2-chloro-N-(4-chlorophenyl)quinazolin-4-amine | 174074-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-chloro-N-(4-chlorophenyl)quinazolin-4-amine
• CAS: 174074-90-9
• 化学式: C₁₄H₉Cl₂N₃
• 分子量: 290.152
• InChiKey: YLYPNGHTTODCQA-UHFFFAOYSA-N

物化性质

• 熔点：
  210-215 °C
• 沸点：
  403.1±45.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(4-chlorophenyl)quinazolin-4-amine 在 盐酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 N-(4-chlorophenyl)-2-(piperazin-1-yl)quinazolin-4-amine
  参考文献：
  名称：

  Discovery of novel potent and selective ligands for 5-HT2A receptor with quinazoline scaffold

  摘要：

  A series of compounds with quinazoline scaffold were designed, synthesized and evaluated as novel potent 5-HT2A receptor ligands. N-(4-Chlorophenyl)-2-(piperazin-1-yl)quinazolin-4-amine (5o) has a K-i value of 14.04 +/- 0.21 nM, with a selectivity more than 10,000 fold over 5-HT1A receptors (D-1 and D-2-like receptors). The functional assay showed that this compound is an antagonist to 5-HT2A receptor with an IC50 value of 1.66 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.030
• 作为产物：
  描述：

  2,4-喹唑啉二酮 在 三正丙胺 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 2-chloro-N-(4-chlorophenyl)quinazolin-4-amine
  参考文献：
  名称：

  Discovery of novel potent and selective ligands for 5-HT2A receptor with quinazoline scaffold

  摘要：

  A series of compounds with quinazoline scaffold were designed, synthesized and evaluated as novel potent 5-HT2A receptor ligands. N-(4-Chlorophenyl)-2-(piperazin-1-yl)quinazolin-4-amine (5o) has a K-i value of 14.04 +/- 0.21 nM, with a selectivity more than 10,000 fold over 5-HT1A receptors (D-1 and D-2-like receptors). The functional assay showed that this compound is an antagonist to 5-HT2A receptor with an IC50 value of 1.66 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.030

文献信息

• 一种含有4-氨基-(1H)-吡唑结构的JAK激酶抑制剂及其制备方法和应用
  申请人：山东大学

  公开号：CN106349224A

  公开（公告）日：2017-01-25

  本发明公开了含有4‑氨基‑(1H)‑吡唑的JAK激酶抑制剂及其制备方法和应用。所述化合物具有通式(Ⅰ)或(Ⅱ)所示的结构，本发明提供了该类化合物的具体制备方法以及在预防或治疗炎症、肿瘤、血液相关疾病的应用；所述的与炎症、肿瘤、血液相关疾病包括：银屑癣、风湿性关节炎、真性红细胞增多症、局限性脱发、原发性血小板增多症、溃疡性结肠炎、化生性骨髓纤维化、严重综合免疫缺陷症、各种白血病、各种实体瘤等。
• Design, Synthesis, and Antitumor Evaluation of 4-Amino-(1<i>H</i>)-pyrazole Derivatives as JAKs Inhibitors
  作者：Xuewu Liang、Jie Zang、Mengyuan Zhu、Qianwen Gao、Binghe Wang、Wenfang Xu、Yingjie Zhang

  DOI：10.1021/acsmedchemlett.6b00247

  日期：2016.10.13

  Abnormalities in the JAK/STAT signaling pathway lead to many diseases such as immunodeficiency, inflammation, and cancer. Herein, we designed and synthesized a series of 4-amino-(1H)-pyrazole derivatives as potent JAKs inhibitors for cancer treatment. Results from in vitro protein kinase inhibition experiments indicated that compounds 3a-f and 11b are potent JAKs inhibitors. For example, the IC50 values of compound 3f against JAK1, JAK2, and JAK3 were 3.4, 2.2, and 3.5 nM, respectively. In cell culture experiments, compound 3f showed potent antiproliferative activity against various cell lines (PC-3, HEL, K562, MCF-7, and MOLT4) at low micromolar levels, while compound 11b showed selective cytotoxicity at submicromolar levels against HEL (IC50: 0.35;, mu M) and K562 (IC50: 0.37 mu M) cell lines. It is worth noting that both 3f and 11b showed more potent antiproliferative activities than the approved JAKs inhibitor Ruxolitinib.
• Curd et al., Journal of the Chemical Society, 1948, p. 1759,1765
  作者：Curd et al.

  DOI：——

  日期：——
• US2488379
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] HETEROARYL DERIVATIVES<br/>[FR] DERIVES HETEROARYLES
  申请人：NOVARTIS AG

  公开号：WO1997020821A1

  公开（公告）日：1997-06-12

  (EN) The invention relates to a method of treatment of disorders and diseases associated with NPY receptor subtype Y5 comprising administering to a warm-blooded animal, including man, in need of such treatment a therapeutically effective amount of a compound of formula (I), the variables are as defined and relates to new compounds of formula (I) or a salt thereof, to pharmaceutical compositions, and to the manufacture of new compounds of formula (I) and salts thereof.(FR) L'invention concerne une méthode de traitement de troubles et maladies associés au sous-type Y5 du récepteur du neuropeptide Y, laquelle consiste à administrer à un animal à sang chaud nécessitant un tel traitement, notamment à l'homme, une dose efficace sur le plan thérapeutique d'un composé de la formule (I) dont le variables sont telles que définies. L'invention se rapporte également à des nouveaux composés de la formule (I), à un sel de ceux-ci, à des compositions pharmaceutiques ainsi qu'à la production de ces nouveaux composés et des sels de ceux-ci.