T. I. Lavrikova

Synthesis of 2-aryl-1-hydroxy-1H-naphtho[2,3-d]imidazole-4,9-diones by reaction of 2-benzylamino-1,4-naphthoquinones with nitric acid

Abstract2-Aryl-1-hydroxy-1H-naphtho[2,3-d]imidazole-4,9-diones were synthesized by treatment of 2-benzylamino-1,4-naphthoquinones with a mixture of nitric and sulfuric acids in acetic acid.

Cyclization of 2-arylamino-1,4-naphthoquinones to benzo[b]phenazine-6,11-dione 5-oxides

A method for the synthesis of a new group of tetracyclic diazaquinones, viz., benzo[b]-phenazine-6,11-dione 5-oxides, was developed and the pathways of their further modifications were outlined.

Synthesis of 2-amino(alkylamino)-3-nitro-1,4-naphthoquinones

The reaction of 2-amino(alkylamino)-1,4-naphthoquinones with nitrating mixture in concentrated sulfuric acid leads to the formation of 2-amino(alkylamino)-3-nitro-1,4-naphthoquinones.

Transformation of 2-alkylamino-1,4-naphthoquinones into 2-alkylnaphtho[2,1-d][1,3]oxazole-4,5-dione 4-oximes by the action of nitrosylsulfuric acid

Abstract2-Alkylnaphtho[2,1-d][1,3]oxazole-4,5-dione 4-oximes were synthesized by reaction of 2-alkylamino-1,4-naphthoquinones with nitrosylsulfuric acid in acetic acid.

Isomerization of 4-arylamino-1,2-naphthoquinones to 2-arylamino-1,4-naphthoquinones

Abstract4-Arylamino-1,2-naphthoquinones isomerize into 2-arylamino-1,4-naphthoquinones upon refluxing in acetic acid. The isomerization follows two routes via intermediate 2-hydroxy-1,4-naphthoquinone and 2-arylamino-1,4-naphthoquinone 4-N-arylimines.

POLYCYCLIC QUINOID COMPOUNDS AS ANTITUMOR PREPARATIONS

Сведения об авторах Гильмиярова Фрида Насыровна, Самарский государственный медицинский университет; адрес: Российская Федерация, 443099, г.Самара, ул.Чапаевская, 89; тел.: +7(846)3370463; e-mail: bio-sam@yandex.ru Рыскина Елена Анатольевна, Российский университет дружбы народов; адрес: Российская Федерация, 117198, г. Москва, ул. Миклу хо-Маклая, д. 6, тел.: +7(916)5220133; e-mail: dar31@mail.ru Колотьева Наталия Александровна, Самарский государственный медицинский университет; адрес: Российская Федерация, 443099, г.Самара, ул.Чапаевская, 89; тел.:+7(846)3370463; e-mail: bio-sam@yandex.ru Потехина Валерия Игоревна, Самарский государственный медицинский университет; адрес: Российская Федерация, 443099, г.Самара, ул.Чапаевская, 89; тел.:+7(846)3370463; e-mail: bio-sam@yandex.ru Горбачева Ирина Васильевна, Самарский государственный медицинский университет; адрес: Российская Федерация, 443099, г.Самара, ул.Чапаевская, 89; тел.:+7(846)3370463; e-mail: bio-sam@yandex.ru

DNA fluorescent labeling with naphtho[1,2,3-cd]indol-6(2H)-one for investigation of protein-DNA interactions

Fluorescently labeled DNA to study protein-DNA interactions was synthesized using the Cu(I)-catalysed cycloaddition (CuAAC) reaction. For this purpose, a new azido-containing fluorophore based on the naphtho[1,2,3-cd]indol-6(2H)-one derivative was obtained. The fluorescent properties of naphtho[1,2,3-cd]indol-6(2H)-one derivatives and labeled DNA were studied. The new fluorescent DNA conjugate was shown to be a useful tool to study complex mechanisms of protein-DNA interactions.

The Oxime Derivatives of 1-R-1H-Naphtho[2.3-d][1.2.3]triazole-4.9-dione 2-oxides: Synthesis and Properties

OBJECTIVE To synthesize a novel chemotype based on the naphthoquinone scaffold with retained cytotoxicity and provisionally low intracellular oxidation potential. BACKGROUND Derivatives of naphthoquinone, although potent anticancer agents, can exert heart toxicity due to generation of free oxygen species. METHODS In this study, we modified the scaffold by replacing one carbonyl group with the oxime moiety. Interestingly, only one carbonyl group in 1-R-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione 2-oxides reacted with hydroxylamine. The spatial structure was determined by X-ray analysis. New compounds were tested for the ability to form stable complexes with double stranded DNA by spectroscopy and molecular docking and to induce death of tumor cell lines and non-malignant counterparts. RESULTS The resulting 1-R-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione 4-oxime 2-oxides were further acylated to produce a series of 1-R-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione 4-(O-acyloxime) 2-oxides. Newly synthesized compounds demonstrated a higher (in submicromolar or low micromolar range) cytotoxic potency against human colon and breast adenocarcinoma cell lines than to non-malignant skin fibroblasts. Spectroscopic measurements revealed that, unlike other classes of quinone derivatives, new naphthotriazoledione oxides did not form stable complexes with double stranded DNA regardless of their fitting to the DNA minor groove (as determined by molecular modeling). CONCLUSION Thus, our chemical modifications yielded a new chemotype with good cytotoxic properties and yet-to-be-identified intracellular target(s).

Transformations of 2-alkylamino-1,4-naphthoquinones under the action of nitrating mixture in acetic acid

Reactions of 2-alkylamino-1,4-naphthoquinones with a nitrating mixture in acetic acid afforded 2-alkyl-1-hydroxy-1H-naphtho[2,3-d]imidazole-4,9-diones.

On the reactivity of benzo[a]phenazine-5,6-dione 7-oxides with methanolic alkali and pyrrolidine

When treated with methanolic alkali, benzo[а]phenazine-5,6-dione 7-oxides convert into 11Н-indeno[1,2-b]quinoxalin-11-ones, whereas 11-hydroxy-11-(pyrrolidine-1-carbonyl)-11Н-indeno[1,2-b]quinoxaline 10-oxides form upon treatment with pyrrolidine.