Design, synthesis, spectroscopic characterization, single crystal X-ray analysis, in vitro α-amylase inhibition assay, DPPH free radical evaluation and computational studies of naphtho[2,3-d]imidazole-4,9-dione appended 1,2,3-triazoles

Devi, Meena; Kumar, Parvin; Singh, Rahul; Sindhu, Jayant; Kataria, Ramesh

doi:10.1016/j.ejmech.2023.115230

Cited by 11 publications

(2 citation statements)

References 59 publications

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“…As expected, the literature mentions benzimidazole-triazole hybrids with other biological properties than those studied in this review, such as antitumor [15,48,[75][76][77][78][79][80][81][82][83][84][85][86][87][88][89][90][91][92], antioxidant [93][94][95], anti-Alzheimer [96][97][98][99], antidiabetic [100][101][102][103][104], and anti-inflammatory [105] properties, which is additional proof of the therapeutic potential of these hybrids and the need to study these hybrids on the topic proposed in the title. As expected, the study refers to both 1,2,3-triazole-benzimidazole hybrids and 1,2,4-triazole-benzimidazole hybrids, even if it seems that the literature is richer in the second category in terms of antimicrobial activity.…”

Section: Introductionsupporting

confidence: 70%

Benzimidazole-Triazole Hybrids as Antimicrobial and Antiviral Agents: A Systematic Review

Marinescu

2023

Antibiotics

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Bacterial infections have attracted the attention of researchers in recent decades, especially due to the special problems they have faced, such as their increasing diversity and resistance to antibiotic treatment. The emergence and development of the SARS-CoV-2 infection stimulated even more research to find new structures with antimicrobial and antiviral properties. Among the heterocyclic compounds with remarkable therapeutic properties, benzimidazoles, and triazoles stand out, possessing antimicrobial, antiviral, antitumor, anti-Alzheimer, anti-inflammatory, analgesic, antidiabetic, or anti-ulcer activities. In addition, the literature of the last decade reports benzimidazole-triazole hybrids with improved biological properties compared to the properties of simple mono-heterocyclic compounds. This review aims to provide an update on the synthesis methods of these hybrids, along with their antimicrobial and antiviral activities, as well as the structure–activity relationship reported in the literature. It was found that the presence of certain groups grafted onto the benzimidazole and/or triazole nuclei (-F, -Cl, -Br, -CF3, -NO2, -CN, -CHO, -OH, OCH3, COOCH3), as well as the presence of some heterocycles (pyridine, pyrimidine, thiazole, indole, isoxazole, thiadiazole, coumarin) increases the antimicrobial activity of benzimidazole-triazole hybrids. Also, the presence of the oxygen or sulfur atom in the bridge connecting the benzimidazole and triazole rings generally increases the antimicrobial activity of the hybrids. The literature mentions only benzimidazole-1,2,3-triazole hybrids with antiviral properties. Both for antimicrobial and antiviral hybrids, the presence of an additional triazole ring increases their biological activity, which is in agreement with the three-dimensional binding mode of compounds. This review summarizes the advances of benzimidazole triazole derivatives as potential antimicrobial and antiviral agents covering articles published from 2000 to 2023.

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Section: Introductionsupporting

confidence: 70%

Benzimidazole-Triazole Hybrids as Antimicrobial and Antiviral Agents: A Systematic Review

Marinescu

2023

Antibiotics

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“…According to their place of origin and structural makeup, proteinaceous amylase inhibitors are divided into seven categories, [43] namely the knottin-like type, the thaumatin-like type, the Kunitz type, the cereal type, the γthionin-like type, the lectin-like type, and the microbial type. The non-proteinaceous α-amylase inhibitor includes a variety of organic compounds such as imidazole, [44] pyrazole, [45] thiazolidinone, [34b] chalcone, [46] thiazoles, [47] flavones, [48] spirooxidnoles, [34a] etc. α-Amylase is a crucial therapeutic target that has been used to create a number of synthetic commercial drugs, including acarbose, voglibose, and miglitol [49] (Figure 10).…”

Section: Classification Of α-Amylase Inhibitorsmentioning

confidence: 99%

α‐Amylase Inhibitors Based on Thiazolidinone Skeleton: A Promising Approach in Diabetes Management

Singh,

Sindhu,

Kumar

et al. 2023

ChemistrySelect

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Thiazolidinone scaffold has become a promising scaffold when it comes to therapeutic importance, and researchers are quite interested in it because of its wide range of applications in the different fields of chemistry. The capacity of this nucleus to interact with a variety of biological targets, including the peroxisome proliferator‐activated receptor (PPAR), protein tyrosine phosphatase 1B, aldose reductase, α‐glucosidase, and α‐amylase, has led to the observation of its antidiabetic effect. α‐Amylase (α‐1,4‐glucan‐4‐glucanohydrolase, EC 3.2.1.1) is one of the most important industrial endoamylases capable of hydrolyzing the internal α‐1,4‐glycosidic bonds in polysaccharides with net retention of α‐anomeric configuration in low molecular weight products, such as glucose, maltose, and maltotriose units. The inhibitors of α‐amylase have the ability to lower endogenous activity, which is crucial for the management of agricultural pests as well as the treatment and prevention of human disorders. In the present review, we attempted to compile the most recent studies on thiazolidinone‐based α‐amylase inhibitors, investigate their therapeutic potential in treating diabetes, comprehend the relationships between structure and activity, offer suggestions for future research and translation of these findings into clinical applications. This comprehensive review strives to be a valuable resource for researchers, medicinal chemists, and healthcare professionals involved in developing and applying novel therapeutics for treating metabolic disorders.

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Recent pharmacological insights about imidazole hybrids: a comprehensive review

Poyraz,

Yıldırım,

Ersatir

2024

Med Chem Res

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Design, synthesis, spectroscopic characterization, single crystal X-ray analysis, in vitro α-amylase inhibition assay, DPPH free radical evaluation and computational studies of naphtho[2,3-d]imidazole-4,9-dione appended 1,2,3-triazoles

Cited by 11 publications

References 59 publications

Benzimidazole-Triazole Hybrids as Antimicrobial and Antiviral Agents: A Systematic Review

Benzimidazole-Triazole Hybrids as Antimicrobial and Antiviral Agents: A Systematic Review

α‐Amylase Inhibitors Based on Thiazolidinone Skeleton: A Promising Approach in Diabetes Management

Recent pharmacological insights about imidazole hybrids: a comprehensive review

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