Synthesis, structure, and antimicrobial activity of a series of novel heterocyclic azo-colorants derived from α-dicarbonyl compounds

Synthesis, structure, and antimicrobial activity of a series of novel heterocyclic azo-colorants derived from α-dicarbonyl compounds Full article

Journal

RSC Advances
ISSN: 2046-2069

Output data

Year: 2026, Volume: 16, Number: 26, Pages: 24128-24140 Pages count : 13 DOI: 10.1039/d5ra10033j

Authors

Vu Thi Ngoc Anh ^1,2 , Polyanskaya Nadezhda ^3,4,5 , Bozhenkova Svetlana ^3,6 , Khrustalev Viktor ^4,7 , Utenyshev Andrey ^3,8 , Shetnev Anton ⁹ , Filenko Igor ⁶ , Huynh Minh Chin ¹⁰ , Nguyen Anh Van ¹¹ , Kovalchukova Olga ^3,4

Affiliations

1	Faculty of Applied Sciences, Ton Duc Thang University, No. 19 Nguyen Huu Tho Street, Tan Phong Ward, District 7, Ho Chi Minh City, 700000, Vietnam
2	Laboratory of Advanced Materials Chemistry, Institute for Advanced Study in Technology, Ton Duc Thang University, No. 19 Nguyen Huu Tho Street, Tan Phong Ward, District 7, Ho Chi Minh City, 700000, Vietnam
3	A.N. Kosygin Russian State University, 1-3, Malaya Kaluzhskaya Str., Moscow 117997, Russia
4	Peoples' Friendship University of Russia (RUDN University), 6, Miklukho-Maklaya Str., Moscow 117197, Russia
5	Petrovsky Medical University, 3, Tsuriupy Str., Moscow 117418, Russia
6	Russian Institute for Scientific and Technical Information (VINITI RAS), 20, Usievich Str., Moscow, 125315, Russia
7	Zelinsky Institute of Organic Chemistry of RAS, 47 Leninsky Prospect, 119991 Moscow, Russian Federation
8	Federal Research Center of Problem of Chemical Physics and Medicinal Chemistry RAS, 1, Academician Semenov Avenue, Chernogolovka, Moscow Region, 142432, Russia
9	Yaroslavl State Pedagogical University Named After K.D. Ushinsky, 108, Respublikanskaya Str., Yaroslavl, 150000, Russia
10	Ho Chi Minh City Department of Health, Ho Chi Minh City, 700000, Vietnam
11	Faculty of Food Science and Technology, Ho Chi Minh City University of Industry and Trade, Ho Chi Minh City, 700000, Vietnam

Six novel azo-compounds derived from α-dicarbonyl species, such as 9,10-phenanthrene quinone, squaric acid and ammonium 2,3,5,6-tetraoxo-4-nitropyridinate, were isolated by reactions with a series of heterocyclic hydrazides and characterized by a set of methods. The spectral studies (FT-IR and 1H NMR), together with theoretical DFT modeling and X-ray structure description, of two compounds revealed the hydrazone tautomeric forms of the molecules. Antimicrobial activity against biofilm-forming bacteria was assessed using a turbidimetric method. Growth inhibition was monitored to determine the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) for both Gram-positive and Gram-negative strains. The possibility of a hemolytic effect of the compounds on human red blood cells was evaluated. The ADMET analysis indicated that all the studied compounds obeyed Lipinski's and Veber's rules of the drug discovery pipeline and offered oral bioavailability and positive blood–brain barrier permeability, indicating their potential as therapeutic lead-like compounds. According to the Toxtree analysis, all investigated compounds were categorized as Class I, indicating they belong to the low-toxicity group. The molecular interactions and inhibitory potential underlying the antimicrobial activities of the selected compounds were investigated using molecular docking methods.

Vu T.N.A. , Polyanskaya N. , Bozhenkova S. , Khrustalev V. , Utenyshev A. , Shetnev A. , Filenko I. , Huynh M.C. , Nguyen A.V. , Kovalchukova O.
Synthesis, structure, and antimicrobial activity of a series of novel heterocyclic azo-colorants derived from α-dicarbonyl compounds
RSC Advances. 2026. V.16. N26. P.24128-24140. DOI: 10.1039/d5ra10033j OpenAlex

Submitted:	Dec 26, 2025
Published online:	May 8, 2026

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