Crystal Growth, Single Crystal Structure, and Biological Activity of Thiazolo-Pyridine Dicarboxylic Acid Derivatives

Hamdi Ben Yahia; Souhir Sabri; Rachid Essehli; Peter Kasak; Joanna Drogosz-Stachowicz; Anna Janecka; Brahim El Bali

doi:10.1021/acsomega.0c01769

Crystal Growth, Single Crystal Structure, and Biological Activity of Thiazolo-Pyridine Dicarboxylic Acid Derivatives

ACS Omega. 2020 Oct 22;5(43):27756-27765. doi: 10.1021/acsomega.0c01769. eCollection 2020 Nov 3.

Authors

Hamdi Ben Yahia¹, Souhir Sabri¹, Rachid Essehli², Peter Kasak³, Joanna Drogosz-Stachowicz⁴, Anna Janecka⁴, Brahim El Bali⁵

Affiliations

¹ Qatar Environment and Energy Research Institute (QEERI 2.0), Hamad Bin Khalifa University, Qatar Foundation, P.O. Box 34110 Doha, Qatar.
² Energy and Transportation Science Division, Oak Ridge National Laboratory, Oak Ridge, 37831-2008 Tennessee, United States.
³ Centre for Advanced Materials (CAM), Qatar University, 2713 Doha, Qatar.
⁴ Department of Biomolecular Chemistry, Medical University of Lodz, Mazowiecka 6/8, 92-215 Lodz, Poland.
⁵ Independent scientist, LMSAC, Po. Box 717, Oujda 60000, Morocco.

Abstract

Four novel TPDCA derivatives were prepared via a supersaturation method combining TPDCA with water, N-methyl-2-pyrrolidone (NMP), Na(PO₂H₂), and ammonia solution: 2(C₉H₇NO₅S)H₂O (1), (C₉H₇NO₅S)C₅H₉NO (2), (C₉H₇NO₅S)Na(PO₂H₂) (3), and (C₉H₅NO₅S)(NH₄)₂(H₂O) (4). Their crystal structures were determined by single-crystal X-ray diffraction. Compounds (1) and (2) crystallize in the monoclinic space groups P2₁ and P2₁/c, respectively, whereas compounds (3) and (4) crystallize in the triclinic space group P1̅. Weak and moderate hydrogen bonds were detected in the four compounds. In the biological tests, (1) and (3) exhibited significant antibacterial activity against Escherichia coli and Staphylococcus aureus; in addition, (1) was cytotoxic against leukemia HL-60 cells with the IC₅₀ value of 158.5 ± 12.5 μM.