Supplementary Material
for
SYNTHESIS, STRUCTURAL CHARACTERIZATION AND BIOLOGICAL
EVALUATION OF NOVEL SUBSTITUTED 1,3-THIAZOLE DERIVATIVES
CONTAINING SCHIFF BASES
Hakan Tahtaci,a Mustafa Er,b* Tuncay Karakurt,c Abdurrahman Onarand
a
Department of Polymer Engineering, Faculty of Technology, Karabuk University, 78050
Karabuk, Turkey.
E-mail address: hakantahtaci@karabuk.edu.tr
b
*Department of Chemical Engineering, Faculty of Engineering, Karabuk University, 78050
Karabuk, Turkey. Tel: +90 370 433 83 74, Fax: +90 370 433 83 34
E-mail address: mustafaer@karabuk.edu.tr
c
Department of Chemical Engineering, Faculty of Engineering and Architecture, Ahi Evran
University, 40100, Kırşehir, Turkey.
E-mail address: tuncay-karakurt@hotmail.com
d
Department of Plant Protection, Faculty of Agriculture, Ahi Evran University, 40100, Kırşehir,
Turkey. E-mail address: abdonaran@hotmail.com
S1
Effect of the compounds on the antifungal activity of in vitro
The antifungal activities of the compounds were determined by agar well diffusion method [1].
Different compound of concentration (10 mg, 5 mg and 2,5 mg/mL) was obtained with dissolved
in dimethyl sulfoxide (DMSO). DMSO (100 µL/well-1) was used as a negative control (C-).
Thiram 80% (Commercial dose, Hekthiram Forte, Hektas Group) was used as a positive control
(C+). The PDA was poured into 90 mm petri plates (~20 mL/plate-1). Four (5 mm diameter)
wells were opened by sterile cork borer, 30 mm far from centre, on the PDA plate. Each plate
was contained 3 different concentration (10 mg, 5 mg and 2,5 mg/mL) of compound and one
negative control (DMSO). Each dose (100 µL/well-1) was added the well and kept at room
temperatures during 2 hours for diffusing. The PDA plates were incubated (in the centre of PDA)
with 5 mm plugs from 7-day-old cultures. The plates were incubated at 22±2 oC for 7 d.
Experiment was set up 3 replicates and repeated 2 times. All data were recorded. All antifungal
activities values were determined by measuring inhibition zone distance between pathogen and
well (compounds filled).
Antifungal activity determination: The activity index of the compounds was determined by the
following formula [2].
The activity index = Inhibition zone of compounds / Inhibition zone of standarda
a
Standard: Inhibition zone of positive control
Percentage inhibition: Percentage of inhibition was calculated according to the following
formula; [3]
% Inhibition= Inhibition zone in treatment /Controlb x 100
b
Control: Inhibition zone of positive control
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REFERENCES
[1] Grammar, A. 6th edition, Collins C. H.; Lyne P. M.; Grange J. M. (Eds.), Bulterworths and
Co. Ltd., London, 235 pp. 1976.
[2] Jain, N.; Sharma, M. Curr Sci 2005, 85(1), 30.
[3] Vyas, Y. K.; Bhatnagar, M.; Sharma, K. J. J Cell Tissue Res 2006, 6(1), 639.
S3
Figure S1. Part of the crystal structure of the compound 3b, showing C-H…O stacking
interactions. For the sake of clarity, H atoms not involved in the motifs shown have been
omitted.
Table S1. Hydrogen bonding geometry (Å, º) for the compound 3b.
D–H….A
D–H
H….A
D….A
D–H….A
C2–H2… O3i
0.96(2)
2.56(2)
3.52(3)
170(3)
Symmetry code: i = x, 1/2-y, -1/2+z
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Figure S2. Crystal packing of the compound 3b, crystal structure projected into bc plane. The
dashed lines indicate the intermolecular hydrogen bonds.
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Figure S3. 1H NMR Spectrum (DMSO-d6) (3a)
Figure S4. 13C NMR Spectrum (DMSO-d6) (3a)
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Figure S5. 1H NMR Spectrum (DMSO-d6) (3b)
Figure S6. 13C NMR Spectrum (DMSO-d6) (3b)
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Figure S7. 1H NMR Spectrum (DMSO-d6) (3c)
Figure S8. 13C NMR Spectrum (DMSO-d6) (3c)
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Figure S9. 1H NMR Spectrum (DMSO-d6) (5a)
Figure S10. 1H NMR Exchange Spectrum (DMSO-d6 + D2O) (5a)
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Figure S11. 13C NMR Spectrum (DMSO-d6) (5a)
Figure S12. 1H NMR Spectrum (DMSO-d6) (5b)
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Figure S13. 1H NMR Exchange Spectrum (DMSO-d6 + D2O) (5b)
Figure S14. 13C NMR Spectrum (DMSO-d6) (5b)
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Figure S15. 1H NMR Spectrum (DMSO-d6) (5c)
Figure S16. 1H NMR Exchange Spectrum (DMSO-d6 + D2O) (5c)
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Figure S17. 13C NMR Spectrum (DMSO-d6) (5c)
Figure S18. 1H NMR Spectrum (DMSO-d6) (7a)
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Figure S19. 13C NMR Spectrum (DMSO-d6) (7a)
Figure S20. 1H NMR Spectrum (DMSO-d6) (7b)
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Figure S21. 13C NMR Spectrum (DMSO-d6) (7b)
Figure S22. 1H NMR Spectrum (DMSO-d6) (7c)
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Figure S23. 13C NMR Spectrum (DMSO-d6) (7c)
Figure S24. 1H NMR Spectrum (DMSO-d6) (7d)
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Figure S25. 13C NMR Spectrum (DMSO-d6) (7d)
Figure S26. 1H NMR Spectrum (DMSO-d6) (7e)
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Figure S27. 13C NMR Spectrum (DMSO-d6) (7e)
Figure S28. 1H NMR Spectrum (DMSO-d6) (7f)
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Figure S29. 13C NMR Spectrum (DMSO-d6) (7f)
Figure S30. 1H NMR Spectrum (DMSO-d6) (8a)
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Figure S31. 13C NMR Spectrum (DMSO-d6) (8a)
Figure S32. 1H NMR Spectrum (DMSO-d6) (8b)
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Figure S33. 13C NMR Spectrum (DMSO-d6) (8b)
Figure S34. 1H NMR Spectrum (DMSO-d6) (8c)
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Figure S35. 13C NMR Spectrum (DMSO-d6) (8c)
Figure S36. 1H NMR Spectrum (DMSO-d6) (8d)
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Figure S37. 13C NMR Spectrum (DMSO-d6) (8d)
Figure S38. 1H NMR Spectrum (DMSO-d6) (8e)
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Figure S39. 13C NMR Spectrum (DMSO-d6) (8e)
Figure S40. 1H NMR Spectrum (DMSO-d6) (8f)
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Figure S41. 13C NMR Spectrum (DMSO-d6) (8f)
Figure S42. 1H NMR Spectrum (DMSO-d6) (9a)
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Figure S43. 13C NMR Spectrum (DMSO-d6) (9a)
Figure S44. 1H NMR Spectrum (DMSO-d6) (9b)
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Figure S45. 13C NMR Spectrum (DMSO-d6) (9b)
Figure S46. 1H NMR Spectrum (DMSO-d6) (9c)
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Figure S47. 13C NMR Spectrum (DMSO-d6) (9c)
Figure S48. 1H NMR Spectrum (DMSO-d6) (9d)
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Figure S49. 13C NMR Spectrum (DMSO-d6) (9d)
Figure S50. 1H NMR Spectrum (DMSO-d6) (9e)
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Figure S51. 13C NMR Spectrum (DMSO-d6) (9e)
Figure S52. 1H NMR Spectrum (DMSO-d6) (9f)
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Figure S53. 13C NMR Spectrum (DMSO-d6) (9f)
S31