Synthesis, Characterization and Bioactivity Research of a Derivative of Secnidazole: 1-(2-Chloropropyl)-2-methyl-5-nitro-1H-imidazole

Huang, Xi-Shou; Wang, Lisheng; Yin, Yuan‐Qi; Li, Wan-Mei; Duan, Man; Wei, Ran; Zhu, Hai‐Liang

doi:10.1007/s10870-011-0104-9

Cited by 5 publications

(2 citation statements)

References 11 publications

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“…Lots of research showed that structural modification of the imidazole ring by suitable alkyl side chain was favorable for effective interaction with the hydrophobic parts of target enzymes and thereby resulted in enhanced antibacterial activities. Numerous imidazole derivatives characterized with a certain length of alkyl linkers between the imidazole ring and an additional function group have been reported to manifest good antibacterial activities …”

Section: Imidazoles As Antibacterial Agentsmentioning

confidence: 99%

Comprehensive Review in Current Developments of Imidazole-Based Medicinal Chemistry

et al. 2013

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Imidazole ring is an important five-membered aromatic heterocycle widely present in natural products and synthetic molecules. The unique structural feature of imidazole ring with desirable electron-rich characteristic is beneficial for imidazole derivatives to readily bind with a variety of enzymes and receptors in biological systems through diverse weak interactions, thereby exhibiting broad bioactivities. The related research and developments of imidazole-based medicinal chemistry have become a rapidly developing and increasingly active topic. Particularly, numerous imidazole-based compounds as clinical drugs have been extensively used in the clinic to treat various types of diseases with high therapeutic potency, which have shown the enormous development value. This work systematically gives a comprehensive review in current developments of imidazole-based compounds in the whole range of medicinal chemistry as anticancer, antifungal, antibacterial, antitubercular, anti-inflammatory, antineuropathic, antihypertensive, antihistaminic, antiparasitic, antiobesity, antiviral, and other medicinal agents, together with their potential applications in diagnostics and pathology. It is hoped that this review will be helpful for new thoughts in the quest for rational designs of more active and less toxic imidazole-based medicinal drugs, as well as more effective diagnostic agents and pathologic probes.

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Section: Imidazoles As Antibacterial Agentsmentioning

confidence: 99%

Comprehensive Review in Current Developments of Imidazole-Based Medicinal Chemistry

et al. 2013

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“…Secnidazole (SNZ) is known as an antimicrobial drug that can be used against some kinds of bacteria and parasites of anaerobicity, like trichomonas, giardia, and ameba, which are responsible for somewhat neglected diseases. It is named (hydroxyl-2-propyl)-1-methyl-2-nitro-5-imidazole) (Figure 1) as stated by the classification of IUPAC, It is part of the chemical class of 5-nitro-imidazoles, and its structure is related to the tinidazole and metronidazole [1][2][3][4], that used against an assortment of 𝐺𝐺 + /𝐺𝐺 − bacteria, but with severe side effects as to make use of it in high concentrations [5]. This medicine is provided as a white powder crystalline, and although it has been sold for a few decades, thus with a consolidated request, this active substance is not listed at all by the pharmacopeias.…”

Section: Introductionmentioning

confidence: 99%

DFT modelling studies of spectroscopic properties and Medium Effects on Molecular Reactivity of Secnidazole in different solvents

Hssain

2022

Journal of Physical Chemistry and Functional Materials

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The spectroscopic and optoelectronic investigations of (hydroxyl-2-propyl)-1-methyl-2-nitro-5-imidazole (secnidazole, C_7 H_11 N_3 O_3) molecule were performed using C13 and H1 NMR chemical shifts, FT-IR spectroscopies. Molecular geometric optimizations, HOMO-LUMO properties and molecular electrostatic potential (MPE) were studied using B3LYP functional in DFT method at the cc-pVDZ basis set. UV-Vis spectra of the titled molecule in several solvents (water, dimethyl sulfoxide (DMSO), nitromethane, acetone, and tetrahydrofuran (THF) were investigated theoretically with the aforementioned model method. The solvents have an effective role in the optoelectronic properties of the secnidazole molecule. From non-polar to polar solvents, the (HOMO and LUMO) bandgap energy of secnidazole was found to be decreased except THF solvent. Furthermore, the research aims at investigating the medium effects on solvation free energy, polarizability, dipole moment, first-order hyper-polarizability as well as several molecular properties such as chemical potential, electronegativity, chemical hardness and softness, electrophilicity index of secnidazole (SNZ). The aforementioned method and basis set was used for all kinds of computations in the gas phase and solution. The Solvation Model on Density (SMD) was applied to the aforementioned solvent systems to calculate the solvent polarity effect on dipole moment, free energy, and molecular properties of the (SNZ) molecule. The free energies have gradually increased with a decrease in the solvent dielectric constant i.e. as solvent polarity decreases, the solvation energy increases. From polar to non-polar solvents, the dipole moment of secnidazole was found to be decreased. In various solvents, the dipole moment of secnidazole was greater than that of the gas phase. With the decrease of the solvent dielectric constant, the first-order hyperpolarizability and polarizability have also been decreased. Besides, electronegativity, the chemical potential, and electrophilicity index were decreased continuously from polar to non-polar solvent, except in THF. Secnidazole’s electronegativity, chemical potential, and electrophilicity index were higher in THF than in acetone. However, with increasing solvent polarity, chemical hardness decreased and the inverse relationship was noticed in the case of chemical softness. The obtaining results in this computational investigation may lead to a better understanding of the stability and reactivity of secnidazole and will be helpful for the use of the title compound as reaction intermediates and pharmaceuticals.

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Imidazole heterocycles: Therapeutically potent lead compounds as antimicrobials

Sahiba

Sethiya

Agarwal

2022

Imidazole-Based Drug Discovery

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Synthesis, Characterization and Bioactivity Research of a Derivative of Secnidazole: 1-(2-Chloropropyl)-2-methyl-5-nitro-1H-imidazole

Cited by 5 publications

References 11 publications

Comprehensive Review in Current Developments of Imidazole-Based Medicinal Chemistry

Comprehensive Review in Current Developments of Imidazole-Based Medicinal Chemistry

DFT modelling studies of spectroscopic properties and Medium Effects on Molecular Reactivity of Secnidazole in different solvents

Imidazole heterocycles: Therapeutically potent lead compounds as antimicrobials

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