2,5-dimethoxybenzaldene-4-phenylthiosemicarbazone | 328044-97-9

• 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: 2,5-dimethoxybenzaldene-4-phenylthiosemicarbazone
• 英文别名: 1-[(2,5-Dimethoxyphenyl)methylideneamino]-3-phenylthiourea
• CAS: 328044-97-9
• 化学式: C₁₆H₁₇N₃O₂S
• 分子量: 315.396
• InChiKey: SHQLGJWVXITHRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-dimethoxybenzaldene-4-phenylthiosemicarbazone 在 iron(III) chloride 、 sodium acetate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 N¹-benzylidene-N²-[3-(2,5-dimethoxyphenyl)-4-(1,4-benzoquinon-2-yl)-1,3-thiazol-2-ylidene]hydrazine
  参考文献：
  名称：

  Synthesis and biological evaluation of novel benzoquinones as potential antimicrobial agents

  摘要：

  New series of 2,5-dihydroxyphenyl-1,3-thiazoles 4a-l was synthesized by reacting 2,5-dihydroxyphenacyl bromide with various 4-aryl thiosemicarbazones 3a-l that on oxidation with ferric chloride yielded the corresponding N (1)-substituted benzylidene-N (2)-[3-aryl-4-(1,4-benzoquinon-2-yl)-1,3-thiazol-2-ylidene]hydrazines 5a-l. They were evaluated for antibacterial activity against Staphylococcus aureus and Bacillus subtilis as Gram-positive bacteria, Escherichia coli and Pseudomonas aeruginosa as Gram-negative bacteria. They were also evaluated for their in vitro antifungal potential against Candida albicans. Almost all tested compounds were found to possess variable degrees of antimicrobial activity. The obtained data revealed that compounds 4b-h and 5e, 5f and 5l exhibited promising antimicrobial activity against the tested organisms of which compound 4b proved to be the most active.

  DOI：

  10.1007/s00044-012-0076-0
• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 、 4-苯基-3-硫代氨基脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以82%的产率得到2,5-dimethoxybenzaldene-4-phenylthiosemicarbazone
  参考文献：
  名称：

  钯 (II) 与硫缩硫脲配合物的合成与表征

  摘要：

  缩氨基硫脲衍生物是独特的 N,S-供体，因为它们具有混合的硬-软特性、可变的结合模式、灵活性、选择性和对中心金属原子的敏感性 [1]。由于亚胺基团 (-N=CH-) 的存在，这些配体与天然生物物质的结构相似，因此这些配体获得了极大的关注，亚胺基团赋予生物活性，包括抗真菌、抗菌、抗炎、抗病毒、抗惊厥、抗抑郁、抗癌以及良好的抗 HIV 活性，因此在药理学和核医学中得到广泛应用 [2-6]。这些配体还可以作为分析试剂，用于测定、固定和捕获重金属离子 [7,8]。过渡金属掺入缩氨基硫脲导致其药理活性增强[9]，随后涉及金属和缩氨基硫脲的协同作用导致其生物活性提高并降低金属离子和配体的细胞毒性[10] . 它们以中性或阴离子形式与过渡金属中心结合。据报道，亚胺基团碳原子上的取代基（-HC=N）会影响与金属卤化物的结合，这决定了单核、二核和多核配合物的形成。有机锡(IV)、铁(II)、铜(II)、锌(

  DOI：

  10.14233/ajchem.2018.21117
• 作为试剂：
  描述：

  咪唑 、 3-甲基苯硼酸 在 2,5-dimethoxybenzaldene-4-phenylthiosemicarbazone 、 copper(II) acetate monohydrate 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以78%的产率得到1-(间甲苯)咪唑
  参考文献：
  名称：

  苯硫脲Cu(II)配合物：室温下不同N基亲核试剂与芳基硼酸形成CN键的原位催化剂

  摘要：

  AbstractWe have reported here a new synthetic protocol for the formation of C‐N bond catalyzed by a thiosemicarbazone complex of copper. This in situ complex has been found to be very effective for Chan‐Lam C‐N cross‐coupling reaction of anilines and various imidazoles at room temperature. Pyrazole and 4‐bromoindole were also activated for C‐N bond formation by using this protocol at room temperature. This catalytic system gave good‐to‐excellent yield using a mixture of DMF and water as solvent in a 1:1 proportion.

  DOI：

  10.1002/hc.21414

文献信息

• Synthesis and Characterization of Palladium(II) Complexes with Thiosemicarbazones
  作者：Samim Sultana、Jayantajit Baruah、Geetika Borah

  DOI：10.14233/ajchem.2018.21117

  日期：——

  poly-nuclear complexes. Various transition metals such as organotin(IV), iron(II), copper(II), zinc(II), nickel(II), palladium, platinum, ruthenium, etc. have been incorporated into thiosemicarbazones and their applications have been studied [11-15]. Palladium(II) derivatives were found to be more preferred for cancer treatment because of their structural analogy with Pt(II) complexes and some complexes show

  缩氨基硫脲衍生物是独特的 N,S-供体，因为它们具有混合的硬-软特性、可变的结合模式、灵活性、选择性和对中心金属原子的敏感性 [1]。由于亚胺基团 (-N=CH-) 的存在，这些配体与天然生物物质的结构相似，因此这些配体获得了极大的关注，亚胺基团赋予生物活性，包括抗真菌、抗菌、抗炎、抗病毒、抗惊厥、抗抑郁、抗癌以及良好的抗 HIV 活性，因此在药理学和核医学中得到广泛应用 [2-6]。这些配体还可以作为分析试剂，用于测定、固定和捕获重金属离子 [7,8]。过渡金属掺入缩氨基硫脲导致其药理活性增强[9]，随后涉及金属和缩氨基硫脲的协同作用导致其生物活性提高并降低金属离子和配体的细胞毒性[10] . 它们以中性或阴离子形式与过渡金属中心结合。据报道，亚胺基团碳原子上的取代基（-HC=N）会影响与金属卤化物的结合，这决定了单核、二核和多核配合物的形成。有机锡(IV)、铁(II)、铜(II)、锌(
• Cu(II) complex of phenylthiosemicarbazone: An in situ catalyst for formation of C-N bond between different N-based neucleophiles with arylboronic acids at room temperature
  作者：Nibedita Gogoi、Geetika Borah、Pradip K. Gogoi

  DOI：10.1002/hc.21414

  日期：2018.3

  AbstractWe have reported here a new synthetic protocol for the formation of C‐N bond catalyzed by a thiosemicarbazone complex of copper. This in situ complex has been found to be very effective for Chan‐Lam C‐N cross‐coupling reaction of anilines and various imidazoles at room temperature. Pyrazole and 4‐bromoindole were also activated for C‐N bond formation by using this protocol at room temperature. This catalytic system gave good‐to‐excellent yield using a mixture of DMF and water as solvent in a 1:1 proportion.
• Synthesis and biological evaluation of novel benzoquinones as potential antimicrobial agents
  作者：Ibrahim Chaaban、El Sayeda M. El Khawass、Mona A. Mahran、Heba A. Abd El Razik、Nehad S. El Salamouni、Abeer E. Abdel Wahab

  DOI：10.1007/s00044-012-0076-0

  日期：2013.2

  New series of 2,5-dihydroxyphenyl-1,3-thiazoles 4a-l was synthesized by reacting 2,5-dihydroxyphenacyl bromide with various 4-aryl thiosemicarbazones 3a-l that on oxidation with ferric chloride yielded the corresponding N (1)-substituted benzylidene-N (2)-[3-aryl-4-(1,4-benzoquinon-2-yl)-1,3-thiazol-2-ylidene]hydrazines 5a-l. They were evaluated for antibacterial activity against Staphylococcus aureus and Bacillus subtilis as Gram-positive bacteria, Escherichia coli and Pseudomonas aeruginosa as Gram-negative bacteria. They were also evaluated for their in vitro antifungal potential against Candida albicans. Almost all tested compounds were found to possess variable degrees of antimicrobial activity. The obtained data revealed that compounds 4b-h and 5e, 5f and 5l exhibited promising antimicrobial activity against the tested organisms of which compound 4b proved to be the most active.