4-氯-8-硝基喹啉 | 23833-99-0

• 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-氯-8-硝基喹啉
• 英文名称: 4-chloro-8-nitroquinoline
• CAS: 23833-99-0
• 化学式: C₉H₅ClN₂O₂
• mdl: MFCD00457008
• 分子量: 208.604
• InChiKey: AOATVJLAFLBGPZ-UHFFFAOYSA-N

物化性质

• 熔点：
  127-128 °C
• 沸点：
  339.9±27.0 °C(Predicted)
• 密度：
  1.484±0.06 g/cm3(Predicted)
• 溶解度：
  >31.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件为2-8°C，并需保存在惰性气体中。

反应信息

• 作为反应物：
  描述：

  4-氯-8-硝基喹啉 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 、 silver carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 8,9-dimethoxy-1-nitro-5-[2-(N,N-dimethylamino)ethyl]-5H-dibenzo[c,h][1,6]naphthyridin-6-one
  参考文献：
  名称：

  Nitro and amino substitution within the A-ring of 5H-8,9-dimethoxy-5-(2-N,N-dimethylaminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: influence on topoisomerase I-targeting activity and cytotoxicity

  摘要：

  Recently, 5H-8 9-dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3-methylenedioxydibenzo[c,h][1,6]naphthyridin-6-one, 1, was identified as a TOP1-targeting agent with pronounced antitumor activity. In the present study, the effect on activity of substituting, a single nitro or amino group in the A-ring in lieu of the methylenedioxy moiety of 1 was evaluated. The presence of either a nitro or amino substituent at the 4-position had a pronounced adverse affect on both TOP1-targeting activity and cytotoxicity. To a lesser extent, derivatives with a nitro or amino substituent at the 1-position were also less active than 1. Replacement of the methylenedioxy moiety of 1 with either a nitro or amino substituent at either the 2- and 3-position did result in analogues with potent TOP1-targeting activity and cytotoxicity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.076
• 作为产物：
  描述：

  2,2-dimethyl-5-(((2-nitrophenyl)amino)methylene)-1,3-dioxane-4,6-dione 在 三氯氧磷 作用下， 以 二苯醚 为溶剂， 反应 4.5h， 生成 4-氯-8-硝基喹啉
  参考文献：
  名称：

  通过芳香氢的亲核置换直接胺化硝基喹啉衍生物

  摘要：

  研究了缺电子硝基喹啉中氢（VNS）反应的亲核取代。所有新产品的性能已通过多种技术进行了表征：MS，HRMS，FTIR，GC-MS，电子吸收光谱和多核NMR。4-氯-8-硝基喹啉，8-（的结构叔丁基）-2-甲基-5-硝基喹啉，9-（8-硝基喹啉-7-基）-9 ħ -咔唑和（Ž）-7-通过单晶X射线衍射测定来确定（9 H-咔唑-9-基）-8-（羟基亚氨基）喹啉-5（8 H）-1。9-（8-硝基喹啉-7-基）-9 ħ -咔唑和（Ž）-7-（9 ħ咔唑-9-基）-8-（羟基亚氨基）喹啉-5-（8H）-一说明了VNS反应中的硝基/亚硝基转化。另外，9-（8-异丙基-2 - （（8-异丙基-2-甲基-5-硝基喹啉-6-基）甲基）-5- nitrosoquinolin -6-基）-9 ħ咔被呈现为双VNS产品。据推测，钾抗衡离子与硝基上的氧相互作用，从而可能以这种方式影响亲核试剂的攻击。

  DOI：

  10.3390/molecules26071857

文献信息

• Novel Sulfonaminoquinoline Hepcidin Antagonists
  申请人：Buhr Wilm

  公开号：US20120214803A1

  公开（公告）日：2012-08-23

  The present invention relates to novel hepcidin antagonists, pharmaceutical compositions comprising them and the use thereof as medicaments for the use in the treatment of iron metabolism disorders, such as, in particular, iron deficiency diseases and anemias, in particular anemias in connection with chronic inflammatory diseases.

  本发明涉及新型肝铁蛋白拮抗剂，包括它们的药物组合物以及将其用作药物治疗铁代谢紊乱，特别是铁缺乏病和贫血等疾病，特别是与慢性炎症性疾病相关的贫血。
• Novel Quinolinylaminoisoquinoline Bioisosteres of Sorafenib as Selective RAF1 Kinase Inhibitors: Design, Synthesis, and Antiproliferative Activity against Melanoma Cell Line
  作者：Hye Jung Cho、Mohammed Ibrahim El-Gamal、Chang-Hyun Oh、So Ha Lee、Taebo Sim、Garam Kim、Hong Seok Choi、Jung Hoon Choi、Kyung Ho Yoo

  DOI：10.1248/cpb.c13-00283

  日期：——

  Design and synthesis of a new series of quinolinylaminoisoquinoline derivatives as conformationally restricted bioisosteres of Sorafenib are described. Their in vitro antiproliferative activity against A375P melanoma cell line was tested. Compounds 1b, 1d, 1g, and 1j showed the highest potency against A375P cell line with IC50 values in sub-micromolar scale. In addition, compound 1d exerted high selectivity towards RAF1 serine/threonine kinase with 96.47% inhibition at 10 µM, and IC50 of 0.96 µM. This compound can possess antiproliferative activity against melanoma cells through inhibition of RAF1 kinase.

  报道了一种新型喹啉基氨基异喹啉衍生物的设计与合成，这些衍生物作为索拉非尼的构象限制性生物等排体。测定了它们对A375P黑色素瘤细胞系的体外抗增殖活性。化合物1b、1d、1g和1j显示出对A375P细胞系最高的活性，IC50值在亚微摩尔范围内。此外，化合物1d对RAF1丝氨酸/苏氨酸激酶表现出高选择性，在10微摩尔浓度下抑制率达到96.47%，IC50为0.96微摩尔。该化合物通过抑制RAF1激酶对黑色素瘤细胞具有抗增殖活性。
• [EN] QUINOLINE DERIVATIVES AS CASPASE-3 INHIBITOR, PREPARATION FOR PRODUCING THE SAME AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME<br/>[FR] DERIVES DE LA QUINOLINE INHIBITEURS DE LA CASPASE-3, PREPARATION SERVANT A LES OBTENIR, ET PREPARATIONS PHARMACEUTIQUES LES COMPRENANT
  申请人：YUNGJIN PHARMACEUTICAL CO LTD

  公开号：WO2003093240A1

  公开（公告）日：2003-11-13

  The present invention relates to new quinoline derivatives of formula (1) or their pharmaceutically acceptable salts with caspase-3 inhibitory activity and their preparation methods, wherein R2 is H; halogen; C1-6 alkyl; C 1-6 alkoxy; C1-6 alkoxyalkyl; or C3-6 cycloalkyl; R1 is formula (a); -CN; or formula (b); R is H; C6-14 aryl unsubstituted or substituted by halogen, C1-6 alkyl, C1-6 alkoxy or amino; 5 - 15 membered heterocyclic group unsubstituted or substituted by halogen, C1-6 alkyl, C1-6 alkoxy or amino; or -(CH2)n-CHR4R5. The present invention relates to a pharmaceutical composition for treating caspase-associated diseases by inhibiting the activity of caspase-3 which comprises the compound of formula (1) or its pharmaceutically acceptable salt.

  本发明涉及公式（1）的新喹啉衍生物或其与caspase-3抑制活性有关的药用盐，以及其制备方法，其中R2为H；卤素；C1-6烷基；C1-6烷氧基；C1-6烷氧基烷基；或C3-6环烷基；R1为公式（a）；-CN；或公式（b）；R为H；C6-14芳基，未取代或取代的，取代基为卤素，C1-6烷基，C1-6烷氧基或氨基；5-15成员的杂环基，未取代或取代，取代基为卤素，C1-6烷基，C1-6烷氧基或氨基；或-(CH2)n-CHR4R5。本发明涉及一种治疗caspase相关疾病的药物组合物，通过抑制caspase-3的活性，其中包括公式（1）的化合物或其药用盐。
• BICYCLIC COMPOUNDS AS mPGES-1 INHIBITORS
  申请人：Glenmark Pharmaceuticals S.A.

  公开号：US20130210844A1

  公开（公告）日：2013-08-15

  The present disclosure is directed to compounds of formula (I), and pharmaceutically acceptable salts thereof, as mPGES-1 inhibitors. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (mPGES-1) enzyme and are therefore useful in the treatment of pain and/or inflammation from a variety of diseases or conditions, such as asthma, osteoarthritis, rheumatoid arthritis, acute or chronic pain and neurodegenerative diseases.

  本公开涉及式(I)的化合物及其药学上可接受的盐，作为mPGES-1抑制剂。这些化合物是微粒体前列腺素E合成酶-1（mPGES-1）酶的抑制剂，因此在治疗各种疾病或症状引起的疼痛和/或炎症方面具有用途，如哮喘、骨关节炎、类风湿性关节炎、急性或慢性疼痛和神经退行性疾病。
• Toll样受体-7小分子抑制剂及其制备方法
  申请人：清华大学

  公开号：CN112390751B

  公开（公告）日：2022-07-05

  本发明属于化学小分子领域，尤其涉及一种Toll样受体‑7的小分子抑制剂。提供一种Toll样受体‑7小分子抑制剂，本发明以筛选得到的TLR7和TLR8的共抑制剂为研究对象，通过对母体化合物的结构优化和构效关系(SAR)的研究，实现了对TLR7和TLR8的选择性调控，进而开发出了对TLR7有一定选择性的高效、无毒、特异性的小分子抑制剂。该类TLR7小分子抑制剂在自身免疫疾病(系统性红斑狼疮)中有一定的效果和潜在的药用价值。