ethyl 4-oxo-6-phenyl-1,4-dihydroquinoline-2-carboxylate | 5428-31-9

• 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
• 英文名称: ethyl 4-oxo-6-phenyl-1,4-dihydroquinoline-2-carboxylate
• 英文别名: ethyl 4-oxo-6-phenyl-1H-quinoline-2-carboxylate
• CAS: 5428-31-9
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: CIKFPAYTONMDRZ-UHFFFAOYSA-N

物化性质

• 熔点：
  253-255 °C (decomp)(Solv: ethanol (64-17-5))
• 沸点：
  513.9±45.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  ethyl 4-oxo-6-phenyl-1,4-dihydroquinoline-2-carboxylate 在 sodium hydroxide 作用下， 生成 4-hydroxy-6-phenyl-quinoline-2-carboxylic acid
  参考文献：
  名称：

  Phenylquinolines¹

  摘要：

  DOI：

  10.1021/ja01154a525
• 作为产物：
  描述：

  以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以4221 mg的产率得到ethyl 4-oxo-6-phenyl-1,4-dihydroquinoline-2-carboxylate
  参考文献：
  名称：

  新型 C-3 取代犬尿酸衍生物的合成

  摘要：

  犬尿烯酸 (KYNA) 作为富电子芳香体系在改良曼尼希反应中的应用已得到研究。通过使用存在于许多生物活性产物中的胺，如吗啉、哌啶或 N-甲基哌嗪和反应性明显不同的醛，如甲醛和苯甲醛，测试了反应的扩展可能性。还研究了连接到 3 位的取代基对氨基烷基化的影响。因此，还测试了 3-氨基甲酰基取代的前体与含有侧链的叔胺的反应，以提供具有两个潜在阳离子中心的新 KYNA 衍生物。通过由 DFT 计算支持的 NMR 光谱测量，还确定了 KYNA 衍生物的主要互变异构体形式。

  DOI：

  10.3390/molecules25040937

文献信息

• Types of C-3 substituted kynurenic acid derivatives with improved neuroprotective activity
  申请人：SZEGEDI TUDOMÁNYEGYETEM

  公开号：US10870633B2

  公开（公告）日：2020-12-22

  The invention relates to C-3 substituted kynurenic acid derivatives with the general formula (I) wherein R1 is C1-7alkyl-, R6R7N—C1-7alkyl-, C6-10aryl-C1-7alkyl group; R2 is H or C1-7alkyl group; or R1 and R2 with the nitrogen atom to which they are attached form a saturated or partially saturated 5-7 membered, optionally benzofused heterocyclic ring, optionally comprising additional N, O, S heteroatoms and optionally being substituted; R3 is —OH, C1-7alkyl-O—, —NH2, C1-7alkyl-NH—, C6-10aryl-C1-7alkyl-NH— or —NH— —(CH2)n—NR8R9 group wherein n is an integer from 1 to 3; R4 is H, C1-7alkyl-, C6-10aryl group or a halogen atom; R5 is H or C6-10aryl group; R6 is C1-7alkyl group; R7 is C1-7alkyl group; or R6 and R7 with the nitrogen atom to which they are attached form a saturated or partially saturated 5-7 membered, optionally benzofused heterocyclic ring, optionally comprising additional N, O, S heteroatoms and optionally being substituted; R8 is C1-7alkyl group; R9 is C1-7alkyl group; R8 and R9 with the nitrogen atom to which they are attached form a saturated or partially saturated 5-7 membered, optionally benzofused heterocyclic ring, optionally comprising additional N, O, S heteroatoms and optionally being substituted; and stereoisomers, tautomers and salts thereof. The invention relates to the pharmaceutical preparations comprising the compounds and stereoisomers, tautomers and pharmaceutically acceptable salts. The compounds of the invention have neuroprotective activity, may be used for the prevention and treatment of neurodegeneration, and for slowing down the development of the conditions and diseases associated with a decline in cognitive abilities.

  本发明涉及具有通式（I）的 C-3 取代的犬尿酸衍生物，其中 R1 是 C1-7 烷基、R6R7N-C1-7烷基、C6-10 芳基-C1-7烷基；R2 是 H 或 C1-7 烷基；或 R1 和 R2 与它们所连接的氮原子形成饱和或部分饱和的 5-7 位元、任选苯并杂环，任选包括额外的 N、O、S 杂原子并任选被取代；R3 是 -OH、C1-7 烷基-O-、-NH2、C1-7 烷基-NH-、C6-10 芳基-C1-7 烷基-NH- 或 -NH- -(CH2)n-NR8R9 基团，其中 n 是 1 到 3 的整数；R4 是 H、C1-7 烷基、C6-10 芳基或卤原子；R5 是 H 或 C6-10 芳基；R6 是 C1-7 烷基；R7 是 C1-7 烷基；或 R6 和 R7 与它们所连接的氮原子形成饱和或部分饱和的 5-7 位元、任选苯并杂环，任选包括额外的 N、O、S 杂原子并任选被取代；R8是C1-7烷基；R9是C1-7烷基；R8和R9与它们所连接的氮原子形成饱和或部分饱和的5-7个成员的、可选地包含额外的N、O、S杂原子并可选地被取代的杂环；以及它们的立体异构体、同系物和盐。本发明涉及包含本发明化合物及其立体异构体、同系物和药学上可接受的盐的药物制剂。本发明的化合物具有神经保护活性，可用于预防和治疗神经变性，以及减缓与认知能力下降相关的病症和疾病的发展。
• 10.1039/d4ra04341c
  作者：Sárik, Julián Robin、Hetényi, Anasztázia、Berkecz, Róbert、Szatmári, István、Lőrinczi, Bálint

  DOI：10.1039/d4ra04341c

  日期：——

  Lactam formation of different KYNA amides and Mannich bases mediated by ortho-quinone methide has been investigated. The efficiency of the two routes of the cyclization process was revealed and the influence of diverse amide side chains was explored. In this regard compounds bearing a tertiary amine function in the amide side chain resulted in the formation of the lactam product, while the formation

  已研究了邻醌甲基化物介导的不同 KYNA 酰胺和曼尼希碱的内酰胺形成。揭示了环化过程的两种途径的效率，并探讨了不同酰胺侧链的影响。在这方面，酰胺侧链带有叔胺官能团的化合物导致内酰胺产物的形成，而在其他KYNA酰胺的情况下观察到二聚体衍生物的形成。此外，合成了KYNA B环上带有不同取代基的衍生物，并研究了它们对闭环反应的影响。
• NOVEL TYPES OF C-3 SUBSTITUTED KINURENIC ACID DERIVATIVES WITH IMPROVED NEUROPROTECTIVE ACTIVITY
  申请人：Szegedi Tudományegyetem

  公开号：EP3423444A1

  公开（公告）日：2019-01-09
• NOVEL TYPES OF C-3 SUBSTITUTED KYNURENIC ACID DERIVATIVES WITH IMPROVED NEUROPROTECTIVE ACTIVITY
  申请人：SZEGEDI TUDOMÁNYEGYETEM

  公开号：US20190106409A1

  公开（公告）日：2019-04-11

  The invention relates to C-3 substituted kynurenic acid derivatives with the general formula (I) wherein R 1 is C 1-7 alkyl-, R 6 R 7 N-C 1-7 alkyl group; C 6-10 aryl-C 1-7 alkyl group; R 2 is H or C 1-7 alkyl group; or R 1 and R 2 with the nitrogen atom to which they are attached form a saturated or partially saturated 5-7 membered, optionally benzofused heterocyclic ring, optionally comprising additional N, O, S heteroatoms and optionally being substituted; R 3 is —OH, C 1-7 alkyl-O—, —NH 2 , C 1-7 alkyl-NH—, C 6-10 aryl-C 1-7 alkyl-NH— or —NH—(CH 2 ) n —NR 8 R 9 group wherein n is an integer from 1 to 3; R 4 is H, C 6-10 aryl group or a halogen atom; R 5 is H or C 6-10 aryl group; R6 is C 1-7 alkyl group; R 7 is C 1-7 alkyl group; or R 6 and R 7 with the nitrogen atom to which they are attached form a saturated or partially saturated 5-7 membered, optionally benzofused heterocyclic ring, optionally comprising additional N, O, S heteroatoms and optionally being substituted; R 8 is C 1-7 alkyl group; R 9 is C 1-7 alkyl group; R 8 and R 9 with the nitrogen atom to which they are attached form a saturated or partially saturated 5-7 membered, optionally benzofused heterocyclic ring, optionally comprising additional N, O, S heteroatoms and optionally being substituted; and stereoisomers, tautomers and salts thereof. The invention relates to the pharmaceutical preparations comprising the compounds and stereoisomers, tautomers and pharmaceutically acceptable salts. The compounds of the invention have neuroprotective activity, may be used for the prevention and treatment of neurodegeneration, and for slowing down the development of the conditions and diseases associated with a decline in cognitive abilities.
• Synthesis of New C-3 Substituted Kynurenic Acid Derivatives
  作者：Bálint Lőrinczi、Antal Csámpai、Ferenc Fülöp、István Szatmári

  DOI：10.3390/molecules25040937

  日期：——

  substituents attached to position 3 on the aminoalkylation was also investigated. Thus, reactions of 3-carbamoyl-substituted precursors with tertiary amine containing side-chains were also tested to afford new KYNA derivatives with two potential cationic centers. By means of NMR spectroscopic measurements, supported by DFT calculations, the dominant tautomer form of KYNA derivatives was also determined.

  犬尿烯酸 (KYNA) 作为富电子芳香体系在改良曼尼希反应中的应用已得到研究。通过使用存在于许多生物活性产物中的胺，如吗啉、哌啶或 N-甲基哌嗪和反应性明显不同的醛，如甲醛和苯甲醛，测试了反应的扩展可能性。还研究了连接到 3 位的取代基对氨基烷基化的影响。因此，还测试了 3-氨基甲酰基取代的前体与含有侧链的叔胺的反应，以提供具有两个潜在阳离子中心的新 KYNA 衍生物。通过由 DFT 计算支持的 NMR 光谱测量，还确定了 KYNA 衍生物的主要互变异构体形式。