5-nitro-salicylaldehyde-N¹-methyl-thiosemicarbazone | 41377-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-nitro-salicylaldehyde-N¹-methyl-thiosemicarbazone
• 英文别名: 1-(5-Nitrosalicyliden)-4-methyl-thiosemicarbazon；1-[(2-Hydroxy-5-nitrophenyl)methylideneamino]-3-methylthiourea
• CAS: 41377-25-7
• 化学式: C₉H₁₀N₄O₃S
• 分子量: 254.269
• InChiKey: LHTHURNBOXNCKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  428.7±55.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  5-nitro-salicylaldehyde-N¹-methyl-thiosemicarbazone 、 cobalt(II) chloride 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.0h， 以60.5%的产率得到
  参考文献：
  名称：

  Synthesis, Characterization and Antibacterial Activity of Co(II), Cu(II) and Zn(II) Complexes Derived from 4-Methylthiosemicarbazide and 5-Nitrosalicylaldehyde

  摘要：

  通过5-硝基水杨醛与4-甲基氨基硫脲缩合反应得到的NS供体配体与钴(II)、铜(II)和锌(II)进行了反应。NS供体配体的结构通过单晶X射线衍射分析确定。晶体属于单斜晶系，空间群C2/c，晶胞参数为：a = 1.31165(5) nm，b = 0.71876(3) nm，c = 2.38370(7) nm，α = 90º，β = 90.855º(3)，γ = 90º，V = 2.24701(14) nm³，Z = 8，F(000) = 1056，Mr = 254.27，Dc = 1.503 g/cm³，μ(MoKa) = 0.291 mm⁻¹，R1 = 0.0462，wR2 = 0.1202。晶体结构分析表明，该化合物具有通过氢键和静电相互作用形成的三维网络结构。通过元素分析、红外光谱、紫外光谱和抗菌活性测定了配体及其金属配合物。结论是配体的硫化硫和席夫碱氮原子与金属离子配位。抗菌活性结果表明，所有配体及其配合物都能抑制细菌活性。

  DOI：

  10.14233/ajchem.2013.13272
• 作为产物：
  描述：

  2-甲基-3-硫代氨基脲 、 5-硝基水杨醛 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以83%的产率得到5-nitro-salicylaldehyde-N¹-methyl-thiosemicarbazone
  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
• The Effect of C‐2 Substituents of Salicylaldehyde‐Based Thiosemicarbazones on the Synthesis, Spectroscopy, Structures, and Fluorescence of Nickel(II) Complexes
  作者：Tarlok S. Lobana、Poonam Kumari、Alfonso Castineiras、Ray J. Butcher

  DOI：10.1002/ejic.201300209

  日期：2013.7.2

  bonding patterns, geometry, and fluorescence properties of nickel(II) complexes with salicylaldehyde-based thiosemicarbazones [(2-OH-5-R1-C6H3)C(R2)=NNHC(=S)NHR3, LH2] by invoking the effect of substituents at the C-2 and N-1 atoms of the thio ligands and by using bipyridines/phenanthrolines as auxiliary ligands. The methodology used for the preparation of complexes involved initial binding of NiII

  本研究的目的是研究镍 (II) 配合物与水杨醛基缩氨基硫脲 [(2-OH-5-R1-C6H3)C(R2)=NNHC(=S) 的键合模式、几何形状和荧光特性NHR3, LH2] 通过在硫代配体的 C-2 和 N-1 原子上调用取代基的作用并使用联吡啶/菲咯啉作为辅助配体。用于制备复合物的方法包括 NiII 与硫代配体在有机溶剂中的初始结合，以产生经验成分 [NiL] 的不溶性固体，该固体与 N,N 供体配体进一步反应。这样，我们制备了一系列双核配合物和两种单核配合物，化学计量比为[Ni2L2(bipy)(D)] [bipy = 2,2'-bipyridine, L = L1 (R1, R2, R3 = H), D = H2O 1；L = L2（R1，R2 = H，R3 = Me），D = CH3OH 2；L = L3 (R1, R2 = H, R3 = Et)，D = CH3OH 4；L=L3，D=
• 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
• 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.