Synthesis of Benzimidazole–Based Analogs as Anti Alzheimer’s Disease Compounds and Their Molecular Docking Studies

Adalat, Bushra; Taha, Muhammad; Alshamrani, Foziah; Anouar, El Hassane; Uddin, Nizam; Ali, Zarshad; Zakaria, Zainul Amiruddin

doi:10.3390/molecules25204828

Cited by 24 publications

(10 citation statements)

References 27 publications

(26 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%

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%

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

Alheety,

Mohammed,

Farhan

et al. 2023

SynOpen

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“…6, 144.6, 132.8, 130.3, 122.0, 119.2, 110.5, 35.0; MS (EI, 70 eV) m/z 265,232,207,188,174,156,121,91,imidazol-2-yl)thio)methyl)benzoate (4i). 25 Eluent: petroleum ether/ethyl acetate (v/v = 5:1). White solid: 61% yield (36.4 mg, 0.12 mmol); m.p.…”

Section: The Journal Of Organic Chemistrymentioning

confidence: 99%

DBU-Promoted Deaminative Thiolation of 1H-Benzo[d]imidazol-2-amines and Benzo[d]oxazol-2-amines

et al. 2022

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A facile and efficient catalyst-/metal-/oxidant-free DBU-promoted deaminative thiolation reaction of 1H-benzo[d]imidazol-2-amines and benzo[d]oxazol-2-amines has been developed at room temperature conditions in a one-pot protocol. This practical three-component strategy represents a novel and environmentally friendly reaction pathway toward the straightforward synthesis of various 2-thio-1H-benzo[d]imidazoles and 2thiobenzo[d]oxazoles using carbon disulfide as a sulfur source through C−N bond cleavage and C−S bond formation process. Different types of 1H-benzo[d]imidazol-2-amines, benzo[d]oxazol-2-amines, and organic bromides are suitable substrates. The gram-scale and late-stage modification experiments provide the potential applications based on this methodology in the field of organic and medicinal chemistry.

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“…Dementia is one of the major global challenges today. This dementia is mainly caused by Alzheimer’s disease (AD) [ 1 ]. The number of Alzheimer’s patients increases day by day as the population and age increase, by 2023 it will be up to 74.7 million people suffering from AD [ 2 ].…”

Section: Introductionmentioning

confidence: 99%

Biologically Potent Benzimidazole-Based-Substituted Benzaldehyde Derivatives as Potent Inhibitors for Alzheimer’s Disease along with Molecular Docking Study

et al. 2023

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Twenty-one analogs were synthesized based on benzimidazole, incorporating a substituted benzaldehyde moiety (1–21). These were then screened for their acetylcholinesterase and butyrylcholinesterase inhibition profiles. All the derivatives except 13, 14, and 20 showed various inhibitory potentials, ranging from IC50 values of 0.050 ± 0.001 µM to 25.30 ± 0.40 µM against acetylcholinesterase, and 0.080 ± 0.001 µM to 25.80 ± 0.40 µM against butyrylcholinesterase, when compared with the standard drug donepezil (0.016 ± 0.12 µM and 0.30 ± 0.010 µM, against acetylcholinesterase and butyrylcholinesterase, respectively). Compound 3 in both cases was found to be the most potent compound due to the presence of chloro groups at the 3 and 4 positions of the phenyl ring. A structure-activity relationship study was performed for all the analogs except 13, 14, and 20, further, molecular dynamics simulations were performed for the top two compounds as well as the reference compound in a complex with acetylcholinesterase and butyrylcholinesterase. The molecular dynamics simulation analysis revealed that compound 3 formed the most stable complex with both acetylcholinesterase and butyrylcholinesterase, followed by compound 10. As compared to the standard inhibitor donepezil both compounds revealed greater stabilities and higher binding affinities for both acetylcholinesterase and butyrylcholinesterase.

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Synthesis of Benzimidazole–Based Analogs as Anti Alzheimer’s Disease Compounds and Their Molecular Docking Studies

Cited by 24 publications

References 27 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

DBU-Promoted Deaminative Thiolation of 1H-Benzo[d]imidazol-2-amines and Benzo[d]oxazol-2-amines

Biologically Potent Benzimidazole-Based-Substituted Benzaldehyde Derivatives as Potent Inhibitors for Alzheimer’s Disease along with Molecular Docking Study

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