(E)-2-(2-(2-bromobenzylidene)hydrazinyl)-4-phenylthiazole

• 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-(2-bromobenzylidene)hydrazinyl)-4-phenylthiazole
• 英文别名: N-[(E)-(2-bromophenyl)methylideneamino]-4-phenyl-1,3-thiazol-2-amine
• 化学式: C₁₆H₁₂BrN₃S
• 分子量: 358.261
• InChiKey: YXJBGPKCNKZENH-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 、 邻溴苯甲醛 以 乙醇 为溶剂， 反应 3.0h， 以78%的产率得到(E)-2-(2-(2-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

文献信息

• Rust-derived Fe₂O₃ nanoparticles as a green catalyst for the one-pot synthesis of hydrazinyl thiazole derivatives
  作者：Rutikesh Gurav、Santosh Kumar Surve、Santosh Babar、Prafulla Choudhari、Devashree Patil、Vikramsinh More、Sandeep Sankpal、Shankar Hangirgekar

  DOI：10.1039/d0ob00109k

  日期：——

  the present work, novel one-pot multicomponent reactions of tosylates, aryl aldehydes and thiosemicarbazide are reported for the synthesis of hydrazinyl thiazoles, using Fe2O3 NPs derived from rusted iron as a catalyst. The Fe2O3 NPs were characterized using XRD, SEM, VSM, HR-TEM, EDX and FT-IR techniques. The structures of all of the synthesized hydrazinyl thiazole derivatives were confirmed by 1H NMR

  在本工作中，报道了甲苯磺酸盐，芳基醛和硫代氨基脲的新型一锅多组分反应，用于使用衍生自生锈的铁的Fe 2 O 3 NPs催化合成肼基噻唑。用XRD，SEM，VSM，HR-TEM，EDX和FT-IR技术对Fe 2 O 3 NPs进行了表征。通过1 H NMR，13 C NMR，FT-IR和质谱确认所有合成的肼基噻唑衍生物的结构。磁性Fe 2 O 3使用外磁体可以轻松地从反应中回收NP，并在优化的反应条件下经过四个循环检查了回收的催化剂的催化活性。它表现出最小的产量损失。为了探索潜在的应用，对合成分子的抗菌，抗真菌和抗氧化活性进行了研究，并显示出令人鼓舞的结果。分子对接研究进一步支持了该结果。