2-(4-nitrobenzylidene)hydrazino-4-phenylthiazole | 73753-32-9

• 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-(4-nitrobenzylidene)hydrazino-4-phenylthiazole
• 英文别名: 2-[N'-(4-nitrobenzylidene)hydrazino]-4-phenylthiazole；(E)-2-(2-(4-nitrobenzylidene)hydrazinyl)-4-phenylthiazole；p-Nitrobenzalverbindung von 4-Phenyl-thiazolyl-2-hydrazin Ia；4-nitro-benzaldehyde-(4-phenyl-thiazol-2-ylhydrazone)；4-Nitro-benzaldehyd-(4-phenyl-thiazol-2-ylhydrazon)；2-[(2E)-2-(4-nitrobenzylidene)hydrazinyl]-4-phenyl-1,3-thiazole；N-[(E)-(4-nitrophenyl)methylideneamino]-4-phenyl-1,3-thiazol-2-amine
• CAS: 73753-32-9
• 化学式: C₁₆H₁₂N₄O₂S
• 分子量: 324.363
• InChiKey: ZTWZTAARPLNDKN-LICLKQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 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：
  111
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-nitrobenzylidene)hydrazino-4-phenylthiazole 、 氯乙酰氯 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以85%的产率得到2-[N-chloroacetyl-N'-(4-nitrobenzylidene)hydrazino]-4-phenylthiazole
  参考文献：
  名称：

  Acylation and Carbamoylation of 2-Hydrazinothiazole Derivatives. Identification of Isomeric Structures

  摘要：

  对2-(芳基亚甲基肼)-和2-(芳酰肼)噻唑进行酰化和氨基甲酰化，并确定了产物的结构。

  DOI：

  10.1007/s11178-005-0208-9
• 作为产物：
  描述：

  [2-(4-硝基苄基亚基)亚肼基](氨基)甲硫醇 、 2-溴苯乙酮 以 乙醇 为溶剂， 反应 1.0h， 以89%的产率得到2-(4-nitrobenzylidene)hydrazino-4-phenylthiazole
  参考文献：
  名称：

  Bromination of 4-substituted thiazolylhydrazones

  摘要：

  DOI：

  10.1007/bf01170750

文献信息

• Beyer et al., Chemische Berichte, 1956, vol. 89, p. 1095,1099
  作者：Beyer et al.

  DOI：——

  日期：——
• Synthesis of phenyl thiazole hydrazones and their activity against glycation of proteins
  作者：Khalid Mohammed Khan、Muhammad Irfan、Mahwish Ashraf、Muhammad Taha、Syed Muhammad Saad、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.1007/s00044-015-1349-1

  日期：2015.7

  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.
• NALEPA K.; BULKA E., ACTA UNIV. PALACK. OLOMUC. FAC. RERUM NATUR., 1978, 57, 191-196
  作者：NALEPA K.、 BULKA E.

  DOI：——

  日期：——