5-nitrosalicylidene-4-phenylthiosemicarbazone | 41377-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-nitrosalicylidene-4-phenylthiosemicarbazone
• 英文别名: 5-nitro-salicylaldehyde-N¹-phenyl-thiosemicarbazone；5-NO₂-salicyliden-4-phenylthiosemicarbazone；1-(5-Nitrosalicyliden)-4-phenyl-thiosemicarbazon；1-[(2-Hydroxy-5-nitrophenyl)methylideneamino]-3-phenylthiourea
• CAS: 41377-31-5
• 化学式: C₁₄H₁₂N₄O₃S
• 分子量: 316.34
• InChiKey: MBQALLXEFNLQIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  506.8±60.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二氧化三碳 、 5-nitrosalicylidene-4-phenylthiosemicarbazone 以 1,4-二氧六环 、 乙腈 为溶剂， 以78%的产率得到6-Nitro-2-oxo-2H-chromene-3-carboxylic acid (4,6-dioxo-3-phenyl-2-thioxo-tetrahydro-pyrimidin-1-yl)-amide
  参考文献：
  名称：

  Artizzu; Bonsignore; Loy, Il Farmaco, 1995, vol. 50, # 12, p. 853 - 856

  摘要：

  DOI：
• 作为产物：
  描述：

  5-硝基水杨醛 、 苯胺基硫脲 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以80%的产率得到5-nitrosalicylidene-4-phenylthiosemicarbazone
  参考文献：
  名称：

  Synthesis, structures and antimicrobial activity of 5-nitro-salicylaldehyde-thiosemicarbazonates of zinc(II) coordinated to substituted bipyridines/phenanthrolines

  摘要：

  Reactions of zinc(II) with 5-nitro-salicylaldehyde-N-1 -substituted thiosemicarbazones {(5-NO2-2-HO-C6H4)C-2(H)=N-3-(NH)-H-2-C-1(=S)-(NHR)-H-1; R = H, H2L1; Me, H2L2; Et, H2L3; Ph, H2L4 ) and 4,4'-dimethyl-2,2'-bipyridine (dm-bipy), 2,9-dimethyl-1,10-phenanthroline (dm-phen) and 3,4,7,8-tetramethyl-1, 10-phenanthroline (tm-phen) as co-ligands, have yielded complexes of stoichiometry, [Zn(L-n)(L)] {n = 1-4; L = dm-bipy, 1, 4, 7, 10; dm-phen, 2, 5, 8, 11; tm-phen, 3, 6, 9, 12) characterized by elemental analysis, infrared and electronic absorption spectroscopy and single crystal X-ray crystallography. Complexes 9 and 10 have distorted trigonal bipyramidal geometry (tau = 0.529-0.580), while complexes 5, 8 and 11 have distorted square pyramidal geometry (tau = 0.004-0.250). They displayed fluorescence bands at lambda(max) - 430-440 nm. In comparison to unsubstituted bipyridines/phenanthrolines, these zinc(II) complexes have shown higher antimicrobial activity with low minimum inhibitory concentration (MIC) against the clinical isolate methicillin resistant Staphylococcus aureus (MRSA), Gram positive bacteria, namely, Staphylococcus aureus (MTCC740), Enterococcus faecalis (MTCC439), Gram negative bacteria, namely, Klebsiella pneumonia 1 (MTCC109), Escherichia coli (MTCC119), Salmonella typhimurium 1 (MTCC98) and one yeast strain Candida albicans (MTCC227). These complexes tested were found to be cytotoxic to microorganisms (bactericidal/fungicidal). (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2018.03.027

文献信息

• Synthesis, spectroscopy, structures and antimicrobial activity of mixed-ligand zinc(<scp>ii</scp>) complexes of 5-nitro-salicylaldehyde thiosemicarbazones
  作者：Shikha Indoria、Tarlok S. Lobana、Henna Sood、Daljit S. Arora、Geeta Hundal、Jerry P. Jasinski

  DOI：10.1039/c5nj02822a

  日期：——

  development in antimicrobial investigations vis-à-vis lack of activity of gentamicin against MRSA or low antimicrobial activity against S. aureus as per literature reports. All complexes are active against K. pneumoniae and S. typhimurium, while complexes reported in the literature were found to be inactive. Complexes tested were found to be cytotoxic to microorganisms (bactericidal/fungicidal).

  锌（II）与5-硝基-水杨醛-N 1取代的硫代半氨基甲酮5-NO 2 -C 6 H 4（2-OH）-C 2（H）N 3 –N 2 H– C 1（S）–N 1 HR；H 2 L 1 –NHR，R = H，Me，Et，Ph：分别使用联吡啶/菲咯啉（L'）作为共配体的硫代配体}，并通过元素分析，红外，NMR，电子吸收和荧光光谱和单晶X射线晶体学。硫代配体以双阴离子（O，N，SL-NHR）的形式与金属中心配合2-在它们的复合物，[锌（κ 3 -O，N，SL-NHR）（κ 2 - Ñ， Ñ -L'）] R，（ Ñ， Ñ -L'）：H，联吡啶1，苯， 2 ; 我，bipy 3，phen 4；Et，bipy 5，phen， 6 ; Ph，bipy， 7，phen 8 }。复合物的几何形状可分为三类：扭曲三角双锥（ 1 -molecule II， 5， 7）; 变形四方锥（ 4， 6和8-分子II）和
• Synthesis and Characterization of Some New Cu(II), Ni(II) and Zn(II) Complexes with Salicylidene Thiosemicarbazones: Antibacterial, Antifungal and in Vitro Antileukemia Activity
  作者：Elena Pahontu、Valeriu Fala、Aurelian Gulea、Donald Poirier、Victor Tapcov、Tudor Rosu

  DOI：10.3390/molecules18088812

  日期：——

  Thirty two new Cu(II), Ni(II) and Zn(II) complexes (1–32) with salicylidene thiosemicarbazones (H2L1–H2L10) were synthesized. Salicylidene thiosemicarbazones, of general formula (X)N-NH-C(S)-NH(Y), were prepared through the condensation reaction of 2-hydroxybenzaldehyde and its derivatives (X) with thiosemicarbazide or 4-phenylthiosemicarbazide (Y = H, C6H5). The characterization of the new formed compounds was done by 1H-NMR, 13C-NMR, IR spectroscopy, elemental analysis, magnetochemical, thermoanalytical and molar conductance measurements. In addition, the structure of the complex 5 has been determined by X-ray diffraction method. All ligands and metal complexes were tested as inhibitors of human leukemia (HL-60) cells growth and antibacterial and antifungal activities.

  合成了32个新的Cu(II)、Ni(II)和Zn(II)配合物(1-32)与水杨醛缩硫代氨基脲(H2L1-H2L10)。水杨醛缩硫代氨基脲，通式为(X)N-NH-C(S)-NH(Y)，通过2-羟基苯甲醛及其衍生物(X)与硫代氨基脲或4-苯基硫代氨基脲(Y=H, C6H5)的缩合反应制备。新形成的化合物的表征通过1H-NMR、13C-NMR、IR光谱、元素分析、磁化学、热分析和摩尔电导测量进行。此外，配合物5的结构通过X射线衍射方法确定。所有配体和金属配合物都作为抑制人白血病(HL-60)细胞生长以及抗菌和抗真菌活性的抑制剂进行了测试。
• Synthesis and structures of 5-nitro-salicylaldehyde thiosemicarb-azonates of copper(<scp>ii</scp>): molecular spectroscopy, ESI-mass studies, antimicrobial activity and cytotoxicity
  作者：Tarlok S. Lobana、Shikha Indoria、Harpreet Kaur、Daljit S. Arora、Amanpreet K. Jassal、Jerry P. Jasinski

  DOI：10.1039/c4ra15006f

  日期：——

  infections and among these, methicillin resistant Staphylococcus aureus (MRSA) is the most frequent nosocomial pathogen. Likewise, Candida albicans (fungi) are found to have developed resistance against a number of antifungal agents. In this context, compounds of copper(II) with salicylaldehyde based thiosemicarbazones 5-R′-2-HO–C6H4–C2(H)N3–N2H–C1(S)–N1HR; R = H, Me, Et, Ph: H2L1, H2L2, H2L3, H2L4 respective

  这项研究的基本目的是探索基于金属硫代半氨基甲酸酯的潜在金属有机抗菌剂。鉴于革兰氏阳性和革兰氏阴性细菌表现出的耐药性已成为一个严重的全球性医学问题，这项研究具有重要意义。耐药菌的增加是造成各种医院感染的原因，其中，耐甲氧西林的金黄色葡萄球菌（MRSA）是最常见的医院病原体。同样，发现白色念珠菌（真菌）对多种抗真菌剂产生了抗药性。在这种情况下，铜（II）与水杨醛基的硫代半氨基偶氮化合物5-R'-2-HO–C 6 H4 –C 2（H）N 3 –N 2 H–C 1（S）–N 1 HR；R = H，Me，Et，Ph：H 2 L 1，H 2 L 2，H 2 L 3，H 2 L 4分别为硫代配体]各种微生物（细菌/真菌）。对于R'=甲氧基，最近针对革兰氏阳性细菌，如金黄色葡萄球菌（MTCC740），耐甲氧西林的金黄色葡萄球菌测试了几种配合物（五配位配合物）（MRSA），革兰氏阴性细菌，弗氏志贺氏菌（M
• Silicon-containing diorganotin complexes with salicylaldehyde thiosemicarbazone and their anticancer activity
  作者：Qian Liu、Bo Xie、Sen Lin、Qihua Liao、Ruihong Deng、Yan Zhaohua

  DOI：10.1007/s12039-019-1650-5

  日期：2019.8

  characterized by \(^1}\hbox H NMR}\), \(^13}\hbox C NMR}\), IR spectra, elemental analysis and X-ray single-crystal diffraction. Spectroscopic and X-rays studies indicated that the thiosemicarbazone Schiff base and tin atom were coordinated as a parallel five- and six-membered heterocyclic structure. In addition, the bioassay of the synthesized complexes was performed and the results show that the silicon-containing

  摘要合成了八种新型的含硅二有机锡与水杨醛硫代半乳糖苷复合物。它们的特征在于\（^ 1} \ hbox H NMR} \），\（^ 13} \ hbox C NMR} \），红外光谱，元素分析和X射线单晶衍射。光谱和X射线研究表明，硫半脲席夫碱和锡原子被协调为平行的五元和六元杂环结构。此外，对合成的复合物进行了生物测定，结果表明，含硅的二有机锡复合物与水杨醛硫半乳糖苷对人乳腺癌细胞具有良好的抗癌活性。 图形摘要合成了八种含有水杨醛硫半脲衍生物的含硅有机锡配合物。络合物中的Sn原子以扭曲的三角双锥体构型五配位，通过氧，氮，硫原子的配位形成五元和六元螯合环。所有复合物均显示出显着的抗癌活性，尤其是复合物3cb和3ab。
• Synthesis of 5-nitro-salicylaldehyde-N-substituted thiosemicarbazonates of copper(II): Molecular structures, spectroscopy, ESI-mass studies and antimicrobial activity
  作者：Tarlok S. Lobana、Shikha Indoria、Henna Sood、Daljit S. Arora、Balwinder S. Randhawa、Isabel Garcia-Santos、Victoria A. Smolinski、Jerry P. Jasinski

  DOI：10.1016/j.ica.2017.02.032

  日期：2017.5

  Equimolar reactions of copper(II) acetate with 5-nitro-salicylaldehyde-N-1-substituted thiosemi carbazones, [5-NO2-2-HO-C6H4-C-2(H)@ N-3-(NH)-H-2-C-1(@ S)-(NHR)-H-1; R = Me, H2L-NHMe; Et, H2L-NHEt; Ph, H2L-NHPh; H, H2L-NH2], and 4,4'-dimethyl-2,2'-bipyridine (dm-bipy), 2,9-dimethyl-1,10-phenanthroline (dm-phen) and 3,4,7,8-tetramethyl-1,10-phenanthroline (tm-phen) have yielded complexes of stoichiometry, [Cu(kappa(3)-O,N,S-5-NO2-stscN(1)HR)(kappa(2)-N, N-L')] R = H (1, 2, 3), Me (4, 5, 6), Et(7, 8, 9), Ph (10, 11, 12); L0 = dm-bipy (1, 4, 7, 10)/dm-phen (2, 5, 8, 11)/tm-phen (3, 6, 9, 12)}. They have been investigated by analytical data, infrared and electronic absorption spectroscopy, electron spin resonance spectroscopy, fluorescence activity, ESI-mass study and single crystal X-ray crystallography (1, 6, 7). The geometry of complexes is slightly distorted square pyramidal and have displayed weak to intense fluorescence in the region, 370-570 nm. Complexes have shown significant antimicrobial activity against methicillin resistant Staphylococcus aureus (MRSA), Staphylococcus aureus (MTCC740), Klebsiella pneumoniae (MTCC109), Shigella flexneri (MTCC1457), Salmonella typhimurium (MTCC-439), and Candida albicans (MTCC227). Complexes are cytotoxic against living cells and thus they are bactericidal/fungicidal. (C) 2017 Elsevier B. V. All rights reserved.