Nitroimidazoles Part 7. Synthesis and Anti-HIV Activity of New 4-Nitroimidazole Derivatives

Al‐Masoudi, Najim A.; Pfleiderer, Wolfgang; Pannecouque, Christophe

doi:10.5560/znb.2012-0122

Cited by 16 publications

(11 citation statements)

References 17 publications

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“…A perusal of the literature revealed that pyrimidine derivatives and the uracil and thymine nitrogen bases [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 ] are efficient inhibitors to protect steel in acidic solutions [ 15 , 17 ]. 1,2,3-Triazoles have been the subject of considerable research, mainly due to their usefulness in synthetic organic chemistry and also due to their variety of interesting biological activities, forming part of the scaffolds of antibacterial and antituberculosis agents [ 18 , 19 ], neuraminidase inhibitors [ 20 ], anticancer compounds [ 21 , 22 , 23 , 24 ], antiviral agents [ 25 , 26 , 27 ], analgesic compounds [ 28 ], fungicidal activity [ 29 , 30 , 31 ], protein tyrosine phosphatase inhibitors [ 32 , 33 ], and assorted biomolecules (nucleosides and nucleotides) [ 34 , 35 ]. On the other hand, 1,2,3-triazoles have other applications, like in chemosensors [ 36 ] and organocatalysts [ 37 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New 1,2,3-Triazole Derivatives of Uracil and Thymine with Potential Inhibitory Activity against Acidic Corrosion of Steels

et al. 2013

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Ten 1,4-disubstituted 1,2,3-triazoles were synthesized from one of 1-(azido-methyl)benzene, 1-(azidomethyl)-4-fluorobenzene, 1-(azidomethyl)-4-chlorobenzene, 1-(azidomethyl)-4-bromobenzene or 1-(azidomethyl)-4-iodobenzene, generated in situ from sodium azide and the corresponding benzyl halide, and dipropargyl uracil or dipropargyl thymine. Optimal experimental conditions were established for the conventional click chemistry. The corrosion inhibiting properties of some of these compounds, which were determined by means of an electrochemical technique, are also presented.

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Section: Introductionmentioning

confidence: 99%

Synthesis of New 1,2,3-Triazole Derivatives of Uracil and Thymine with Potential Inhibitory Activity against Acidic Corrosion of Steels

et al. 2013

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“…A few years later, other teams were interested in the synthesis of derivatives having a 1,3‐diazepine moiety, as potential HIV protease inhibitors, but these showed only weak activity 113,114 …”

Section: 3‐diazepine Derivatives As Enzyme Inhibitorsmentioning

confidence: 99%

1,3‐Diazepine: A privileged scaffold in medicinal chemistry

Malki

Martinez

Masurier

2021

Medicinal Research Reviews

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Privileged structures have been widely used as effective templates for drug discovery. While benzo‐1,4‐diazepine constitutes the first historical example of such a structure, the 1,3 analogue is just as rich in terms of applications in medicinal chemistry. The 1,3‐diazepine moiety is present in numerous biological active compounds including natural products, and is used to design compounds displaying a large range of biological activities. It is present in the clinically used anticancer compound pentostatin, in several recent FDA approved β‐lactamase inhibitors (e.g., avibactam) and also in coformycin, a natural product known as a ring‐expanded purine analogue displaying antiviral and anticancer activities. Several other 1,3‐diazepine containing compounds have entered into clinical trials. This heterocyclic structure has been and is still widely used in medicinal chemistry to design enzyme inhibitors, GPCR ligands, and so forth. This review endeavours to highlight the main use of the 1,3‐diazepine scaffold and its derivatives, and their applications in medicinal chemistry, drug design, and therapy. We will focus more particularly on the development of enzyme inhibitors incorporating this scaffold, with a strong emphasis on the molecular interactions involved in the inhibition mechanism.

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“…Based on the imidazole pharmacological importance of imidazole derivatives and in contituation of our previous work on imidazole analogues with their antiviral and anticancer activity, [22][23][24][25][26][27][28][29] we report here new derivatives of nitroimidazole-containing piperazine derivatives and evaluation of their anticancer activity as well as the molecular docking study.…”

Section: Introductionmentioning

confidence: 95%

Synthesis, anticancer activity and molecular docking studies of new 4-nitroimidazole derivatives

Al‐Soud¹,

Alhelal²,

Saeed³

et al. 2021

Arkivoc

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Imidazoles have occupied a unique position in heterocyclic chemistry, and its derivatives have attracted considerable interests in recent years for their versatile properties in chemistry and pharmacology. Herein, we report the synthesis of 3-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-ylsulfanyl)-1-(4-substituted phenyl-piperazin-1-yl)-propan-1-one 5a-p by reaction of 3-(1-benzyl-2-methyl-4-nitro-1H-imidazol-5-ylsulfanyl)-propanoyl chloride (3) with piperazine nucleophiles. Eighteen compounds were assessed for their antiproliferative inhibition potency against four human cancer cell lines (MCF-7, PC3, MDA MB231 and Du145). Compounds 5f and 5k were the most potent anticancer agents on MCF-7 cell lines cell line with IC50 value of 1.0 µg/mL, while 5d and 5m exhibited cytotoxic effect on PC3 and DU145 cell lines with IC50 values of 4.0 and 5.0 µg/mL, respectively. The molecular docking of compounds 5f, 5d and 5m has been studied.

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Nitroimidazoles Part 7. Synthesis and Anti-HIV Activity of New 4-Nitroimidazole Derivatives

Cited by 16 publications

References 17 publications

Synthesis of New 1,2,3-Triazole Derivatives of Uracil and Thymine with Potential Inhibitory Activity against Acidic Corrosion of Steels

Synthesis of New 1,2,3-Triazole Derivatives of Uracil and Thymine with Potential Inhibitory Activity against Acidic Corrosion of Steels

1,3‐Diazepine: A privileged scaffold in medicinal chemistry

Synthesis, anticancer activity and molecular docking studies of new 4-nitroimidazole derivatives

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