4-溴-1-甲基-1H-喹啉-2-酮 | 941-72-0

• 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: 4-溴-1-甲基-1H-喹啉-2-酮
• 中文别名: 4-溴-1-甲基-喹啉-2-酮
• 英文名称: 4-bromo-1-methylquinolin-2(1H)-one
• 英文别名: 4-bromo-1-methylquinolin-2-one
• CAS: 941-72-0
• 化学式: C₁₀H₈BrNO
• 分子量: 238.084
• InChiKey: HBHLDFROPPTEDU-UHFFFAOYSA-N

物化性质

• 熔点：
  125-127 °C(Solv: isopropanol (67-63-0))
• 沸点：
  289.2±40.0 °C(Predicted)
• 密度：
  1.592±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  4-溴-1-甲基-1H-喹啉-2-酮 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 20.0h， 生成 6-methylbenzo[i]phenanthridine-1,4,5(6H)-trione
  参考文献：
  名称：

  Novel coumarin- and quinolinone-based polycycles as cell division cycle 25-A and -C phosphatases inhibitors induce proliferation arrest and apoptosis in cancer cells

  摘要：

  Cell division cycle phosphatases CDC25 A, B and C are involved in modulating cell cycle processes and are found overexpressed in a large panel of cancer typology. Here, we describe the development of two novel quinone-polycycle series of CDC25A and C inhibitors on the one hand la-k, coumarin-based, and on the other 2a-g, quinolinone-based, which inhibit either enzymes up to a sub-micro molar level and at single digit micro molar concentrations, respectively. When tested in six different cancer cell lines, compound 2c displayed the highest efficacy to arrest cell viability, showing in almost all cell lines sub-micro molar IC50 values, a profile even better than the reference compound NCS95397. To investigate the putative binding mode of the inhibitors and to develop quantitative structure-activity relationships, molecular docking and 3-D QSAR studies were also carried out. Four selected inhibitors, la, ld, 2a and 2c have been also tested in A431 cancer cells; among them, compound 2c was the most potent one leading to cell proliferation arrest and decreased CDC25C protein levels together with its splicing variant. Compound 2c displayed increased phosphorylation levels of histone H3, induction of PARP and caspase 3 cleavage, highlighting its contribution to cell death through pro-apoptotic effects. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.04.012
• 作为产物：
  描述：

  4-羟基-N-甲基-2-喹啉 在 四磷十氧化物 、 四丁基溴化铵 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 4-溴-1-甲基-1H-喹啉-2-酮
  参考文献：
  名称：

  Novel coumarin- and quinolinone-based polycycles as cell division cycle 25-A and -C phosphatases inhibitors induce proliferation arrest and apoptosis in cancer cells

  摘要：

  Cell division cycle phosphatases CDC25 A, B and C are involved in modulating cell cycle processes and are found overexpressed in a large panel of cancer typology. Here, we describe the development of two novel quinone-polycycle series of CDC25A and C inhibitors on the one hand la-k, coumarin-based, and on the other 2a-g, quinolinone-based, which inhibit either enzymes up to a sub-micro molar level and at single digit micro molar concentrations, respectively. When tested in six different cancer cell lines, compound 2c displayed the highest efficacy to arrest cell viability, showing in almost all cell lines sub-micro molar IC50 values, a profile even better than the reference compound NCS95397. To investigate the putative binding mode of the inhibitors and to develop quantitative structure-activity relationships, molecular docking and 3-D QSAR studies were also carried out. Four selected inhibitors, la, ld, 2a and 2c have been also tested in A431 cancer cells; among them, compound 2c was the most potent one leading to cell proliferation arrest and decreased CDC25C protein levels together with its splicing variant. Compound 2c displayed increased phosphorylation levels of histone H3, induction of PARP and caspase 3 cleavage, highlighting its contribution to cell death through pro-apoptotic effects. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.04.012

文献信息

• IMIDAZOPYRIMIDINE DERIVATIVES
  申请人：Gilead Sciences, Inc.

  公开号：US20200108071A1

  公开（公告）日：2020-04-09

  The present disclosure provides a compound of Formula (I): or a pharmaceutically acceptable salt thereof as described herein. The present disclosure also provides pharmaceutical compositions comprising a compound of Formula I, processes for preparing compounds of Formula I, therapeutic methods for treating cancers.

  本公开提供了一种如下式（I）的化合物： 或其药学上可接受的盐。本公开还提供了包含如下式I的化合物的药物组合物，制备如下式I的化合物的方法，以及治疗癌症的治疗方法。
• A Combined Experimental and Computational Study on the Palladium-Catalyzed Sequential [2+2+1] Spirocyclization/Arene C–H Activation of 4-Iodo-2-quinolones with Diphenylacetylene
  作者：Yoshihiko Yamamoto、Naohiro Hirako、Takeshi Yasui

  DOI：10.1246/bcsj.20200328

  日期：2021.2.15

  The palladium-catalyzed reaction of 4-iodo-2-quinolones with diarylacetylenes in the presence of Ag2CO3 as a base in N,N-dimethylformamide (DMF) at 100 °C afforded unprecedented polyfused 2-quinolones via sequential [2+2+1] spirocyclization/arene C–H activation. A plausible mechanism is suggested based on control experiments and density functional theory (DFT) calculations.

  摘要 以 Ag2CO3 为碱在 N,N-二甲基甲酰胺（DMF）中于 100 ℃催化 4-碘-2-喹啉酮与二芳基乙炔的反应，通过顺序[2+2+1]螺环化/芳烃 C-H 活化，得到了前所未有的多融合 2-喹啉酮。根据对照实验和密度泛函理论（DFT）计算，提出了一种合理的机理。
• [EN] OPTICALLY ACTIVE DEVICES<br/>[FR] DISPOSITIFS OPTIQUEMENT ACTIFS
  申请人：MERCK PATENT GMBH

  公开号：WO2022128832A1

  公开（公告）日：2022-06-23

  The present invention relates to novel ophthalmic devices comprising polymerized compounds comprising a photoactive chromophore, said polymerized compounds, and special monomer compounds being particularly suitable for compositions and ophthalmic devices. The present invention is also directed to a process of changing the optical properties of said ophthalmic device or a precursor article for an ophthalmic device.

  本发明涉及新型眼科装置，其中包括聚合物化合物，其中包括光活性色团，所述聚合物化合物和特殊单体化合物特别适用于组成和眼科装置。本发明还涉及一种改变所述眼科装置或用于眼科装置的前体文章的光学特性的方法。
• [EN] MPRO TARGETING ANTIVIRAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIVIRAUX CIBLANT LES MPRO
  申请人：EXSCIENTIA AI LTD

  公开号：WO2023180189A1

  公开（公告）日：2023-09-28

  Disclosed are novel viral Mpro inhibitors according to Formula (I), their pharmaceutically acceptable salts, and pharmaceutical compositions thereof. Also disclosed are methods of using such compounds and compositions to inhibit Mpro and/or to treat various viral infections; particularly related to coronavirus. The compounds and compositions of the disclosure may be particularly useful in treating a broad spectrum of coronavirus.

  公开了根据式（I）的新型病毒 Mpro 抑制剂、它们的药学上可接受的盐及其药物组合物。还公开了使用此类化合物和组合物抑制 Mpro 和/或治疗各种病毒感染的方法；特别是与冠状病毒有关的病毒感染。本公开的化合物和组合物在治疗广谱冠状病毒方面可能特别有用。
• OPTICALLY ACTIVE DEVICES
  申请人：AMO Ireland

  公开号：EP4015512A1

  公开（公告）日：2022-06-22

  The present invention relates to novel ophthalmic devices comprising polymerized compounds comprising a photoactive chromophore, said polymerized compounds, and special monomer compounds being particularly suitable for compositions and ophthalmic devices. The present invention is also directed to a process of changing the optical properties of said ophthalmic device or a precursor article for an ophthalmic device.

  本发明涉及新型眼科设备，该设备由包含光活性发色团的聚合化合物组成，所述聚合化合物和特殊单体化合物特别适用于组合物和眼科设备。本发明还涉及一种改变所述眼科设备或眼科设备前体制品光学特性的工艺。