Multicomponent Reaction of 2-aminobenzimidazole, Arylglyoxals, and 1,3-cyclohexanedione

Petrova, O. N.; Zamigajlo, Lali L.; Ostras, Konstantin S.; Shishkina, S. V.; Шишкин, Олег В.; Борисов, А. В.; Мусатов, Владимир И.; Широбокова, М. Г.; Липсон, В. В.

doi:10.1007/s10593-015-1700-y

Cited by 21 publications

(17 citation statements)

References 20 publications

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“…Scheme 3 describes the proposed reaction mechanism for the formation of the regioisomers. Initially, the electron pair of the nitrogen exo located in C-2 is introduced and is directed towards the N -3 endo (tautomeric electron transfer to Petrova et al) [ 33 ]. The anion formed nucleophilic ally displaces the chlorine from the amide, where the N 1 enters its electron pair system to regenerate aromaticity, leading to the formation of the reigoisomer mixture.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of 2-(2-Amino-5(6)-nitro-1H-benzimidazol-1-yl)-N-arylacetamides as Antiprotozoal Agents

et al. 2017

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Parasitic diseases are a public health problem affecting millions of people worldwide. One of the scaffolds used in several drugs for the treatment of parasitic diseases is the benzimidazole moiety, a heterocyclic aromatic compound. This compound is a crucial pharmacophore group and is considered a privileged structure in medicinal chemistry. In this study, the benzimidazole core served as a model for the synthesis of a series of 2-(2-amino-5(6)-nitro-1H-benzimidazol-1-yl)-N-arylacetamides 1–8 as benznidazole analogues. The in silico pharmacological results calculated with PASS platform exhibited chemical structures highly similar to known antiprotozoal drugs. Compounds 1–8 when evaluated in silico for acute toxicity by oral dosing, were less toxic than benznidazole. The synthesis of compounds 1–8 were carried out through reaction of 5(6)-nitro-1H-benzimidazol-2-amine (12) with 2-chlroactemides 10a–h, in the presence of K2CO3 and acetonitrile as solvent, showing an inseparable mixture of two regioisomers with the -NO2 group in position 5 or 6 with chemical yields of 60 to 94%. The prediction of the NMR spectra of molecule 1 coincided with the experimental chemical displacements of the regioisomers. Comparisons between the NMR prediction and the experimental data revealed that the regioisomer endo-1,6-NO2 predominated in the reaction. The in vitro antiparasitic activity of these compounds on intestinal unicellular parasites (Giardia intestinalis and Entamoeba histolytica) and a urogenital tract parasite (Trichomonas vaginalis) were tested. Compound 7 showed an IC50 of 3.95 μM and was 7 time more active against G. intestinalis than benznidazole. Compounds 7 and 8 showed 4 times more activity against T. vaginalis compared with benznidazole.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of 2-(2-Amino-5(6)-nitro-1H-benzimidazol-1-yl)-N-arylacetamides as Antiprotozoal Agents

et al. 2017

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“…Orange crystals; yield 86%; mp 213–215°C [lit. , mp 210–212°C]. 1 H‐NMR δ (ppm): 8.30 (d, J = 7.2 Hz, 2H, Ar H), 7.56 (t, J = 6.9 Hz, 1H, Ar H), 7.48 (t, J = 7.2 Hz, 2H, Ar H), 5.44 (s, 1H, CH), 2.71 (t, J = 6.6 Hz, 1H), 2.65 (t, J = 6.6 Hz, 1H), 2.59 (t, J = 6.6 Hz, 1H), 2.53 (t, J = 6.6 Hz, 1H), 2.44–2.28 (m, 4H, 2 × CH 2 ), 2.09–1.99 (m, 4H, 2 × CH 2 ).…”

Section: Methodsmentioning

confidence: 99%

A Facile Synthesis of Xanthene‐1,8(2H)‐dione Derivatives by Using Tetrapropylammonium Bromide as Catalyst

Marjani

Abdollahi

Ezzati

et al. 2018

Journal of Heterocyclic Chem

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“…A multicomponent reaction involving 2-aminobenzimidazole ( 48 ), cyclohexanedione ( 2a ) and arylglyoxales 83 was thoroughly studied by Petrova et al ( 2015b ); all the compounds including intermediates were isolated in individual form, characterized and their structures were proven with the help of X-Ray analysis (Figure 7 ).…”

Section: Main Partmentioning

confidence: 99%

Aminoazole-Based Diversity-Oriented Synthesis of Heterocycles

et al. 2018

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Multicomponent Reaction of 2-aminobenzimidazole, Arylglyoxals, and 1,3-cyclohexanedione

Cited by 21 publications

References 20 publications

Design, Synthesis and Biological Evaluation of 2-(2-Amino-5(6)-nitro-1H-benzimidazol-1-yl)-N-arylacetamides as Antiprotozoal Agents

Design, Synthesis and Biological Evaluation of 2-(2-Amino-5(6)-nitro-1H-benzimidazol-1-yl)-N-arylacetamides as Antiprotozoal Agents

A Facile Synthesis of Xanthene‐1,8(2H)‐dione Derivatives by Using Tetrapropylammonium Bromide as Catalyst

Aminoazole-Based Diversity-Oriented Synthesis of Heterocycles

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