Synthesis and Pharmacological Evaluation of Novel 2,3,4,5-tetrahydro[1,3]diazepino[1,2-a]benzimidazole Derivatives as Promising Anxiolytic and Analgesic Agents

Maltsev, D. V.; Spasov, A. A.; Skripka, Maria O.; Мирошников, М. В.; Eliseeva, Natalya; Lifanova, Yu. V.; Кузьменко, Т. А.; Диваева, Л. Н.; Морковник, А. С.

doi:10.3390/molecules26196049

Cited by 5 publications

(5 citation statements)

References 30 publications

(39 reference statements)

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“…In addition to the above medical applications, benzimidazole derivatives have been widely used as an essential part of biological applications including: antihypertensive activity, 154 155 156 157 158 antiprotozoal activity, 159–163 antiviral activity, 164–167 anthelmintic activity, 168 169 170 171 172 antidiabetic agents, 173 174 175 176 177 analgesic activity, 78 , 178 179 180 181 antispasmodic activity, 182 183 antidepressant activity, 184 185 186 187 188 189 sphingosine kinase 1 inhibitor, 190 191 anti-Alzheimer’s agents, 192 193 194 angiotensin II-AT1 receptor antagonists, 195 196 197 198 199 200 antiulcer activity, 201 202 203 204 anti-tubercular activity, 205 206 207 208 209 210 211 anti-HIV agents, 212 213 214 215 216 217 218 and anti-secretory activity. 219 220 221…”

Section: Biological Activity Of Benzimidazole Derivativesmentioning

confidence: 99%

“…In addition to the above medical applications, benzimidazole derivatives have been widely used as an essential part of biological applications including: antihypertensive activity, [154][155][156][157][158] antiprotozoal activity, [159][160][161][162][163] antiviral activity, [164][165][166][167] anthelmintic activity, [168][169][170][171][172] antidiabetic agents, [173][174][175][176][177] analgesic activity, 78,[178][179][180][181] antispasmodic activity, 182,183 antidepressant activity, [184][185][186][187][188][189] sphingosine kinase 1 inhibitor, 190,191 anti-Alzheimer's agents, [192][193][194] angiotensin II-AT1 receptor antagonists, [195][196][197][198]…”

Section: Other Biological Applicationsmentioning

confidence: 99%

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A Review on Benzimidazole Heterocyclic Compounds: Synthesis and Their Medicinal Activity Applications

Alheety,

Mohammed,

Farhan

et al. 2023

SynOpen

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Benzimidazole is a heterocyclic compound formed by fusing the benzene ring with an imidazole ring that contains two nitrogen atoms. Benzimidazole and its derivatives are prepared in different ways, including condensation of o-phenylenediamine with carbonyl compounds (aldehydes and ketones) or with carboxylic acids and their derivatives. The benzimidazoles can also be prepared by rearranging other heterocyclic compounds such as quinoxaline derivatives, triazole derivatives, etc. In recent decades, benzimidazoles were prepared using green methods such as microwaves, ultrasound, and the use of an environmentally friendly catalyst, as well as photochemical reactions. Benzimidazoles have attracted the interest of scientists and researchers due to the great medical efficacy shown by them for various diseases. The benzimidazole derivatives show many pharmacological activities such as anticancer, anti-inflammatory, antioxidant, anticoagulant, antiviral, etc. This review focuses on shedding light on benzimidazole and its derivatives, the most important methods used to prepare it, as well as the biological applications in our daily lives.

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Section: Biological Activity Of Benzimidazole Derivativesmentioning

confidence: 99%

“…In addition to the above medical applications, benzimidazole derivatives have been widely used as an essential part of biological applications including: antihypertensive activity, [154][155][156][157][158] antiprotozoal activity, [159][160][161][162][163] antiviral activity, [164][165][166][167] anthelmintic activity, [168][169][170][171][172] antidiabetic agents, [173][174][175][176][177] analgesic activity, 78,[178][179][180][181] antispasmodic activity, 182,183 antidepressant activity, [184][185][186][187][188][189] sphingosine kinase 1 inhibitor, 190,191 anti-Alzheimer's agents, [192][193][194] angiotensin II-AT1 receptor antagonists, [195][196][197][198]…”

Section: Other Biological Applicationsmentioning

confidence: 99%

A Review on Benzimidazole Heterocyclic Compounds: Synthesis and Their Medicinal Activity Applications

Alheety,

Mohammed,

Farhan

et al. 2023

SynOpen

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“…Some benzimidazoles are efficient agents in Diabetes mellitus [25][26][27], while astemizole compounds possess anti-prion activity to treat Creutzfeldt-Jakob disease [5,28]. The literature also reports anti-Alzheimer [29,30], psychoactive, anxiolytic, analgesic [31,32], and anticoagulant properties [33,34] of benzimidazole derivatives.…”

Section: Introductionmentioning

confidence: 99%

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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“…These derivatives have wide potential applications such as antibacterial, antiviral, antiparasitic, anthelmintic, antitumor, anti‐inflammatory, antioxidant, antiulcer, antihypertensive, anticoagulant, antidepressant, anticonvulsant, antihistaminic, antiasthmatic, and antidiabetic agents. [ 2–11 ]…”

Section: Introductionmentioning

confidence: 99%

“…have wide potential applications such as antibacterial, antiviral, antiparasitic, anthelmintic, antitumor, anti-inflammatory, antioxidant, antiulcer, antihypertensive, anticoagulant, antidepressant, anticonvulsant, antihistaminic, antiasthmatic, and antidiabetic agents. [2][3][4][5][6][7][8][9][10][11] Although the use of compounds with an aromatic ring derived from benzimidazole as a biological agent is quite old, the study of the antimicrobial properties of these compounds accelerated in the early 1990s. For example, the group of Opferkuch, in vitro, investigated the bactericidal activities of substituted benzimidazoles against Helicobacter pylori, which is responsible for gastric acid secretion.…”

mentioning

confidence: 99%

Design, synthesis, antimicrobial activity and molecular docking study of cationic bis‐benzimidazole‐silver(I) complexes

Üstün

Şahin²,

Günal

et al. 2023

Archiv der Pharmazie

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Two series of bis(1‐alkylbenzimidazole)silver(I) nitrate and bis(1‐alkyl‐5,6‐dimethylbenzimidazole)silver(I) nitrate complexes, in which the alkyl substituent is either an allyl, a 2‐methylallyl, an isopropyl or a 3‐methyloxetan‐3‐yl‐methyl chain, were synthesized and fully characterized. The eight N‐coordinated silver(I) complexes were screened for both antimicrobial activities against Gram‐negative (Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, and Acinetobacter baumannii) and Gram‐positive (Staphylococcus aureus, Staphylococcus aureus MRSA, and Enterococcus faecalis) bacteria and antifungal activities against Candida albicans and Candida glabrata strains. Moderate minimal inhibitory concentrations (MIC) of 0.087 μmol/mL were found when the Gram‐negative and Gram‐positive bacteria were treated with the silver complexes. Nevertheless, MIC values of 0.011 μmol/mL, twice lower than for the well‐known fluconazole, against the two fungi were measured. In addition, molecular docking was carried out with the structure of Escherichia coli DNA gyrase and CYP51 from the pathogen Candida glabrata with the eight organometallic complexes, and molecular reactivity descriptors were calculated with the density functional theory‐based calculation methods.

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Synthesis and Pharmacological Evaluation of Novel 2,3,4,5-tetrahydro[1,3]diazepino[1,2-a]benzimidazole Derivatives as Promising Anxiolytic and Analgesic Agents

Cited by 5 publications

References 30 publications

A Review on Benzimidazole Heterocyclic Compounds: Synthesis and Their Medicinal Activity Applications

A Review on Benzimidazole Heterocyclic Compounds: Synthesis and Their Medicinal Activity Applications

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

Design, synthesis, antimicrobial activity and molecular docking study of cationic bis‐benzimidazole‐silver(I) complexes

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