)ethanol 在 N-溴代丁二酰亚胺(NBS) 、 重铬酸吡啶 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 2-bromo-2-(4-azidophenyl)acetaldehyde
  参考文献：
  名称：

  Side‐Chain Conformational Restriction in Template‐Competitive Inhibitors of E. coliDNA Polymerase I Klenow Fragment: Synthesis, Structural Characterization and Inhibition Activity

  摘要：

  Nucleotide triphosphate alpha-(4-azidophenyl)-1,N-6-etheno-dATP 3 and its monophosphate 3m were synthesized by condensation of 2-halo-2-(4-azidophenyl)acetaldehyes with dATP and dAMP, respectively. Structure analysis shows that the azidophenyl side chain is attached to the alpha-position of the etheno ring (i.e., the carbon attached to N1 of the purine), and conformation calculations show minima in the etheno-phenyl bond rotation at 50 and 130degrees where the bulk of the phenyl ring projects out from the plane of the etheno group. Like DNA Pol inhibitor 2-(4-azidophenacyl)thio-2'-deoxyadenosine 5'-triphosphate 1, nucleotide 3 is a template-competitive DNA polymerase inhibitor (TCPI), with a competitive Ki for Pol I KF of 3.41 muM, but has only weak activity as an HIV RT inhibitor relative to the template-competitive reverse transcriptase inhibitor 2-(4-azidophenacyl)thio-1,N-6-etheno-2'-deoxyadenosine 5'-triphosphate 2. Additionally, 3 photoinactivates KF in a time-dependent manner, confirming the kinetic data that 3 binds to the free form of KF. The TCPI activity of 3 provides evidence for an extended side chain conformational preference in the combined substrate polymerase inhibitors.

  DOI：

  10.1081/ncn-200034042

文献信息

• [EN] INHIBITION OF BACTERIAL BIOFILMS WITH IMIDAZOLE-PHENYL DERIVATIVES<br/>[FR] INHIBITION DE BIOFILMS BACTÉRIENS PAR DES DÉRIVÉS D'IMIDAZOLE-PHÉNYLE
  申请人：UNIV NORTH CAROLINA STATE

  公开号：WO2009123753A1

  公开（公告）日：2009-10-08

  Disclosure is provided for imidazole-phenyl derivative compounds that prevent, remove and/or inhibit the formation of biofilms, compositions comprising these compounds, devices comprising these compounds, and methods of using the same.

  本文提供了一种防止、去除和/或抑制生物膜形成的咪唑-苯衍生物化合物的披露，以及包含这些化合物的组合物、包含这些化合物的设备和使用这些化合物的方法。
• IMAGING AGENTS USEFUL FOR IDENTIFYING AD PATHOLOGY
  申请人：Siemens Medical Solutions USA, Inc.

  公开号：EP2323697A2

  公开（公告）日：2011-05-25
• [EN] IMAGING AGENTS USEFUL FOR IDENTIFYING AD PATHOLOGY<br/>[FR] AGENTS D'IMAGERIE UTILES POUR IDENTIFIER UNE PATHOLOGIE
  申请人：SIEMENS MEDICAL SOLUTIONS

  公开号：WO2010011964A2

  公开（公告）日：2010-01-28

  Provided herein are compounds and compositions which comprise the formulae as disclosed herein, wherein the compound is an amyloid binding compound. An amyloid binding compound according to the invention may be administered to a patient in amounts suitable for in vivo imaging of amyloid deposits, and distinguish between neurological tissue with amyloid deposits and normal neurological tissue. Amyloid probes of the invention may be used to detect and quantitate amyloid deposits in diseases including, for example, Down's syndrome, familial Alzheimer's Disease. In another embodiment, the compounds may be used in the treatment or prophylaxis of neurodegenerative disorders.. Also provided herein are methods of allowing the compound to distribute into the brain tissue, and imaging the brain tissue, wherein an increase in binding of the compound to the brain tissue compared to a normal control level of binding indicates that the mammal is suffering from or is at risk of developing a neurodegenerative disease.
• [EN] PSMA IMAGING AGENTS<br/>[FR] AGENTS D'IMAGERIE DU PSMA
  申请人：SIEMENS MEDICAL SOLUTIONS

  公开号：WO2013028664A1

  公开（公告）日：2013-02-28

  Compounds for targeting and agents for imaging, Prostate-specific membrane antigen (PSMA) are disclosed. Methods of synthesizing compounds and imaging agents, as well as methods for imaging PSMA are also disclosed. The imaging agents disclosed are suitable for PET and SPECT imaging.