Synthesis and properties of carbazole derivatives of 1,4-naphthoquinone
Students Name: Protsiv Dmytro Mykolaiovych
Qualification Level: master (ESP)
Speciality: Pharmacy, Industrial Pharmacy
Institute: Institute of Chemistry and Chemical Technologies
Mode of Study: full
Academic Year: 2020-2021 н.р.
Language of Defence: ukrainian
Abstract: Protsiv D. M.; Khomyak S.V. (supervisor). «Synthesis and properties of carbazole derivatives of 1,4-naphthoquinone». Master`s thesis. – Lviv Polytechnic National University, Lviv, 2021. Extended abstract Study object - amino and amino acid derivatives of carbazole-naphthoquinone. Scope of research – chemistry of quinoid compounds. Goal of research – synthesis, studying of a structure and properties of amino and amino acid derivatives of 1,4-naphthoquinones and clarification of possible ways of their practical application. The growing interest in the study of quinoid systems is due to their wide synthetic capabilities, in addition, many compounds of this class have in their assets a range of practically useful properties, which opens up a wide range of their practical applications. The search for new drugs, pesticides, dyes leads to a relentless interest in the study of these compounds. In addition, quinoid systems are widespread in nature and play an exceptional role in the biochemical processes of a living organism. However, despite many years of studying quinones, there are a number of unresolved issues, including those related to the study of nucleophilic substitution reactions in carbazole-substituted naphthoquinones, followed by the production of compounds with amino and amino acid moieties in their structure, the study of the latter. Despite the purely scientific interest, knowledge of the basic laws of these processes allows them to be used to solve practical problems. The reaction of nucleophilic substitution of 2-(9H-carbazolyl-9)-3-chloro-1,4-naphthoquinone with amines and amino acids with the preparation of 2-carbazolo-3-aminosubstituted 1,4-naphthoquinone derivatives was mainly studied. At the same time the schemes of possible routes of a course of these reactions are offered. Preparative methods of synthesis have been developed and the optimal conditions for obtaining 1,4-naphthoquinone derivatives with amino, amino acid and other fragments in their structure have been determined. The structure of the obtained new compounds is substantiated by modern spectral methods. Among the compounds synthesized in the work were found those that are characterized by the presence of biological activity, in particular, antitubercular, fungicidal, as confirmed by relevant studies. In the calculation part, the material balance of all stages of production of one of the synthesized compounds, namely - 2-(9H-carbazolyl-9)-3-chloro-1,4-naphthoquinone. A basic technological scheme for the production process of 2-(9H-carbazolyl-9)-3-chloro-1,4-naphthoquinone has also been developed and designed. In the economic part of the work, technical-economic indicators were calculated and the economic feasibility of this work was proved. The conclusions formulated in the paper are in accordance with the literature data and are based on experimental material using modern physicochemical research methods (1H NMR, IR spectroscopy). Key words: 1,4-naphthoquinone, carbazole, amino acid derivatives, predicted biological activity, design calculation. References: 1. Hardesh K. Maurya. (2019). Synthetic and biological utility of 2,3-dichloro-1,4-naphthoquinone: a review. International Journal of Research -Granthaalayah, 7(10), 293-347. https://doi.org/10.29121/granthaalayah.v7.i10.2019.399. 2. Ghulam Abbas, Zahid Hassan, Ahmed Al-Harrasi, Ajmal khan, Ahmed Al-Adawi, Majid Ali. (2019). Synthesis, biological evaluation, molecular docking and structure-activity relationship studies of halogenated quinone and naphthoquinone derivatives. Journal of Molecular Structure, Volume 1195, 462-469. https://doi.org/10.1016/j.molstruc.2019.06.002. 3. Sanchez-Calvo, J.M., Barbero, G.R., Guerrero-Vasquez, G. et al. (2016). Synthesis, antibacterial and antifungal activities of naphthoquinone derivatives: a structure–activity relationship study. Med Chem Res 25, 1274–1285 https://doi.org/10.1007/s00044-016-1550-x. 4. Фігурка О.М, Губрій З.В., Губицька І.І, Хом’як С.В. Амінопохідні карбазолзаміщеного 1,4-нафтохінону // Вісник НУ «Львівська політехніка»: Хімія, технологія речовин та їх застосування. – 2016. – № 841. - С. 258–264. http://science.lpnu.ua/uk/node/3840