5-nitro-salicylaldehyde-N¹-ethyl-thiosemicarbazone | 41377-26-8

• 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-ethyl-thiosemicarbazone
• 英文别名: 1-(5-Nitrosalicyliden)-4-ethyl-thiosemicarbazon；1-Ethyl-3-[(2-hydroxy-5-nitrophenyl)methylideneamino]thiourea
• CAS: 41377-26-8
• 化学式: C₁₀H₁₂N₄O₃S
• 分子量: 268.296
• InChiKey: RBMLXWGQAMURNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 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：
  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-ethyl-thiosemicarbazone 、 copper(II) acetate monohydrate 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  铜（ii）的5-硝基-水杨醛醛基硫代氨基甲酸酯-氨基磺酸盐的合成与结构：分子光谱，ESI质谱研究，抗菌活性和细胞毒性†

  摘要：

  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

  DOI：

  10.1039/c4ra15006f
• 作为产物：
  描述：

  ethyl thiosemicarbazide 、 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82%的产率得到5-nitro-salicylaldehyde-N¹-ethyl-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
• Electronic Fine‐Tuning of Oxygen Atom Transfer Reactivity of <i>cis</i> ‐Dioxomolybdenum(VI) Complexes with Thiosemicarbazone Ligands
  作者：Aurélien Ducrot、Bethany Scattergood、Ben Coulson、Robin N. Perutz、Anne‐K. Duhme‐Klair

  DOI：10.1002/ejic.201500059

  日期：2015.7

  A series of six cis-dioxomolybdenum(VI) complexes with thiosemicarbazone ligands was synthesized and characterized. The ligands were obtained by reacting ethyl thiosemicarbazide with salicylaldehydes substituted with a selection of electron-withdrawing and electron-donating groups. The crystal structures, IR, NMR spectroscopic data and oxygen atom transfer activities of the complexes revealed that

  合成并表征了一系列具有氨基硫脲配体的六个顺式-二氧钼 (VI) 配合物。配体是通过乙基氨基硫脲与水杨醛反应获得的，水杨醛被一些吸电子和给电子基团取代。配合物的晶体结构、IR、NMR 光谱数据和氧原子转移活性表明，位于苯酚供体对位的取代基的电子效应传递到钼中心，如哈米特之间的线性关系所反映的。配合物的常数和关键特性，包括钼-苯酚键长和亚胺质子共振的配位位移。与未取代的催化剂相比，吸电子取代基增加了氧原子从二甲基亚砜转移到三苯基膦的速率，而给电子基团具有相反的效果。通过在酚盐供体的对位引入强吸电子的 NO2 取代基，实现了最高的速率增强。
• 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 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.