Design and synthesis of new fused carbazole-imidazole derivatives as anti-diabetic agents: In vitro α-glucosidase inhibition, kinetic, and in silico studies

Adib, Mehdi; Peytam, Fariba; Shourgeshty, Reihaneh; Mohammadi‐Khanaposhtani, Maryam; Jahani, Mehdi; Imanparast, Somaye; Faramarzi, Mohammad Ali; Larijani, Bagher; Moghadamnia, Ali Akbar; Esfahani, Ensieh Nasli; Bandarian, Fatemeh; Mahdavi, Mohammad

doi:10.1016/j.bmcl.2019.01.012

Cited by 35 publications

(13 citation statements)

References 19 publications

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“…The unique structural features of the five-membered imidazole and benzoimidazole moieties distinguish them as important heterocycles and these structures are part of many natural products and synthetic compounds. The electron-rich nature of the imidazole-based derivatives is useful to freely bind with various receptors and enzymes in the biological profile, thus showing broad biological activities [65,66]. Several imidazole-based molecules (oxiconazole, dacarbazine, and clotrimazole) exhibiting antifungal and anticancer activities with high therapeutic potency are clinically used as drugs ( Figure 16).…”

Section: Imidazoles and Benzoimidazolesmentioning

confidence: 99%

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

et al. 2020

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The analogs of nitrogen-based heterocycles occupy an exclusive position as a valuable source of therapeutic agents in medicinal chemistry. More than 75% of drugs approved by the FDA and currently available in the market are nitrogen-containing heterocyclic moieties. In the forthcoming decade, a much greater share of new nitrogen-based pharmaceuticals is anticipated. Many new nitrogen-based heterocycles have been designed. The number of novel N-heterocyclic moieties with significant physiological properties and promising applications in medicinal chemistry is ever-growing. In this review, we consolidate the recent advances on novel nitrogen-containing heterocycles and their distinct biological activities, reported over the past one year (2019 to early 2020). This review highlights the trends in the use of nitrogen-based moieties in drug design and the development of different potent and competent candidates against various diseases.

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Section: Imidazoles and Benzoimidazolesmentioning

confidence: 99%

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

et al. 2020

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“…Nearly two-thirds of the main small molecule drugs have a minimum one aza heterocyclic fragment in their design structures [117]. Whereas nitrogen-based synthetic heterocyclic compounds provide broad therapeutic applications in several medical categories, such as VEGFr-2 inhibitors (91) [118], anti-cancer [119], anti-tubulin (92) [120], anti-inflammatory [121], antiaging [122], anti-tumor (93) [123], anti-influenza [124], anti-tubercular [125], anti-bacterial [126], anti-diabetic [127], anti-dengue virus [128], anti-convulsant and antidepressant [129], promising antioxidant, antifungal and anti-acetylcholinesterase agents (94) [130]. Moreover, they have been widely found as a key structural material and dominate the field of dyestuff synthesis [131], agro-based chemicals [132] and supramolecular chemistry [133].…”

Section: An Overview Of Heterocycles Containing Nitrogen As Possible Therapeutic Candidatesmentioning

confidence: 99%

“…Further, it is used as a solvent for resins and terpenes which are used in paint manufacturing as well as for metallic corrosion inhibition, due to its combination of high electron density [174]. There are a number of natural products (126)(127)(128)(129) with quinoline skeleton isolated from different plant species which are used as a medicine or employed as a lead molecule for the development of newer and potent molecules [175]. Furthermore, several quinoline derivatives have been found to be used as agrochemicals as well as in the processing of dyes, food colorants and pH indicators as well as in the synthesis of other organic substances [176].…”

Section: An Overview Of Quinoline As Possible Therapeutic Candidatesmentioning

confidence: 99%

Recent investigations into synthesis and pharmacological activities of phenoxy acetamide and its derivatives (chalcone, indole and quinoline) as possible therapeutic candidates

2021

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Graphical abstract Medicinal chemistry can rightfully be regarded as a cornerstone in the public health of our modern society that combines chemistry and pharmacology with the aim of designing and developing new pharmaceutical compounds. For this purpose, many chemical techniques as well as new computational chemistry applications are used to study the utilization of drugs and their biological effects. In the biological interface, medicinal chemistry constitutes a group of interdisciplinary sciences, as well as controlling its organic, physical and computational pillars. Therefore, medicinal chemists working to design an integrated and developing system that portends an era of novel and safe tailored drugs either by synthesizing new pharmaceuticals or to improving the processes by which existing pharmaceuticals are made. It includes researching the effects of synthetic, semi-synthetic and natural biologically active substances based on molecular interactions in terms of molecular structure with triggered functional groups or the specific physicochemical properties. The present work focuses on the literature survey of chemical diversity of phenoxy acetamide and its derivatives (Chalcone, Indole and Quinoline) in the molecular framework in order to get complete information regarding pharmacologically interesting compounds of widely different composition. From a biological and industrial point of view, this literature review may provide an opportunity for the chemists to design new derivatives of phenoxy acetamide and its derivatives that proved to be the successful agent in view of safety and efficacy to enhance life quality.

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“…There are many studies in which the imidazole group shows α-glucosidase enzyme inhibition. [42][43][44][45] 3.5 | Photophysical and photochemical studies…”

Section: α-Glucosidase Inhibition Assaymentioning

confidence: 99%

Synthesis of water‐soluble phthalocyanines containing 1‐methyl‐1H‐imidazole‐2‐thiol: Investigation of DNA nuclease, α‐glucosidase inhibitory, and photo‐physicochemical properties

Günsel

Kalkan

Atmaca

et al. 2021

Applied Organom Chemis

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In this work, we have presented on the synthesis and characterization of novel 3-(1-methyl-1H-imidazole-2-thiol)phthalonitrile (1) as a ligand and its nonperipherally (M = 2H (2), Zn(II) (3), and GaCl(III) ( 4)) phthalocyanines and their highly water-soluble hydrochloride derivatives (2a-4a), containing 1-methyl-1H-imidazole-2-thiol substituents. All compounds were supported by FT-IR, UV-Vis, 1 H-NMR, 13 C-NMR, and MALDI-TOF mass spectra. The molecular structure of the novel compound (1) and its intermolecular interactions have been elucidated by analyzing the results of X-ray diffraction measurements. In order to determine the supercoiled pBR322 plasmid DNA nuclease properties of compounds (2a-4a), agarose gel electrophoresis was used. The plasmid DNA nuclease did not observe without light irradiation on increasing concentrations (2a-4a). When irradiated at 10 and 20 J/cm 2 , the band intensities changed on agarose gel, displaying photonuclease activity on supercoiled pBR322 plasmid DNA of compounds (2a-4a); 4a had the highest photonuclease activities in a concentration-dependent manner at 10 and 20 J/cm 2 . The in vitro α-glucosidase inhibitory effects of compounds (2a-4a) were investigated to determine whether they can be used in potential agents for diabetes mellitus. Compounds (2a-4a) showed higher inhibitory effects than acarbose (63.03 ± 2.14 μM) against α-glucosidase enzyme. Lineweaver-Burk analysis showed that K m increased and V max remained the same on increasing concentrations of compounds (2a-4a). The finding results claimed that the compounds inhibited α-glucosidase enzyme via competitive manner. Dixon plots showed that K i values of compounds (2a-4a) were 14.70 ± 0.70, 11.20 ± 0.50, and 12.60 ± 0.20 μM, respectively. Besides, the effect of including metal ion on photochemical and photophysical features of the compounds was studied in DMSO and water, comparatively. The compounds gave high singlet oxygen quantum yields (Φ Δ = 0.86 for (4a), 0.77 for (3a), and 0.59 for (2a)) in DMSO. The results showed that the compounds are also very suitable for photodynamic therapy applications.

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Design and synthesis of new fused carbazole-imidazole derivatives as anti-diabetic agents: In vitro α-glucosidase inhibition, kinetic, and in silico studies

Cited by 35 publications

References 19 publications

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

Recent investigations into synthesis and pharmacological activities of phenoxy acetamide and its derivatives (chalcone, indole and quinoline) as possible therapeutic candidates

Synthesis of water‐soluble phthalocyanines containing 1‐methyl‐1H‐imidazole‐2‐thiol: Investigation of DNA nuclease, α‐glucosidase inhibitory, and photo‐physicochemical properties

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