2-(3,4-difluorobenzylidene)hydrazine-1-carbothioamide | 1570052-89-9

• 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: 2-(3,4-difluorobenzylidene)hydrazine-1-carbothioamide
• 英文别名: (E)-2-(3,4-difluoro-benzylidene)-hydrazine-carbothioamide；[(E)-(3,4-difluorophenyl)methylideneamino]thiourea
• CAS: 1570052-89-9
• 化学式: C₈H₇F₂N₃S
• 分子量: 215.226
• InChiKey: ZPFPTBLLFSISKM-UUILKARUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-溴-4'-(三氟甲基)苯乙酮 、 2-(3,4-difluorobenzylidene)hydrazine-1-carbothioamide 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以70.6%的产率得到EGPI-1
  参考文献：
  名称：

  Design, synthesis and biological evaluation of bromophenol-thiazolylhydrazone hybrids inhibiting the interaction of translation initiation factors eIF4E/eIF4G as multifunctional agents for cancer treatment

  摘要：

  The eukaryotic initiation factor 4E (eIF4E) is an emerging anticancer drug target for specific anticancer therapy as a promising approach to overcome drug resistance and promote chemotherapy antitumor efficacy. A series of bromophenol-thiazotylhydrazone hybrids were designed, synthesized and evaluated for their antitumor activities. Among of them, the most potent compound 3e (EGPI-1) could inhibit the eIF4E/eIF4G interaction. Further mechanism study demonstrated EGPI-1 played an antitumor role in multiple modes of action including regulating the activity of elF4E by inhibiting the phosphorylation of eIF4E and 4EBPI, disrupting mitochondrial function through the mTOR/4EBP1 signaling pathway, and inducing autophagy, apoptosis and ROS generation. Moreover, EGPI-1 showed good safety and favorable pharmacokinetic properties in vivo. These observations demonstrate that EGPI-1 may serve as an excellent lead compound for the development of new anticancer drugs that target the eIF4E/eIF4G interface and as a chemical genetic probe to investigate the role of the eIF4E in biological processes and human diseases. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.05.044
• 作为产物：
  描述：

  3,4-二氟苯甲醛 、 氨基硫脲 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以95%的产率得到2-(3,4-difluorobenzylidene)hydrazine-1-carbothioamide
  参考文献：
  名称：

  氟化硫缩脲的合成和结构表征

  摘要：

  六种新型氟化缩氨基硫脲 RC(R')=N-NH-C(S)NH2 (R = 2,4-C6H3F2, R' = H (1); R = 2,5-C6H3F2, R' = H (2 ); R = 2,6-C6H3F2, R' = H (3); R = 3,4-C6H3F2, R' = H (4); R = 3,5-C6H3F2, R' = H (5) 和R = 4-C6H4F, R' = C6H5, (6)) 已制备。已确定化合物 1 至 6 的分子结构。

  DOI：

  10.3390/molecules181013111

文献信息

• NOVEL QUINOLINE COMPOUND AND USE THEREOF
  申请人：Shenyang Pharmaceutical University

  公开号：EP2915806A1

  公开（公告）日：2015-09-09

  The invention relates to a series of quinoline derivatives of general formula I, pharmaceutically acceptable salts, hydrates, solvates or prodrugs. Thereof M, R1, R2, X, Y and n are defined as claims. And the compounds of general formula I show potent inhibitory activity gainst c-Met kinase. The present invention further relates to the uses of the compounds, pharmaceutically acceptable salts and hydrates for the preparation of medicaments for the treatment and/or prevention of diseases caused by abnormal expression of c-Met kinase, especially for treatment and/or prevention of cancer.

  本发明涉及一系列通式 I 的喹啉衍生物、药学上可接受的盐、水合物、溶液或原药。其中 M、R1、R2、X、Y 和 n 的定义如权利要求所述。通式 I 的化合物对 c-Met 激酶具有强效抑制活性。本发明进一步涉及这些化合物、药学上可接受的盐和水合物用于制备治疗和/或预防由 c-Met 激酶异常表达引起的疾病的药物，特别是用于治疗和/或预防癌症。
• Synthesis and Structural Characterization of Fluorinated Thiosemicarbazones
  作者：Juan Bautista、Marcos Flores-Alamo、Jorge Tiburcio、Rebeca Vieto、Hugo Torrens

  DOI：10.3390/molecules181013111

  日期：——

  Six new fluorinated thiosemicarbazones R-C(R′)=N-NH-C(S)NH2 (R = 2,4-C6H3F2, R′ = H (1); R = 2,5-C6H3F2, R′ = H (2); R = 2,6-C6H3F2, R′ = H (3); R = 3,4-C6H3F2, R′ = H (4); R = 3,5-C6H3F2, R′ = H (5) and R = 4-C6H4F, R′ = C6H5, (6)) have been prepared. The molecular structures of compounds 1 to 6 have been determined.

  六种新型氟化缩氨基硫脲 RC(R')=N-NH-C(S)NH2 (R = 2,4-C6H3F2, R' = H (1); R = 2,5-C6H3F2, R' = H (2 ); R = 2,6-C6H3F2, R' = H (3); R = 3,4-C6H3F2, R' = H (4); R = 3,5-C6H3F2, R' = H (5) 和R = 4-C6H4F, R' = C6H5, (6)) 已制备。已确定化合物 1 至 6 的分子结构。
• Design, synthesis and biological evaluation of bromophenol-thiazolylhydrazone hybrids inhibiting the interaction of translation initiation factors eIF4E/eIF4G as multifunctional agents for cancer treatment
  作者：Lijun Wang、Chuanlong Guo、Xiuxue Li、Xuemin Yu、Xiangqian Li、Kuo Xu、Bo Jiang、Xiaoling Jia、Chao Li、Dayong Shi

  DOI：10.1016/j.ejmech.2019.05.044

  日期：2019.9

  The eukaryotic initiation factor 4E (eIF4E) is an emerging anticancer drug target for specific anticancer therapy as a promising approach to overcome drug resistance and promote chemotherapy antitumor efficacy. A series of bromophenol-thiazotylhydrazone hybrids were designed, synthesized and evaluated for their antitumor activities. Among of them, the most potent compound 3e (EGPI-1) could inhibit the eIF4E/eIF4G interaction. Further mechanism study demonstrated EGPI-1 played an antitumor role in multiple modes of action including regulating the activity of elF4E by inhibiting the phosphorylation of eIF4E and 4EBPI, disrupting mitochondrial function through the mTOR/4EBP1 signaling pathway, and inducing autophagy, apoptosis and ROS generation. Moreover, EGPI-1 showed good safety and favorable pharmacokinetic properties in vivo. These observations demonstrate that EGPI-1 may serve as an excellent lead compound for the development of new anticancer drugs that target the eIF4E/eIF4G interface and as a chemical genetic probe to investigate the role of the eIF4E in biological processes and human diseases. (C) 2019 Elsevier Masson SAS. All rights reserved.