Electrophilic reactions as methods of modification of pyrrolobenzimidazolones and pyrroloquinazolinones
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Electrophilic reactions as methods of modification of pyrrolobenzimidazolones and pyrroloquinazolinones Vyacheslav S. Grinev1,2*, Alevtina Yu. Egorova1 1
Saratov State University named after N. G. Chernyshevsky, 83 Astrakhanskaya St,, Saratov 410012, Russia; e-mail: [email protected] 2 Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 Entuziastov Ave., Saratov 410049, Russia Submitted April 28, 2020 Accepted May 21, 2020
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(7), 923–929
The publication presents a number of modifications based on electrophilic reactions of previously synthesized biologically active benzannulated pyrrolo[1,2-a]imidazolones and pyrrolo[2,1-b]quinazolinones, which make it possible to widely change the physicochemical properties of molecules. Quantitative assessments of the lipophilicity of all synthesized compounds were carried out, on the basis of which conclusions were made regarding the advisability of introducing alkyl and trifluoroacetyl groups to increase the bioavailability of compounds by increasing their lipophilicity to 40%. Keywords: pyrrolo[1,2-a]benzimidazolones, lipophilicity, methylation, trifluoroacylation.
pyrrolo[2,1-b]quinazolinones,
bioavailability,
electrophilic
reactions,
7-arylazo derivatives was structurally characterized.6 Other synthetic possibilities of modification 2,3,3a,4-tetrahydro1H-pyrrolo[1,2-a]benzimidazol-1-ones remain unexplored. Pyrrolo[2,1-b]quinazolinones, benzannulated analogs of pyrrolo[2,1-b]pyrimidinones, exhibit somewhat higher conformational mobility due to the presence of an additional methylene unit in the diazaalkane ring, and therefore the synthesis and study of their properties are also promising.
It is known that polyheterocycles containing a pyrrolidone ring have a high synthetic potential, and the preparation of their functionalized derivatives leads to the formation of extensive libraries of compounds that are used, among other things, in agriculture and medicine.1 At the same time, the chemical properties of condensed bicyclic perhydropyrrolo[2,1-b]oxazolone systems exhibiting pronounced biological activity have been studied in acylation and hydrogenation reactions,2,3 but publications on this topic are sporadic. Benzannulated derivatives, both benzopyrrolo[2,1-b]oxazolones and their nitrogen-containing analogs benzopyrrolo[1,2-a]imidazolones, possess antiinflammatory, antinociceptive, immunomodulatory, and antioxidant effects,4 while at the same time retaining a significant potential for chemical modifications, due to which interest in them has recently grown. Previously, we identified the characteristics of the nitrosation reaction of 3a-substituted 2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-ones, proposed a probable reaction mechanism, including the initial attack by the nitrosonium ion at the secondary amino group followed by the Fischer–Hepp rearrangement leading to the formation of 7-nitroso derivatives (Scheme 1).5 Also, one representative of 0009
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