4-chloro-β-cyanocinnamic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-chloro-β-cyanocinnamic acid
• 英文别名: 3-cyano-3-(4-chlorophenyl)acrylic acid；3-(4-Chlorophenyl)-3-cyanoprop-2-enoic acid
• 化学式: C₁₀H₆ClNO₂
• 分子量: 207.616
• InChiKey: DPCUKSCYGFSXCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 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：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对羟基苯乙胺 、 4-chloro-β-cyanocinnamic acid 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以94%的产率得到(2Z)-3-(4-chlorophenyl)-3-cyano-N-[2-(4-hydroxyphenyl)ethyl]acrylamide
  参考文献：
  名称：

  Structure−Activity Relationship of N-(Phenylalkyl)cinnamides as Novel NR2B Subtype-Selective NMDA Receptor Antagonists

  摘要：

  A novel series of N-(phenylalkyl)cinnamides related to N-(4-phenylbutyl)-3,4-dihydroxy-beta-cyanocinnamide (6, an EGFR-K inhibitor with high antiproliferative activity) was synthesized and tested for antagonism at N-methyl-D-aspartate (NMDA) receptor subtypes. Potency and subunit selectivity were assayed by electrical recordings in Xenopus oocytes expressing three binary combinations of cloned rat NMDA receptor subunits: NR1A expressed in combination with either NR2A, NR2B, or NR2C. The N-(phenylalkyl)cinnamides are selective antagonists of NR1A/2B receptors. Assayed under steady-state conditions, N-(4-phenylbutyl)-4-hydroxycinnamide (16) has an IC50 value of 77 nM and >1000-fold selectivity with respect to NR1A/2A and NR1A/2C receptors. Potency at alpha(1) adrenergic receptors is low for the four cinnamides tested. Inhibition of NR1A/2B receptors does not correlate with EGFR and ErbB2/neu tyrosine kinase inhibitor activity. The N-(phenylalkyl)cinnamide series we describe provides a novel and structurally diverse framework for designing new NR2B-selective NMDA antagonists as potential CNS therapeutics.

  DOI：

  10.1021/jm990199u

文献信息

• Alpha-Cyano-4-Hydroxy-3-Iodocinnamic Acid as a Matrix in Maldi Mass Spectrometry
  申请人：Board of Trustees of Southern Illinois University

  公开号：US20190161438A1

  公开（公告）日：2019-05-30

  A heavy-atom derivative of CHCA, a primary matrix molecule for matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS), is synthesized and purified. This new matrix molecule α-cyano-4-hydroxy-3-iodocinnamic acid (CHICA) is characterized by 1 H NMR and mass spectrometry. CHICA is shown to increase MALDI-MS yield for the test analytes human angiotensin II and sex pheromone inhibitor as compared to both CHCA and an alternative heavy-atom CHCA derivative matrix. An optimal CHICA matrix concentration is determined to be 4 mg/mL. Analyte ion yield is shown to be comparable for CHICA and CHCA for analyte concentrations below 0.001 mg/mL. For analyte concentrations above this threshold, use of CHICA resulted in higher analyte yield and significantly lower relative standard deviation.

  合成并纯化了CHCA的重原子衍生物，这是一种用于基质辅助激光解吸/电离质谱（MALDI-MS）的主要基质分子。这种新的基质分子α-氰基-4-羟基-3-碘基肉桂酸（CHICA）通过1H核磁共振和质谱进行表征。与CHCA和另一种替代重原子CHCA衍生物基质相比，CHICA被证明能够增加对测试样品人类血管紧张素II和性信息素抑制剂的MALDI-MS产量。确定了最佳的CHICA基质浓度为4毫克/毫升。对于分析物浓度低于0.001毫克/毫升的情况，CHICA和CHCA的分析物离子产量是可比较的。对于超过此阈值的分析物浓度，使用CHICA导致更高的分析物产量和显著更低的相对标准偏差。
• [EN] SYNTHESIS OF LACTONE DERIVATIVES AND THEIR USE IN THE MODIFICATION OF PROTEINS<br/>[FR] SYNTHÈSE DE DÉRIVÉS DE LACTONE ET LEUR UTILISATION DANS LA MODIFICATION DE PROTÉINES
  申请人：GENIE BIOTECH UK LTD

  公开号：WO2021123229A1

  公开（公告）日：2021-06-24

  Site-specific modifications of proteins are desirable in biotechnological applications such as biopharmaceuticals, immunotherapy, vaccines, and are useful in chemical biology. Gluconoylation is a non-enzymatic, covalent, post-translational modification commonly observed on N-terminal His-Tags bearing proteins. We synthesized glucono-1,5-lactone derivatives, including azido variants for selective acylation. High yield acylation is achieved by simply mixing derivatives with target protein amidst diverse conditions of temperatures, aqueous buffers, excipients, or complex cell lysate.

  蛋白质的位点特异性修饰在生物技术应用中是可取的，例如生物制药、免疫疗法、疫苗，并且在化学生物学中也非常有用。葡萄糖酸化是一种非酶促的共价后翻译修饰，常见于带有N-末端His-标签的蛋白质上。我们合成了葡萄糖酸-1,5-内酯衍生物，包括用于选择性酰化的叠氮化衍生物。只需将衍生物与目标蛋白质混合在不同的温度、水溶液缓冲剂、辅料或复杂的细胞裂解液条件下，即可实现高产酰化。
• USE OF CYANOCINNAMIC ACID DERIVATIVES AS MATRICS IN MALDI MASS SPECTROMETRY
  申请人：Karas Michael

  公开号：US20110121166A1

  公开（公告）日：2011-05-26

  The present invention relates to the use of cyanocinnamic acid derivatives as a matrix in the MALDI mass spectrometry of an analyte.

  本发明涉及在MALDI质谱分析中将氰基肉桂酸衍生物用作基质的使用。
• DEBONDABLE ADHESIVE COMPOSITION
  申请人：NITTO DENKO CORPORATION

  公开号：EP2957610A1

  公开（公告）日：2015-12-23

  The present invention provides an approach for making adhesive compositions and in particular pressure sensitive adhesive compositions that possess adjustable adhesion level allowing debonding on-demand in an easy, rapid and cost-efficient manner, wherein said approach can be easily applied to a wide variety of different adhesive systems without need for complex adaptation of the adhesive systems. The adhesive compositions of the present invention are characterized by an adhesive system and a debonding component, wherein the debonding component is an organic compound having a molecular weight of from 200 g/mol to 10000 g/mol, which debonding component contains two or more photodimerizable groups.

  本发明提供了一种制造粘合剂组合物，特别是压敏型粘合剂组合物的方法，这种组合物具有可调节的粘合力水平，能够以简单、快速和具有成本效益的方式按需剥离，其中所述方法可轻松应用于各种不同的粘合剂体系，而无需对粘合剂体系进行复杂的调整。本发明的粘合剂组合物的特征是由粘合剂体系和脱粘组分组成，其中脱粘组分是一种有机化合物，其分子量在 200 克/摩尔到 10000 克/摩尔之间，脱粘组分含有两个或两个以上可光二聚化的基团。
• Method of mass spectrometry and a mass spectrometer
  申请人：Micromass UK Limited

  公开号：US10153145B2

  公开（公告）日：2018-12-11

  The present invention relates to a method of mass spectrometry, an apparatus adapted to perform the method and a mass spectrometer. More particularly, but not exclusively, the present invention relates to a method of mass spectrometry comprising the step of associating parent and fragmentation ions from a sample by measuring the parent and fragmentation ions from two or more different areas of the sample and identifying changes in the number of parent ions between the areas in the sample, and corresponding changes in the number of fragmentation ions between the two areas.

  本发明涉及一种质谱分析方法、一种用于执行该方法的仪器和一台质谱仪。更具体地说，但不限于此，本发明涉及一种质谱分析方法，该方法包括以下步骤：通过测量样品中两个或多个不同区域的母离子和碎片离子，将样品中的母离子和碎片离子联系起来，并确定样品中不同区域间母离子数量的变化以及两个区域间碎片离子数量的相应变化。