p-fluorophenylglyoxalmonoxime | 17628-74-9

• 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: p-fluorophenylglyoxalmonoxime
• 英文别名: 4-fluorophenylglyoxal monooxime；Isonitroso-p-fluoracetophenon；4-Fluoro-I+/--oxobenzeneacetaldehyde 1-oxime；1-(4-fluorophenyl)-2-hydroxyiminoethanone
• CAS: 17628-74-9
• 化学式: C₈H₆FNO₂
• 分子量: 167.14
• InChiKey: FTSKJDZBOFFAKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  321.1±44.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  p-fluorophenylglyoxalmonoxime 在 potassium tert-butylate 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 78.67h， 生成 6-(4-氟-苯基)-4-甲氧基-蝶啶-2-基胺
  参考文献：
  名称：

  SUBSTITUTED PTERIDINES USEFUL FOR THE TREATMENT AND PREVENTION OF VIRAL INFECTIONS

  摘要：

  该发明提供了具有特定取代模式的4,6-二取代和2,4,6-三取代的喹啉衍生物，对某些类型的病毒感染表现出显著和选择性的活性，特别是选择性地抑制黄热病病毒等黄病毒科的复制，并且对预防和治疗此类病毒感染有用。

  公开号：

  US20100305117A1
• 作为产物：
  描述：

  4-氟苯甲酰乙酸甲酯 在 sodium hydroxide 、 高氯酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 26.0h， 生成 p-fluorophenylglyoxalmonoxime
  参考文献：
  名称：

  One-pot synthesis of 3-amino-4-aryl- and 3-amino-4-hetarylfurazans

  摘要：

  开发了一种“一锅法”合成3-氨基-4-芳基和3-氨基-4-杂芳基呋咱的方法，该方法利用β-芳基和4-β-杂芳基-β-氧代酸酯。

  DOI：

  10.1007/s11172-005-0359-4

文献信息

• SUBSTITUTED PTERIDINES FOR THE TREATMENT AND PREVENTION OF VIRAL INFECTIONS
  申请人：Herdewijn Piet André Maurits Maria

  公开号：US20090318456A1

  公开（公告）日：2009-12-24

  Tri-substituted pteridines and tetra-substituted pteridines exhibit a significant and selective activity against certain types of viral infections, in particular they selectively inhibit the replication of the hepatitis C virus, and are useful for the prevention and treatment of such infections.

  三取代喹啉和四取代喹啉对某些类型的病毒感染表现出显著和选择性的活性，特别是它们选择性地抑制丙型肝炎病毒的复制，并可用于预防和治疗此类感染。
• Single‐Step Modular Synthesis of Unsaturated Morpholine <i>N</i> ‐Oxides and Their Cycloaddition Reactions
  作者：Jongwoo Son、Ki Hwan Kim、Dong‐Liang Mo、Donald J. Wink、Laura L. Anderson

  DOI：10.1002/anie.201611791

  日期：2017.3.6

  A single‐flask procedure for the generation of α‐keto‐N‐alkenylnitrones through a Chan–Lam coupling and subsequent spontaneous 6π electrocyclization of these intermediates for the synthesis of 2H‐1,4‐oxazine N‐oxides has been developed for a variety of α‐ketooximes and alkenylboronic acids. This transformation provides a new approach to C‐substituted unsaturated morpholine derivatives that are poised

  为的α酮的生成单烧瓶过程Ñ -alkenylnitrones通过浐榄耦合和这些中间体的后续自发6πelectrocyclization 2的合成ħ -1,4-恶嗪Ñ -oxides已为开发各种α-酮肟酸和烯基硼酸。这种转变为C取代的不饱和吗啉衍生物提供了一种新方法，该衍生物准备进行进一步的功能化，以制备各种新颖的杂环结构。除了描述这些新杂环中间体的环加成反应性的初步研究之外，还讨论了合成2 H -1,4-恶嗪N-氧化物的新方法的范围。
• Solvent and substituent effects on the fluorescent properties of coelenteramide analogues
  作者：Ryota Saito、Takashi Hirano、Haruki Niwa、Mamoru Ohashi

  DOI：10.1039/a701156c

  日期：——

  Coelenteramide 1 is the light emitter in aequorin bioluminescence. To establish the fluorescent character of 1, the fluorescence properties of 1 and a series of its analogues, 3a–f, possessing a substituent R [= CF3, F, H, OCH3, OH, N(CH3)2] at the para-position on the 5-phenyl group have been investigated in solvents of various polarity. The fluorescence emission maxima of 1 and 3d–f, possessing an electron-donating group R [= OCH3, OH, N(CH3)2] shift to lower energy with increasing solvent polarity, while those of the analogues 3a–c (R = CF3, F, H) are independent of the solvent polarity. The linear correlation between the fluorescence maxima of 1 and 3d–f and the solvent polarity scales can be explained by formation of the singlet excited state with a charge-transfer (CT) character. The quantum yields of CT fluorescence of 1 and 3d–f have been found to be higher than those of 3a–c. These results indicate that the solvatochromic fluorescence of 1 originates from the CT excited state and the existence of an electron donating hydroxy group on the 5-phenyl group is essential for determining a wavelength and a high fluorescence quantum yield of aequorin bioluminescence.

  腔肠素1是海萤素生物发光中的发光体。为了确定1的荧光特性，在各种极性的溶剂中研究了1及其一系列类似物3a-f的荧光特性，这些类似物在5-苯基基团的对位上具有取代基R（= CF3、F、H、OCH3、OH、N（CH3）2）。1和3d-f的荧光发射最大值具有电子供体基团R（= OCH3、OH、N（CH3）2），随着溶剂极性的增加，其最大值向较低能量移动，而类似物3a-c（R= CF3、F、H）的荧光发射最大值与溶剂极性无关。1和3d-f的荧光最大值与溶剂极性尺度之间的线性相关性可以用具有电荷转移（CT）特征的单线态激发态的形成来解释。1和3d-f的CT荧光量子产率高于3a-c。这些结果表明，1的溶剂致色荧光来自CT激发态，5-苯基基团上存在电子供体羟基对于确定海萤素生物发光的波长和高荧光量子产率至关重要。
• Dornow; Theidel, Chemische Berichte, 1955, vol. 88, p. 1267,1274
  作者：Dornow、Theidel

  DOI：——

  日期：——
• Inhibition of Neuronal Nitric Oxide Synthase by 4-Amino Pteridine Derivatives:  Structure−Activity Relationship of Antagonists of (6<i>R</i>)-5,6,7,8-Tetrahydrobiopterin Cofactor
  作者：Lothar G. Fröhlich、Peter Kotsonis、Hermann Traub、Shahriyar Taghavi-Moghadam、Najim Al-Masoudi、Heinrich Hofmann、Hartmut Strobel、Hans Matter、Wolfgang Pfleiderer、Harald H. H. W. Schmidt

  DOI：10.1021/jm981129a

  日期：1999.10.1

  The family of nitric oxide synthases (NOS) catalyzes the conversion of L-arginine to L-citrulline and nitric oxide (NO), an important cellular messenger molecule which has been implicated in the pathophysiology of septic shock and inflammatory and neurodegenerative disease states. NOS can be maximally activated by the ubiquitous cofactor, (6R)-5,6,7,8-tetrahydrobiopterin (H(4)Bip), and antagonists of H(4)Bip may be of therapeutic importance to inhibit pathologically high NO formation. The 4-amino substituted analogue of H(4)Bip was reported to be a potent NOS inhibit-or. Therefore, we developed a series of novel 4-amino pteridine derivatives, antipterins, to pharmacologically target the neuronal isoform of nitric oxide synthase (NOS-I). To functionally characterize the pterin/anti-pterin interaction and establish a structure-activity relationship (SAR), we systematically altered the substituents in the 2-, 4-, 5-, 6-, and 7-position of the pteridine nucleus. Varying the substitution pattern in the 2-, 5-, and 7-position resulted in no significant inhibitory effect on enzyme activity. In contrast, bulky substituents in the B-position, such as phenyl, markedly increased the inhibitory potency of the reduced 4-amino-5,6,7,8-tetrahydropteridines, possibly as a consequence of hydrophobic interactions within NOS-I. However, this was not the case for the aromatic 4-amino pteridines. Interestingly, chemical modification of the 4-amino substituent by dialkyl/diaralkylation together with 6-arylation of the aromatic 2,4-diamino pteridine resulted in potent and efficacious inhibitors of NOS-I, suggesting possible hydrophilic and hydrophobic interactions within NOS-I. This SAR agrees with (a) the recently published crystal structure of the oxygenase domain of the inducible NOS isoform (NOS-II) and (b) the comparative molecular field analysis of selected NOS-I inhibitors, which resulted in a 3D-QSAR model of the pterin binding site interactions. Further optimization should be possible when the full length structure of NOS-I becomes available.