methyl 2-((2-chloro-5-nitropyrimidin-4-yl)amino)benzoate | 66427-76-7

• 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: methyl 2-((2-chloro-5-nitropyrimidin-4-yl)amino)benzoate
• 英文别名: 4-(2-Carbomethoxyanilino)-2-chloro-5-nitropyrimidin；2-(2-chloro-5-nitro-pyrimidin-4-ylamino)-benzoic acid methyl ester；Methyl 2-[(2-chloro-5-nitropyrimidin-4-yl)amino]benzoate
• CAS: 66427-76-7
• 化学式: C₁₂H₉ClN₄O₄
• 分子量: 308.681
• InChiKey: HHKFILBTVSLJTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-((2-chloro-5-nitropyrimidin-4-yl)amino)benzoate 以69%的产率得到methyl 2-({5-nitro-2-[(3,4,5-trimethoxyphenyl)amino]pyrimidin-4-yl}amino)benzoate hydrochloride
  参考文献：
  名称：

  [EN] PYRIMIDINE COMPOUNDS
  [FR] COMPOSES DE PYRIMIDINE

  摘要：

  公开号：

  WO2004074244A3
• 作为产物：
  描述：

  邻氨基苯甲酸甲酯 以63%的产率得到methyl 2-((2-chloro-5-nitropyrimidin-4-yl)amino)benzoate
  参考文献：
  名称：

  [EN] PYRIMIDINE COMPOUNDS
  [FR] COMPOSES DE PYRIMIDINE

  摘要：

  公开号：

  WO2004074244A3

文献信息

• Pyrimidine compounds
  申请人：Davis-Ward Ronda

  公开号：US20070010668A1

  公开（公告）日：2007-01-11

  The present invention provides compounds of formula (I): wherein all variables are as defined herein, pharmaceutical compositions containing the same, processes for preparing the same and their use as pharmaceutical agents.

  本发明提供以下式(I)的化合物：其中所有变量如此定义，包含它们的制药组合物，制备它们的过程以及它们用作制药剂的用途。
• Design and synthesis of doublecortin-like kinase 1 inhibitors and their bioactivity evaluation
  作者：Pengming Pan、Dengbo Ji、Zhongjun Li、Xiangbao Meng

  DOI：10.1080/14756366.2023.2287990

  日期：2024.12.31

  Doublecortin-like kinase 1 (DCLK) is a microtubule-associated serine/threonine kinase that is upregulated in a wide range of cancers and is believed to be related to tumour growth and development. ...

  双皮质素样激酶 1 (DCLK) 是一种微管相关丝氨酸/苏氨酸激酶，在多种癌症中表达上调，并被认为与肿瘤生长和发展有关。 ...
• Discovery of methyl 3-((2-((1-(dimethylglycyl)-5-methoxyindolin-6-yl)amino)-5-(trifluoro-methyl) pyrimidin-4-yl)amino)thiophene-2-carboxylate as a potent and selective polo-like kinase 1 (PLK1) inhibitor for combating hepatocellular carcinoma
  作者：Zhou Deng、Guyue Chen、Shuang Liu、Yunzhan Li、Jiaji Zhong、Baoding Zhang、Li Li、Huiying Huang、Zheng Wang、Qingyan Xu、Xianming Deng

  DOI：10.1016/j.ejmech.2020.112697

  日期：2020.11

  Hepatocellular carcinoma (HCC) is the second leading cause of cancer-related death worldwide and targeted therapeutics exhibit limited success. Polo-like kinase 1 (PLK1), a Ser/Thr kinase, plays a pivotal role in cell-cycle regulation and is considered a promising target in HCC. Here, via structural optimization using both biochemical kinase assays and cellular antiproliferation assays, we discovered a potent and selective PLK1 kinase inhibitor, compound 31. Compound 31 exhibited biochemical activity with IC50 of < 0.508 nM against PLK1 and a KINOMEscan selectivity score (S(1)) of 0.02 at a concentration of 1 mu M. Furthermore, 31 showed broad antiproliferative activity against a variety of cancer cell lines, with the lowest antiproliferative IC50 (11.1 nM) in the HCC cell line HepG2. A detailed mechanistic study of 31 revealed that inhibition of PLK1 by 31 induces mitotic arrest at the G2/M phase checkpoint, thus leading to cancer cell apoptosis. Moreover, 31 exhibited profound antitumor efficacy in a xenograft mouse model. Collectively, these results establish compound 31 as a good starting point for the development of PLK1 targeted therapeutics for HCC. (C) 2020 Elsevier Masson SAS. All rights reserved.
• INA SHUICHIRO; MORITA KUNIHIKO; NOGUCHI ISAO, YAKUGAKU DZASSI, YAKUGAKU ZASSNI, J. PHARM. SOS. JAR., 1978, 98, NO 1, 72+
  作者：INA SHUICHIRO、 MORITA KUNIHIKO、 NOGUCHI ISAO

  DOI：——

  日期：——
• PYRIMIDINE COMPOUNDS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1597251A2

  公开（公告）日：2005-11-23