5-(4-ethylphenyl)-1,3,4-thiadiazol-2-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-ethylphenyl)-1,3,4-thiadiazol-2-amine
• 英文别名: 5-(4-ethylphenyl)-1,3,4-thidiazol-2-amine
• 化学式: C₁₀H₁₁N₃S
• 分子量: 205.283
• InChiKey: RXTFAFIUEXCNFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-ethylphenyl)-1,3,4-thiadiazol-2-amine 在 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 反应 19.5h， 生成 3-[2-(4-ethylphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl]aniline
  参考文献：
  名称：

  Design, synthesis and antiproliferative activity of novel heterobivalent hybrids based on imidazo[2,1- b ][1,3,4]thiadiazole and imidazo[2,1- b ][1,3]thiazole scaffolds

  摘要：

  Heterobivalent ligands constituted by two different pharmacophores that bind to different molecular targets or to two distinct sites on the same molecular target could be one of the methods used for the treatment of cancer. In view of the importance of imidazo[1,2-6][1,3]thiazole and imidazo[1,2-b][1,3,4] thiadiazole as privileged structures for the preparation of novel anticancer agents, we decided to explore the synthesis and biological evaluation of molecular conjugates comprising these fused bicyclic systems tethered at their C-6 position by a meta-(alpha-bromoacryloylamido)phenyl moiety. We found that most of the hybrid compounds displayed high antiproliferative activity toward a wide panel of cancer cell lines, with one-digit micromolar to submicromolar 50% inhibitory concentrations (IC50). We have observed that selected compounds 7d, 7e, 7n and 8c induced apoptosis, which was associated with the release of cytochrome c and cleavage of multiple caspases. Overexpression of the protective mitochondrial protein Bcl-2 did not confer protection to cell death induced by these compounds. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.042
• 作为产物：
  描述：

  2-(4-ethylbenzylidene)hydrazinecarbothioamide 在 iron(III) chloride 作用下， 以 水 为溶剂， 生成 5-(4-ethylphenyl)-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Synthesis, spectral characterization and DNA interactions of 5-(4-substituted phenyl)-1,3,4-thiadiazol-2-amine scaffolds

  摘要：

  Five 5-(4-Substituted phenyl)-1, 3, 4-thiadiazole-2-amines have been prepared and structure of the compounds confirmed by spectroscopy studies. On the basis of spectroscopic studies, confirmed the formation of compounds. The DNA binding affinity of the prepared compounds was undertaken by absorption titration method and increasing the amount of CT-DNA observed hyperchromism or hypsochromism. The binding affinity compounds (except 5) are in the order of 4[13.341 x 10(4) M-1]>3 [8.505 x 10(4) M-1]>2 [3.567 x 10(4) M-1]>1[3.525 x 10(4) M-1]. The ethidiumbromide quenching results indicates CT-DNA was quenched by thiadiazoles via a static quenching mechanism. The DNA cleavage studies of the compounds were carried out in the presence and absence of H2O2 using gel electrophoresis experiment. (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2019.126999

文献信息

• 6-11 Bicyclic Ketolide Derivatives
  申请人：Or Yat Sun

  公开号：US20070244160A1

  公开（公告）日：2007-10-18

  The present invention discloses compounds of formula I, or pharmaceutically acceptable salts, esters, or prodrugs thereof: which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.
• 6-11 BICYCLIC KETOLIDE DERIVATIVES
  申请人：ENANTA PHARMACEUTICALS, INC.

  公开号：US20140135485A1

  公开（公告）日：2014-05-15

  The present invention discloses compounds of formula I, or pharmaceutically acceptable salts, esters, or prodrugs thereof: which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.
• US7189704B2
  申请人：——

  公开号：US7189704B2

  公开（公告）日：2007-03-13