2,4-diamino-8-chloro-5,7-bis(phenylthio)quinazoline-6-carbonitrile | 1128018-54-1

• 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: 2,4-diamino-8-chloro-5,7-bis(phenylthio)quinazoline-6-carbonitrile
• 英文别名: 2,4-Diamino-8-chloro-5,7-bis(phenylsulfanyl)quinazoline-6-carbonitrile
• CAS: 1128018-54-1
• 化学式: C₂₁H₁₄ClN₅S₂
• 分子量: 435.961
• InChiKey: YXPKLEVASURCHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  152
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,4-diamino-8-chloro-5,7-difluoroquinazoline-6-carbonitrile 、 苯硫酚 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 以82%的产率得到2,4-diamino-8-chloro-5,7-bis(phenylthio)quinazoline-6-carbonitrile
  参考文献：
  名称：

  Synthesis of highly functionalized 2,4-diaminoquinazolines as anticancer and anti-HIV agents

  摘要：

  Novel polyhalo 2,4-diaminoquinazolines 3a-3d were prepared by reacting polyhaloisophthalonitriles with guanidine carbonate under solvent-free conditions and in the absence of a catalyst with good yields (74-95%). A series of highly functionalized 2,4-diaminoquinazolines 4-5 were then synthesized based on 3a-3c. The anticancer activities of compounds 3-5 were evaluated in vitro against human cell lines such as Skov-3, HL-60, A431, A549, and HepG-2. Some of the compounds showed excellent cytotoxic activity and 5a was found to be the most potent derivative, with an IC50 value lower than 2.5 mu g/mL against the five tumor cell lines, making it more active than cisplatin. Representative compounds were also preliminarily evaluated as HIV-1 inhibitors in vitro, and 3c showed the most potent anti-HIV-1 activity with EC50 values of 0.6 and 1.6 mu g/mL, and TI values of >59.6 and 66.6, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.056

文献信息

• Small molecules against cancer
  申请人：Biokine Therapeutics Ltd.

  公开号：US10646465B2

  公开（公告）日：2020-05-12

  Compounds capable of, or usable in, killing cancer cells, and/or modulating a biological activity of a chemokine, and/or inhibiting a kinase, and/or treating diseases and disorders associated with a biological activity of a chemokine and/or cell migration, and/or treating disease and disorders such as cancer and inflammatory diseases and disorders, are provided herein. The compounds are listed in Tables 2, 4 and 5, and/or are represented by Formulae I, IV, V and VI, as defined in the specification. Methods utilizing these compounds are also provided.

  本文提供的化合物能够或可用于杀死癌细胞，和/或调节趋化因子的生物活性，和/或抑制激酶，和/或治疗与趋化因子的生物活性和/或细胞迁移相关的疾病和紊乱，和/或治疗疾病和紊乱，如癌症和炎症性疾病和紊乱。这些化合物列于表 2、表 4 和表 5 中，和/或由式 I、式 IV、式 V 和式 VI 表示，如说明书中所定义。还提供了利用这些化合物的方法。
• SMALL MOLECULES AGAINST CANCER
  申请人：Biokine Therapeutics Ltd.

  公开号：US20190240188A1

  公开（公告）日：2019-08-08

  Compounds capable of, or usable in, killing cancer cells, and/or modulating a biological activity of a chemokine, and/or inhibiting a kinase, and/or treating diseases and disorders associated with a biological activity of a chemokine and/or cell migration, and/or treating disease and disorders such as cancer and inflammatory diseases and disorders, are provided herein. The compounds are listed in Tables 2, 4 and 5, and/or are represented by Formulae I, IV, V and VI, as defined in the specification. Methods utilizing these compounds are also provided.
• [EN] SMALL MOLECULES AGAINST CANCER<br/>[FR] PETITES MOLÉCULES CONTRE LE CANCER
  申请人：BIOKINE THERAPEUTICS LTD

  公开号：WO2017103931A1

  公开（公告）日：2017-06-22

  Compounds capable of, or usable in, killing cancer cells, and/or modulating a biological activity of a chemokine, and/or inhibiting a kinase, and/or treating diseases and disorders associated with a biological activity of a chemokine and/or cell migration, and/or treating disease and disorders such as cancer and inflammatory diseases and disorders, are provided herein. The compounds are listed in Tables 2, 4 and 5, and/or are represented by Formulae I, IV, V and VI, as defined in the specification. Methods utilizing these compounds are also provided.
• Synthesis of highly functionalized 2,4-diaminoquinazolines as anticancer and anti-HIV agents
  作者：Sheng-Jiao Yan、Han Zheng、Chao Huang、Yu-Yun Yan、Jun Lin

  DOI：10.1016/j.bmcl.2010.06.056

  日期：2010.8

  Novel polyhalo 2,4-diaminoquinazolines 3a-3d were prepared by reacting polyhaloisophthalonitriles with guanidine carbonate under solvent-free conditions and in the absence of a catalyst with good yields (74-95%). A series of highly functionalized 2,4-diaminoquinazolines 4-5 were then synthesized based on 3a-3c. The anticancer activities of compounds 3-5 were evaluated in vitro against human cell lines such as Skov-3, HL-60, A431, A549, and HepG-2. Some of the compounds showed excellent cytotoxic activity and 5a was found to be the most potent derivative, with an IC50 value lower than 2.5 mu g/mL against the five tumor cell lines, making it more active than cisplatin. Representative compounds were also preliminarily evaluated as HIV-1 inhibitors in vitro, and 3c showed the most potent anti-HIV-1 activity with EC50 values of 0.6 and 1.6 mu g/mL, and TI values of >59.6 and 66.6, respectively. (C) 2010 Elsevier Ltd. All rights reserved.