2-amino-3-(1-phenylethoxy)pyridine | 81066-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-3-(1-phenylethoxy)pyridine
• 英文别名: 3-(1-Phenylethoxy)pyridin-2-amine
• CAS: 81066-64-0
• 化学式: C₁₃H₁₄N₂O
• mdl: MFCD19578491
• 分子量: 214.267
• InChiKey: PPDXZQYCEONNNJ-UHFFFAOYSA-N

物化性质

• 熔点：
  85-88 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  360.2±27.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  48.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-3-(1-phenylethoxy)pyridine 在 N-溴代丁二酰亚胺(NBS) 、 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 potassium acetate 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 18.25h， 生成 6-amino-1'-methyl-5-(1-phenylethoxy)-[3,4'-bipyridine]-2'(1'H)-one
  参考文献：
  名称：

  Discovery of 2-aminopyridines bearing a pyridone moiety as potent ALK inhibitors to overcome the crizotinib-resistant mutants

  摘要：

  Despite the initial benefit demonstrated in clinical setting with ALK inhibitors, the challenging resistant mutants (F1174L, L1196M and G1202R) invariably developed. In this work, a series of 2-aminopyridine derivatives were designed and synthesized by C-5 position incorporation of a 2-pyridone moiety and bioisosteric replacement of the C-3 position linkers. Optimization of the 2-aminopyridine derivatives led to the identification of hit 18d displaying a significant growth inhibition against a variety of ALK-addicted cancer cells. Especially in the case of ALK-positive Karpas-299 cell, 18d exhibited excellent anti-proliferative potency with an IC50 value of about 40 nM. Moreover, 18d demonstrated encouraging activities against wild-type ALK (19 nM), ROS1 (2.3 nM) as well as challenging crizotinib-resistant ALK(L1196M) and ALK(G1202R) mutants with IC50 values of 45 nM and 22 nM, respectively. Additionally flow cytometric analysis indicates that 18d inhibited Karpas-299 cell viability via G1 phase arrest. Taken together, this work provided a promising ALK inhibitor to circumvent the clinical crizotinib-resistant mutants. (C) 2019 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.111734
• 作为产物：
  描述：

  3-羟基-2-硝基吡啶 在 铁粉 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.0h， 生成 2-amino-3-(1-phenylethoxy)pyridine
  参考文献：
  名称：

  Discovery of 2-aminopyridines bearing a pyridone moiety as potent ALK inhibitors to overcome the crizotinib-resistant mutants

  摘要：

  Despite the initial benefit demonstrated in clinical setting with ALK inhibitors, the challenging resistant mutants (F1174L, L1196M and G1202R) invariably developed. In this work, a series of 2-aminopyridine derivatives were designed and synthesized by C-5 position incorporation of a 2-pyridone moiety and bioisosteric replacement of the C-3 position linkers. Optimization of the 2-aminopyridine derivatives led to the identification of hit 18d displaying a significant growth inhibition against a variety of ALK-addicted cancer cells. Especially in the case of ALK-positive Karpas-299 cell, 18d exhibited excellent anti-proliferative potency with an IC50 value of about 40 nM. Moreover, 18d demonstrated encouraging activities against wild-type ALK (19 nM), ROS1 (2.3 nM) as well as challenging crizotinib-resistant ALK(L1196M) and ALK(G1202R) mutants with IC50 values of 45 nM and 22 nM, respectively. Additionally flow cytometric analysis indicates that 18d inhibited Karpas-299 cell viability via G1 phase arrest. Taken together, this work provided a promising ALK inhibitor to circumvent the clinical crizotinib-resistant mutants. (C) 2019 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.111734

文献信息

• [(alkoxy)pyridinyl]amine compounds which are useful in the treatment of
  申请人：SmithKline Beecham Intercredit B.V.

  公开号：US05409943A1

  公开（公告）日：1995-04-25

  The present invention relates to N-pyridylamidine and N-pyridylguanidine derivatives of general formula (I) in which: Ar.sup.1 is an optionally substituted phenyl ring; Ar.sup.2 is an optionally substituted phenyl ring; R.sup.1 is hydrogen or C.sub.1-4 alkyl; R.sup.2 is hydrogen or C.sub.1-4 alkyl; R.sup.3 is hydrogen or C.sub.1-4 alkyl; R.sup.4 is hydrogen, halogen, C.sub.1-6 alkyl or C.sub.1-6 alkoxy; X is CH.sub.2 or NR.sup.5, and R.sup.5 is hydrogen or C.sub.1-4 alkyl, and the salts thereof, and their use in therapy as gastric acid secretion inhibitors.

  本发明涉及一般式(I)的N-吡啶基脒和N-吡啶基胍衍生物，其中：Ar.sup.1是可选择取代的苯环；Ar.sup.2是可选择取代的苯环；R.sup.1是氢或C.sub.1-4烷基；R.sup.2是氢或C.sub.1-4烷基；R.sup.3是氢或C.sub.1-4烷基；R.sup.4是氢，卤素，C.sub.1-6烷基或C.sub.1-6烷氧基；X是CH.sub.2或NR.sup.5，R.sup.5是氢或C.sub.1-4烷基，以及它们的盐，以及它们在治疗中作为胃酸分泌抑制剂的用途。
• ENANTIOMERICALLY PURE AMINOHETEROARYL COMPOUNDS AS PROTEIN KINASE INHIBITORS
  申请人：CUI Jingrong Jean

  公开号：US20140288086A1

  公开（公告）日：2014-09-25

  Enantiomerically pure compound of formula 1 are provided, as well as methods for their synthesis and use. Preferred compounds are potent inhibitors of the c-Met protein kinase, and are useful in the treatment of abnormal cell growth disorders, such as cancers.

  本发明提供了公式1的对映纯化合物，以及它们的合成和使用方法。首选化合物是c-Met蛋白激酶的强效抑制剂，可用于治疗异常细胞增生性疾病，例如癌症。
• Aminoheteroaryl compounds as protein kinase inhibitors
  申请人：Cui Jean Jingrong

  公开号：US20070072874A1

  公开（公告）日：2007-03-29

  Aminopyridine and aminopyrazine compounds of formula ( 1 ), compositions including these compounds, and methods of their use are provided. Preferred compounds of formula 1 have activity as protein kinase inhibitors, including as inhibitors of c-MET.

  提供了公式（1）的氨基吡啶和氨基吡嗪化合物，包括这些化合物的组合物以及它们的使用方法。公式1的优选化合物具有作为蛋白激酶抑制剂的活性，包括作为c-MET抑制剂。
• An Improved Synthesis of 2-Amino-3-alkyloxypyridines by a Phase-Transfer Catalyzed Ether Synthesis
  作者：James A. Bristol、Irwin Gross、Raymond G. Lovey

  DOI：10.1055/s-1981-29663

  日期：——
• BRISTOL, J. A.;GROSS, I.;LOVEY, R. G., SYNTHESIS, BRD, 1981, N 12, 971-973
  作者：BRISTOL, J. A.、GROSS, I.、LOVEY, R. G.

  DOI：——

  日期：——