3-chloro-4-fluorophenylurea | 343247-57-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-chloro-4-fluorophenylurea
• 英文别名: (3-Chloro-4-fluorophenyl)urea
• CAS: 343247-57-4
• 化学式: C₇H₆ClFN₂O
• mdl: MFCD11183381
• 分子量: 188.589
• InChiKey: PAIOBGQOUSRSNN-UHFFFAOYSA-N

物化性质

• 熔点：
  228 °C
• 沸点：
  268.9±30.0 °C(Predicted)
• 密度：
  1.498±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-4-fluorophenylurea 在 乙醇 、 sodium 、 溶剂黄146 作用下， 生成 5-((3-fluoro-4-(6-methoxy-7-(3-morpholinopropoxy)quinolin-4-yloxy)phenylamino)methylene)-1-(3-chloro-4-fluorophenyl)pyrimidine-2,4,6-trione
  参考文献：
  名称：

  Discovery of novel 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 5-(aminomethylene)pyrimidine-2,4,6-trione moiety as c-Met kinase inhibitors

  摘要：

  A series of novel quinoline derivatives bearing 5-(aminomethylene)pyrimidine-2,4,6-trione moiety were designed, synthesized, and evaluated for their c-Met kinase inhibitory activities and antiproliferative activities against 5 cancer cell lines (HT-29, H460, MKN-45, A549, and U87MG) in vitro. Most compounds showed moderate to excellent potency, with the most promising analogue 45 (c-Met half-maximal inhibitory concentration [IC50] = 1.15 nM) showing high selectivity versus 5 other tyrosine kinases, VEGFR-2, Flt-3, PDGFR-beta, c-Kit, and EGFR. Structure-activity relationship studies indicated that electron-donating groups on the phenyl ring at the 3-position of pyrimidine-2,4,6-trione were required to increase the electron density on the 5-(aminomethylene) pyrimidine-2,4,6-trione moiety. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.014
• 作为产物：
  描述：

  异氰酸- 3-氯-4-氟苯酯 在 氨 、 水 作用下， 以 丙酮 为溶剂， 生成 3-chloro-4-fluorophenylurea
  参考文献：
  名称：

  N-（3-苄氨基-2-氰基-3-甲基硫代丙烯酰基）-N'-（取代苯基）脲的合成及晶体结构

  摘要：

  将苯脲基引入传统的氰基丙烯酸酯骨架中，合成了一系列的N-（3-苄氨基-2-氰基-3-甲基硫代丙烯酰基）-N'-（取代的苯基）脲。所有化合物均为新化合物，其结构通过1 H NMR，13 C NMR和质谱分析确定。关键词：合成，氰基丙烯酸酯，苯脲衍生物。化学 Soc。埃塞俄比亚。2013，27（2），295-300。DOI：http：//dx.doi.org/10.4314/bcse.v27i2.15

  DOI：

  10.4314/bcse.v27i2.15

文献信息

• [EN] PYRIDINE DERIVATIVES AS JNK INHIBITORS AND THEIR USE<br/>[FR] DERIVES PYRIDINE SERVANT D'INHIBITEURS DE JNK ET UTILISATION
  申请人：ASTRAZENECA AB

  公开号：WO2004052880A1

  公开（公告）日：2004-06-24

  The present invention relates to new compounds of formula (I) whrein: R1 is aryl or heteroaryl, each of which is optionally substituted with one or more of R3, OR3, OCOR3, COOR3, COR3, CONR3R4, NHCOR3, NR3R4, NHSO2R3, SO2R3, SO2NR3R4, SR3, CN, halogeno or NO2; R2 is R5, R6, COR5, COR6, CONHR5, CONHR6, CON(R6)2, COOR5, COOR6, SO2R5 or SO2R6; a process for their preparation and new intermediates used therein, pharmaceutical formulations containing said therapeutically active compounds and to the use of said active compounds in therapy.

  本发明涉及公式（I）的新化合物，其中：R1是芳基或杂环芳基，每个都可以选择地用一个或多个R3，OR3，OCOR3，COOR3，COR3，CONR3R4，NHCOR3，NR3R4，NHSO2R3，SO2R3，SO2NR3R4，SR3，CN，卤素或NO2取代；R2是R5，R6，COR5，COR6，CONHR5，CONHR6，CON（R6）2，COOR5，COOR6，SO2R5或SO2R6；一种用于它们的制备的方法和在其中使用的新中间体，含有所述治疗活性化合物的药物配方以及所述活性化合合物在治疗中的使用。
• Design and biological evaluation of novel 4-(2-fluorophenoxy)quinoline derivatives bearing an imidazolone moiety as c-Met kinase inhibitors
  作者：Weike Liao、Gang Hu、Zhuang Guo、Deyu Sun、Lixia Zhang、Yanxin Bu、Yingxiu Li、Yajing Liu、Ping Gong

  DOI：10.1016/j.bmc.2015.06.026

  日期：2015.8

  A series of 4-(2-fluorophenoxy)quinoline derivatives containing an imidazolone moiety were designed, synthesized and evaluated for their in vitro biological activities against c-Met kinase and four cancer cell lines (A549, H460, HT-29 and MKN-45). Most compounds showed moderate to excellent activities in enzyme and cellular assays. The most promising analog, 58 (c-Met IC50 = 1.42 nM), displayed 2.1-

  设计，合成并评估了一系列含咪唑酮部分的4-（2-氟苯氧基）喹啉衍生物对c-Met激酶和四种癌细胞系（A549，H460，HT-29和MKN-45）的体外生物学活性）。大多数化合物在酶和细胞分析中均显示中等至出色的活性。 与福瑞替尼相比，最有前途的类似物58（c-Met IC 50 = 1.42 nM）对H460和MKN-45细胞株分别显示出2.1倍，8.6倍的增长。对结构-活性关系的分析表明，邻位取代的苯环以及N-未取代的咪唑啉酮连接基有利于抗肿瘤活性。
• Multi-Component Synthesis of Dihydropyrimidines by Iodine Catalyst at Ambient Temperature and<i>in-vitro</i>Antimycobacterial Activity
  作者：Paresh Zalavadiya、Satish Tala、Jignesh Akbari、Hitendra Joshi

  DOI：10.1002/ardp.200800224

  日期：2009.8

  and simple three‐component domino synthesis of some new dihydropyrimidines (DHPMs) from aromatic aldehydes, 1,3‐dicarbonyl compounds and N‐(3‐chloro‐4‐fluorophenyl)urea using molecular iodine as catalyst is described. The 1‐substituted dihydropyrimidines were isolated in good to excellent yields (78‐90%) within a short reaction time (4‐6 h) at ambient temperature. The biological evaluation revealed

  描述了使用分子碘作为催化剂，由芳香醛、1,3-二羰基化合物和 N-(3-氯-4-氟苯基)脲有效且简单地三组分多米诺合成一些新的二氢嘧啶 (DHPM)。在环境温度下，在很短的反应时间内（4-6 小时），1-取代的二氢嘧啶以良好到极好的产率（78-90%）被分离出来。生物学评估表明，新合成的化合物（4a-i 和 5a-i）对结核分枝杆菌 H37 RV 表现出中等的抗分枝杆菌活性。
• Green Synthesis of Oxoquinoline-1(2H)-Carboxamide as Antiproliferative and Antioxidant Agents: An Experimental and In-Silico Approach to High Altitude Related Disorders
  作者：Amena Ali、Abuzer Ali、Musarrat Husain Warsi、Mohammad Akhlaquer Rahman、Mohamed Jawed Ahsan、Faizul Azam

  DOI：10.3390/molecules27010309

  日期：——

  promising anticancer activity. Compound 5a also demonstrated promising DPPH free radical scavenging activity with an IC50 value of 14.16 ± 0.42 µM. The epidermal growth factor receptor (EGFR) and carbonic anhydrase (CA), two prospective cancer inhibitor targets, were used in the molecular docking studies. Molecular docking studies of ligand 5a (docking score = −8.839) against the active site of EGFR revealed

  在高海拔地区，氧气浓度的下降会导致产生活性氧和氮（RONS），从而引起各种健康问题。我们解决了这些健康问题，并报告了一系列 10 种氧代喹啉的合成、表征和生物活性。根据报道的方法，在超声照射下分两步获得 N-Aryl-7-hydroxy-4-methyl-2-oxoquinoline-1(2H)carboxamides (5a-j)。根据美国国家癌症研究所 (NCI US) 的方案，在 10 µM 下针对从九个不同面板获得的总共 5 打癌细胞系进行了抗癌活性测试。化合物 5a（TK-10（肾癌）；%GI = 82.90）和 5j（CCRF-CEM（白血病）；%GI = 58.61）显示出最有希望的抗癌活性。化合物 5a 还表现出有希望的 DPPH 自由基清除活性，IC50 值为 14.16 ± 0.42 µM。表皮生长因子受体 (EGFR) 和碳酸酐酶 (CA) 这两个前瞻性癌症抑制剂靶点被用于分子对接研究。配体
• [EN] CERTAIN CHEMICAL ENTITIES, COMPOSITIONS, AND METHODS<br/>[FR] ENTITÉS CHIMIQUES, COMPOSITIONS ET PROCÉDÉS
  申请人：NEUPHARMA INC

  公开号：WO2013040515A1

  公开（公告）日：2013-03-21

  Chemical entities based on quinoxaline that are kinase inhibitors are described. Specifically quinoxaline derivatives of Formula I, containing a diarylamide or diarylurea substructure that inhibit Braf mutant kinase activity, pharmaceutical compositions containing the inhibitor compounds and methods of treatment of cancer comprising administering an effective amount of the Braf inhibitor compound are described.

  描述了基于喹啉的化合物，这些化合物是激酶抑制剂。具体来说，描述了含有二芳胺或二芳基脲亚结构的式I的喹啉衍生物，这些衍生物能够抑制Braf突变激酶活性，以及含有这些抑制剂化合物的药物组合物和包括给予有效量Braf抑制剂化合物的治疗癌症方法。