5-甲氧基喹啉-2(1H)-酮 | 160893-04-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 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
• 中文名称: 5-甲氧基喹啉-2(1H)-酮
• 英文名称: 5-methoxyquinolin-2(1H)-one
• 英文别名: 5-methoxy-2(1H)-quinolinone；5-methoxy-1H-quinolin-2-one
• CAS: 160893-04-9
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: HJEKDEFGMGFUBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-甲氧基喹啉-2(1H)-酮 在 sodium hydride 、 三乙胺 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 1-{3-[4-(3-Bromo-phenyl)-piperazin-1-yl]-propyl}-5-methoxy-1H-quinolin-2-one (HCl)
  参考文献：
  名称：

  3,4-Dihydro-2(1H)-quinolinone as a Novel Antidepressant Drug:  Synthesis and Pharmacology of 1-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-3,4- dihydro-5-methoxy-2(1H)-quinolinone and Its Derivatives

  摘要：

  To develop a novel antidepressant drug with central nervous system-stimulating activity, me prepared a series of 1-[w-(4-substituted phenyl-1-piperazinyl)alkyl]-3,4-dihydro-2(1H)-quinlinone derivatives and examined their activities by their effects at 30 and 100 mg/kg po on the sleeping time of mice anesthetized with halothane and on the time required for recovery from coma induced in mice by cerebral concussion. We examined their binding affinities for a receptors by evaluating their ability to inhibit [H-3]-1,3-di(o-tolyl)guanidine ([H-3]DTG) binding to the rat whole brain membrane in comparison with three putative a receptor agonists: 1,3-di(o-tolyl)guanidine (DTG, 66), (+)-1,2,3,4,5,6-hexahydro-6,11-dimethylmethano-3-benzazecin-8-ol (SKF10,047, 67), and (+)-1,2,3,4,5,6-hexahydro-6, 11-dimethyl-3(3 -methyl-2-butenyl)-2,6-methano-3-benzazecin-8-ol (pentazocine, 68). Among the series of derivatives, 1-3-[4-(3-chlorophenyl)-1-piperazinyl]-3p linone hydrochloride (34b) and its mesylate (34c), at a dose of 30 mg/kg po, reduced the sleeping time and the time for recovery from coma and they inhibited [H-3]DTG binding for a receptors. The putative a receptor agonists reduced the sleeping time and the time for recovery from coma whereas two a receptor antagonists, alpha-(4-fluorophenyl)-4-(5-fluoro-2-pyrimidinyl) piperazinebutanol hydrochloride (BMY14802, 69) and cis-9-[3-(3,5-dimethyl-1-piperazinyl)propyl]carbazole dihydrochloride (rimcazole, 70), were inactive in the two tests. Preadministration of the putative a receptor antagonists 69 (3 mg/kg po) and 70 (30 mg/kg po) completely antagonized the actions of 34b and the a receptor agonists in the test for recovery from coma. These results suggested that 34b and 34c are a receptor agonists. Furthermore, a single administration of 1 and 10 mg/kg po 34b and 34c showed antidepressant-like activity by reducing the immobility time in the forced-swimming test with mice, while a tricyclic antidepressant, 10,11-dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine hydrochloride (imipramine, 1) (10 and 30 mg/kg po), did not reduce the time after a single administration. 1 reduced the time after repeated administration of 30 mg/kg po once a day for 4 days. The structure-activity relationship of the series of compounds is also discussed.

  DOI：

  10.1021/jm980333v
• 作为产物：
  描述：

  5-甲氧基-3,4-二氢-1H-喹啉-2-酮 在 sodium persulfate 、 iron(III) chloride hexahydrate 作用下， 以 水 、 乙腈 为溶剂， 以91%的产率得到5-甲氧基喹啉-2(1H)-酮
  参考文献：
  名称：

  取代喹啉-2(1H)-酮化合物的制备方法和用途

  摘要：

  本发明属于药物化学和化学合成领域，具体涉及一类取代喹啉‑2(1H)‑酮化合物的制备方法。本发明提供了一种取代喹啉‑2(1H)‑酮化合物的制备方法，其将式I表示的化合物和氧化剂在溶剂中发生氧化反应，得到式II表示的化合物。该制备方法具有以下优点：方法简便、收率高、成本低、适于工业化生产，通式II表示的取代喹啉‑2(1H)‑酮为多种药物活性成分的重要中间体。

  公开号：

  CN110467569B

文献信息

• Palladium-catalyzed synthesis of quinolin-2(1<i>H</i>)-ones: the unexpected reactivity of azodicarboxylate
  作者：Jin-Bao Peng、Bo Chen、Xinxin Qi、Jun Ying、Xiao-Feng Wu

  DOI：10.1039/c8ob00199e

  日期：——

  Quinolin-2(1H)-one is a useful structure unit present in a wide range of natural products and pharmaceuticals. A Pd(II)-catalyzed synthesis of quinolin-2(1H)-ones from quinoline N-oxides was developed with azodicarboxylates which act as both the activating agent and oxidant. The reaction proceeded under mild conditions and no protection against air and moisture was needed.

  喹啉-2（1 H）-1是存在于多种天然产物和药物中的有用的结构单元。用偶氮二羧酸酯开发了Pd（II）催化由喹啉N-氧化物合成喹啉-2（1 H）-酮的方法，偶氮二羧酸盐既起活化剂作用，又起氧化剂作用。反应在温和的条件下进行，不需要防空气和湿气。
• Synthesis of Methoxy-2-quinolones via Pummerer-type Cyclization of N-Aryl-N-methyl-3-(phenylsulfinyl)propionamides.
  作者：Jun TODA、Michiya SAKAGAMI、Yoko GOAN、Mina SIMAKATA、Toshiaki SAITOH、Yoshie HORIGUCHI、Takehiro SANO

  DOI：10.1248/cpb.48.1854

  日期：——

  The thionium ions 10 generated by Pummerer reaction of N-aryl-N-methyl-3-(phenylsulfinyl)propionamides 4 caused not only an electrophilic cyclization reaction producing 2-quinolones 8, but also the formation of the vinyl sulfides 5 and 6 in favor of the latter reaction. On the other hand, the treatment of the vinyl sulfides 5 and 6 with p-toluenesulfonic acid induced cyclization to afford the 2-quinolones

  由N-芳基-N-甲基-3-（苯基亚磺酰基）丙酰胺Pummerer反应产生的硫鎓离子10不仅引起产生2-喹诺酮8的亲电环化反应，而且有利地形成了乙烯基硫化物5和6。后一种反应。另一方面，取决于芳环的电子性质，用对甲苯磺酸对乙烯基硫化物5和6的处理引起环化，从而以优异至中等的收率得到2-喹诺酮8，从而提供了一种方便的方法用于合成甲氧基-2-喹诺酮。
• 2-Anilinoquinoline based arylamides as broad spectrum anticancer agents with B-RAFV600E/C-RAF kinase inhibitory effects: Design, synthesis, in vitro cell-based and oncogenic kinase assessments
  作者：Ashraf K. El-Damasy、Md Mamunul Haque、Jung Woo Park、Sang Chul Shin、Jun-Seok Lee、Eunice EunKyeong Kim、Gyochang Keum

  DOI：10.1016/j.ejmech.2020.112756

  日期：2020.12

  identification of new anticancer agents with improved potency and efficacy, a new series of arylamides incorporating the privileged 2-anilinoquinoline scaffold has been designed, synthesized, and biologically assessed. Aiming at extensive evaluation of the target compounds’ potency and spectrum, a panel of 60 clinically important cancer cell lines representing nine cancer types has been used. Compounds

  迫切需要鉴定具有增强的效力和功效的新抗癌剂，已经设计，合成和生物学评估了结合特权2-苯胺基喹啉骨架的一系列新的芳基酰胺。为了广泛评估目标化合物的效能和光谱，已使用一组代表9种癌症的60种临床上重要的癌细胞系。具有哌嗪取代的苯环的化合物9a和9c作为最活跃的成员出现，超过了FDA批准的伊马替尼药物的抗癌能力。他们引发了亚微摩尔或一位数微摩尔GI 50在大多数测试的癌细胞（包括结肠癌HCT-15，肾脏TK-10和UO-31，以及卵巢NCI / ADR-RES）中的多药耐药（MDR）细胞中，其值均保持不变。体外机理研究表明，化合物9a和9c可以触发HCT-116结肠癌细胞的形态变化，凋亡和细胞周期停滞。此外，化合物9c以与紫杉醇相似的方式改变了微管聚合模式。9c的激酶筛选显示了其对B-RAF V600E和C-RAF激酶的抑制活性，IC 50值分别为0.888μM和0.229μM。综上所述，本报告
• 신규 퀴놀린 화합물 및 이를 포함하는 암의 예방 또는 치료용 약학 조성물
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY 한국과학기술연구원(319980077518) BRN ▼209-82-03522

  公开号：KR101778938B1

  公开（公告）日：2017-09-18

  본 발명은 암세포에 대한 우수한 항 증식 효능을 나타내는 퀴놀린 화합물, 이의 약학적으로 허용 가능한 염, 또는 수화물과, 이의 제조 방법 및 이를 유효성분으로 함유하는 암 질환의 예방 또는 치료용 의약 조성물에 관한 것으로서, 상기 본 발명에 따른 화합물, 이의 약학적으로 허용 가능한 염, 또는 수화물은 우수한 암세포 억제 활성과 단백질 키나아제 및 돌연변이 키나아제의 억제 활성을 나타내고 있으므로, 부작용이 적은 새로운 항암제로 유용하게 사용될 수 있다.

  本发明涉及一种对癌细胞具有优异抑制增殖作用的喹诺啉化合物，其药学上可接受的盐或水合物，以及其制备方法和用作抗癌疾病预防或治疗的药物组合物，该化合物、其药学上可接受的盐或水合物根据本发明具有优异的抗癌细胞抑制活性和蛋白激酶及突变激酶的抑制活性，因此可以作为副作用较少的新型抗癌药物得到有益应用。
• [EN] QUINOLONES AS INHIBITORS OF CLASS IV BROMODOMAIN PROTEINS<br/>[FR] QUINOLONES À TITRE D'INHIBITEURS DE PROTÉINES À BROMODOMAINES DE CLASSE IV
  申请人：UCL BUSINESS PLC

  公开号：WO2016034512A1

  公开（公告）日：2016-03-10

  The present invention provides compounds of formula (I) as described herein and pharmaceutically acceptable salts, hydrates and solvates thereof for use in medicine, for example in the treatment of acute myeloid leukaemia:

  本发明提供了如下所述的化合物(I)及其药用可接受的盐、水合物和溶剂合物，用于医学上的应用，例如用于治疗急性髓样白血病：