The aminopyrimidines so obtained were converted into Schiff bases by treating with different substituted aldehydes, The study of novel heterocyclic Schiff base ligands 3-{[(4,6-dihydroxy pyrimidin-2-yl)Imino]methyl}Napthalen-2-ol or 2-(((2-hydroxynaphthalen-1-yl)methylene)amino)pyrimidine-4,6-diol derived from 2-amino-4, 6-dihydroxypyrimidine and 2-hydroxy-1-naphthaldehyde (L) were synthesized. These ligands have been used in the synthesis of Cr(II) complexes. The ligand coordinates to the metal ions in the ratio 2L: 1M, through the azomethine N and napthol O atoms, resulting in N2O2 chromophores around the central metal atom. The structures of synthesized compounds were confirmed by physical parameters and spectral studies. The synthesized compounds were characterized using FT-IR, 1H-NMR, UV-Vis techniques for the ligands, Thin layer chromatography (TLC) for all reactions, and molar conductivity and magnetic susceptibility measurements for the corresponding reactions. The general formula of the complexes is [Cr(L)2(H2O)2]. The complexes are paramagnetic in nature. Molar conductivity measurements showed that all complexes in (DMSO) are non electrolytes. Octahedral geometry of all complexes. The ligands are bidentate (L) due to the phenolic (OH) nitrogen and the azomethine nitrogen. The ligands and their complexes were examined for antifungal and antibacterial activity against Aspergillus niger, Penicillium chrysogenum, Fusarium moneriforme, and Aspergillus flavus, as well as Escherichia coli, Salmonella typhi, Staphylococcus aureus, and Bacillus subtilis. The results showed that the complexes have excellent antifungal and antibacterial effects.
Published in | Science Journal of Chemistry (Volume 13, Issue 1) |
DOI | 10.11648/j.sjc.20251301.11 |
Page(s) | 1-10 |
Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
Copyright |
Copyright © The Author(s), 2025. Published by Science Publishing Group |
Schiff Base, 2-Hydroxy-1-Naphthaldehyde, 2-Amino-4,6-Dihydroxypyrimidine, Antibacterial Activity
Compound Molecular formula | Mol. Wt. | M. P. Decomp temp.°C | Colour | Molar Conduc. Mho. Cm2mol-1 |
---|---|---|---|---|
L | 281 | 221 | Yellow | --- |
Cr-L | 618 | >300 | Dark Brown | 10.25 |
Compound | % Found (Calculated) | |||
---|---|---|---|---|
C | H | N | M | |
L | 51.54 (53.21) | 3.57 (3.85) | 16.64 (16.89) | ---- |
Cr-L | 44.43 (44.35) | 3.37 (3.29) | 14.17 (14.15) | 9.90 (9.88) |
Bond vibrational modes | O-H Free Stretching( ) | C = N Azomethine Stretching( ) | C = C Aromatic ring stretching( ) | C -- N Aryl azomethine stretch ( ) | C -- O Enolic stretching ( ) | M--O | M--N |
---|---|---|---|---|---|---|---|
L | 3430 | 1654 | 1486 | 1209 | 1038 | -- | -- |
Cr-L | 3625.55 | 1633.23 | 1351.21 | 1290.22 | 1130.31 | 561.30 | 451.23 |
Complex | Step | Decomp. Temp. (°C) | n | Ea (kJmole-1) | Z (S-1) | S (JK-1mole-1) | G (kJmole-1) | Correlation coefficient |
---|---|---|---|---|---|---|---|---|
Cr-L | I | 432 | 0.9 | 11.13 | 1.27 104 | -173.57 | 26.09 | 0.970 |
Peak No. | 2 (observed) | 2 (calculated) | d (observed) | d (calculated) | Miller indices of Planes | Relative intensities (%) | ||
---|---|---|---|---|---|---|---|---|
h | k | l | ||||||
1 | 6.49527 | 6.49993 | 6.80483 | 6.80464 | -1 | 0 | 1 | 100.00 |
2 | 11.91296 | 11.91217 | 3.73022 | 3.73185 | -1 | 3 | 0 | 2.24 |
3 | 16.56698 | 16.57711 | 2.7008 | 2.69991 | 2 | 0 | 4 | 12.74 |
4 | 19.22149 | 19.22346 | 2.33924 | 2.33953 | 2 | 2 | 2 | 17.75 |
5 | 25.96779 | 25.97817 | 1.75893 | 1.75856 | -3 | 5 | 5 | 5.76 |
6 | 29.5445 | 29.55077 | 1.56194 | 1.56186 | 4 | 1 | 4 | 8.57 |
7 | 31.37724 | 31.37821 | 1.47925 | 1.4794 | -1 | 2 | 10 | 4.04 |
8 | 35.13069 | 35.12972 | 1.33847 | 1.33865 | -6 | 1 | 1 | 2.51 |
9 | 36.34332 | 36.35103 | 1.29968 | 1.29958 | -6 | 1 | 3 | 2.93 |
Test Compound | Antifungal Growth | |||||||
---|---|---|---|---|---|---|---|---|
Aspergillus niger | Penicillium chrysogenum | Fusarium moneliforme | Aspergillus flavus | |||||
1% | 2% | 1% | 2% | 1% | 2% | 1% | 2% | |
L | -ve | -ve | -ve | -ve | -ve | -ve | -ve | -ve |
Cr-L | -ve | -ve | -ve | -ve | -ve | -ve | -ve | -ve |
+ve control | +ve | +ve | +ve | +ve | +ve | +ve | +ve | +ve |
-ve control (Griseofulvin) | -ve | -ve | -ve | -ve | -ve | -ve | -ve | -ve |
Test Compound | Diameter of inhibition zone (mm) | |||||||
---|---|---|---|---|---|---|---|---|
E. coli | Salmonella typhi | Staphylococcu saureus | Bacillus subtlis | |||||
1% | 2% | 1% | 2% | 1% | 2% | 1% | 2% | |
L | -ve | 16mm | -ve | 17mm | -ve | 19mm | -ve | 21mm |
Cr-L | 14mm | 19mm | 14mm | 18mm | 16mm | 21mm | 12mm | 16mm |
DMSO | -ve | -ve | -ve | -ve | -ve | -ve | -ve | -ve |
Penicillin | 14mm | 18mm | 18mm | 18mm | 31mm | 31mm | 19mm | 21mm |
IR | Infrared Spectra (IR) |
FTIR | Fourier-Transform Infrared |
TGA | Thermal Gravimetric Analysis |
UV-Vis | Ultraviolet Visible Spectroscopy |
XRD | X Ray Diffraction |
1H-NMR | Hydrogen Nuclear Magnetic Resonance |
TLC | Thin Layer Chromatography |
STIC | Advanced Laboratory Instrumentation Centre |
SAIF | Advanced Analytical Instrumentation Facility |
CHN | Carbon, Hydrogen, Nitrogen |
UG, PG | Under Graduate & Post Graduate Research |
D. T. | Dhondiram Tukaram |
[1] | D. T. Sakhare, Synthesis, characterization of some transition metal complexes of bidentate Schiff base and their antifungal and antimicrobial studies, Advances in Applied Science Research, 2015, 6(6): 10-16. |
[2] | C. Chandramouli, M. R. Shivanand, T. B. Nayanbhai, B. Bheemachari, R. H. Udupi, Synthesis and biological screening of certain new triazole schiff bases and their derivatives bearing substituted benzothiazole moiety, J Chem Pharm Res, 2012, 4, 1151-1159. |
[3] | D. T. Sakhare, Synthesis, Characterization and Antimicrobial Activity of Schiff Base Derived from 2-Hydroxybenzaldehyde with 2-Amino-4,6-Dimethylpyrimidine And Their Transition Metal Complexes, GIS Science Journal, 2022, 9(4), 82-94. |
[4] | R. Sliverstien, G. Bassler, T. Morrill, Spectrometric Identification of Organic Compounds. 7th addition, John Wiley, New York, 2005. |
[5] | D. T. Sakhare, Copper Metal Complexes of a Pyrimidine Based Schiff Base Ligand Synthesis, Characterization and Biological Activity, Journal of Xidian University, 2022, 16(3), 191-201. |
[6] | D. T. Sakhare, Synthesis, Characterization And Biological Studies of Aminopyrimidine Schiff Bases And Their Transition Metal Complexes, Dickensian Journal, 202, 22(4), 65-77. |
[7] | D. T. Sakhare, Synthesis, characterization and biological activities of new bidentate Schiff base ligand and their Co (II) metal complexes, Materials Today: Proceedings, online, 2024. |
[8] | Harshalata D., Dhongade H. J., Kavita C., Pharmacological potentials of pyrimidine derivatives: A review, Asian J. Pharm. Clin. Res., 2015, 8, 171-177. |
[9] | D. T. Sakhare, Synthesis, Characterization and Antimicrobial Activity of Cu(II) Complexes Derived from Heterocyclic Schiff Bases Ligands, Asian Journal of Organic & Medicinal Chemistry, 2022, 7(2), 41-47. |
[10] | Rana K., Kaur B., Kumar B., Synthesis and antihypertensive activity of some dihydropyrimidines, Indian J. Chem. B, 2004, 43, 1553–1557. |
[11] | Atkins M., Jones C. A., Kirkpatrick P. Sunitinib maleate. Nat. Rev. Drug Discov., 2006. 5, 279-280. |
[12] | D. T. Sakhare, Synthesis, Characterization And In-Vitro Biological Activities of Novel Bidentate Schiff Base Ligand And Their Cobalt (II) Complexes. Juni Khyat, 2023, 13(07), No. 03, 134-143. |
[13] | Ramaling S., Belani C. P., Role of bevacizumab for the treatment of non-small-cell lung cancer. Future oncology, 2007, 3, 131-139. |
[14] | Harris P. A., Boloor A., Cheung M., Kumar R., Crosby R. M., Davis-Ward R. G., et al., Discovery of 5-[[4-[(2,3-dimethyl-2Hindazol-6-yl) methylamino]-2-pyrimidinyl] amino]-2-methylbenzenesulfonamide (Pazopanib), a Novel and potent vascular endothelial growth factor receptor inhibito, J. Med. Chem, 2008, 51, 4632-4640. |
[15] | D. T. Sakhare, Synthesis, Characterization and Biological Activity of New Schiff Bases Derived from Aminopyrimidine and Their Metal Complexes, International Journal of Scientific Research in Science and Technology, 2022, 9(17), 160-173. |
[16] | Lascombe M. B., Ponchet M., Venard P., Milat M. L., Blein J. P., Prange T., The 1.45 A resolution structure of the cryptogeincholesterol complex: a close-up view of a sterol carrier protein (SCP) active site, Acta Crystallogr. Sect. D, 2002. 58, 1442-1447. |
[17] | Kappe C. O., 100 years of the biginelli dihydropyrimidine synthesis, Tetrahedron, 1993, 49, 6937-6963. |
[18] | Espinet P., Esteruelas M. A., Oro L. A., Serrano J. L., Sola E., Transition metal liquid crystals: advanced materials within the reach of the coordination chemist, Coord. Chem. Reviews, 1992, 117, 215-274. |
[19] | D. T. Sakhare, Synthesis, Characterization of some Cu (II) complexes of bidentate Schiff base and their antimicrobial studies, Journal of Medicinal Chemistry and Drug Discovery, 2016, 2(1), 583-597. |
[20] | Osowole A. A., Festus C., Synthesis, Characterization, antibacterial and antioxidant activities of some heteroleptic metal(II) complexes of 3-{[-(pyrimidin-2-yl) Imino] methyl} napthalen-2-ol, J. Chem. Bio. Phy. Sci., 2015, 6, 080-089. |
[21] | D. T. Sakhare, Synthesis, Characterization and Antimicrobial Activity of Novel 2-Amino-4, 6- Dimethylpyrimidine and 2- Hydroxy-5- Nitrobenzaldehyde Schiff Base Ligand and Their Transition Metal Complexes, International Journal of Advance and Applied Research, 2024, 5(40), 35-44. |
[22] | Gulcan M., Özdemir S., Dündar A., Ispir E., Kurtog ̆lu M., Mononuclear complexes based on pyrimidine ring azo Schiff-Base ligand: synthesis, characterization, antioxidant, antibacterial, and thermal investigations, Z. Anorg. Allg. Chem, 2014, 640, 1754-1762. |
[23] | D. T. Sakhare, Synthesis, Characterization And Antimicrobial Studies of Some Transition Metal Complexes of Schiff Bases, International Journal of Current Research In Chemistry And Pharmaceutical Sciences, 2015, 2(6), 28–34. |
[24] | D. T. Sakhare, Synthesis, characterization and antimicrobial activities of some transition metal complexes of biologically active bidentate ligands, Inorganic Chemistry An Indian Journal, 2015, 10(4), 142-147. |
[25] | Tetteh S., Dodoo D. K., Appiah-Opong, R., Tuffour, I., Spectroscopic cha racterization, in vitro cytotoxicity, and antioxidant activity of mixed ligand palladium(II) chloride complexes bearing nucleobases, J. Inorg. Chem., 2014. 2014, 7 pages, Article ID 586131, |
[26] | D. T. Sakhare, Synthesis, characterization and in-vitro biological activities of Co (II) complexes of 2-(4-Methaylbenzylideneamino) Pyrimidine-4, 6-Diol. Current Pharma Research. 2019, 9(4), 3335-3344. |
[27] | D. T. Sakhare, Synthesis, Spectral, Thermal And Antimicrobial Activities of Mn (II) And Fe (III) Schiff Base Metal Complexes. International Journal of Current Research In Chemistry And Pharmaceutical Sciences, 2(7), (2015), 1-8. |
[28] | D. T. Sakhare, Synthesis, Charecterization And Biological Evaluation for Some Divalent Metal Complexes with New Pyrimidine Schiff Base Ligand, Alochana Journal, 2024, 13(2), 1-14. |
[29] | A A Osowole. and R O Yoade, Scientific Journal Of Applied Research. 2013; 4: 101-106. |
[30] | D. T. Sakhare, Synthesis, characterization and antimicrobial activities of some Mn(II) and Fe(III) complexes of biologically active bidentate ligands, Journal of Chemical and Pharmaceutical Research, 2015, 7(6), 198-204. |
[31] | M Usharani. E Akila, And R Rajavel. International Journal of Recent Scientific Research, 2013; 4(9): 1385- 1390. |
[32] | D. T. Sakhare, Synthesis, Characterization And Biological Evaluation of Schiff Base Ligand And Their Fe(III) Complexes, International Journal of Advanced Science and Engineering, 2024, 11(1), 3788-3797. |
[33] | Housecroft, C. E., Sharpe, A. G.: Inorganic Chemistry, 2nd edn. Pearson, England (2005). |
[34] | D. T. Sakhare, Synthesis, Characterization And Biological Activity of New Schiff Bases 1-(((4,6-Dimethylpyrimidin-2-yl)imino)Methyl)Naphthalen-2-ol And Their Fe (III) Complexes, Juni Khyat, 2024, 14(9), 2, 101-111. |
[35] | Avaji P G, Reddy B N and Patil S A, Trans. Met. Chem., 2006, 31, 842. |
[36] | D. T. Sakhare,. Synthesis, Characterization And Antimicrobial Studies On Schiff Base Derived From 2-Amino 4, 6- Dihydroxypyrimidine And Benzaldehyde And Its Cobalt Complexes, International Journal of Food And Nutrition Science, 11(S1), 2022, 970-982. |
[37] | D. T. Sakhare, Syntheses, characterization of some transition metal complexes of bidentate schiff base and their antimicrobial activities, Der Chemica Sinica, 2015, 6(6): 1-6. |
[38] | D. T. Sakhare, Synthesis, Characterization And Spectroscopic Study of New 3-{[(4,6-Dihydroxy Pyrimidin-2-yl)imino]methyl}Napthalen-2-ol Schiff-Base Ligand And It’s Transition Metal Complexes, International Journal of Scientific Research in Chemical Sciences, 2024, 11(5), 6-12. |
APA Style
Sakhare, D. T. (2025). Green Synthesis, Characterization and Biological Evaluation of Divalent Transition Metal Complexes of Substituted Aminopyrimidine Novel Schiff Base Ligand. Science Journal of Chemistry, 13(1), 1-10. https://doi.org/10.11648/j.sjc.20251301.11
ACS Style
Sakhare, D. T. Green Synthesis, Characterization and Biological Evaluation of Divalent Transition Metal Complexes of Substituted Aminopyrimidine Novel Schiff Base Ligand. Sci. J. Chem. 2025, 13(1), 1-10. doi: 10.11648/j.sjc.20251301.11
@article{10.11648/j.sjc.20251301.11, author = {Dhondiram Tukaram Sakhare}, title = {Green Synthesis, Characterization and Biological Evaluation of Divalent Transition Metal Complexes of Substituted Aminopyrimidine Novel Schiff Base Ligand}, journal = {Science Journal of Chemistry}, volume = {13}, number = {1}, pages = {1-10}, doi = {10.11648/j.sjc.20251301.11}, url = {https://doi.org/10.11648/j.sjc.20251301.11}, eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20251301.11}, abstract = {The aminopyrimidines so obtained were converted into Schiff bases by treating with different substituted aldehydes, The study of novel heterocyclic Schiff base ligands 3-{[(4,6-dihydroxy pyrimidin-2-yl)Imino]methyl}Napthalen-2-ol or 2-(((2-hydroxynaphthalen-1-yl)methylene)amino)pyrimidine-4,6-diol derived from 2-amino-4, 6-dihydroxypyrimidine and 2-hydroxy-1-naphthaldehyde (L) were synthesized. These ligands have been used in the synthesis of Cr(II) complexes. The ligand coordinates to the metal ions in the ratio 2L: 1M, through the azomethine N and napthol O atoms, resulting in N2O2 chromophores around the central metal atom. The structures of synthesized compounds were confirmed by physical parameters and spectral studies. The synthesized compounds were characterized using FT-IR, 1H-NMR, UV-Vis techniques for the ligands, Thin layer chromatography (TLC) for all reactions, and molar conductivity and magnetic susceptibility measurements for the corresponding reactions. The general formula of the complexes is [Cr(L)2(H2O)2]. The complexes are paramagnetic in nature. Molar conductivity measurements showed that all complexes in (DMSO) are non electrolytes. Octahedral geometry of all complexes. The ligands are bidentate (L) due to the phenolic (OH) nitrogen and the azomethine nitrogen. The ligands and their complexes were examined for antifungal and antibacterial activity against Aspergillus niger, Penicillium chrysogenum, Fusarium moneriforme, and Aspergillus flavus, as well as Escherichia coli, Salmonella typhi, Staphylococcus aureus, and Bacillus subtilis. The results showed that the complexes have excellent antifungal and antibacterial effects.}, year = {2025} }
TY - JOUR T1 - Green Synthesis, Characterization and Biological Evaluation of Divalent Transition Metal Complexes of Substituted Aminopyrimidine Novel Schiff Base Ligand AU - Dhondiram Tukaram Sakhare Y1 - 2025/01/07 PY - 2025 N1 - https://doi.org/10.11648/j.sjc.20251301.11 DO - 10.11648/j.sjc.20251301.11 T2 - Science Journal of Chemistry JF - Science Journal of Chemistry JO - Science Journal of Chemistry SP - 1 EP - 10 PB - Science Publishing Group SN - 2330-099X UR - https://doi.org/10.11648/j.sjc.20251301.11 AB - The aminopyrimidines so obtained were converted into Schiff bases by treating with different substituted aldehydes, The study of novel heterocyclic Schiff base ligands 3-{[(4,6-dihydroxy pyrimidin-2-yl)Imino]methyl}Napthalen-2-ol or 2-(((2-hydroxynaphthalen-1-yl)methylene)amino)pyrimidine-4,6-diol derived from 2-amino-4, 6-dihydroxypyrimidine and 2-hydroxy-1-naphthaldehyde (L) were synthesized. These ligands have been used in the synthesis of Cr(II) complexes. The ligand coordinates to the metal ions in the ratio 2L: 1M, through the azomethine N and napthol O atoms, resulting in N2O2 chromophores around the central metal atom. The structures of synthesized compounds were confirmed by physical parameters and spectral studies. The synthesized compounds were characterized using FT-IR, 1H-NMR, UV-Vis techniques for the ligands, Thin layer chromatography (TLC) for all reactions, and molar conductivity and magnetic susceptibility measurements for the corresponding reactions. The general formula of the complexes is [Cr(L)2(H2O)2]. The complexes are paramagnetic in nature. Molar conductivity measurements showed that all complexes in (DMSO) are non electrolytes. Octahedral geometry of all complexes. The ligands are bidentate (L) due to the phenolic (OH) nitrogen and the azomethine nitrogen. The ligands and their complexes were examined for antifungal and antibacterial activity against Aspergillus niger, Penicillium chrysogenum, Fusarium moneriforme, and Aspergillus flavus, as well as Escherichia coli, Salmonella typhi, Staphylococcus aureus, and Bacillus subtilis. The results showed that the complexes have excellent antifungal and antibacterial effects. VL - 13 IS - 1 ER -