3-Nitropyrimido[1,2-a]benzimidazol-4-ones: synthesis and study of alkylation reaction

Fedotov, Victor V.; Ulomskiy, E. N.; Gorbunov, Evgeny B.; Eltsov, Oleg S.; Воинков, Е. К.; Саватеев, Константин В.; Дрокин, Роман А.; Kotovskaya, S. K.; Русинов, В. Л.

doi:10.1007/s10593-017-2095-8

Cited by 8 publications

(7 citation statements)

References 23 publications

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“…In the reaction with isopropyl iodide, this ratio is 1:0.5. 74 By changing the catalyst and solvent, a team of Indian researchers obtained pyrimidobenzimidazole derivatives 133a-k via the reaction of Morita-Baylis-Hillman acetates 132a-k and 2-aminobenzimidazole (1a) (Scheme 33). 78 Another approach for the construction of polycyclic derivatives of pyrimidobenzimidazoles is the synthesis of hexacyclic derivative 135 was demonstrated in a publication from 2014.…”

Section: Scheme 29mentioning

confidence: 99%

Pyrimido[1,2-a]benzimidazoles: synthesis and perspective of their pharmacological use

Fedotov

Русинов

Ulomsky

et al. 2021

Chem Heterocycl Comp

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Nitrogen-containing heterocyclic compounds are the basis of many natural and synthetic biologically active substances. 1 More than two-thirds of the known drugs used in clinical practice contain heterocyclic and, above all, nitrogen-containing fragments within their structure. Over the past decades, the chemistry of aza-heterocycles has received considerable attention due to the wide spectrum of their biological activity and numerous therapeutic applications in medicine.Of nitrogenous heterocycles, azoloazines containing fragments similar to the natural heterocycles purines and pyrimidines are currently of great practical importance. Thus, non-natural nucleosides abacavir, famciclovir, remdesivir are known, which are the products of structural modifications of all the components of the nucleotide exhibiting excellent indicators of antiviral action (Fig. 1). [2][3][4] In addition to the generally accepted nucleoside forms, the azoloazines themselves are relevant in the search for means of combating diseases on a global scale. Nitroazolo- [5,1-c][1,2,4]triazines and nitroazolo [1,5-a]pyrimidines, a new family of antiviral compounds has been found. 5 The

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Section: Scheme 29mentioning

confidence: 99%

Pyrimido[1,2-a]benzimidazoles: synthesis and perspective of their pharmacological use

Fedotov

Русинов

Ulomsky

et al. 2021

Chem Heterocycl Comp

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“…The monitoring of the reaction progress was performed by using TLC on Silufol UV254 plates (eluent is CHCl3). Heterocycles 3b, 3d, 3e, 7, 10a, 10b were synthesized in accordance with literature data: 3b [16], 3d, 3e [17], 7 [18], 10a, 10b [19]. All synthesized compounds are >95% pure by elemental analysis.…”

Section: Chemistrymentioning

confidence: 99%

Azolo[1,5-a]pyrimidines and Their Condensed Analogs with Anticoagulant Activity

Саватеев¹,

Fedotov²,

Русинов³

et al. 2021

Preprint

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Hypercytokinemia, or cytokine storm, is one of the severe complications of viral and bacterial infections, involving the release of abnormal amounts of cytokines, resulting in a massive inflammatory response. Cytokine storm is associated with COVID-19 and sepsis high mortality rate by developing epithelial dysfunction and coagulopathy, leading to thromboembolism and multiple organ dysfunction syndrome. The anticoagulant therapy is an important tactic to prevent thrombosis in sepsis and COVID-19, but recent data show the incompatibility of modern direct oral anticoagulants and antiviral agents. It seems relevant to develop dual-action drugs with antiviral and anticoagulant properties. At the same time it was shown that azolo[1,5-a]pyrimidines are heterocycles with a broad spectrum of antiviral activity. We have synthesized a new family of azolo[1,5-a]pyrimidines and their condensed polycyclic analogs by cyclocondensation reactions and direct CH-functionalization and studied their anticoagulant properties. Five compounds among 1,2,4-triazolo[1,5-a]pyrimidin-7-ones and 5-alkyl-1,3,4-thiadiazolo[3,2-a]purin-8-ones demonstrated higher anticoagulant activity than the reference drug, dabigatran etexilate. Antithrombin activity of lead compounds was confirmed using lipopolysaccharide (LPS) treated blood to mimic conditions of cytokine release syndrome. The studied compounds affected only the thrombin time value, reliably increasing it 6.5–15.2 times as compared to LPS-treated blood.

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“…The second group contains structurally more different products (Scheme 10) that are formed by reaction with usually amino heterocycles as 1,3-binucleophiles. 36,37,62,63 The reaction was studied on trisubstituted nitroalkenes with two different nucleophiles 35,63 (Scheme 11). In both examples, a base was required to form a C-nucleophile in the first SNV step.…”

Section: Reactions With 13-binucleophiles (G)mentioning

confidence: 99%

Trisubstituted push-pull nitro alkenes

Pavilek¹,

Milata²

2021

Arkivoc

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Properties, preparations, and utilization in the organic synthesis of the trisubstituted push-pull nitroalkenes are summarized from all the relevant results published until 2020. Preparation of these nitroalkenes is versatile due to numerous of the starting materials. The importance of reviewed nitroalkenes is outlined by their frequent exploitation in the synthesis of biologically active compounds, as well as a vast range of heterocyclic derivatives.

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3-Nitropyrimido[1,2-a]benzimidazol-4-ones: synthesis and study of alkylation reaction

Cited by 8 publications

References 23 publications

Pyrimido[1,2-a]benzimidazoles: synthesis and perspective of their pharmacological use

Pyrimido[1,2-a]benzimidazoles: synthesis and perspective of their pharmacological use

Azolo[1,5-a]pyrimidines and Their Condensed Analogs with Anticoagulant Activity

Trisubstituted push-pull nitro alkenes

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