Hydrazinolysis Products of Selected Sugar Lactones—Crystal Structure and Microbiological Activity
Abstract
:1. Introduction
2. Results and Discussion
2.1. Crystal Structure and Analysis of Intermolecular Interactions
2.2. Microbiological Testing
3. Materials and Methods
3.1. General Section
3.2. NMR Measurements
3.3. MS Spectrometry
3.4. TG Analysis
3.5. Elemental Analysis
3.6. Polarimetry
3.7. Single-Crystal X-ray Diffraction
3.8. Antimicrobial Activity
3.9. General Procedure for the Preparation of Lactones
3.10. General Procedure for the Preparation of Hydrazides
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Compound | 1 | 2 | 3 | 4 | 5 | 6 |
---|---|---|---|---|---|---|
Chemical formula | C5H12N2O5 | C5H12N2O4 | C6H14N2O6 | C6H14N2O5 | C6H14N2O5 | C6H12N2O6 |
FW/g·mol−1 | 180.17 | 164.17 | 210.19 | 194.19 | 194.19 | 208.18 |
Crystal system | orthorhombic | monoclinic | orthorhombic | triclinic | triclinic | monoclinic |
Space group | P212121 | P21 | P212121 | P1 | P1 | P21 |
a/Å | 5.2059(2) | 8.777(2) | 5.6086(7) | 4.7524(12) | 4.7391(6) | 8.9247(12) |
b/Å | 9.4219(5) | 4.8499(6) | 9.1664(12) | 5.7522(14) | 5.7382(9) | 5.1153(7) |
c/Å | 15.3276(9) | 9.719(3) | 18.223(3) | 8.6708(17) | 8.6287(15) | 9.4937(14) |
α/° | 90 | 90 | 90 | 72.83(2) | 72.967(14) | 90 |
β/° | 90 | 114.87(3) | 90 | 76.43(2) | 76.462(13) | 97.139(12) |
γ/° | 90 | 90 | 90 | 75.41(2) | 75.323(12) | 90 |
V/Å3 | 751.81(7) | 375.33(17) | 936.8(2) | 215.85(9) | 213.77(6) | 430.05(10) |
Z | 4 | 2 | 4 | 1 | 1 | 2 |
T/K | 293(2) | 293(2) | 293(2) | 293(2) | 293(2) | 293(2) |
λMo/Å | 0.71073 | 0.71073 | 0.71073 | 0.71073 | 0.71073 | 0.71073 |
ρcalc/g·cm−3 | 1.592 | 1.453 | 1.490 | 1.494 | 1.508 | 1.608 |
µ/mm−1 | 0.142 | 0.125 | 0.133 | 0.129 | 0.131 | 0.144 |
F(000) | 384 | 176 | 448 | 104 | 104 | 220 |
θ range/° | 3.43–25.00 | 4.10–25.00 | 3.80–25.00 | 3.78–25.00 | 3.79–25.00 | 3.35–25.00 |
Completeness of θ/% | 99.8 | 99.6 | 99.7 | 99.9 | 99.9 | 99.6 |
Reflections collected | 4849 | 2260 | 6675 | 1317 | 2722 | 2670 |
Reflections unique | 1322 (Rint = 0.0453) | 1187 (Rint = 0.0843) | 1652 (Rint = 0.1731) | 1024 (Rint = 0.0542) | 1511 (Rint = 0.0227) | 1450 (Rint = 0.0327) |
Data/restraints/parameters | 1322/7/130 | 1187/7/118 | 6675/8/1652 | 1024/10/140 | 1511/10/140 | 1450/9/151 |
Goodness of fit on F2 | 1.025 | 0.972 | 0.993 | 1.140 | 1.085 | 0.997 |
Final R1 value (I > 2σ(I)) | 0.0345 | 0.0640 | 0.0849 | 0.0753 | 0.0287 | 0.0414 |
Final wR2 value (I > 2σ(I)) | 0.0652 | 0.1192 | 0.0961 | 0.1977 | 0.0706 | 0.0771 |
Final R1 value (all data) | 0.0428 | 0.1211 | 0.1835 | 0.0887 | 0.0299 | 0.0537 |
Final wR2 value (all data) | 0.0675 | 0.1462 | 0.1219 | 0.2292 | 0.0718 | 0.0810 |
CCDC number | 2262959 | 2262961 | 2262964 | 2262963 | 2262960 | 2262962 |
Compound | dC=O (Å) | dC-N ([Å) | dN-N (Å) | ∠ O–C–N–H (°) |
---|---|---|---|---|
1 | 1.232 | 1.327 | 1.420 | −172.2 |
2 | 1.220 | 1.345 | 1.427 | 171.5 |
3 | 1.223 | 1.325 | 1.420 | −173.5 |
4 | 1.227 | 1.336 | 1.427 | 165.6 |
5 | 1.234 | 1.324 | 1.414 | 173.2 |
Compound | dC1=O * | dC1-C2 | dC2-O | dC2-C3 | dC3-O | dC3-C4 |
---|---|---|---|---|---|---|
6 | 1.231 | 1.409 | 1.375 | 1.349 | 1.287 | 1.499 |
AA | 1.216 | 1.452 | 1.361 | 1.338 | 1.326 | 1.493 |
Compound | MIC90 Values of the Synthesized Compounds 1–6 (µg/mL) | |||
---|---|---|---|---|
Gram-Negative Bacteria | Gram-Positive Bacteria | |||
Escherichia coli ATCC 25922 | Pseudomonas aeruginosa ATCC 27853 | Staphylococcus aureus ATCC 25923 | Staphylococcus aureus ATCC 29213 | |
1 | 128 | 128 | >512 | >512 |
2 | 512 | 512 | >512 | >512 |
3 | 64 | 256 | >512 | >512 |
4 | 128 | 256 | >512 | >512 |
5 | 128 | 256 | >512 | >512 |
6 | 256 | 256 | 512 | 512 |
Compound | MIC90 Values of the Synthesized Compounds 1–6 (µg/mL) | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
Candida albicans SC5314 | Candida glabrata DSM 11226 | Candida krusei DSM 6128 | Candida parapsilosis DSM 5784 | |||||||||
Medium | Medium | Medium | Medium | |||||||||
RPMI + GLC | GPMI − GLC | YNB | RPMI + GLC | GPMI − GLC | YNB | RPMI + GLC | GPMI − GLC | YNB | RPMI + GLC | GPMI − GLC | YNB | |
1 | 64 | 64 | 128 | 512 | 256 | >512 | 512 | 256 | >512 | 512 | 256 | 512 |
2 | 128 | 64 | >512 | >512 | >512 | >512 | >512 | >512 | >512 | >512 | >512 | >512 |
3 | 32 | 32 | 256 | 512 | 128 | >512 | 512 | 128 | >512 | 512 | 256 | 512 |
4 | 128 | 64 | 512 | >512 | 256 | >512 | >512 | 256 | >512 | >512 | 256 | 512 |
5 | 128 | 64 | 256 | >512 | 512 | >512 | 512 | 256 | >512 | 512 | 512 | >512 |
6 | 32 | 32 | 128 | >512 | 256 | >512 | >512 | 256 | >512 | >512 | 256 | >512 |
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Samaszko-Fiertek, J.; Sikorski, A.; Dmochowska, B.; Szweda, P.; Madaj, J. Hydrazinolysis Products of Selected Sugar Lactones—Crystal Structure and Microbiological Activity. Int. J. Mol. Sci. 2023, 24, 12114. https://doi.org/10.3390/ijms241512114
Samaszko-Fiertek J, Sikorski A, Dmochowska B, Szweda P, Madaj J. Hydrazinolysis Products of Selected Sugar Lactones—Crystal Structure and Microbiological Activity. International Journal of Molecular Sciences. 2023; 24(15):12114. https://doi.org/10.3390/ijms241512114
Chicago/Turabian StyleSamaszko-Fiertek, Justyna, Artur Sikorski, Barbara Dmochowska, Piotr Szweda, and Janusz Madaj. 2023. "Hydrazinolysis Products of Selected Sugar Lactones—Crystal Structure and Microbiological Activity" International Journal of Molecular Sciences 24, no. 15: 12114. https://doi.org/10.3390/ijms241512114