Additional file 1 of Synthesis, antimicrobial and antioxidant activity of triazole, pyrazole containing thiazole derivatives and molecular docking studies on COVID-19
Creators: name: Matta, Raghavender
name: Pochampally, Jalapathi
name: Dhoddi, Bala Narsimha
name: Bhookya, Shankar
name: Bitla, Sampath
name: Akkiraju, Anjini Gayatri
Publisher: name: figshare
Year: 2023
Subjects: subject: Organic Chemistry
subject: FOS: Chemical sciences

description: Additional file 1: Fig. S1. 1H-NMR of 1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-pyrazole-4-carbaldehyde (8a, C25H19N5O2). Fig. S2. 13C-NMR of 1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-pyrazole-4-carbaldehyde (8a,C25H19N5O2). Fig. S3. 1H-NMR of 3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde (8b, C25H18ClN5O2). Fig. S4. 13C-NMR of 3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde (8b, C25H18ClN5O2). Fig. S5. 1H-NMR of 3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde (8c, C27H23N5O2). Fig. S6. 13C-NMR of 3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde (8c, C27H23N5O2). Fig. S7. 1H-NMR of 4-(4-bromophenyl)-2-(2-((1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)meth-oxy)-phenyl)-1H-pyrazol-4-yl)methylene) hydrazinyl) thiazole (12a, C34H25BrN8OS). Fig. S8. 13C-NMR of 4-(4-bromophenyl)-2-(2-((1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)meth-oxy)-phenyl)-1H-pyrazol-4-yl)methylene) hydrazinyl) thiazole (12a, C34H25BrN8OS). Fig. S9. FT-IR of 4-(4-bromophenyl)-2-(2-((1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)meth-oxy)-phenyl)-1H-pyrazol-4-yl)methylene) hydrazinyl) thiazole (12a, C34H25BrN8OS). Fig. S10. Mass of 4-(4-bromophenyl)-2-(2-((1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)meth-oxy)-phenyl)-1H-pyrazol-4-yl)methylene) hydrazinyl) thiazole (12a, C34H25BrN8OS). Fig. S11. 1H-NMR of 4-(4-chlorophenyl)-2-(2-((1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)meth-oxy)-phenyl)-1H-pyrazol-4-yl)methylene)hydrazinyl) thiazole (12b, C34H25ClN8OS). Fig. S12. 13C-NMR of 4-(4-chlorophenyl)-2-(2-((1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)meth-oxy)-phenyl)-1H-pyrazol-4-yl)methylene)hydrazinyl) thiazole (12b, C34H25ClN8OS). Fig. S13. FT-IR of 4-(4-chlorophenyl)-2-(2-((1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)meth-oxy)-phenyl)-1H-pyrazol-4-yl)methylene)hydrazinyl) thiazole (12b, C34H25ClN8OS). Fig. S14. ESI-Mass of 4-(4-chlorophenyl)-2-(2-((1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)meth-oxy)-phenyl)-1H-pyrazol-4-yl)methylene)hydrazinyl) thiazole (12b, C34H25ClN8OS). Fig. S15. 1H-NMR of 4-(4-methoxyphenyl)-2-(2-((1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)meth-oxy)-phenyl)-1H-pyrazol-4-yl)methylene)hydrazinyl) thiazole (12c,C35H28N8O2S). Fig. S16. 13C-NMR of 4-(4-methoxyphenyl)-2-(2-((1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)meth-oxy)-phenyl)-1H-pyrazol-4-yl)methylene)hydrazinyl) thiazole (12c,C35H28N8O2S). Fig. S17. FT-IR of 4-(4-methoxyphenyl)-2-(2-((1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)meth-oxy)-phenyl)-1H-pyrazol-4-yl)methylene)hydrazinyl) thiazole (12c,C35H28N8O2S). Fig. S18. ESI-Mass of 4-(4-methoxyphenyl)-2-(2-((1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)meth-oxy)-phenyl)-1H-pyrazol-4-yl)methylene) hydrazinyl)thiazole (12c,C35H28N8O2S). Fig. S19. 1H-NMR of 4-phenyl-2-(2-((1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-pyrazol-4-yl)methylene)hydrazinyl)thiazole (12d, C34H26N8OS). Fig. S20. 13C-NMR of 4-phenyl-2-(2-((1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-pyrazol-4-yl)methylene)hydrazinyl)thiazole (12d, C34H26N8OS). Fig. S21. ESI-Mass of 4-phenyl-2-(2-((1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-pyrazol-4-yl)methylene)hydrazinyl)thiazole (12d, C34H26N8OS). Fig. S22. ESI-Mass of 4-phenyl-2-(2-((1-phenyl-3-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-pyrazol-4-yl)methylene)hydrazinyl)thiazole (12d, C34H26N8OS). Fig. S23. 1H-NMR of 4-(4-chlorophenyl)-2-(2-((3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazinyl)thiazole (12e, C34H24Cl2N8OS). Fig. S24. 13C-NMR of 4-(4-chlorophenyl)-2-(2-((3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazinyl)thiazole (12e, C34H24Cl2N8OS). Fig. S25. FT-IR of 4-(4-chlorophenyl)-2-(2-((3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazinyl)thiazole (12e, C34H24Cl2N8OS). Fig. S26. ESI-Mass of 4-(4-chlorophenyl)-2-(2-((3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazinyl)thiazole (12e, C34H24Cl2N8OS). Fig. S27. 1H-NMR of 4-(4-bromophenyl)-2-(2-((3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazinyl)thiazole (12f, C34H24BrClN8OS). Fig. S28. 13C-NMR of 4-(4-bromophenyl)-2-(2-((3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazinyl)thiazole (12f, C34H24BrClN8OS). Fig. S29. FT-IR of 4-(4-bromophenyl)-2-(2-((3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazinyl)thiazole (12f, C34H24BrClN8OS). Fig. S30. ESI-Mass of 4-(4-bromophenyl)-2-(2-((3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazinyl)thiazole (12f, C34H24BrClN8OS). Fig. S31. 1H-NMR of 2-(2-((3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)-4-(4-methoxyphenyl)thiazole(12g, C35H27ClN8O2S). Fig. S32. 13C-NMR of 2-(2-((3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)-4-(4-methoxyphenyl)thiazole(12g, C35H27ClN8O2S). Fig. S33. FT-IR of 2-(2-((3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)-4-(4-methoxyphenyl)thiazole(12g, C35H27ClN8O2S). Fig. S34. ESI-Mass of 2-(2-((3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)-4-(4-methoxyphenyl)thiazole(12g, C35H27ClN8O2S). Fig. S35. 1H-NMR of 2-(2-((3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)-4-phenylthiazole(12h, C34H25ClN8OS). Fig. S36. 13C-NMR of 2-(2-((3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)-4-phenylthiazole(12h, C34H25ClN8OS). Fig. S37. FT-IR of 2-(2-((3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)-4-phenylthiazole(12h, C34H25ClN8OS). Fig. S38. ESI-Mass of 2-(2-((3-(4-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)-4-phenylthiazole(12h, C34H25ClN8OS). Fig. S39. 1H-NMR of 2-(2-((3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)-4-(4-methoxyphenyl)thiazole (12i, C37H32N8O2S). Fig. S40. 13C-NMR of 2-(2-((3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)-4-(4-methoxyphenyl)thiazole (12i, C37H32N8O2S). Fig. S41. FT-IR of 2-(2-((3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)-4-(4-methoxyphenyl)thiazole (12i, C37H32N8O2S). Fig. S42. ESI-Mass of 2-(2-((3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)-4-(4-methoxyphenyl)thiazole (12i, C37H32N8O2S). Fig. S43. 1H-NMR of 4-(4-chlorophenyl)-2-(2-((3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)thiazole(12j,C36H29ClN8OS). Fig. S44. 13C-NMR of 4-(4-chlorophenyl)-2-(2-((3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)thiazole(12j,C36H29ClN8OS). Fig. S45. FT-IR of 4-(4-chlorophenyl)-2-(2-((3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)thiazole(12j,C36H29ClN8OS). Fig. S46. ESI-Mass of 4-(4-chlorophenyl)-2-(2-((3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)thiazole(12j,C36H29ClN8OS). Fig. S47. 1H-NMR of 4-(4-bromophenyl)-2-(2-((3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)thiazole(12k, C36H29BrN8OS). Fig. S48. 13C-NMR of 4-(4-bromophenyl)-2-(2-((3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)thiazole(12k, C36H29BrN8OS). Fig. S49. FT-IR of 4-(4-bromophenyl)-2-(2-((3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)thiazole(12k, C36H29BrN8OS). Fig. S50. ESI-Mass of 4-(4-bromophenyl)-2-(2-((3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)thiazole(12k, C36H29BrN8OS). Fig. S51. 1H-NMR of 2-(2-((3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl) methylene)hydrazinyl)-4-phenylthiazole(12l,C36H30N8OS). Fig. S52. 13C-NMR of 2-(2-((3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl) methylene)hydrazinyl)-4-phenylthiazole(12l,C36H30N8OS). Fig. S53. FT-IR of 2-(2-((3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl) methylene)hydrazinyl)-4-phenylthiazole(12l,C36H30N8OS). Fig. S54. ESI-Mass of 2-(2-((3-(4-((1-(3,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-phenyl-1H-pyrazol-4-yl) methylene)hydrazinyl)-4-phenylthiazole(12l,C36H30N8OS). Fig. S55. Zone of inhibition test for antimicrobial activity. Table S1. MIC of synthesized 12a-lcompounds (μg/ml) against gram-positive and gram-negative bacterial strains