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Synthesis of 4-aminoantipyrine Schiff bases and their antimicrobial activities

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Journal of Chinese Pharmaceutical Sciences 2018年第11期27卷 753-766页

作者： Olatunde S.Oladeji monisola i.ikhile Carine M.D.Fotsing Messai Mamo Patrick G.Ndungu Derek T.Ndinteh Department of Applied Chemistry Faculty of Science University of Johannesburg

Various compounds of 4-aminoantipyrine Schiff bases(M1–M12) were synthesized via a condensation reaction of 4-aminoantipyrine with different benzaldehydes through a conventional method of refluxing the mixture for 3–4 h. The synthesized Schiff bases were characterized by using elemental analyses, FT-iR, UV-Vis, Mass, 1 H and 13 C NMR spectroscopy. The antimicrobial activity of the synthesized Schiff bases was investigated against 12 bacterial strains(Mycobacterium smegmatis, Bacillus cereus, Bacillus subtilis, Enterococcus faecalis, Staphylococcus epidermidis, Klebsiella pneumonia, Escherichia coli, Enterobacter cloacae, Klebsiella oxytoca, Proteus vulgaris, Enterobacter aerogenes, and Pseudomonas aeruginosa), and antifungal activities were tested against seven fungal strains(Aspergillus flavus, Aspergillus carbonarious, Aspergillus parasiticus, Aspergillus fumigatus, Aspergillus niger, Fusarium verticillioides and Fusarium proliferatum). The antimicrobial activities of the synthesized compounds were compared with standard streptomycin and nalidixic acid. The results obtained from antibacterial assay indicated that M1–M12 inhibited potential growth of Proteus vulgaris with minimum inhibitory concentrations(MiCs) ranging from 15.6–250 μg/mL compared with the standard nalidixic acid with an MiC of 500 μg/mL. Moreover, we could conclude that most of the tested compounds experienced mild to low activities at 15.6 μg/mL. Their activities could be attributed to their low concentration s. The antifungal analysis showed that the tested fungi were not sensitive to the prepared Schiff bases at the prepared concentration of 500 μg/mL. Therefore, we recommended further analysis on both cytotoxicity and minimum bactericidal concentration(MBC) to ascertain their potential effects against human cells.

关键词： 4-Aminoantipyrine Antibacterial Schiffbases Antifungal Synthesis inhibition

Towards eradicating antibiotic-resistant bacteria: synthesis and antibacterial activities of substituted N-(2-nitrophenyl)pyrrolidine-and piperidine-2-carboxylic acids

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Journal of Chinese Pharmaceutical Sciences 2019年第10期28卷 704-715页

作者： Jocelyn A.Odusami monisola i.ikhile Marthe C.D.Fotsing idris A.O.lasupo Josephat U.izunobi Elizabeth O.Bamgbade Thierry Y.Fonkui Olayinka T.Asekun Oluwole B.Familoni Derek T.Ndinteh Department of Chemical Sciences Yaba College of TechnologyYabaLagosNigeria Department of Applied Chemistry P.O Box 17011Doornfontein Campus 2028University of JohannesburgSouth Africa Department of Chemistry University of LagosAkokaLagosNigeria Department of Biotechnology and Food Technology P.O Box 17011Doornfontein Campus 2028University of JohannesburgSouth Africa

Antibacterial resistance is a source of great concern in the effective prevention and treatment of infections caused by bacteria,making the development of requisite therapeutics a major challenge.N-(Nitrophenyl)cycloamino acids are important compounds in the synthesis of poly-condensed nitrogen-containing heterocycles with marked activities in many biological systems.A series of substituted N-(o-nitrophenyl)cycloamino-2-carboxylic acids 3a–3g were synthesized via the condensation reaction of substituted o-halogenonitrobenzenes with L-proline 2a and D,L-pipecolinic acid 2b,under refluxing alcoholic basic conditions in excellent *** synthesized compounds were characterised by FT-iR,(1H&13C)NMR,UV-Vis,mass spectroscopy and elemental *** antibacterial activities were evaluated against five Gram-positive and five Gram-negative bacterial strains using the broth micro-dilution *** antibacterial activities of the synthesized compounds were compared with streptomycin and nalidixic acid as standard antibiotic *** minimum inhibitory concentration(MiC)values of compounds 3a–3g revealed good antibacterial activities against the tested *** 3a–3g were more potent than nalidixic acid against Enterococcus faecalis,Mycobacterium smegmatis,Escherichia coli and Proteus vulgaris and also more potent than streptomycin against Enterobacter cloacae and Staphylococcus *** 3a,3c and 3g displayed the highest antibacterial potency with an MiC value of 15.6μg/mL against ***,*** and ***,*** results indicated that these aryl cycloamino acids with antibacterial activities had potential applications as substitutes for antimicrobial peptide antibiotics,which are not susceptible to bacterial resistance,to solve the problem of drug resistance.

关键词： Antibiotics Bacteria Cyclic amino acids o-Halogenonitrobenzene

各种二茂铁基席夫碱的合成、表征和对革兰氏阳性和革兰氏阴性细菌的抗菌筛选

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无机化学学报 2022年第4期38卷 705-715页

作者： Oladeji S.Olatunde ikhile i.monisola Mamo Messai Ndungu G.Patrick Ndinteh T.Derek Department of Chemical Sciences Faculty of ScienceUniversity of JohannesburgJohannesburgSouth Africa

合成了10种二茂铁基席夫碱1~10,并采用UV⁃Vis光谱、FT⁃iR、元素分析、1 H和13C NMR谱对其进行了表征。评价了所合成的化合物对11种细菌菌株(枯草芽孢杆菌ATCC19659、产气克雷伯氏菌肠杆菌ATCC13882、粪肠球菌ATCC13047、耻垢分枝杆菌MC2... 详细信息

合成了10种二茂铁基席夫碱1~10,并采用UV⁃Vis光谱、FT⁃iR、元素分析、1 H和13C NMR谱对其进行了表征。评价了所合成的化合物对11种细菌菌株(枯草芽孢杆菌ATCC19659、产气克雷伯氏菌肠杆菌ATCC13882、粪肠球菌ATCC13047、耻垢分枝杆菌MC2155、表皮葡萄球菌ATCC14990、金黄色葡萄球菌ATCC25923、大肠杆菌ATCC25922、阴沟肠杆菌ATCC13047、产酸克雷伯氏菌ATCC8724、奇异变形杆菌ATCC7002、普通变形杆菌ATCC6380)的抗菌活性。抗菌试验结果表明,与标准物萘啶酸和硫酸链霉素对比,合成的席夫碱1~10可抑制产气克雷伯氏菌和粪肠球菌的潜在生长,最低抑菌浓度(MiC)分别为15.6~31.25和31.25~125μg·mL^(-1)。

关键词：抗菌席夫碱萘啶合成抑制

一些二茂铁苯基亚胺化合物的合成与表征（英文）

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无机化学学报 2015年第10期31卷 2079-2088页

作者： ikhile monisola i Ngila J Catherine Department of Applied Chemistry University of Johannesburg Doornfontein Campus

通过回流对应的二茂铁苯胺和芳香醛的混合物的同样路径合成了一系列新颖的二茂铁苯基亚胺化合物（5-12）。当暴露于空气时化合物5-12稳定,不发生任何分解。所有化合物均用1H、13C NMR,MS,iR,UV-Vis和元素分析表征。还报导了化合物N-（3-... 详细信息

通过回流对应的二茂铁苯胺和芳香醛的混合物的同样路径合成了一系列新颖的二茂铁苯基亚胺化合物（5-12）。当暴露于空气时化合物5-12稳定,不发生任何分解。所有化合物均用1H、13C NMR,MS,iR,UV-Vis和元素分析表征。还报导了化合物N-（3-bromo-2-hydroxylbenzylidene）-4-ferrocenylimine（10）的单晶结构,其结晶属单斜晶系P21/c空间群。

关键词：二茂铁合成表征亚胺 X-射线衍射

Synthesis, characterization and biological activities of Schiff bases derived from 2-hydroxy-3-nitrobenzaldehyde

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Journal of Chinese Pharmaceutical Sciences 2017年第12期26卷 858-871页

作者： monisola itohan ikhile Marthe Carine Djuidje Fotsing Charmaine Ardeme Jane Catherine Ngila Derek Tantoh Ndinteh Department of Applied Chemistry University of JohannesburgDoornfontein CampusPO 17011Johannesburg 2028South Africa Department of Chemistry University of JohannesburgP O Box 524Auckland ParkJohannesburg 2006South Africa

Four novel Schiff bases were synthesized by the condensation reaction of 2-hydroxyl-3-nitrobenzaldehyde with either benzothiazoles or benzimidazolamines. The compounds 1–4 were characterized by spectroscopic and analytical methods. The crystal structures of 6-methoxy-1,3-benzothiazol-2-amine and compound 2 are reported only. The 6-methoxy-1,3-benzothiazol-2-amine was found to crystallize in the orthorhombic crystal system in the space group Pbca, having eight molecules in the unit cell, while compound 2 was found to crystallize in the monoclinic crystal system in the space group P2_1/c. The biological activities of these compounds were investigated by evaluating their antibacterial, antifungal, antimalarial, anti-HiV and anti-trypanosomiasis activities. These compounds displayed very interesting antibacterial, antifungal, antimalarial, anti-trypanosomiasis, anti-HiV and low cytotoxicity activity against HeLa cells.

关键词： Schiff bases Biological activity Synthesis X-ray diffraction Characterization

Synthesis, characterization and biological applications of novel Schiff bases of 2-(trifluoromethoxy) aniline

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Journal of Chinese Pharmaceutical Sciences 2018年第5期27卷 307-323页

作者： Thierry Youmbi Fonkui monisola itohan ikhile Freddy Munyololo Muganza Marthe Carine Djuidje Fotsing Charmaine Arderne Xavier Siwe-Noundou Rui Werner Macedo Krause Derek Tantoh Ndinteh Patrick Berka Njobeh Department of Biotechnology and Food Technology University of Johannesburg Department of Applied Chemistry University of Johannesburg Department of Chemistry Sefako Makgatho Health Sciences University Department of Chemistry University of Johannesburg Department of Chemistry Rhodes University

A series of five new Schiff bases(1–5) were synthesized by reacting 2-(trifluoromethoxy) aniline with different aromatic aldehydes. The Schiff base compounds were characterized by spectroscopic and analytical methods. Crystal structure of one new compound was also reported. The pharmacological properties, including antibacterial(14 bacterial species), antifungal(7 strains), antimalarial, anti-trypanosomal and anti-HiV activities of the compounds, were investigated. Cytotoxicity of the tested compounds was evaluated against human cervix adernocarcinoma cells(He La). Bacterial minimum inhibitory concentration(MiC) results by broth microdilution method showed that Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Staphylococcus epidermidis, Proteus vulgaris, Klebsiella oxytoc and Klebsiella pneumonia were more sensitive in the presence of tested compounds with an MiC value of 15.6 μg/m L. All the tested compounds showed good to moderate activity against fungi. The sensitivity of Aspergillus fumigatus was higher than other strains with a minimum cell death concentration(MFC) of 15.6 μg/m L. Compound 1 showed greater antimalarial and anti-trypanosomal properties with very low to no cytotoxic effects against He La cells as compared with compound 5, while other compounds exhibited poor activity. Compounds 1–5 demonstrated good activity against HiV type-1. These Schiff base compounds could be used as good antimicrobial agents.

关键词： Synthesis Biological activity Schiff bases Antimicrobial 2-(Trifluoromethoxy) aniline