2,4-dimethyl 6-chloroquinoline-2,4-dicarboxylate | 438590-44-4

• 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: 2,4-dimethyl 6-chloroquinoline-2,4-dicarboxylate
• 英文别名: dimethyl 6-chloroquinoline-2,4-dicarboxylate
• CAS: 438590-44-4
• 化学式: C₁₃H₁₀ClNO₄
• 分子量: 279.68
• InChiKey: AFFRIWTUOYSJFU-UHFFFAOYSA-N

物化性质

• 沸点：
  409.3±40.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 储存条件：
  存于室温下，密封保存，并确保环境干燥。

反应信息

• 作为反应物：
  描述：

  2,4-dimethyl 6-chloroquinoline-2,4-dicarboxylate 在 水 作用下， 以 四氢呋喃 为溶剂， 生成 6-氯喹啉-2,4-二羧酸
  参考文献：
  名称：

  Quinoline-2,4-dicarboxylic acids: Synthesis and evaluation as inhibitors of the glutamate vesicular transport system

  摘要：

  Twenty-six quinoline-2,4-dicarboxylic acids (QDC's) were synthesized by a modified Doebner-von Miller pathway and tested as inhibitors against the glutamate vesicular transport (GVT) protein. The QDC's were active as inhibitors with the most potent QDC's found to contain halogens at the 6-/8-position, a hydroxyl at the 8-position, or a tethered aromatic moiety at the 6- or 7-position of the quinoline. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00444-8
• 作为产物：
  描述：

  alpha-酮戊二酸 在 氯化亚砜 、 2-甲基苯磺酸 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 27.5h， 生成 2,4-dimethyl 6-chloroquinoline-2,4-dicarboxylate
  参考文献：
  名称：

  Synthesis and in Vitro Pharmacology of Substituted Quinoline-2,4-dicarboxylic Acids as Inhibitors of Vesicular Glutamate Transport

  摘要：

  The vesicular glutamate transport (VGLUT) system selectively mediates the uptake of L-glutamate into synaptic vesicles. Uptake is linked to an H+-ATPase that provides coupling among ATP hydrolysis, an electrochemical proton gradient, and glutamate transport. Substituted quinoline-2,4-dicarboxylic acids (QDCs), prepared by condensation of dimethyl keto-glutaconate (DKG) with substituted anilines and subsequent hydrolysis, were investigated as potential VGLUT inhibitors in synaptic vesicles. A brief panel of substituted QDCs was previously reported (Carrigan et al. Bioorg. Med. Chem. Lett. 1999, 9, 2607-2612), and showed that certain substituents led to more potent competitive inhibitors of VGLUT. Using these compounds as leads, an expanded series of QDC analogues were prepared either by condensation of DKG with novel anilines or via aryl-coupling (Suzuki or Heck) to dimethyl 6-bromoquino-linedicarboxylate. From the panel of almost 50 substituted QDCs tested as inhibitors of the VGLUT system, the 6-PhCH=CH-QDC (K-i = 167 muM), 6-PhCH2CH2-QDC (K-i = 143 muM), 6-(4'-phenylstyryl)-QDC (K-i = 64 AM), and 6-biphenyl-4-yl-QDC (K-i = 41 muM) were found to be the most potent blockers. A preliminary assessment of the key elements needed for binding to the VGLUT protein based on the structure-activity relationships for the panel of substituted QDCs is discussed herein. The substituted QDCs represent the first synthetically derived VGLUT inhibitors and are promising templates for the development of selective transporter inhibitors.

  DOI：

  10.1021/jm010261z

文献信息

• [EN] GLUCOSE TRANSPORT INHIBITORS<br/>[FR] INHIBITEURS DE TRANSPORT DU GLUCOSE
  申请人：BAYER PHARMA AG

  公开号：WO2015091428A1

  公开（公告）日：2015-06-25

  The present invention relates to chemical compounds that selectively inhibit glucose transporter 1 (GLUT1), to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, as well as to intermediate compounds useful in the preparation of said compounds.

  本发明涉及选择性抑制葡萄糖转运蛋白1（GLUT1）的化合物，涉及制备该类化合物的方法，包括含有该类化合物的药物组合物和药物组合物，以及利用该类化合物制造用于治疗或预防疾病的药物组合物的用途，还涉及在制备该类化合物中有用的中间体化合物。
• Metal-free synthesis of quinoline-2,4-dicarboxylate derivatives using aryl amines and acetylenedicarboxylates through a pseudo three-component reaction
  作者：Saghir Ali、Abu T. Khan

  DOI：10.1039/d1ob01188j

  日期：——

  scaffolds is accomplished from aryl amines and dimethyl/diethyl acetylenedicarboxylates using 20 mol% molecular iodine as a catalyst in acetonitrile at 80 °C. In addition, the mechanistic explanation for the formation of the desired products is disclosed. The pivotal role of molecular iodine in the formation of the major products, diester quinoline derivatives, and the minor product, triesters, in two cases

  在 80 °C 下，使用 20 mol% 分子碘在乙腈中作为催化剂，由芳基胺和乙炔二羧酸二甲酯/二乙酯完成了一种高效、有用且一锅法的 quinoline-2,4-dicarboxylate 支架合成方案。此外，还公开了形成所需产物的机理解释。在机理中描述了分子碘在主要产物二酯喹啉衍生物和次要产物三酯形成中的关键作用，在两种情况下。该方法的显着优点是不涉及金属催化剂，避免最终产品中的金属污染以及废物产生，使用低成本和环保的催化剂，易于处理，区域选择性高，反应时间更短,
• Cascade embedding triethyltryptophanium iodide ionic liquid ( <scp> TrpEt ₃ </scp> ⁺ I ⁻ ) on silicated titanomagnetite core ( <scp> Fe _3‐x Ti _x O ₄ ‐SiO ₂ </scp> @ <scp> TrpEt ₃ </scp> ⁺ I ⁻ ): A novel nano organic–inorganic hybrid to prepare a library of 4‐substituted quinoline‐2‐carboxylates and 4,6‐disubstituted quinoline‐2‐carboxylates
  作者：Kobra Nikoofar、Fatemeh Molaei Yielzoleh

  DOI：10.1002/jccs.202000444

  日期：2021.8

  dialkyl acetylenedicarboxylates; and (c) pseudo three-component reaction of anilines and methyl propiolate under solvent-free conditions at 100°C. The promoter of these annulation processes is a novel inorganic–organic core–shell that was obtained from silicated titanomagnetite, tryptophan amino acid, and ethyl iodide. The tryptophan embedded on the silicated titanomagnetite core (Fe3-xTixO4-SiO2) followed

  取代喹诺酮-2-羧酸酯库（4,6-二取代喹诺酮-2-羧酸酯、6-取代喹啉二烷基-2,4-二羧酸酯和6-取代4-[2-甲氧基-2-氧乙基]喹啉- 2-甲基羧酸盐）是通过不同范围的一锅一步 MCRs 获得的，例如 (a) 芳香胺、乙炔二羧酸二烷基酯和末端烯烃/酮的三组分反应；(b) 苯胺与乙炔二羧酸二烷基酯的拟三组分反应；(c) 苯胺和丙炔酸甲酯在 100°C 无溶剂条件下的假三组分反应。这些环化过程的促进剂是一种新型的无机-有机核-壳，它是从硅化钛磁铁矿、色氨酸氨基酸和碘乙烷中获得的。嵌入在硅化钛磁铁矿核上的色氨酸（Fe3-x Ti x O 4 -SiO 2 )，随后用乙基碘烷基化，随后导致原位制备碘化三乙基色氨酸离子液体(TrpEt 3 + I - )。最终的纳米杂化物（Fe 3-x Ti x O 4 -SiO 2 @TrpEt 3 + I -) 通过场发射扫描电子显微镜、EDAX、FT-IR、TGA/DTG、振动样品磁强计和
• GLUCOSE TRANSPORT INHIBITORS
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：EP3083598A1

  公开（公告）日：2016-10-26
• Quinoline-2,4-dicarboxylic acids: Synthesis and evaluation as inhibitors of the glutamate vesicular transport system
  作者：Christina N. Carrigan、C. Sean Esslinger、Richard D. Bartlett、Richard J. Bridges、Charles M. Thompson

  DOI：10.1016/s0960-894x(99)00444-8

  日期：1999.9

  Twenty-six quinoline-2,4-dicarboxylic acids (QDC's) were synthesized by a modified Doebner-von Miller pathway and tested as inhibitors against the glutamate vesicular transport (GVT) protein. The QDC's were active as inhibitors with the most potent QDC's found to contain halogens at the 6-/8-position, a hydroxyl at the 8-position, or a tethered aromatic moiety at the 6- or 7-position of the quinoline. (C) 1999 Elsevier Science Ltd. All rights reserved.