SYNTHESIS AND ANTIMICROBIAL EVALUATION OF BIS-NAPHTHALIMIDE DERIVATIVES

Assoc. Prof. Marin Marinov, PhD

Faculty of Plant Protection and Agroecology Department of Chemistry, Phytopharmacy, Ecology and Environmental Protection Agricultural University - Plovdiv

E-mail: m_n_marinov@abv.bg

Chief Assist. Prof. Iliana Nikolova, PhD

Department of Chemical, Food and Biotechnologies “Angel Kanchev” University of Ruse, Razgrad Branch

ORCID: 0000-0003-0191-3189

E-mail: inikolova@uni-ruse.bg

Chief Assist. Prof. Rumyana Prodanova, PhD

Faculty of Plant Protection and Agroecology Department of Chemistry, Phytopharmacy, Ecology and Environmental Protection Agricultural University - Plovdiv

E-mail: ru_prodanovakam@abv.bg

Assoc. Prof. Iliana Kostova, PhD

Department of Chemical, Food and Biotechnologies “Angel Kanchev” University of Ruse, Razgrad Branch

ORCID: 0000-0003-1595-773X

E-mail: ikostova@uni-ruse.bg

Abstract

This work presents a new method for the synthesis of bis-naphthalimide derivatives based on the reaction of 2- (2-aminoethyl)-1H-benzo[de]isoquinoline-1,3(2H)-diones with 1H,3H-naphtho[1,8-cd]pyran-1,3-diones. The structures of the newly synthesized products were confirmed by melting points, R_f values, IR, ¹H NMR, ¹³C NMR, and ¹³C DEPT 135 spectroscopy. The antimicrobial activity of the obtained bis-naphthalimides was evaluated against Gram-positive and Gram-negative bacteria.

Keywords

bis-naphthalimides, IR, ¹H NMR, ¹³C NMR, ¹³C DEPT 135, antimicrobial activity

REFERENCES

Bagale, S. M. (2011). Synthesis of fluorescent analogs of neurotransmitters. Thesis, University of Miami.
Braña, M. F., Cacho, M., Ramos, A., Domínguez, M. T., Pozuelo, J. M., Abradelo, C., Rey-Stolle, M. F., Yuste, M., Carrasco, C. & Bailly, C. (2003). Synthesis, biological evaluation and DNA binding properties of novel mono and bisnaphthalimides. Organic & Biomolecular Chemistry, 1 (4), 648-654.
Braña, M. F., Castellano, J. M., Perron, D., Maher, C., Conlon, D., Bousquet, P. F., George, J., Qian , X.-D. & Robinson, S. P. (1997). Chromophore-modified bis-naphthalimides: synthesis and anti-tumor activity of bis-dibenz[de,h]isoquinoline-1,3-diones. Journal of Medicinal Chemistry, 40 (4), 449-454.
Georgiev, N. I., Bojinov, V. B. & Nikolov, P. S. (2009). Design and synthesis of a novel pH sensitive core and peripherally 1,8-naphthalimide-labeled PAMAM dendron as light harvesting antenna. Dyes and Pigments, 81 (1), 18-26.
Hussein, K. N., Molnár, T., Pinter R., Toth, A., Ayari, E., Friedrich, L., Dalmadi, I. & Kiskó, G. (2021). In vitro antimicrobial activity of plant active components against Pseudomonas lundensis and Listeria monocytogenes. Progress in Agricultural Engineering Sciences, 16, 163-172.
Kazhoka, Kh. A. & Meyrovits, I. A. (1983). N-Zameshchennyye imidy 4-bromnaftalevoy kisloty. Izvestiya Akademii nauk Latviyskoy SSR, Seriya khimicheskaya, 2, 238-240 (in Russian).
Marinov, M., Nikolova, I. & Kostova, I. Synthesis and antimicrobial study of 6-phenothiazin-10-yl- benzo[de]isoquinoline-1,3-dione derivatives. In press.
Palhares, D. R. (2015). Synthesis and biological evaluation of mono and bis-naphthalimide derivatives against SH-SY5Y, human brain cancer cells. Master Thesis, Universidade do Minho.
Rule, H. G. & Thompson, S. B. (1937). Bromo- and nitro-derivatives of naphthalic acid. Journal of the Chemical Society, 1764-1767.
Zhong, K., Liu, H., Jin, S. & Chen, X. (2021). Design of fluorescence turn-on sensors with novel response mechanism based on C=N isomerization. Dyes and Pigments, 195, 109714.