ethyl 3-(diethylamino)acrylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 3-(diethylamino)acrylate
• 英文别名: Ethyl 3-diethylaminoacrylate；ethyl 3-(diethylamino)prop-2-enoate
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: ANTPVARYELNKNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-(diethylamino)acrylate 在 三乙胺 作用下， 以 乙醚 、 乙醇 、 甲苯 为溶剂， 反应 8.0h， 生成 3-Cyclopropylamino-2-(2,4,5-trifluorbenzoyl)acrylsaeure-ethylester
  参考文献：
  名称：

  Synthesis of Novel Ciprofloxacin-Based Hybrid Molecules toward Potent Antimalarial Activity

  摘要：

  Antimalarial drug resistance is a serious obstacle in the persistent quest to eradicate malaria. There is a need for potent chemical agents that are able to act on drug-resistant Plasmodium falciparum populations at reasonable concentrations without any related toxicity to the host. By rational drug design, we envisaged to address this issue by generating a novel hybrid drug possessing two pharmacophores that can act on two unique and independent targets within the cell. We synthesized a new class of ciprofloxacinbased hybrid molecules, which have been integrated with acridine, quinolone, sulphonamide, and cinnamoyl pharmacophores (1-4). We realized a potent chloroquinolone-ciprofloxacin-based antimalarial hybrid (2, CQ-CFX) whose mechanism of action is unlike that of its parent molecules indicating a unique biological target. CQ-CFX is not only potent against CQ-resistant and susceptible strains of Plasmodium falciparum at low nanomolar concentrations (IC50 values are 63.17 +/- 1.2 nM and 25.52 +/- 4.45 nM, respectively) but is also not toxic to mammalian and bacterial systems up to 20 mu M and 1 mu M, respectively.

  DOI：

  10.1021/acsmedchemlett.0c00196
• 作为产物：
  描述：

  二乙胺 、 丙炔酸乙酯 以 乙腈 为溶剂， 反应 24.0h， 以88.3%的产率得到ethyl 3-(diethylamino)acrylate
  参考文献：
  名称：

  使用双前药/生物有机金属方法增强环丙沙星的抗疟活性

  摘要：

  氟喹诺酮环丙沙星的衍生化通过结合生物有机金属化学和前药方法大大提高了其抗疟活性。发现两种新的非手性化合物2和4对恶性疟原虫对氯喹敏感和对氯喹耐药的菌株的活性比环丙沙星高10到100倍。与环丙沙星相比，这些非手性衍生物杀死寄生虫的速度更快。化合物2和4被证明是有前途的先导，创建了一个新的抗疟药家族。

  DOI：

  10.1021/jm901357n

文献信息

• The C=C Bond Decomposition Initiated by Enamine‐Azide Cycloaddition for Catalyst‐ and Additive‐Free Synthesis of <i>N</i> ‐Sulfonyl Amidines
  作者：Xixi Zheng、Jie‐Ping Wan

  DOI：10.1002/adsc.201901054

  日期：2019.12.17

  The chemo‐selective synthesis of N‐sulfonyl amidines is realized via the decomposition of the enamine C=C bond of enaminoesters through an in situ generated triazoline intermediate. Control experiments prove that the electron withdrawing ester group in the enamine component is crucial in inducing the chemo‐selective formation of amidines. The method is featured with high efficiency and sustainability

  N-磺酰基am的化学选择性合成是通过原位生成的三唑啉中间体将烯胺酯的烯胺C = C键分解而实现的。对照实验证明，烯胺成分中的吸电子酯基对于诱导am的化学选择性形成至关重要。该方法以纯水为介质，无需任何催化剂或添加剂，具有高效，可持续的特点。
• [EN] IMIDAZOPYRIDAZINES AS MODULATORS OF IL-17<br/>[FR] IMIDAZOPYRIDAZINES EN TANT QUE MODULATEURS DE L'IL-17
  申请人：JANSSEN BIOTECH INC

  公开号：WO2021222404A1

  公开（公告）日：2021-11-04

  The present application discloses compounds having the following formula: (I), or pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4 and R5 are defined in the specification, as well as methods of making and using the compounds disclosed herein for treating or ameliorating an IL-17 mediated syndrome, disorder and/or disease.

  本申请公开了具有以下公式(I)的化合物，或其药用可接受的盐，其中R1、R2、R3、R4和R5在说明书中定义，以及制造和使用所公开化合物的方法，用于治疗或改善IL-17介导的综合征、紊乱和/或疾病。
• Enhancement of the Antimalarial Activity of Ciprofloxacin Using a Double Prodrug/Bioorganometallic Approach
  作者：Faustine Dubar、Guillaume Anquetin、Bruno Pradines、Daniel Dive、Jamal Khalife、Christophe Biot

  DOI：10.1021/jm901357n

  日期：2009.12.24

  The derivatization of the fluoroquinolone ciprofloxacin greatly increases its antimalarial activity by combining bioorganometallic chemistry and the prodrug approach. Two new achiral compounds 2 and 4 were found to be 10- to 100-fold more active than ciprofloxacin against Plasmodium falciparum chloroquine-susceptible and chloroquine-resistant strains. These achiral derivatives killed parasites more

  氟喹诺酮环丙沙星的衍生化通过结合生物有机金属化学和前药方法大大提高了其抗疟活性。发现两种新的非手性化合物2和4对恶性疟原虫对氯喹敏感和对氯喹耐药的菌株的活性比环丙沙星高10到100倍。与环丙沙星相比，这些非手性衍生物杀死寄生虫的速度更快。化合物2和4被证明是有前途的先导，创建了一个新的抗疟药家族。
• [EN] IMIDAZOPYRIMIDINES AS MODULATORS OF IL-17<br/>[FR] IMIDAZOPYRIMIDINES EN TANT QUE MODULATEURS DE L'IL-17
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2021220183A1

  公开（公告）日：2021-11-04

  The present application discloses compounds of Formula I or pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R4, and R5 are defined in the specification, as well as methods of making and using the compounds disclosed herein for treating or ameliorating an IL-17 mediated syndrome, disorder and/or disease.

  本申请公开了化合物I的化学式或其药用盐，其中R1、R2、R3、R4和R5在规范中有定义，以及制备和使用此处公开的化合物的方法，用于治疗或改善IL-17介导的综合症、紊乱和/或疾病。
• Synthesis of new fluoroquinolones and evaluation of their in vitro activity on Toxoplasma gondii and Plasmodium spp
  作者：G. Anquetin、M. Rouquayrol、N. Mahmoudi、M. Santillana-Hayat、R. Gozalbes、J. Greiner、K. Farhati、F. Derouin、R. Guedj、P. Vierling

  DOI：10.1016/j.bmcl.2004.03.070

  日期：2004.6

  6-amino-3-azabicyclo[3.1.0]hexyl side chain of trovafloxacin. The four compounds are also inhibitory for blood stages of Plasmodium falciparum though at high concentration. These results confirm the potential of quinolones as anti-T. gondii and antimalarial drugs but also show that the QSAR models for T. gondii cannot be reliably extended for screening antimalarial activity.

  描述了四种新的计算机设计的氟喹诺酮的合成，这些合成的氟喹诺酮已通过QSAR分析预测对弓形虫原虫具有活性。这些化合物在体外对弓形虫有抑制作用。这些化合物之一具有与曲伐沙星相当的高活性。它结合了加替沙星或莫西沙星的基本环丙基喹啉结构与托伐沙星的C-7 6-氨基-3-氮杂双环[3.1.0]己基侧链。这四种化合物即使在高浓度下也对恶性疟原虫的血液阶段具有抑制作用。这些结果证实了喹诺酮类药物具有抗T的潜力。刚地和抗疟药，但也表明不能可靠地扩展刚地弓形虫的QSAR模型来筛选抗疟活性。