ethyl 7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylate | 84088-84-6

• 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 7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylate
• 英文别名: Ethyl 4-hydroxy-2-oxo-1-azatricyclo[7.3.1.0^{5,13}]trideca-3,5(13),6,8-tetraene-3-carboxylate；ethyl 4-hydroxy-2-oxo-1-azatricyclo[7.3.1.05,13]trideca-3,5,7,9(13)-tetraene-3-carboxylate
• CAS: 84088-84-6
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: XPXAPFWWBARBHC-UHFFFAOYSA-N

物化性质

• 熔点：
  102-104 °C(Solv: hexane (110-54-3))
• 沸点：
  434.0±45.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylate 在 三乙胺 、 三氯氧磷 作用下， 反应 3.0h， 以90%的产率得到ethyl 7-chloro-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylate
  参考文献：
  名称：

  4-azido-2-oxoquinoline-3-羧酸盐和4-azidocoumarin-3羧酸盐的闭环和重排反应† ‡

  摘要：

  通过相应的4-羟基衍生物1经由4-甲苯磺酸酯2或4-氯化合物4从相应的4-羟基衍生物1中获得4-叠氮基-2-氧代喹啉-3-羧酸盐和4-叠氮杂多古灵-3-羧酸盐6，将它们在热解后环化成3-烷氧基异恶唑[ 4,3- c ]喹啉-4（5 H）-或相应的香豆素8，而在稍高的温度下，发生3- O，4- O重排，得到4-烷氧基-异恶唑[4]。 ，3- c ]-喹啉-3-酮和相应的香豆素9.借助差示扫描量热法可以容易地获得必要的反应条件。

  DOI：

  10.1002/jhet.5570350322
• 作为产物：
  描述：

  ethyl 2-bromo-1,3-dioxo-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate 在 丙酮 作用下， 以97%的产率得到ethyl 7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylate
  参考文献：
  名称：

  4-Hydroxy-2-Quinolones. 233*. Synthesis and Diuretic Activity of 9-Bromo-7-Hydroxy-5-Oxo-2,3-Dihydro-1H,5H-Pyrido[3,2,1-ij]Quinoline-6-Carboxylic Acid Anilides

  摘要：

  The ethyl ester of 7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylic acid reaction with bromine in anhydrous acetic acid producing a mixture of the 9-bromo-substituted product and 6-ethoxycarbonyl-5,7-dihydroxy-2,3-dihydro-1H-pyrido[3,2,1-ij]quinolinium tribromide in a 1:1 ratio. It has been established experimentally that the diuretic activity of 9-bromo-7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxanilides increases substantially in comparison with their non-brominated analogs.

  DOI：

  10.1007/s10593-013-1381-3

文献信息

• A ‘sulfonyl-azide-free’ (SAFE) aqueous-phase diazo transfer reaction for parallel and diversity-oriented synthesis
  作者：Dmitry Dar’in、Grigory Kantin、Mikhail Krasavin

  DOI：10.1039/c9cc02042j

  日期：——

  Diazo transfer reactions are notoriously associated with the use of potentially explosive sulfonyl azides. The first ‘sulfonyl-azide-free’ (SAFE) protocol for producing diazo compounds from their active-methylene precursors via the Regitz diazo transfer reaction was developed and has displayed a remarkable substrate scope. It can be applied to generating arrays of diazo compounds for further evolution

  众所周知，重氮转移反应与潜在爆炸性磺酰叠氮化物的使用有关。研发了第一个通过Regitz重氮转移反应从其活性亚甲基前体生产重氮化合物的“无磺酰叠氮”（SAFE）方案，该方案已显示出显着的底物范围。它可用于产生重氮化合物的阵列，以通过组合化学和一系列支架产生的转化进一步进化。
• Methanetricarboxylates as key reagents for the simple preparation of heteroarylcarboxamides with potential biological activity. Part<b>1</b>reaction of methanetricarboxylates with indoline and 1,2,3,4-tetrahydroquinoline
  作者：Alexander Kutyrev、Thomas Kappe

  DOI：10.1002/jhet.5570340340

  日期：1997.5

  The reaction of methanetricarboxylates 2a,b with indoline as well as 1,2,3,4-tetrahydroquinoline yields tricyclic 4-hydroxy-2(1H)-quinolones with an ester group in position 3 (3, 8a,b). These heterocyclic esters condense with primary aliphatic, aromatic, and heteroaromatic amines to give the corresponding amides 5a-e and 10a-t.

  甲烷三羧酸酯2a，b与二氢吲哚以及1,2,3,4-四氢喹啉的反应产生在位置3（3，8a，b）具有酯基的三环4-羟基-2（1 H）-喹诺酮。这些杂环酯与脂族，芳族和杂芳族伯胺缩合，得到相应的酰胺5a-e和10a-t。
• 다이하이드로퀴놀린 카복스아마이드 유도체 또는 이의 약학적으로 허용 가능한 염을 유효성분으로 포함하는 폐렴의 예방 또는 치료용 약학적 조성물
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY 한국화학연구원(319980077651)

  公开号：KR20190067546A

  公开（公告）日：2019-06-17

  다이하이드로퀴놀린 카복스아마이드 유도체 또는 이의 약학적으로 허용 가능한 염을 유효성분으로 포함하는 폐렴의 예방 또는 치료용 약학적 조성물이 개시된다. 상기 약학적 조성물은 우수한 항균활성을 가질 뿐만 아니라, 종래 일반적으로 사용되고 있는 에리트로마이신과 같은 항균제와는 달리 약물내성을 가지는 폐렴균에 대하여 항균 활성이 뛰어나므로 이들 폐렴균에 의해서 발생되는 폐렴 질환의 예방 또는 치료용 약학적 조성물로써 유용하게 사용될 수 있다.

  二羟基喹诺啉羧酰胺衍生物或其药学上允许的盐作为有效成分，用于预防或治疗肺炎的药学组合物已经公开。该药学组合物不仅具有优异的抗菌活性，而且对于对传统抗生素如红霉素等常用抗菌剂具有药物耐药性的肺炎菌具有出色的抗菌活性，因此可以作为预防或治疗由这些肺炎菌引起的肺炎疾病的药学组合物而被有益地使用。
• Heterocyclic carboxamides, compositions containing such compounds,
  申请人：Aktiebolaget Leo

  公开号：US04547511A1

  公开（公告）日：1985-10-15

  This invention relates to novel heterocyclic carboxamides which increase the activity of the immune system and to the preparation thereof. The invention is also concerned with pharmaceutical compositions containing the said compounds and methods of treatment therewith.

  本发明涉及一种新型杂环羧酰胺，其能够增强免疫系统的活性，以及其制备方法。本发明还涉及含有上述化合物的药物组合物和治疗方法。
• 4-Hydroxy-2-quinolones. 220*. Bromination of ethyl 7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylate
  作者：I. V. Ukrainets、N. Yu. Golik、I. N. Chernenok、S. V. Shishkina、V. A. Parshikov

  DOI：10.1007/s10593-013-1190-8

  日期：2013.2

  7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylate with bromine in aqueous acetic acid solution gave not only the expected ethyl 2-bromo-1,3-dioxo-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate, but also an admixture of its 9-bromo-substituted isomer. The structural features of the major and minor reaction products are discussed.

  在乙酸水溶液中用溴处理7-羟基-5-氧代-2,3-二氢-1 H，5 H-吡啶并[3,2,1- ij ]喹啉-6-羧酸乙酯2-溴-1,3-二氧杂-2-乙基，3,6,7-四氢-1 H，5 H-吡啶基[3,2,1- ij ]喹啉-2-羧酸乙酯，也可以是其9的混合物-溴取代的异构体。讨论了主要和次要反应产物的结构特征。