(E)-3-(喹啉-4-基)丙烯酸 | 81124-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: (E)-3-(喹啉-4-基)丙烯酸
• 英文名称: (E)-3-(quinolin-4-yl)acrylic acid
• 英文别名: 3-(Quinolin-4-yl)prop-2-enoic acid；(E)-3-quinolin-4-ylprop-2-enoic acid
• CAS: 81124-52-9
• 化学式: C₁₂H₉NO₂
• 分子量: 199.209
• InChiKey: GDCNAOKZXWMIJA-AATRIKPKSA-N

物化性质

• 沸点：
  408.0±20.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(喹啉-4-基)丙烯酸 在 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醚 、 二氯甲烷 、 氯仿 为溶剂， 反应 48.17h， 生成 perfluorophenyl (2R,3S,4R)-2-(2-oxoethyl)-4-(quinolin-4-yl)-2,3,4,5-tetrahydro-[1,1'-biphenyl]-3-carboxylate
  参考文献：
  名称：

  2,4-二烯醛和 α,β-不饱和酯之间的有机催化对映和非对映选择性 Diels-Alder 反应

  摘要：

  尽管催化不对称狄尔斯-阿尔德反应的发展取得了进展，但引入α,β-不饱和酯作为亲二烯体仍然具有挑战性，因为它们的反应活性较低。在此，我们报道手性氨基催化剂与手性异硫脲催化剂或布朗斯台德酸结合可以促进2,4-二醛和α,β-不饱和酯之间的对映选择性和非对映选择性狄尔斯-阿尔德反应。该方法通过形成手性三烯胺中间体来与活化的亲二烯体、α,β-不饱和酰基铵物质或质子化的N-杂芳基取代的烯烃进行外环加成。通过二烯和酯亲二烯体的协同活化，可以得到具有多个立构中心的密集官能化环己烯，其dr高达>25:1，ee>99%。此外，我们表明手性催化剂的构型和烯烃几何形状的变化允许对映体纯外型产物的四种立体异构体的立体发散制备。

  DOI：

  10.1002/adsc.202300756
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 (E)-3-(喹啉-4-基)丙烯酸
  参考文献：
  名称：

  613.一些三核花青染料。第五部分：尝试合成与新花青类异构体的染料

  摘要：

  DOI：

  10.1039/jr9520003197

文献信息

• Acrylamide derivatives as antiallergic agents. I. Synthesis and structure-activity relationships of N-((4-substituted 1-piperazinyl)alkyl)-3-(aryl and heteroaryl)acrylamides.
  作者：Yoshinori NISHIKAWA、Tokuhiko SHINDO、Katsumi ISHI、Hideo NAKAMURA、Tatsuya KON、Hitoshi UNO

  DOI：10.1248/cpb.37.100

  日期：——

  A new series of acrylamide derivatives (7-10) were synthesized. Antiallergic activity of these compounds was evaluated and their structure-activity relationships were examined. Compounds 10d, N[4-(4-diphenylmethyl-1-piperazinyl)buthyl]3-(3-pyridyl)acrylamide, showed antiallergic activity equivalent or superior to that of ketotifen in the rat passive cutaneous anaphylaxis (PCA) test by oral administration. Compound 10d, unlike ketotifen, had more potent in vitro 5-lipoxygenase inhibitory activity than caffeic acid, whereas its in vitro antihistamine activity was weaker than that of ketotifen. In addition, its inhibitory activity against histamine release from rat mast cells was approximately two-thirds as potent as that of disodium cromoglycate (DSCG). Compound 10d is a promising agent for treating a variety of allergic diseases.

  一系列新的丙烯酰胺衍生物（7-10）被合成。对这些化合物的抗过敏活性进行了评估，并考察了它们的结构-活性关系。化合物10d，即N[4-(4-二苯甲基-1-哌嗪基)丁基]3-(3-吡啶基)丙烯酰胺，在口服给药的大鼠被动皮肤过敏反应（PCA）测试中显示出与酮替芬相当或更优越的抗过敏活性。与酮替芬不同，10d在体外对5-脂氧合酶的抑制活性比咖啡酸更强，而其体外抗组胺活性则弱于酮替芬。此外，它对大鼠肥大细胞释放组胺的抑制活性约为色甘酸二钠（DSCG）的三分之二。化合物10d是一种有前途的多种过敏性疾病治疗药物。
• Heteroarylacrylamides and their use as pharmaceuticals for the stimulation of the expression of endothelial NO synthase
  申请人：sanofi-aventis

  公开号：EP1939180A1

  公开（公告）日：2008-07-02

  The present invention relates to heteroarylacrylamides of the formula I, in which Het, X, Ra, Rb, R1, R2 and R3 have the meanings indicated in the claims, which modulate the transcription of endothelial nitric oxide (NO) synthase and are valuable pharmacologically active compounds. Specifically, the compounds of the formula I upregulate the expression of the enzyme endothelial NO synthase and can be applied in conditions in which an increased expression of said enzyme or an increased NO level or the normalization of a decreased NO level is desired. The invention further relates to processes for the preparation of compounds of the formula I, to pharmaceutical compositions comprising them, and to the use of compounds of the formula I for the manufacture of a medicament for the stimulation of the expression of endothelial NO synthase or for the treatment of various diseases including cardiovascular disorders such as atherosclerosis, thrombosis, coronary artery disease, hypertension and cardiac insufficiency, for example.

  本发明涉及式I的杂环丙烯酰胺， 其中Het、X、Ra、Rb、R1、R2和R3具有权利要求中所示的含义，这些化合物调节内皮型一氧化氮（NO）合酶的转录，并且是有价值的药理活性化合物。具体地，式I的化合物上调内皮型一氧化氮合酶的表达，并可应用于需要增加该酶的表达或增加NO水平或恢复降低的NO水平的情况。本发明还涉及制备式I化合物的方法，包括它们的药物组合物，以及利用式I化合物制造用于刺激内皮型一氧化氮合酶表达或治疗各种疾病的药物，包括心血管疾病，如动脉粥样硬化、血栓形成、冠状动脉疾病、高血压和心脏功能不全等。
• Synthesis of Enantiomerically Pure Ring-Substituted <scp>l</scp>-Pyridylalanines by Biocatalytic Hydroamination
  作者：Syed T. Ahmed、Fabio Parmeggiani、Nicholas J. Weise、Sabine L. Flitsch、Nicholas J. Turner

  DOI：10.1021/acs.orglett.6b02559

  日期：2016.11.4

  Current routes to nitrogen-containing heteroarylalanines involve complex multistep synthesis and are often reliant on protection/deprotection steps and wasteful chromatographic purifications. In order to complement existing methodologies, a convenient telescopic strategy was developed for the synthesis of l-pyridylalanine analogues (12 examples) and other l-heteroarylalanines (5 examples) starting

  目前获得含氮杂芳基丙氨酸的路线涉及复杂的多步合成，并且通常依赖于保护/脱保护步骤和浪费的色谱纯化。为了补充现有方法，开发了一种方便的伸缩策略，用于从相应的醛开始合成l-吡啶基丙氨酸类似物（12 个实例）和其他l-杂芳基丙氨酸（5 个实例）。来自Anabaena variabilis的苯丙氨酸解氨酶 (PAL)被用作生物催化剂，通过在必要时使用额外的去消旋化级联反应，转化率在 88% 到 95% 之间，分离产率为 32-60% 和完美的对映纯度 (>99% ee) .
• Auxiliary ligand-controlled supramolecular assembly of three Cd(ii) coordination polymers based on a (E)-3-(quinolin-4-yl) acrylic acid: syntheses, structures and photoluminescent properties
  作者：Gui-lei Liu、Hui Li

  DOI：10.1039/c3ce40864g

  日期：——

  Reactions of deprotonated (E)-3-(quinolin-4-yl) acrylic acid (QCA) with nitrates of cadmium, in the presence or absence of auxiliary 4,4′-bipyridine (4,4′-bipy) ligand in CH3OH–DMF–H2O, produce three novel compounds with the formula of [Cd(QCA)2(H2O)]n (1), [Cd(QCA)2(4,4′-bipy)]n (2) and[Cd(QCA)2(4,4′-bipy)1.5]·2.5H2O}n (3). Their structures have been determined by single-crystal X-ray diffraction analysis and further characterized by elemental analysis, IR spectra, thermogravimetric (TGA) and powder X-ray diffraction (PXRD) analysis. Compounds 1 and 2 displays 2D undulated and planar layered structures respectively, which are further connected by intermolecular hydrogen bonds to form a 3D supramolecular architecture. In compound 3, QCA and 4,4′-bipy ligands link Cd centers to generate 1D ladder-like chain. An unusual uudd cyclic water tetramer in the crystal lattice of 3 is observed as the second example reported until now. Obviously, the structural differences among them are attributable to the different molar ratio of QCA to auxiliary 4,4′-bipy ligand. Moreover, the photoluminescent properties of all the compounds have been investigated.

  在 CH3OH 中存在或不存在辅助 4,4'-联吡啶 (4,4'-bipy) 配体的情况下，去质子化 (E)-3-(喹啉-4-基) 丙烯酸 (QCA) 与硝酸镉的反应–DMF–H2O，生成三种新型化合物，其分子式为 [Cd(QCA)2( )]n (1)、[Cd(QCA)2(4,4′-bipy)]n (2) 和[ Cd(QCA)2(4,4′-bipy)1.5]·2.5 }n (3)。它们的结构已通过单晶 X 射线衍射分析确定，并通过元素分析、红外光谱、热重 (TGA) 和粉末 X 射线衍射 (PXRD) 分析进一步表征。化合物1和2分别显示出2D波状和平面层状结构，它们进一步通过分子间氢键连接形成3D超分子结构。在化合物 3 中，QCA 和 4,4'-bipy 配体连接 Cd 中心，生成一维梯状链。迄今为止报道的第二个例子是在3的晶格中观察到不寻常的uudd环状水四聚体。显然，它们之间的结构差异归因于QCA与辅助4,4'-联吡啶配体的摩尔比不同。此外，还研究了所有化合物的光致发光性质。
• Polyazasteroids. III. 1,2,4-triazolo[3,4-<i>a</i>]benzo[<i>f</i>]isoquinoline. Synthesis of the diazaphenanthrene alkaloid perlolidine and its 1,8-phenanthroline isomer
  作者：I. Lalezari、S. Nabahi

  DOI：10.1002/jhet.5570170825

  日期：1980.12

  A series of 1,2,4-triazolo[3,4-a]benzo[f]isoquinolines, which constitutes a new class of polyazasteroidal compounds, were synthesized. A simple synthesis of the diazaphenanthrene alkaloid perlolidine as well as 1,8-phenanthrolin-7-(8H)one is reported.

  合成了一系列1,2,4-三唑并[3,4- a ]苯并[ f ]异喹啉，它们构成了一类新型的聚氮杂甾类化合物。据报道，简单地合成了二氮杂菲生物碱perlolidine以及1,8-菲林-7-（8 H）one。