ethyl 6-hydroxy-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-5-carboxylate | 84088-82-4

• 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: ethyl 6-hydroxy-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-5-carboxylate
• 英文别名: 1-hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[3,2,1-i,j]quinoline-2-carboxylic acid ethyl ester；ethyl 9-hydroxy-11-oxo-1-azatricyclo[6.3.1.04,12]dodeca-4(12),5,7,9-tetraene-10-carboxylate
• CAS: 84088-82-4
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: UFMJUWOLIFFYKD-UHFFFAOYSA-N

物化性质

• 熔点：
  140-142 °C(Solv: heptane (142-82-5))
• 沸点：
  417.8±45.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)
• 溶解度：
  >38.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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 6-hydroxy-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-5-carboxylate 在 吡啶 、 苯胺 作用下， 生成 6-hydroxy-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid anilide
  参考文献：
  名称：

  Heterocyclic carboxamides, compositions containing such compounds,

  摘要：

  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。

  公开号：

  US04547511A1
• 作为产物：
  描述：

  2-(indoline-1-carbonyl)malonic acid diethyl ester 在 二苯醚 作用下， 反应 0.25h， 以94%的产率得到ethyl 6-hydroxy-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-5-carboxylate
  参考文献：
  名称：

  4-Hydroxy-2-quinolones. 107. Reaction of triethyl methanetricarboxylate with indoline

  摘要：

  DOI：

  10.1007/s10593-006-0200-5

文献信息

• 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。
• 4-Hydroxy-2-quinolones 138. Synthesis and study of structure-biological activity relationships in a series of 1-hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid anilides
  作者：I. V. Ukrainets、E. V. Mospanova、N. L. Bereznyakova、O. I. Naboka

  DOI：10.1007/s10593-007-0237-0

  日期：2007.12
• Discovery of 4-hydroxy-2-oxo-1,2-dihydroquinolines as potential inhibitors of Streptococcus pneumoniae, including drug-resistant strains
  作者：Srigouri Huddar、Chul Min Park、Hyung Jun Kim、Soojin Jang、Sunkyung Lee

  DOI：10.1016/j.bmcl.2020.127071

  日期：2020.5

  New therapies for treating drug-resistant pneumococcal infections are urgently needed. The novel scaffold 6hydroxy-4-oxo-1,2-dihydro-4H-quinoline was shown to have similar efficacies against all three different serotypes of S. pneumoniae, ATCC 49617 (TM) (19F), ATCC BAA-1663 (TM) (15B), and ATCC 700904 (TM) (19A), in a resazurin-based high-throughput screen using the Korea Chemical Bank library. Further studies to identify a new lead with this scaffold, including tricyclic pyrrolo[3,2,1-ij]quinolone and pyrido[3,2,1-ij]quinolone derivatives, led to the identification of 6d, 7d and 12a. Compound 6d (IC50 = 0.92, 0.75, and 0.77 mu M), 7d (IC50 = 0.57, 0.66, and 0.38 mu M) and 12a (IC50, = 0.27, 1.03, and 0.62 mu M) showed submicromolar IC50, values against 19F, 15B, and 19A, respectively, and thus serve as a starting point for further optimization. While some of compounds in this series exhibited acceptable pharmacokinetic profiles in preliminary in vivo rat experiments, the most active compound 12a showed poor solubility and high plasma protein binding. Our current research efforts are focused on optimizing compounds to improve physicochemical properties as well as potency.
• 4-Hydroxy-2-quinolones. 122. 1-Hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[3,2,1-ij]-quinoline-2-carboxylic acid hetarylamides as potential antitubercular agents
  作者：I. V. Ukrainets、E. V. Mospanova、L. V. Sidorenko

  DOI：10.1007/s10593-007-0137-3

  日期：2007.7