2,4-dihydroxybenzaldehyde 4-ethylthiosemicarbazone | 477731-20-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,4-dihydroxybenzaldehyde 4-ethylthiosemicarbazone
• 英文别名: 1-[(2,4-Dihydroxyphenyl)methylideneamino]-3-ethylthiourea
• CAS: 477731-20-7
• 化学式: C₁₀H₁₃N₃O₂S
• 分子量: 239.298
• InChiKey: BOUUUWDFYPBCSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-联吡啶 、 2,4-dihydroxybenzaldehyde 4-ethylthiosemicarbazone 、 zinc(II) acetate dihydrate 以 乙醇 为溶剂， 以75%的产率得到(4-hydroxy-2-oxidobenzaldehyde 4-ethylthiosemicarbazonato)-(2,2'-bipyridine)zinc(II)
  参考文献：
  名称：

  Towards a selective cytotoxic agent for prostate cancer: Interaction of zinc complexes of polyhydroxybenzaldehyde thiosemicarbazones with topoisomerase I

  摘要：

  Four thiosemicarbazones ligands, H3T(1), H3M(2), H3E(3) and H3P(4) have been prepared with good yield by refluxing 2,4-dihydroxybenzaldehyde with N(4)-substituted thiosemicarbazide in ethanol (H3T(1) = 2,4-dihydroxybenzaldehyde thiosemicarbazone: H3M(2) = 2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazone; H3E(3) = 2,4-dihydroxybenzaldehyde 4-ethylthiosemicarbazone and H3P(4) = 2,4-dihydroxybenzaldehyde 4-phenylthiosemicarbazone). Reactions of these ligands with zinc acetates in the presence of 2,2'-bipyridine lead to the formation of zinc(II) complexes of formulation [Zn(bpy)L](5-8) (bpy = 2,2'-bipyridine; L = doubly deprotonated thiosemicarbazones = HT(5); HM(6); HE(7) and HP(8)). These compounds were characterized and their cytotoxicity and topoisomerase I inhibition activities studied. X-ray diffraction study indicates that complex 8 is five coordinated and the coordination geometry around zinc(II) is trigonal bipyramidal distorted square based pyramid (TBDSBP). The doubly deprotonated thiosemicarbazone acts as a tridentate ONS-donor ligand while 2,2-bipyridne as the NN-donor ligand. Complexes 6,7 and 8 are more cytotoxic towards PC3 (prostate cancer cell line) than RWPE-1 (prostate normal cell line). The cytotoxicity and topoisomerase I inhibition activities seem to be dependent on the N(4) substituent of the thiosemicarbazone moiety. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.03.014
• 作为产物：
  描述：

  4-乙基-3-硫代氨基脲 、 2,4-二羟基苯甲醛 以 乙醇 为溶剂， 反应 2.0h， 以78%的产率得到2,4-dihydroxybenzaldehyde 4-ethylthiosemicarbazone
  参考文献：
  名称：

  一系列钼 (VI) 配合物与一些 N(4) 甲基和乙基缩氨基硫脲配体的结构、DNA 结合、DNA 切割和抗肿瘤研究

  摘要：

  通过 [MoO2(acac)2] 与衍生自 5-烯丙基-2-羟基-3-甲氧基苯甲醛 (1)、2-羟基萘甲醛 (2)、2,3-二羟基苯甲醛 ( 3) 或 5-叔丁基-2-羟基苯甲醛 (4)。配体与作为三齿 ONS 供体的钼配位。X 射线晶体学表明，钼的扭曲八面体配位由 1a、3a 和 4a 中的甲醇 (D) 或 2a 中的 H2O 完成。1、3和4的分子结构和配合物通过单晶X射线晶体学确定。配体和复合物与小牛胸腺 DNA 的结合通过 UV、荧光滴定和粘度测量进行研究。凝胶电泳显示所有复合物都能切割pBR322质粒DNA。复合物对人结肠直肠 (HCT 116) 细胞系的细胞毒特性显示出较强的抗增殖活性，相对顺序为 4a > 3a > 1a > 2a，IC50 值分别为 1.6、4.0、4.8 和 6.7 μM。该复合物比标准参考药物 5-氟尿嘧啶 (IC50 7.3 μM) 表现出更高的活性。这些研究表明二氧钼

  DOI：

  10.1080/00958972.2014.893430

文献信息

• Towards a selective cytotoxic agent for prostate cancer: Interaction of zinc complexes of polyhydroxybenzaldehyde thiosemicarbazones with topoisomerase I
  作者：Kong Wai Tan、Hoi Ling Seng、Fei Shen Lim、Shiau-Chuen Cheah、Chew Hee Ng、Kong Soo Koo、Mohd. Rais Mustafa、Seik Weng Ng、Mohd. Jamil Maah

  DOI：10.1016/j.poly.2012.03.014

  日期：2012.5

  Four thiosemicarbazones ligands, H3T(1), H3M(2), H3E(3) and H3P(4) have been prepared with good yield by refluxing 2,4-dihydroxybenzaldehyde with N(4)-substituted thiosemicarbazide in ethanol (H3T(1) = 2,4-dihydroxybenzaldehyde thiosemicarbazone: H3M(2) = 2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazone; H3E(3) = 2,4-dihydroxybenzaldehyde 4-ethylthiosemicarbazone and H3P(4) = 2,4-dihydroxybenzaldehyde 4-phenylthiosemicarbazone). Reactions of these ligands with zinc acetates in the presence of 2,2'-bipyridine lead to the formation of zinc(II) complexes of formulation [Zn(bpy)L](5-8) (bpy = 2,2'-bipyridine; L = doubly deprotonated thiosemicarbazones = HT(5); HM(6); HE(7) and HP(8)). These compounds were characterized and their cytotoxicity and topoisomerase I inhibition activities studied. X-ray diffraction study indicates that complex 8 is five coordinated and the coordination geometry around zinc(II) is trigonal bipyramidal distorted square based pyramid (TBDSBP). The doubly deprotonated thiosemicarbazone acts as a tridentate ONS-donor ligand while 2,2-bipyridne as the NN-donor ligand. Complexes 6,7 and 8 are more cytotoxic towards PC3 (prostate cancer cell line) than RWPE-1 (prostate normal cell line). The cytotoxicity and topoisomerase I inhibition activities seem to be dependent on the N(4) substituent of the thiosemicarbazone moiety. (C) 2012 Elsevier Ltd. All rights reserved.
• Structures, DNA binding, DNA cleavage, and antitumor investigations of a series of molybdenum(VI) complexes with some N(4) methyl and ethyl thiosemicarbazone ligands
  作者：Mouayed A. Hussein、Teoh S. Guan、Rosenani A. Haque、Mohamed B. Khadeer Ahamed、Amin M.S. Abdul Majid

  DOI：10.1080/00958972.2014.893430

  日期：2014.2.16

  Four dioxomolybdenum(VI) complexes were synthesized by reaction of [MoO2(acac)2] with thiosemicarbazones derived from 5-allyl-2-hydroxy-3-methoxybenzaldehyde (1), 2-hydroxynaphthaldehyde (2), 2,3-dihydroxybenzaldehyde (3), or 5-tert-butyl-2-hydroxybenzaldehyde (4). The ligands were coordinated to molybdenum as tridentate ONS donors. X-ray crystallography showed that the distorted octahedral coordination

  通过 [MoO2(acac)2] 与衍生自 5-烯丙基-2-羟基-3-甲氧基苯甲醛 (1)、2-羟基萘甲醛 (2)、2,3-二羟基苯甲醛 ( 3) 或 5-叔丁基-2-羟基苯甲醛 (4)。配体与作为三齿 ONS 供体的钼配位。X 射线晶体学表明，钼的扭曲八面体配位由 1a、3a 和 4a 中的甲醇 (D) 或 2a 中的 H2O 完成。1、3和4的分子结构和配合物通过单晶X射线晶体学确定。配体和复合物与小牛胸腺 DNA 的结合通过 UV、荧光滴定和粘度测量进行研究。凝胶电泳显示所有复合物都能切割pBR322质粒DNA。复合物对人结肠直肠 (HCT 116) 细胞系的细胞毒特性显示出较强的抗增殖活性，相对顺序为 4a > 3a > 1a > 2a，IC50 值分别为 1.6、4.0、4.8 和 6.7 μM。该复合物比标准参考药物 5-氟尿嘧啶 (IC50 7.3 μM) 表现出更高的活性。这些研究表明二氧钼