(E)-3-(quinolin-4-yl) acrylic acid | 13026-20-5

• 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
• 英文名称: (E)-3-(quinolin-4-yl) acrylic acid
• 英文别名: 3-Quinolin-4-ylprop-2-enoic acid
• CAS: 13026-20-5
• 化学式: C₁₂H₉NO₂
• mdl: MFCD00137153
• 分子量: 199.209
• InChiKey: GDCNAOKZXWMIJA-UHFFFAOYSA-N

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-(quinolin-4-yl) acrylic acid 在 palladium 10% on activated carbon 、 氢气 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 85.0h， 生成
  参考文献：
  名称：

  From tryptophan-based amides to tertiary amines: Optimization of a butyrylcholinesterase inhibitor series

  摘要：

  DOI：

  10.1016/j.ejmech.2022.114248
• 作为产物：
  描述：

  4-喹啉甲醛 、 三甲基膦酰基乙酸酯 在 sodium hydride 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 24.17h， 以35.2%的产率得到(E)-3-(quinolin-4-yl) acrylic acid
  参考文献：
  名称：

  From tryptophan-based amides to tertiary amines: Optimization of a butyrylcholinesterase inhibitor series

  摘要：

  DOI：

  10.1016/j.ejmech.2022.114248

文献信息

• Asymmetric synthesis and cytotoxicity of (−)-saframycin A analogues
  作者：Wenfang Dong、Wei Liu、Zheng Yan、Xiangwei Liao、Baohe Guan、Nan Wang、Zhanzhu Liu

  DOI：10.1016/j.ejmech.2012.01.017

  日期：2012.3

  (−)-Saframycin A and its nineteen analogues were prepared from l-tyrosine in 24 steps, and their structures were confirmed through NMR and HRMS. The cytotoxicities of these compounds were tested against HCT-8, BEL-7402, Ketr3, A2780, MCF-7, A549, BGC-803, Hela, HELF and KB cell lines. The IC50 values of the cytotoxicity of most compounds were at the level of nM. Compound 7d with 2-furan amide side

  由1-酪氨酸分24步制备（-）-沙弗霉素A及其19个类似物，并通过NMR和HRMS确认其结构。测试了这些化合物对HCT-8，BEL-7402，Ketr3，A2780，MCF-7，A549，BGC-803，Hela，HELF和KB细胞系的细胞毒性。大多数化合物的细胞毒性的IC 50值为nM。具有2-呋喃酰胺侧链的化合物7d在所有这些化合物中显示出最强的细胞毒性，平均IC 50值为6.06 nM。
• 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 and antibacterial activity of a series of novel 9-O-acetyl- 4′-substituted 16-membered macrolides derived from josamycin
  作者：Zhehui Zhao、Longlong Jin、Yanpeng Xu、Di Zhu、Yi Liu、Chao Liu、Pingsheng Lei

  DOI：10.1016/j.bmcl.2013.12.029

  日期：2014.1

  A series of novel 9-O-acetyl-4′-substituted 16-membered macrolides derived from josamycin has been designed and synthesized by cleavage of the mycarose of josamycin and subsequent modification of the 4′-hydroxyl group. These derivatives were evaluated for their in vitro antibacterial activities against a panel of Staphylococcus aureus and Staphylococcus epidermidis. 15 (4′-O-(3-Phenylpropanoyl)-9-

  已设计和合成了一系列新的衍生自交联霉素的9 - O-乙酰基-4'-取代的16元大环内酯类化合物，方法是通过裂解交联霉素的直链淀粉和随后修饰4'-羟基基团来合成。对这些衍生物的体外抗菌活性进行了评价，对一组金黄色葡萄球菌和表皮葡萄球菌的抗菌活性。15（4'- ø - （3-苯基丙酰基）-9- ø -乙酰基desmycarosyl交沙霉素）和16（4'- ö丁酰基-9- ø -乙酰基desmycarosyl交沙霉素）显示出可比较的活动，以交沙霉素针对金黄色葡萄球菌（MSSA）和表皮葡萄球菌（MSSE）。
• Tetrazole amide derivatives of heterocyclic alkenyl acids and their use as antiallergic substances
  申请人：VALEAS S.p.A. INDUSTRIA CHIMICA E FARMACEUTICA

  公开号：EP0384450A1

  公开（公告）日：1990-08-29

  Tetrazole amide derivatives of heterocyclic alkenyl acids, of general formula (I): in which Y = NH, O or S when m = 1; Y = N when m = 2; m = 1 or 2; l = 0 or 4; R = H, C₁₋₄ alkyl, Cl, Br, CF₃, CH₂OCOCH₃, or OCH₂-Ph; R₁ = H, alkaline metal or alkaline earth metal; the double bond of the alkenyl chain being of trans or cis configuration and the possible benzene ring being unsubstituted or substituted. Said derivatives possess high antiallergic activity.

  杂环烯烃酸的四唑酰胺衍生物，一般式（I）如下：其中Y = NH、O或S，当m = 1 时；Y = N，当m = 2 时；m = 1 或 2；l = 0 或 4；R = H、C₁₋₄烷基、Cl、Br、CF₃、CH₂OCOCH₃或OCH₂-Ph；R₁ = H、碱金属或碱土金属；烯烃链的双键为顺式或反式构型，可能的苯环未取代或取代。这些衍生物具有很高的抗过敏活性。
• [EN] MACROLIDES<br/>[FR] MACROLIDES
  申请人：GLAXO GROUP LTD

  公开号：WO2002032917A1

  公开（公告）日：2002-04-25

  The present invention relates to a compound of formula (I) wherein R1 is hydrogen or together with R2 is oxo; R2 represents hydroxy, OC(O)XR7, OC(O)NHXR7 or R2 together with R1 is an oxo group; R3 is hydrogen or a hydroxyl protecting group; R4 is hydrogen or XR7; R5 is hydrogen, XR7 or C(O)NHXR7; R6 is hydrogen or R5 and R6 taken together with the intervening atoms form a cyclic carbonate having the following structure and pharmaceutically acceptable salts and solvates thereof and solvates thereof; to processes for their preparation and their use in the therapy or prophylaxis of systemic or topical bacterial infections in a human or animal body.

  本发明涉及一种化合物，其化学式为（I），其中R1代表氢原子或与R2一起代表氧原子；R2代表羟基、OC（O）XR7、OC（O）NHXR7或R2与R1一起形成氧原子基团；R3代表氢原子或羟基保护基团；R4代表氢原子或XR7；R5代表氢原子、XR7或C（O）NHXR7；R6代表氢原子或R5和R6连同介于其间的原子形成以下结构的环状碳酸酯，并且涉及其药学上可接受的盐和溶剂合物及其溶剂合物的制备方法和在人体或动物体内治疗或预防系统性或局部细菌感染中的应用。