N’-(2-cyano-5-(3-chloropropoxy)-4-methoxyphenyl)-N,N-dimethylformamidine | 385785-04-6

• 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: N’-(2-cyano-5-(3-chloropropoxy)-4-methoxyphenyl)-N,N-dimethylformamidine
• 英文别名: N'-[5-(3-chloro-propoxy)-2-cyano-4-methyoxy-phenyl]-N,N-dimethyl-formamidine；N'-(5-(3-chloropropoxy)-2-cyano-4-methoxyphenyl)-N,N-dimethylimidoformamide；N'-[5-(3-chloropropoxy)-2-cyano-4-methoxyphenyl]-N,N-dimethylmethanimidamide
• CAS: 385785-04-6
• 化学式: C₁₄H₁₈ClN₃O₂
• 分子量: 295.769
• InChiKey: OJKLCBOXHNFGJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N’-(2-cyano-5-(3-chloropropoxy)-4-methoxyphenyl)-N,N-dimethylformamidine 在 盐酸 、 copper(l) iodide 、 水 、 potassium carbonate 、 copper(l) chloride 、 sodium hydroxide 、 sodium nitrite 作用下， 以 甲醇 、 乙醚 、 异丙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 西地尼布
  参考文献：
  名称：

  治疗非小细胞肺癌、肾癌的药物西地尼布及其中间体的制备方法

  摘要：

  本发明公开了治疗非小细胞肺癌、肾癌的药物西地尼布及其中间体的制备方法，所述治疗非小细胞肺癌、肾癌的药物西地尼布的化学名称为4‑(4‑氟‑2‑甲基吲哚‑5‑基氧基)‑6‑甲氧基‑7‑[3‑(吡咯烷‑1‑基)丙氧基]喹唑啉，结构式为：；本发明制备工艺过程简洁，通过缩合反应使得西地尼布中间体与5‑羟基‑4‑氟‑2‑甲基吲哚合成西地尼布，提高了原子经济性、反应的选择性和操作的可控性，使西地尼布的制备工艺更加可控，提高了产品质量，促进了原料药的经济技术发展。

  公开号：

  CN107935941A
• 作为产物：
  描述：

  4-(3-chloropropoxy)-5-methoxy-2-nitrobenzonitrile 在 sodium dithionite 、 溶剂黄146 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 2.75h， 生成 N’-(2-cyano-5-(3-chloropropoxy)-4-methoxyphenyl)-N,N-dimethylformamidine
  参考文献：
  名称：

  Quinazoline-1-deoxynojirimycin hybrids as high active dual inhibitors of EGFR and α-glucosidase

  摘要：

  A series of novel quinazoline-1-deoxynojirimycin hybrids were designed, synthesized and evaluated for their inhibitory activities against two drug target enzymes, epidermal growth factor receptor (EGFR) tyrosine kinase and alpha-glucosidase. Some synthesized compounds exhibited significantly inhibitory activities against the tested enzymes. Comparing with reference compounds gefitinib and lapatinib, compounds 7d, 8d, 9b and 9d showed higher inhibitory activities against EGFR (IC50: 1.79-10.71 nM). Meanwhile the inhibitory activities of 7d, 8d and 9c against alpha-glucosidase (IC50 = 0.14, 0.09 and 0.25 mu M, respectively) were obvious higher than that of miglitol (IC50 = 2.43 mu M), a clinical using alpha-glucosidase inhibitor. Interestingly, compound 9d as a dual inhibitor showed high inhibitory activity to EGFR(wt) tyrosine kinase (IC50 = 1.79 nM), also to alpha-glucosidase (IC50 = 0.39 mu M). The work could be very useful starting point for developing a new series of enzyme inhibitors targeting EGFR and/or alpha-glucosidase. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.08.035

文献信息

• [EN] QUINAZOLINE COMPOUNDS<br/>[FR] COMPOSES DE QUINAZOLINE
  申请人：ASTRAZENECA AB

  公开号：WO2004058752A1

  公开（公告）日：2004-07-15

  Quinazoline derivatives of formula (I) wherein A is 5-membered heteroaryl containing a sulphur atom and optionally containing one or more nitrogen atoms; compositions containing them, processes for their preparation and their use in therapy.

  式(I)中的喹唑啉衍生物，其中A是含有硫原子并且可选地含有一个或多个氮原子的5-成员杂芳基；含有它们的组合物，其制备方法以及它们在治疗中的用途。
• [EN] PHOSPHONOOXY QUINAZOLINE DERIVATIVES AND THEIR PHARMACEUTICAL USE<br/>[FR] DERIVES DE PHOSPHONOOXY QUINAZOLINE ET LEUR UTILISATION PHARMACEUTIQUE
  申请人：ASTRAZENECA AB

  公开号：WO2004058781A1

  公开（公告）日：2004-07-15

  Quinazoline derivatives of formula (I) wherein A is 5-membered heteroaryl containing a nitrogen atom and one or two further nitrogen atoms; compositions containing them, processes for their preparation and their use in therapy.

  式(I)中的喹唑啉衍生物，其中A是含有一个氮原子和一个或两个进一步氮原子的5-成员杂环芳基；含有它们的组合物，其制备方法以及它们在治疗中的用途。
• Phosphonooxy quinazoline derivatives and their pharmaceutical use
  申请人：Heron Murdoch Nicola

  公开号：US20060116357A1

  公开（公告）日：2006-06-01

  Quinazoline derivatives of formula (I) wherein A is 5-membered heteroaryl containing a nitrogen atom and one or two further nitrogen atoms; compositions containing them, processes for their preparation and their use in therapy.

  公式（I）中的喹唑啉衍生物，其中A是含有一个或两个进一步的氮原子的5-成员杂环芳基；包含它们的组合物，它们的制备过程以及它们在治疗中的用途。
• Substituted quinazoline derivatives as inhibitors of aurora kinases
  申请人：Jung Henri Frederic

  公开号：US20050070561A1

  公开（公告）日：2005-03-31

  The invention provides quinazoline derivatives of formula (I): in the preparation of a medicament for use in the inhibition of Aurora kinase and also novel quinazoline derivatives, processes for their preparation, pharamceutical compositions containing them and their use in therapy.

  该发明提供了化学式（I）的喹唑啉衍生物：在制备用于抑制极化丝激酶的药物时，以及新的喹唑啉衍生物，它们的制备过程，包含它们的药物组合物以及它们在治疗中的使用。
• PHOSPHONOXY QUINAZOLINE DERIVATIVES AND THEIR PHARMACEUTICAL USE
  申请人：Heron Nicola Murdoch

  公开号：US20100069412A1

  公开（公告）日：2010-03-18

  Quinazoline derivatives of formula (I): wherein A is 5-membered heteroaryl containing a nitrogen atom and one or two further nitrogen atoms; compositions containing them, processes for their preparation and their use in therapy.

  公式（I）的喹唑啉衍生物： 其中A是含有一个氮原子和一个或两个进一步的氮原子的5-成员杂环芳基；包含它们的组合物，制备它们的过程以及它们在治疗中的用途。