(E)-2-(2-(4-bromobenzylidene)hydrazinyl)-4-phenylthiazole | 1322209-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-2-(2-(4-bromobenzylidene)hydrazinyl)-4-phenylthiazole
• 英文别名: 4-Bromobenzaldehyde (4-phenyl-1,3-thiazol-2-yl)hydrazone；N-[(E)-(4-bromophenyl)methylideneamino]-4-phenyl-1,3-thiazol-2-amine
• CAS: 1322209-67-5
• 化学式: C₁₆H₁₂BrN₃S
• 分子量: 358.261
• InChiKey: BRNREFAZMCBAEM-VCHYOVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4-苯基-2-噻唑)-肼 、 对溴苯甲醛 以 乙醇 为溶剂， 反应 3.0h， 以81%的产率得到(E)-2-(2-(4-bromobenzylidene)hydrazinyl)-4-phenylthiazole
  参考文献：
  名称：

  Synthesis of phenyl thiazole hydrazones and their activity against glycation of proteins

  摘要：

  Phenyl thiazole hydrazone derivatives 1-21 have been synthesized and screened for their in vitro antiglycation activity. Hydrazones 1-21 displayed assorted antiglycation activities having IC50 values in the range of 187.61 +/- A 1.12-886.98 +/- A 5.29 A mu M as compared to standard rutin (IC50 = 269.07 +/- A 3.79 A mu M). Compounds 5 (IC50 = 187.61 +/- A 1.12 A mu M), 3 (IC50 = 191.92 +/- A 3.08 A mu M), 4 (IC50 = 193.77 +/- A 3.06 A mu M), 6 (IC50 = 217.90 +/- A 2.48 A mu M), 15 (IC50 = 221.98 +/- A 2.34 A mu M), 2 (IC50 = 226.59 +/- A 1.19 A mu M), 21 (IC50 = 229.67 +/- A 1.95 A mu M), 18 (IC50 = 231.09 +/- A 0.38 A mu M), 12 (IC50 = 242.94 +/- A 2.05 A mu M), and 1 (IC50 = 264.22 +/- A 5.60 A mu M), respectively, showed excellent antiglycation activities superior to standard rutin. Compound 17 (IC50 = 269.94 +/- A 1.11 A mu M) demonstrated a comparable activity to the standard. Compounds 7, 8, 9, 10, 11, 13, 14, and 16 exhibited weaker activities than standard. However, compounds 19 and 20 showed no activity. When evaluated for cytotoxicity against rat fibroblast cell line (3T3 cell line), all compounds were found to be non-toxic in cellular model.

  DOI：

  10.1007/s00044-015-1349-1