1-(benzyloxy)-2-chloro-4-isothiocyanatobenzene | 1430796-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(benzyloxy)-2-chloro-4-isothiocyanatobenzene
• 英文别名: 1-(Benzyloxy)-2-chloro-4-isothiocyanatobenzene；2-chloro-4-isothiocyanato-1-phenylmethoxybenzene
• CAS: 1430796-84-1
• 化学式: C₁₄H₁₀ClNOS
• 分子量: 275.759
• InChiKey: CXSZPTDVXUSHES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  53.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(benzyloxy)-2-chloro-4-isothiocyanatobenzene 在 sodium methylate 、 肼 作用下， 以 甲醇 、 乙醇 为溶剂， 20.0~75.0 ℃ 、101.33 kPa 条件下， 反应 2.25h， 生成 N³-(4-benzyloxy-3-chlorophenyl)-1H-[1,2,4]triazole-3,5-diamine
  参考文献：
  名称：

  [EN] TRIAZOLE COMPOUNDS AS ANTIVIRALS
  [FR] COMPOSÉS TRIAZOLES EN TANT QU'ANTIVIRAUX

  摘要：

  本发明公开了公式I的化合物：其中公式I中的变量定义如本文所述。还公开了包含此类化合物的药物组合物以及使用公式I化合物预防或治疗HCV感染的方法。

  公开号：

  WO2014006066A1
• 作为产物：
  描述：

  4-benzyloxy-3-chloroaniline 在 三光气 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 1.17h， 生成 1-(benzyloxy)-2-chloro-4-isothiocyanatobenzene
  参考文献：
  名称：

  Design, Synthesis, X-ray Crystallographic Analysis, and Biological Evaluation of Thiazole Derivatives as Potent and Selective Inhibitors of Human Dihydroorotate Dehydrogenase

  摘要：

  Human dihydroorotate dehydrogenase (HsDHODH) is a flavin-dependent mitochondrial enzyme that has been certified as a potential therapeutic target for the treatment of rheumatoid arthritis and other autoimmune diseases. On the basis of lead compound 4, which was previously identified as potential HsDHODH inhibitor, a novel series of thiazole derivatives were designed and synthesized. The X-ray complex structures of the promising analogues 12 and 33 confirmed that these inhibitors bind at the putative ubiquinone binding tunnel and guided us to explore more potent inhibitors, such as compounds 44, 46, and 47 which showed double digit nanomolar activities of 26, 18, and 29 nM, respectively. Moreover, 44 presented considerable anti-inflammation effect in vivo and significantly alleviated foot swelling in a dose-dependent manner, which disclosed that thiazole-scaffold analogues can be developed into the drug candidates for the treatment of rheumatoid arthritis by suppressing the bioactivity of HsDHODH.

  DOI：

  10.1021/jm501127s

文献信息

• ANTIVIRAL COMPOUNDS
  申请人：Hoffmann-La Roche Inc.

  公开号：US20140010783A1

  公开（公告）日：2014-01-09

  The present invention discloses compounds of Formula I: wherein the variables in Formula I are defined as described herein. Also disclosed are pharmaceutical compositions containing such compounds and methods for using the compounds of Formula I in the prevention or treatment of HCV infection.

  本发明公开了I式化合物：其中I式中的变量根据本文所述定义。还公开了包含这些化合物的药物组合物，并公开了使用I式化合物预防或治疗HCV感染的方法。
• TRIAZOLE COMPOUNDS AS ANTIVIRALS
  申请人：F.Hoffmann-La Roche AG

  公开号：EP2870143A1

  公开（公告）日：2015-05-13
• Design, Synthesis, X-ray Crystallographic Analysis, and Biological Evaluation of Thiazole Derivatives as Potent and Selective Inhibitors of Human Dihydroorotate Dehydrogenase
  作者：Junsheng Zhu、Le Han、Yanyan Diao、Xiaoli Ren、Minghao Xu、Liuxin Xu、Shiliang Li、Qiang Li、Dong Dong、Jin Huang、Xiaofeng Liu、Zhenjiang Zhao、Rui Wang、Lili Zhu、Yufang Xu、Xuhong Qian、Honglin Li

  DOI：10.1021/jm501127s

  日期：2015.2.12

  Human dihydroorotate dehydrogenase (HsDHODH) is a flavin-dependent mitochondrial enzyme that has been certified as a potential therapeutic target for the treatment of rheumatoid arthritis and other autoimmune diseases. On the basis of lead compound 4, which was previously identified as potential HsDHODH inhibitor, a novel series of thiazole derivatives were designed and synthesized. The X-ray complex structures of the promising analogues 12 and 33 confirmed that these inhibitors bind at the putative ubiquinone binding tunnel and guided us to explore more potent inhibitors, such as compounds 44, 46, and 47 which showed double digit nanomolar activities of 26, 18, and 29 nM, respectively. Moreover, 44 presented considerable anti-inflammation effect in vivo and significantly alleviated foot swelling in a dose-dependent manner, which disclosed that thiazole-scaffold analogues can be developed into the drug candidates for the treatment of rheumatoid arthritis by suppressing the bioactivity of HsDHODH.
• [EN] TRIAZOLE COMPOUNDS AS ANTIVIRALS<br/>[FR] COMPOSÉS TRIAZOLES EN TANT QU'ANTIVIRAUX
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014006066A1

  公开（公告）日：2014-01-09

  The present invention discloses compounds of Formula I: wherein the variables in Formula I are defined as described herein. Also disclosed are pharmaceutical compositions containing such compounds and methods for using the compounds of Formula I in the prevention or treatment of HCV infection.

  本发明公开了公式I的化合物：其中公式I中的变量定义如本文所述。还公开了包含此类化合物的药物组合物以及使用公式I化合物预防或治疗HCV感染的方法。