Current Researches and Applications of Azole-BasedSupermolecules as Medicinal Agents

Abstract

Noncovalent bond forces-based supramolecular chemistry grows quite rapidly and has been revealed to have extensively potential applications and huge development values in chemistry, physics, materials and information science, medicine and so on. Azole compounds such as imidazoles, thiazoles, oxazoles, pyrazoles, triazoles, tetrazoles and carbazoles containing special nitrogen aromatic heterocyclic structure, can exert non-covalent forces to form supramolecular complexes with inorganic and/or organic compounds and exhibit broad biological activity. In recent years, heterocyclic azole-based supramolecular complexes have been expeditiously expanding in the field of medicine, and have become a quite hot topic. Combined with our work and referring to other literature in recent 5 years, this paper systematically reviews the researches and applications of azole-based supermolecules as medicinal agents including anticancer, antibacterial, antifungal, antiparasitic, antidiabetic, antihypertensive, anti-inflammatory drugs and other ones. Finally, the perspectives of the future development of azole-based supermolecules as medicinal agents are also presented.

Synthesis and Biological Evaluation of Quinazolonethiazoles as New Potential Conquerors towards Pseudomonas Aeruginosa

“…All purchased reagents and solvents were used directly without further purification. Melting points: X-6 melting point apparatus; TLC analysis: pre-coated silica gel plates; 1 H NMR and 13 C NMR spectra: AVANCE III 600 MHz spectrometer with tetramethylsilane (TMS) as reference. Coupling constants (J): hertz (Hz); Signals: singlet (s), doublet (d), triplet (t), quartet (q) as well as multiplet (m); Mass spectra: LCMS-2010A; High-resolution mass spectra (HRMS): IonSpec FTICR mass spectrometer with ESI resource.…”

“…[11] This could be attributed to the unique structure of thiazole ring with both electron-donating groups (NH or S) and electron-withdrawing group (C=N), which endows it to have the multi-binding ability to functional targets through diverse weak interactions. [12][13] The successful exploitation of numerous thiazole-based medications has been stimulating immense efforts to develop the conjugates of thiazole with various pharmacophores. This conjugation strategy has occupied a prominent place in discovery of new bioactive species.…”

“…thiazole-5-H), 5.38 (s, 2H, CH 2 ), 3.78-3.73 (m, 1H, CH), 1.15-1.10 (m, 2H, cyclopropylimino-CH 2 ), 1.07 (d, J = 2.9 Hz, 2H, cyclopropylimino-CH 2 ); 13 C NMR (151 MHz, CDCl 3 ) δ: 169.94 (C=N), 160.41 (quinazolinone-4-C), 153.80, 148.98, 143.38, 140.74, 128.37, 128.00, 127.19, 122.12, 120.48, 50.92, 41.64, 35.59, 11. 16, 152.83, 149.08, 148.86, 143.25, 140.59, 128.16, 127.85, 127.05, 122.30, 120.33, 62.40, 50.79, 41.87, 34.90, 34.78, 24.95, 24.56 8.36 (s,1H,8.25 (d,J = 8.5 Hz,1H,7.99 (d,J = 3.1 Hz,1H,7.72 (d,J = 1.5 Hz,1H,7.45 (dd,J = 8.5,1.6 Hz,1H,7.38 (d,J = 3.2 Hz,1H,2H,7.16 (d,J = 8.0 Hz, 2H, Ph-2,6-H), 6.94 (t, J = 7.2 Hz, 1H, Ph-4-H), 5.27 (s, 2H, CH 2 ); 13 C NMR (151 MHz, CDCl 3 ) δ: 161. 19, 160.50, 149.20, 147.68, 143.62, 143.24, 140.78, 129.49, 128.56, 128.08, 127.34, 124.44, 122.11, 120.63, 118.65, 113.97, 48.46 (2,4-dinitrophenyl)hydrazineylidene-3-H), 8.81 (s, 1H, quinazolinone-2-H), 8.56 (dd,J = 9.4,2.3 Hz,1H,(2,hydrazineylidene-5-H), 8.13 (d,J = 8.6 Hz,1H,(2,hydrazineylidene-6-H), 2H,7.88 (d,J = 3.0 Hz,1H,7.78 (s,1H,7.58 (d,J = 8.6 Hz,1H,5.38 (s,2H,…”

“…177-178 °C; Purity: 97% 38, 152.37, 150.07, 149.01, 144.65, 142.58, 139.08, 128.18, 127.33, 126.38, 125.28, 120.26, 63.12, 46.16 Hz, 2H, OCH 2 ), 1.36 (t, J = 7.1 Hz, 3H, CH 3 ); 13 C NMR (151 MHz, CDCl 3 ) δ: 160. 33, 153.40, 148.76, 144.05, 143.33, 142.42, 140.45, 128.41, 127.80, 127.73, 126.93, 123.51, 120.68, 71.99, 46.86, 14.50 ), 0.88 (t, J = 7.4 Hz, 3H, CH 3 ); 13 C NMR (151 MHz, CDCl 3 ) δ: 162.74, 160.10, 148.83, 148.79, 148.53, 147.58, 143.31, 140.49, 128.25, 128.13, 128.06, 127.82, 126.91, 126.88, 120.57, 76.08, 50.78, 31.00, 30.74, 18.91, 13. 159.86, 152.96, 150.63, 149.58, 144.75, 143.14, 139.58, 128.70, 127.83, 127.80, 126.91, 126.81, 125.71, 120.81, 75.97, 46.73, 31.26, 28.87, 25.45, 22.29, 14.26 . 13 C NMR (151 MHz, CDCl 3 ) δ: 160.34 (C=N), 152.37, 148.43, 147.74, 143.72, 142.98, 140.69, 128.33, 127.93, 127.12, 125.08, 120.53, 114.69, 60.07, 46.97 34, 153.27, 148.69, 144.51, 143.37, 142.49, 140.44, 132.76, 132.71, 128.39, 128.24, 127.79, 127.72, 126.96, 123.76, 120.69, 119.08, 118.94, 46.83, 30.…”

Discovery of Alkaloid Quinazolone‐Derived Imidazolenones with Novel Structural Scaffolds of Multitargeting Antibacterial Potential

“…The introduction of lipophilic and hydrophilic groups could not only improve the ability of membrane targeting and hydrogen bond formation, respectively, but also regulate molecular scaffold rigidity and three‐dimensional structure. [ 15 ] Therefore, various lipophilic and hydrophilic substituents were incorporated to investigate their contribution to the antimicrobial potential.…”