E-4-(p-nitrostyryl)benzoic acid | 74519-02-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: E-4-(p-nitrostyryl)benzoic acid
• 英文别名: 4-(4-Nitro-trans-styryl)-benzoesaeure；4-carboxy-4'-nitrostilbene；Benzoic acid, 4-[2-(4-nitrophenyl)ethenyl]-；4-[(E)-2-(4-nitrophenyl)ethenyl]benzoic acid
• CAS: 74519-02-1
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: VUMCZJBCQAAOPK-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  E-4-(p-nitrostyryl)benzoic acid 在 盐酸 、 sodium tetrahydroborate 、 硫酸 、 calcium chloride 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 42.0h， 生成 {4-[(E)-2-(4-Amino-phenyl)-vinyl]-phenyl}-methanol
  参考文献：
  名称：

  代谢N-羟基化。利用取代基变化来调节4-乙酰氨基苯乙二酸酯的体外生物活化。

  摘要：

  N-羟基化是致癌性芳基酰胺生物活化中的重要步骤。该实验室以前的报道表明，反式-4-乙酰氨基二苯乙烯（1）的4​​'取代基的变化对其体外微粒体N-羟基化的速率有显着影响。为了进一步研究电负性和脂肪族取代基的作用，合成了1的4'-CN，4'-CH3、4'-C（CH3）3和4'-CF3类似物，并通过仓鼠进行了代谢转化肝微粒体。每种化合物均以放射性标记形式合成，并通过TLC，质谱和液体闪烁计数对代谢物进行鉴定和定量。4'-CN类似物的N-羟基化的Vmax为24％，Km为1的11％。乙醇酰胺是4'-CN的次要代谢物。-CN化合物。4'-CH3化合物的主要代谢产物是4'-CH2OH衍生物，少量生成N-羟基化产物。类似地，代谢4'-C（CH3）3类似物以产生反式-4'-[2-（羟甲基）-2-丙基] -4-乙酰氨基sti（26）以及痕量的异羟肟酸。4'-CF3底物产生少量的N-羟基化物质，作为唯一可检测的

  DOI：

  10.1021/jm00183a014
• 作为产物：
  描述：

  trans-4'-carbethoxy-4-nitrostilbene 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 E-4-(p-nitrostyryl)benzoic acid
  参考文献：
  名称：

  Synthesis and evaluation of stilbenylbenzoxazole and stilbenylbenzothiazole derivatives for detecting β-amyloid fibrils

  摘要：

  This paper describes a novel series of stilbenylbenzoxazole ( SBO) and stilbenylbenzothiazole ( SBT) derivatives for beta- amyloid specific binding probes. These 24 compounds were synthesized and evaluated by competitive binding assay against beta- amyloid 1 - 42 ( A beta 42) aggregates using [I-125] TZDM. All the derivatives displayed higher binding affinities with K-i value in the subnanomolar range ( 0.10 - 0.74 nM) than Pittsburgh Compound- B ( PIB) ( 0.77 nM). Among these derivatives, SBT- 2, 5-. uoroethoxy- 2-{ 4-[ 2-( 4- methylaminophenyl) vinyl] phenyl} benzothiazole, showed lowest K-i value ( 0.10 nM). In conclusion, the preliminary results suggest that these compounds are implying a possibility as a probe for detection of A beta fibrils in Alzheimer's disease (AD) patients. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.004

文献信息

• Synthesis of Two Novel Flavonoid Derivatives with Extended p-System: Possible UV-B and UV-A Sunscreens
  作者：Saleh N. Al-Busafi、Asma M. Al-Buraiki、Monther H. Al-Qarni

  DOI：10.14233/ajchem.2017.20430

  日期：——

  Two novel flavonoid derivatives 5 and 6 were synthesized and characterized by IR, 1H, 13C NMR spectroscopy and mass spectrometry. The core structure of the two flavonoids was constructed by applying Baker-Venkataraman rearrangement on 2-acylphenyl ester intermediate. The two compounds exhibited remarkable UV-visible absorption activities compared to flavone. Flavonoid 5 showed a bathochromic shift of 75.6 nm when the size of the cinnamic acid was increased by phenylbutadienyl group and hence it is a good UVA sunscreen. The 4-nitrostyryl group introduced in the cinnamic acid subchromophore of flavonoid 6 causes the compound to absorb at 308.3 and at 345.8 nm which will make it a broad-spectrum sunscreen.

  两种新型黄酮类衍生物5和6被合成并通过红外光谱、核磁共振氢谱和碳谱以及质谱进行了表征。这两类黄酮的核心结构是通过在2-酰基苯酯中间体上应用Baker-Venkataraman重排构建的。与黄酮相比，这两种化合物展示了卓越的紫外-可见吸收活性。黄酮5在增加肉桂酸结构中的苯丁二烯基团后，其吸收峰向长波方向移动了75.6纳米，因此它是一种优秀的UVA防晒剂。在黄酮6的肉桂酸亚显色团中引入4-硝基苯乙烯基团，使得该化合物在308.3纳米和345.8纳米处有吸收，这将使其成为一种广谱防晒剂。
• Nitrodiarylethenes as fluorescence quenchers for nucleic acid probes
  申请人：ELITechGroup, Inc.

  公开号：US10738346B2

  公开（公告）日：2020-08-11

  Fluorescence quenching nitrodiarylethene analogs are useful in oligonucleotide conjugates and probes. These analogs, whose absorption spectra are substantially blue-shifted relatively to emission spectra of common fluorophores (such as fluorescein), do not need to rely on spectral overlap of quencher absorbance and fluorophore's emission for their quenching abilities. The oligonucleotide-quencher conjugates may be used in detection methods for nucleic acid targets.

  荧光淬灭硝基二叔丁烯类似物可用于寡核苷酸共轭物和探针。与普通荧光团（如荧光素）的发射光谱相比，这些类似物的吸收光谱基本上是蓝移的，因此其淬灭能力无需依赖淬灭剂吸收光谱与荧光团发射光谱的重叠。寡核苷酸-淬灭剂共轭物可用于核酸靶标的检测方法。
• NITRODIARYLETHENES AS FLUORESCENCE QUENCHERS FOR NUCLEIC ACID PROBES
  申请人：ElitechGroup B.V.

  公开号：US20180258471A1

  公开（公告）日：2018-09-13

  Fluorescence quenching nitrodiarylethene analogs are useful in oligonucleotide conjugates and probes. These analogs, whose absorption spectra are substantially blue-shifted relatively to emission spectra of common fluorophores (such as fluorescein), do not need to rely on spectral overlap of quencher absorbance and fluorophore's emission for their quenching abilities. The oligonucleotide-quencher conjugates may be used in detection methods for nucleic acid targets.
• US4261855A
  申请人：——

  公开号：US4261855A

  公开（公告）日：1981-04-14
• US5298575A
  申请人：——

  公开号：US5298575A

  公开（公告）日：1994-03-29