Biomedical applications of selective metal complexes of indole, benzimidazole, benzothiazole and benzoxazole: A review (From 2015 to 2022)

Awadh, Ahmed Abdullah Al

doi:10.1016/j.jsps.2023.101698

Cited by 11 publications

(6 citation statements)

References 102 publications

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“…The complex showed the highest activity against A. niger (16 mm) and low activity against E. coli fungal strains (15 mm) (Table 2) [60]. The improved activity of the complexes in relation to their ligands can be explained based on Overtone's concept and Tweedy's chelation theory [46,56]. Kavitha et al evaluated 34 (Scheme 5) for its antibacterial and antifungal activity against Gram-positive Staphylococcus Sp.…”

Section: Singh Et Al Synthesized An Imine Ligand By the Condensation ...mentioning

confidence: 99%

“…The fungus C. albicans was resistant to both iron complexes and showed no significant antifungal activity (Table 2). Overtone's permeability concept and Tweedy's chelation theory can both be used to explain why coordination compounds have more activity than their parent ligands [46,56]. The complexes become more permeable when a metal ion is present because they dissolve in lipids and enter the cell more readily, causing negative changes in the cell environment and its enzymes, further hindering the microbe's growth.…”

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Iron–Imine Cocktail in Drug Development: A Contemporary Update

Anane,

Owusu,

Rivera

et al. 2024

IJMS

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Organometallic drug development is still in its early stage, but recent studies show that organometallics having iron as the central atom have the possibility of becoming good drug candidates because iron is an important micro-nutrient, and it is compatible with many biological systems, including the human body. Being an eco-friendly Lewis acid, iron can accept the lone pair of electrons from imino(sp2)-nitrogen, and the resultant iron–imine complexes with iron as a central atom have the possibility of interacting with several proteins and enzymes in humans. Iron–imine complexes have demonstrated significant potential with anticancer, bactericidal, fungicidal, and other medicinal activities in recent years. This article systematically discusses major synthetic methods and pharmacological potentials of iron–imine complexes having in vitro activity to significant clinical performance from 2016 to date. In a nutshell, this manuscript offers a simplistic view of iron complexes in medicinal inorganic chemistry: for instance, iron is presented as an “eco-friendly non-toxic” metal (as opposed to platinum) that will lead to non-toxic pharmaceuticals. The abundant literature on iron chelators shows that many iron complexes, particularly if redox-active in cells, can be quite cytotoxic, which can be beneficial for future targeted therapies. While we made every effort to include all the related papers, any omission is purely unintentional.

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Section: Singh Et Al Synthesized An Imine Ligand By the Condensation ...mentioning

confidence: 99%

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confidence: 99%

Iron–Imine Cocktail in Drug Development: A Contemporary Update

Anane,

Owusu,

Rivera

et al. 2024

IJMS

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“…Benzimidazole is widely used in antihypertensive, antituberculous, anti-inflammatory, antibacterial, antiviral, analgesic, antihypertensive, antibacterial, and rare applications in cardiovascular diseases. ,− Vitamin B12 consists of benzimidazole, and also thiabendazole, azomycin, chlotrimazole, mebendazole, Omeprazole and albendazole, rabeprazole are the important drugs composed of benzimidazole derivatives. , The synthesis of benzimidazole and quinazoline is 100% atom efficient due to 100% utilization of CO 2 and other substrates . Traditionally, benzimidazole was synthesized from DMF (dimethylformamide) derivatives, formic acid, esters, and methanol. − Benzimidazole was synthesized using a basic medium or strong medium, toxic reagents and high temperatures, but nowadays the synthesis is more environmentally friendly and sustainable by using catalysts. , Another important intermediate used in the pharmaceutical industry is quinazolines-2,4(1 H ,3 H )-diones synthesized by harmful chemicals such as anthranilamide with phosgene, anthranilic acid with urea, and antranilic acid with chlorosulfonyl isocyanate or potassium cyanate (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Fixation of CO₂ into Quinazoline and Benzimidazole

Rajanna,

Srinivasappa,

Sudhakaran

et al. 2024

Energy Fuels

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CO 2 is an important component of the atmosphere that helps in balancing the Earth's atmospheric temperature and channelizes the food cycles. However, an increase or decrease in the concentration will severely affect the climate. Particularly, the rise in CO 2 levels has immensely contributed to global warming, resulting in elevated atmospheric temperature, altered precipitation patterns, glacier melting, and subsequent rises in sea levels, impacting human well-being. In response, researchers are exploring strategies to capture and convert CO 2 into valuable products, such as methanol, formic acid, and organic compounds. Particularly, the synthesis of organic compounds using CO 2 , like benzimidazole and quinazolines, has a high impact. Benzimidazole, widely used in medicinal chemistry for treating cancer and stomach ulcers, also exhibits antiviral and antifungal properties. Quinazoline derivatives, essential in drugs like prazosin and doxazosin, have applications in treating post-traumatic stress disorder and Alzheimer's disease. These compounds were synthesized mainly using environmentally harmful synthons such as phosgene and potassium cyanide. To address both environmental and health concerns, researchers are delving into the chemical fixation of CO 2 for sustainable and green production. Catalysis emerges as a key principle in green chemistry, with catalysts reducing activation energy and facilitating sustainable processes. This review discusses recent state of the art on the development of various catalysts for conversion of CO 2 to quinazoline and benzimidazole, through various homogeneous and heterogeneous catalysts. Notably, while homogeneous catalysts lack industrial recyclability, heterogeneous catalysts show promise for large-scale implementation. This comprehensive review discusses the mechanistic aspects with DFT studies in understanding the catalysts better. Toward the end, it gives the future scope and aspects on this subject.

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“…Over the past two decades, benzothiazole compounds have attracted considerable research attention due to their distinctive structure and diverse biological activities, including anti-tumor (Kamal et al, 2010;Kamal et al, 2011;El-Helby et al, 2019;Makowska et al, 2019;Mokesch et al, 2020), anti-inflammatory (Lee et al, 2011;Kumar and Singh, 2021), neuroprotective (Choi et al, 2007), antibacterial (Al-Tel et al, 2011;Racané et al, 2020), and antiparasitic (Awadh, 2023) activities, etc. In recent years, extensive research has focused on modifying the benzothiazole nucleus to enhance its anti-tumor activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of novel benzothiazole derivatives as potential anticancer and antiinflammatory agents

Xu,

Zhu,

Chen

et al. 2024

Front. Chem.

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Introduction: Cancer, a significant global health concern, necessitates innovative treatments. The pivotal role of chronic inflammation in cancer development underscores the urgency for novel therapeutic strategies. Benzothiazole derivatives exhibit promise due to their distinctive structures and broad spectrum of biological effects. This study aims to explore new anti-tumor small molecule drugs that simultaneously anti-inflammatory and anticancer based on the advantages of benzothiazole frameworks.Methods: The compounds were characterized by nuclear magnetic resonance (NMR), liquid chromatograph-mass spectrometer (LC-MS) and high performance liquid chromatography (HPLC) for structure as well as purity and other related physicochemical properties. The effects of the compounds on the proliferation of human epidermoid carcinoma cell line (A431) and human non-small cell lung cancer cell lines (A549, H1299) were evaluated by MTT method. The effect of compounds on the expression levels of inflammatory factors IL-6 and TNF-α in mouse monocyte macrophages (RAW264.7) was assessed using enzyme-linked immunosorbent assay (ELISA). The effect of compounds on apoptosis and cell cycle of A431 and A549 cells was evaluated by flow cytometry. The effect of compounds on A431 and A549 cell migration was evaluated by scratch wound healing assay. The effect of compounds on protein expression levels in A431 and A549 cells was assessed by Western Blot assay. The physicochemical parameters, pharmacokinetic properties, toxicity and drug similarity of the active compound were predicted using Swiss ADME and admetSAR web servers.Results: Twenty-five novel benzothiazole compounds were designed and synthesized, with their structures confirmed through spectrogram verification. The active compound 6-chloro-N-(4-nitrobenzyl) benzo[d] thiazol-2-amine (compound B7) was screened through a series of bioactivity assessments, which significantly inhibited the proliferation of A431, A549 and H1299 cancer cells, decreased the activity of IL-6 and TNF-α, and hindered cell migration. In addition, at concentrations of 1, 2, and 4 μM, B7 exhibited apoptosis-promoting and cell cycle-arresting effects similar to those of the lead compound 7-chloro-N-(2, 6-dichlorophenyl) benzo[d] thiazole-2-amine (compound 4i). Western blot analysis confirmed that B7 inhibited both AKT and ERK signaling pathways in A431 and A549 cells. The prediction results of ADMET indicated that B7 had good drug properties.Discussion: This study has innovatively developed a series of benzothiazole derivatives, with a focus on compound B7 due to its notable dual anticancer and anti-inflammatory activities. B7 stands out for its ability to significantly reduce cancer cell proliferation in A431, A549, and H1299 cell lines and lower the levels of inflammatory cytokines IL-6 and TNF-α. These results position B7B7 as a promising candidate for dual-action cancer therapy. The study’s mechanistic exploration, highlighting B7’s simultaneous inhibition of the AKT and ERK pathways, offers a novel strategy for addressing both the survival mechanisms of tumor cells and the inflammatory milieu facilitating cancer progression.

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Biomedical applications of selective metal complexes of indole, benzimidazole, benzothiazole and benzoxazole: A review (From 2015 to 2022)

Cited by 11 publications

References 102 publications

Iron–Imine Cocktail in Drug Development: A Contemporary Update

Iron–Imine Cocktail in Drug Development: A Contemporary Update

Recent Advances in the Fixation of CO₂ into Quinazoline and Benzimidazole

Synthesis and biological evaluation of novel benzothiazole derivatives as potential anticancer and antiinflammatory agents

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Biomedical applications of selective metal complexes of indole, benzimidazole, benzothiazole and benzoxazole: A review (From 2015 to 2022)

Cited by 11 publications

References 102 publications

Iron–Imine Cocktail in Drug Development: A Contemporary Update

Iron–Imine Cocktail in Drug Development: A Contemporary Update

Recent Advances in the Fixation of CO2 into Quinazoline and Benzimidazole

Synthesis and biological evaluation of novel benzothiazole derivatives as potential anticancer and antiinflammatory agents

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Product

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Recent Advances in the Fixation of CO₂ into Quinazoline and Benzimidazole