Research Article

Design, Synthesis and Structural Characterization of Novel Thioanthraquinone Analogues from 1,5-Dichloroanthraquinone

Volume: 10 Number: 3 August 30, 2023
EN

Design, Synthesis and Structural Characterization of Novel Thioanthraquinone Analogues from 1,5-Dichloroanthraquinone

Abstract

Anthraquinone and its derivatives are considered intermediate agents with superior properties due to their activities in chemical and biological reaction. A new, economical, practical and one-step synthesis method was developed by our research team for the synthesis of amino and thioanthraquinones in previous studies (1). With this synthesis method, thioanthraquinone analogs 2(a-d) were obtained from 1,5-Dichloroanthraquinone (1) and bioactive thiols. The synthesized organic molecules were purified by column chromatography and their structures were identified with spectroscopic methods. Fluorescence analyzes of synthesized thioanthraquinone analogues were performed. It was determined that all thioanthraquinone analogues synthesized and characterized in the study showed fluorescence activity. These new analogues with fluorescence are expected to find application in drug delivery systems and sensor studies.

Keywords

Thanks

I am grateful to Istanbul University-Cerrahpaşa Chemistry Department, Eskişehir Osmangazi University Central Research Laboratory Application and Research Center (ARUM) and Kastamonu University Central Research Laboratory Application and Research Center for laboratory and analysis.

References

  1. 1. Ozkok F, Şahin YM. Biyoaktif antrakinon anologlarının sentezine yönelik özgün metot geliştirilmesi. TURKEY; TR 2016/19610; 2016.
  2. 2. Lytle NK, Barber AG, Reya T. Stem cell fate in cancer growth, progression and therapy resistance. Nat Rev Cancer [Internet]. 2018 Nov 18;18(11):669–80.
  3. 3. Stasevich M V., Zvarich VI, Novikov VP, Zagorodnyaya SD, Povnitsa OY, Chaika MA, et al. 9,10-Anthraquinone Dithiocarbamates as Potential Pharmaceutical Substances with Pleiotropic Actions: Computerized Prediction of Biological Activity and Experimental Validation. Pharm Chem J [Internet]. 2020 Jan 16;53(10):905–13.
  4. 4. Mohamadzadeh M, Zarei M, Vessal M. Synthesis, in vitro biological evaluation and in silico molecular docking studies of novel β-lactam-anthraquinone hybrids. Bioorg Chem [Internet]. 2020 Jan;95:103515.
  5. 5. Zvarych V, Stasevych M, Novikov V, Rusanov E, Vovk M, Szweda P, et al. Anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones as a New Class of Antistaphylococcal Agents: Synthesis and Biological Evaluation. Molecules [Internet]. 2019 Dec 13;24(24):4581.
  6. 6. Comini LR, Núñez Montoya SC, Páez PL, Argüello GA, Albesa I, Cabrera JL. Antibacterial activity of anthraquinone derivatives from Heterophyllaea pustulata (Rubiaceae). J Photochem Photobiol B Biol [Internet]. 2011 Feb 7;102(2):108–14.
  7. 7. Wang Q, Wang Y, Li Y, Wen B, Dai Z, Ma S, et al. Identification and characterization of the structure–activity relationships involved in UGT1A1 inhibition by anthraquinone and dianthrone constituents of Polygonum multiflorum. Sci Rep [Internet]. 2017 Dec 20;7(1):17952.
  8. 8. Shadrack DM, K. Ndesendo VM. Molecular Docking and ADMET Study of Emodin Derivatives as Anticancer Inhibitors of NAT2, COX2 and TOP1 Enzymes. Comput Mol Biosci [Internet]. 2017 Mar 16;07(01):1–18.

Details

Primary Language

English

Subjects

Organic Chemistry, Organic Chemical Synthesis

Journal Section

Research Article

Publication Date

August 30, 2023

Submission Date

January 22, 2023

Acceptance Date

June 22, 2023

Published in Issue

Year 2023 Volume: 10 Number: 3

APA
Özkök, F. (2023). Design, Synthesis and Structural Characterization of Novel Thioanthraquinone Analogues from 1,5-Dichloroanthraquinone. Journal of the Turkish Chemical Society Section A: Chemistry, 10(3), 671-676. https://doi.org/10.18596/jotcsa.1240673
AMA
1.Özkök F. Design, Synthesis and Structural Characterization of Novel Thioanthraquinone Analogues from 1,5-Dichloroanthraquinone. JOTCSA. 2023;10(3):671-676. doi:10.18596/jotcsa.1240673
Chicago
Özkök, Funda. 2023. “Design, Synthesis and Structural Characterization of Novel Thioanthraquinone Analogues from 1,5-Dichloroanthraquinone”. Journal of the Turkish Chemical Society Section A: Chemistry 10 (3): 671-76. https://doi.org/10.18596/jotcsa.1240673.
EndNote
Özkök F (August 1, 2023) Design, Synthesis and Structural Characterization of Novel Thioanthraquinone Analogues from 1,5-Dichloroanthraquinone. Journal of the Turkish Chemical Society Section A: Chemistry 10 3 671–676.
IEEE
[1]F. Özkök, “Design, Synthesis and Structural Characterization of Novel Thioanthraquinone Analogues from 1,5-Dichloroanthraquinone”, JOTCSA, vol. 10, no. 3, pp. 671–676, Aug. 2023, doi: 10.18596/jotcsa.1240673.
ISNAD
Özkök, Funda. “Design, Synthesis and Structural Characterization of Novel Thioanthraquinone Analogues from 1,5-Dichloroanthraquinone”. Journal of the Turkish Chemical Society Section A: Chemistry 10/3 (August 1, 2023): 671-676. https://doi.org/10.18596/jotcsa.1240673.
JAMA
1.Özkök F. Design, Synthesis and Structural Characterization of Novel Thioanthraquinone Analogues from 1,5-Dichloroanthraquinone. JOTCSA. 2023;10:671–676.
MLA
Özkök, Funda. “Design, Synthesis and Structural Characterization of Novel Thioanthraquinone Analogues from 1,5-Dichloroanthraquinone”. Journal of the Turkish Chemical Society Section A: Chemistry, vol. 10, no. 3, Aug. 2023, pp. 671-6, doi:10.18596/jotcsa.1240673.
Vancouver
1.Funda Özkök. Design, Synthesis and Structural Characterization of Novel Thioanthraquinone Analogues from 1,5-Dichloroanthraquinone. JOTCSA. 2023 Aug. 1;10(3):671-6. doi:10.18596/jotcsa.1240673

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