2-(2,3-dihydroxybenzylidene)-N-phenylhydrazine-1-carbothioamide | 479513-53-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(2,3-dihydroxybenzylidene)-N-phenylhydrazine-1-carbothioamide
• 英文别名: N-(2,3-dihydroxybenzylidene)-4-phenylthiosemicarbazide；2-(2,3-dihydroxybenzylidene)-N-phenylhydrazinecarbothioamide
• CAS: 479513-53-6
• 化学式: C₁₄H₁₃N₃O₂S
• 分子量: 287.342
• InChiKey: UKKZJZNCWSQFMI-UHFFFAOYSA-N

物化性质

• 沸点：
  478.4±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.88
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [osmium(II)dichloride(η6-p-cymene)]2 、 2-(2,3-dihydroxybenzylidene)-N-phenylhydrazine-1-carbothioamide 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以72%的产率得到
  参考文献：
  名称：

  半夹心芳烃钌 (II) 和锇 (II) 缩氨基硫脲复合物：溶液行为和抗增殖活性。

  摘要：

  我们报告了有机锇(II)和有机钌(II)半夹心配合物[(η6-p-cym)Os(L)Cl]Cl（1和2）和[的合成、表征和抗增殖活性。 (η6-p-cym)Ru(L)Cl]Cl（3 和 4），其中 L = N-(2-羟基)-3-甲氧基亚苄基氨基硫脲 (L1) 或 N-(2,3-二羟基亚苄基)-3-分别为氨基硫脲(L2)。 X射线晶体学表明，所有四种配合物均具有半夹心假八面体“三足琴凳”结构，其中中性N,S螯合缩氨基硫脲配体和末端氯占据三个配位。在甲醇中，观察到配位缩氨基硫脲配体的 E/Z 异构化，而在丙酮等非质子溶剂中，配体发生部分解离，在更配位的溶剂（如 DMSO）中达到完全置换。一般来说，该复合物对 A2780 卵巢癌细胞、A2780Cis 顺铂耐药卵巢癌细胞、A549 肺癌细胞、HCT116 结肠癌细胞和 PC3 前列腺癌细胞表现出良好的活性。特别是，钌络合物3在A2780人卵巢癌细

  DOI：

  10.1021/acs.organomet.7b00875
• 作为产物：
  描述：

  2,3-二羟基苯甲醛 、 4-苯基-3-硫代氨基脲 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以81%的产率得到2-(2,3-dihydroxybenzylidene)-N-phenylhydrazine-1-carbothioamide
  参考文献：
  名称：

  半夹心芳烃钌 (II) 和锇 (II) 缩氨基硫脲复合物：溶液行为和抗增殖活性。

  摘要：

  我们报告了有机锇(II)和有机钌(II)半夹心配合物[(η6-p-cym)Os(L)Cl]Cl（1和2）和[的合成、表征和抗增殖活性。 (η6-p-cym)Ru(L)Cl]Cl（3 和 4），其中 L = N-(2-羟基)-3-甲氧基亚苄基氨基硫脲 (L1) 或 N-(2,3-二羟基亚苄基)-3-分别为氨基硫脲(L2)。 X射线晶体学表明，所有四种配合物均具有半夹心假八面体“三足琴凳”结构，其中中性N,S螯合缩氨基硫脲配体和末端氯占据三个配位。在甲醇中，观察到配位缩氨基硫脲配体的 E/Z 异构化，而在丙酮等非质子溶剂中，配体发生部分解离，在更配位的溶剂（如 DMSO）中达到完全置换。一般来说，该复合物对 A2780 卵巢癌细胞、A2780Cis 顺铂耐药卵巢癌细胞、A549 肺癌细胞、HCT116 结肠癌细胞和 PC3 前列腺癌细胞表现出良好的活性。特别是，钌络合物3在A2780人卵巢癌细

  DOI：

  10.1021/acs.organomet.7b00875

文献信息

• Nickel(II) complexes of polyhydroxybenzaldehyde N4-thiosemicarbazones: synthesis, structural characterization and antimicrobial activities
  作者：Hana Bashir Shawish、Mohammadjavad Paydar、Chung Yeng Looi、Yi Li Wong、Elaheh Movahed、Siti Nadiah Abdul Halim、Won Fen Wong、Mohd-Rais Mustafa、Mohd Jamil Maah

  DOI：10.1007/s11243-013-9777-6

  日期：2014.2

  Nickel(II) complexes with 2,3-dihydroxybenzaldehyde N4-substituted thiosemicarbazone ligands (H3L1–H3L4) have been synthesized and characterized with the aim of evaluating the effect of N4 substitution in the thiosemicarbazone moiety on their coordination behavior and biological activities. Two series of nickel(II) complexes with the general formulae [Ni(H3L)(H2L)]ClO4 and [Ni2(HL)2] were characterized by analytical and spectral techniques. The molecular structure of one of the complexes, namely, [Ni(H3L4)(H2L4)]ClO4 was established by single crystal X-ray diffraction studies. The crystal structure of this complex revealed that two H3L4 ligands are coordinated to nickel(II) in different modes; one as a neutral tridentate ONS ligand and the other is as a monoanionic tridentate (ONS−) ligand. The antimicrobial activities of the compounds were tested against 25 bacterial strains via the disc diffusion method, and their minimum inhibitory concentration (MIC) and minimum microbicidal concentration were evaluated using microdilution methods. With a few exceptions, most of the compounds exhibited low-to-moderate inhibitory activities against the tested bacterial strains. However, the complexes [Ni2(HL3)2] (7) and [Ni2(HL4)2] (8) indicated higher inhibitory activity against Salmonella enterica ATCC 9068 (MIC values 15.7 and <15.7 μg/ml, respectively), compared with gentamicin as the positive control (MIC 25 μg/ml). Complex (7) also inhibited Streptococcus pneumoniae more efficiently (MIC 31.2 μg/ml), compared with gentamicin (MIC > 50 μg/ml). The toxicities of the compounds were tested on brine shrimp (Artemia salina), where no meaningful toxicity level was noted for both the free ligands and the complexes. The cytotoxicities of the compounds on cell viability were determined on MCF7, PC3, A375, and H413 cancer cells in terms of IC50; complexes [Ni(H3L3)(H2L3)]ClO4 (3), [Ni2(HL3)2] (7) and [Ni2(HL4)2] (8) exhibited significant cytotoxicity on the tested cell lines.

  合成了具有2,3-二羟基苯甲醛N4取代硫半缩二氨基脲配体（H3L1~H3L4）的镍（II）配合物，并对其进行了表征，旨在评估硫半缩二氨基脲部分的N4取代对其配位行为和生物活性的影响。通过分析和光谱技术表征了两系列镍（II）配合物，其通式分别为[Ni(H3L)(H2L)]ClO4和[Ni2(HL)2]。其中一个配合物[Ni(H3L4)(H2L4)]ClO4的分子结构通过单晶X射线衍射研究确定。该配合物的晶体结构揭示了两个H3L4配体以不同的方式与镍（II）配位；一个作为中性三齿ONS配体，另一个作为单阴离子三齿（ONS−）配体。通过纸片扩散法测试了这些化合物对25种细菌菌株的抗菌活性，并使用微量稀释法评估了它们的最小抑制浓度（MIC）和最小杀菌浓度。除少数例外，大多数化合物对测试的细菌菌株表现出低至中等的抑制活性。然而，配合物[Ni2(HL3)2]（7）和[Ni2(HL4)2]（8）对沙门氏菌ATCC 9068表现出较高的抑制活性（MIC值分别为15.7和<15.7 μg/ml），相较于阳性对照庆大霉素（MIC 25 μg/ml）。配合物（7）对肺炎链球菌的抑制效率也更高（MIC 31.2 μg/ml），相较于庆大霉素（MIC > 50 μg/ml）。这些化合物对卤虫（Artemia salina）的毒性进行了测试，自由配体和配合物均未显示出有意义的毒性水平。通过IC50评估了这些化合物对MCF7、PC3、A375和H413癌细胞的细胞毒性，配合物[Ni(H3L3)(H2L3)]ClO4（3）、[Ni2(HL3)2]（7）和[Ni2(HL4)2]（8）对测试的细胞系表现出显著的细胞毒性。
• Tin(IV) compounds of tridentate thiosemicarbazone Schiff bases: Synthesis, characterization, in-silico analysis and in vitro cytotoxicity
  作者：Enis Nadia Md Yusof、Alister J. Page、Jennette A. Sakoff、Michela I. Simone、Abhi Veerakumarasivam、Edward R.T. Tiekink、Thahira B.S.A. Ravoof

  DOI：10.1016/j.poly.2020.114729

  日期：2020.10

  Twelve tin(IV) compounds (5-16) derived from four tridentate thiosemicarbazone Schiff bases of 4-methyl-3-thiosemicarbazide with 2-hydroxy-3-methoxybenzaldehyde (1, 2) and 4-phenyl-3-thiosemicarbazide with 2,3 dihydroxybenzaldehyde (3, 4) of the general formulae [R2Sn(L-n)] and [Sn(L-n)(2)] (where R = Ph or Me; L-n = 1, 2, 3 and 4) were synthesized and characterized by elemental analysis, IR, UV-vis, mass spectrometry and multinuclear NMR (H-1, C-13 and Sn-119) spectroscopy. X-ray crystallographic data was obtained for 11', a 2:1 co-crystal between Ph2Sn(L-2) (11) and 3-methoxysalicylaldehyde azine, and Me2Sn(L-2) (12) where (LH2)-H-2 is 2-(2-hydroxy-3-methoxybenzylidene)-N-phenylhydrazinecarbothioamide. The analysis revealed distinct coordination geometries for 11 and 12 approaching trigonal-bipyramidal. In the crystal of 11', supramolecular dimers arising from amine-N-H center dot center dot center dot S(thiolate) hydrogen bonding and center dot center dot center dot HNCS}(2) synthons are evident; pi(chelate ring)center dot center dot center dot pi(oxidobenzylidene) stacking is also apparent. In the crystal of 12, supramolecular, helical chains are generated by a combination of amine-N-H center dot center dot center dot O(phenoxide) hydrogen bonding and Sn S secondary bonding. The cytotoxic activity of the compounds against a panel of ten cancer cell lines, [HT29 (colon), U87 and SJ-G2 (glioblastoma), MCF-7 (breast), A2780 (ovarian), H460 (lung), A431 (skin), DU145 (prostate), BE2-C (neuroblastoma) and MIA (pancreas), and one normal cell line, MCF-10A (normal breast)] were investigated. The thiosemicarbazone Schiff bases 1 and 4 as well as the diphenyltin(IV) compounds showed a strong ability to inhibit the growth of cancer cells, with particular selectivity against HT29, MCF-7, A2780, A431, BE2-C, SJ-G2 and MIA cell lines. The structure-activity relationship of all these compounds were studied by evaluating the effect of alkyl and aryl groups attached on the thiosemicarbazone backbone, the methoxy/hydroxyl groups present at the meta-position of the phenyl ring and alkyl or aryl groups bound to the tin center. (C) 2020 Elsevier Ltd. All rights reserved.