(E)-2-(2-(4-chlorobenzylidene)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-(4-chlorobenzylidene)hydrazinyl)-4-phenylthiazole
• 英文别名: Tyrosinase-IN-12；N-[(E)-(4-chlorophenyl)methylideneamino]-4-phenyl-1,3-thiazol-2-amine
• 化学式: C₁₆H₁₂ClN₃S
• 分子量: 313.81
• InChiKey: YQKYELGBAMTOTP-VCHYOVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 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 、 4-氯苯甲醛 以 乙醇 为溶剂， 反应 3.0h， 以79%的产率得到(E)-2-(2-(4-chlorobenzylidene)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

• Synthesis and Single-Crystal X-Ray Diffraction Studies of an Arylidenethiosemicarbazone and Hydrazonyl-phenylthiazole
  作者：El Ashry、Sammer Yousuf、Hayat Hassan、Magdy Zahran、Ali Hebishy

  DOI：10.2174/15701786113106660065

  日期：2014.1.31

  The reaction of aromatic aldehydes with thiosemicarbazide gives arylidene hydrazinecarbothioamide, whose reaction with phenacyl bromide, yielded (arylidenehydrazonyl)-4-phenylthiazole. The structures of 3 and 7 were fully characterized by using 1H-NMR and mass spectroscopic techniques. The spectral analysis agreed with the assigned structures. The assigned structures were further supported by single-crystal X-ray diffraction studies and summarized as follows: (3) Triclinic, P-1, a=7.6319(4) Å, b= 8.7099(4) Å, c=10.7145(5) Å, α= 77.7400 (10)°, β= 74.0160 (10)°, and γ= 72.8270 (10)°, V= 647.47(5) Å3, and Z = 2; (7) Orthorhombic, Pna21, a = 9.3760(13), b = 14.029(2), c = 23.591(3)Å, α=90, β= 90, and γ= 90o, V = 3103.0(7)Å3, and Z = 4.

  芳香醛与氨基硫脲反应生成亚苯基酰肼硫酰胺，其与苯乙酰溴反应生成（亚苯基酰肼基）-4-苯基噻唑。通过1H-NMR和质谱技术全面表征了3和7的结构。光谱分析与所指派的结构一致。所指派的结构进一步得到了单晶X射线衍射研究的支持，总结如下：3为三斜晶系，P-1空间群，a=7.6319(4) Å，b=8.7099(4) Å，c=10.7145(5) Å，α=77.7400(10)°，β=74.0160(10)°，γ=72.8270(10)°，V=647.47(5) ų，Z=2；7为正交晶系，Pna21空间群，a=9.3760(13) Å，b=14.029(2) Å，c=23.591(3) Å，α=90°，β=90°，γ=90°，V=3103.0(7) ų，Z=4。
• 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。
• Facile and convenient synthesis of 2,4-disubstituted and 2,3,4-trisubstituted 1,3-thiazoles
  作者：Alaa A. Hassan、Shaaban K. Mohamed、Nasr K. Mohamed、Kamal M.A. El-Shaieb、Ahmed T. Abdel-Aziz、Joel T. Mague、Mehmet Akkurt

  DOI：10.1080/17415993.2015.1114621

  日期：2016.3.3

  ABSTRACT An efficient route for the synthesis of (E)-2-(2-(2-nitrobenzylidene)-hydrazinyl)-4-phenylthiazol-3-ium bromide, (E)-2-(2(substituted benzylidene)hydrazinyl)-4-phenylthiazoles and (E)-4-(4-bromophenyl)-2-(cycloalkylidenehydrazono)-3-phenyl-2,3-dihydrothiazoles by reaction of 1-aryl-2-bromoethanones with 2-(1-substituted methylidene)hydrazinecarbothioamides and cycloalkylidene-N-phenyl-hyd

  摘要 一种合成 (E)-2-(2-(2-nitrobenzylidene)-hydrazinyl)-4-phenylthiazol-3-ium bromide, (E)-2-(2(取代的苯亚甲基)hydrazinyl)-的有效途径4-苯基噻唑和 (E)-4-(4-溴苯基)-2-(亚环烷基肼基)-3-苯基-2,3-二氢噻唑通过 1-芳基-2-溴乙酮与 2-(1-取代的亚甲基)反应肼碳硫酰胺和亚环烷基-N-苯基-肼碳硫酰胺。产物的结构已通过红外、核磁共振、质谱和单晶X射线分析确定。图形概要
• 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.