• SAHAR B. AL-JUBOORI Department of Pharmacy, College of Al-Rafidain University, Baghdad, Iraq.
  • AMMAR A. RAZZAK MAHMOOD Department of Pharmaceutical Chemistry, College of Pharmacy, University of Baghdad, Bab-Al-Mouadam, 10001, Baghdad, Iraq.


Objective: Pyrimidine derivatives are reported to possess antibacterial, antifungal, anticancer, and anticonvulsant activities. Encouraged by this remarks, we decided to synthesize novel compounds of new 2-macraptopyrimidine linked to Schiffs̕ bases.

Methods: The present work involves the synthesis of new 2-mercaptopyrimidine linked to Schiffs̕ bases. The starting, 2-mercaptopyrimidine, compound (1) reacted with thiourea to afford the corresponding 1-(pyrimidin-2-yl) thiourea (2). Then compound (2) was used as the key intermediate to prepare the -1-(2-hydroxy benzylidene)-3-(pyrimidin-2-yl) thiourea (3), and (1-benzylidine)-3-(pyrimidin-2-yl) thiourea (4), through the reaction with 2-hydroxybenzaldehyde, and benzaldehyde, respectively.

Results: All the synthesized compounds were characterized by Fourier-transform infrared and1H-nuclear magnetic resonance spectroscopy. The synthesized derivatives were screened for their in vitro, antibacterial activity against two Gram-positive bacteria: Bacillus subtilis and Staphylococcus aureus and four Gram-negative bacteria: Klebsiella pneumoniae, Escherichia coli, and Salmonella typhi, and the results showed that most of them have good antibacterial activity. While their antifungal activity against three fungi species (Aspergillus fumigates, Aspergillus niger, Aspergillus terrus and Rhizopus) revealed that compounds (2-4) displayed the most potent antifungal activity. Density functional theory (DFT) calculations for the synthesized 2-mercapto pyrimidine derivatives were conducted, using a molecular structure with optimized geometry. Highest occupied molecular orbital/lowest unoccupied molecular orbital energies and structures are demonstrated.

Conclusion: The antimicrobial activity indicates that compounds (3) and (4) are the most active than the compounds (1) and (2). Molecular docking revealed that compounds (3) and (4), with bulky phenyl groups are essential to blocking the active centers of glucose -6-phosphate synthase in the bacteria and fungi.

Keywords: Antimicrobial, Density functional theory, 2-Mercaptopyrimidine, Schiff bases, Glucose-6-phosphate synthase.

Author Biography

SAHAR B. AL-JUBOORI, Department of Pharmacy, College of Al-Rafidain University, Baghdad, Iraq.

Associated Prof

Dept of Pharmaceutical  Chemistry


1. Stuart AL, Ayisi NK, Tourigny G, Gupta VS. Antiviral activity, antimetabolic activity, and cytotoxicity of 3’-substituted deoxypyrimidine nucleosides. J Pharm Sci 1985;74:246-9.
2. Agarwal A, Ramesh, Ashutosh, Goyal N, Chauhan PM, Gupta S, et al. Dihydropyrido[2,3-d]pyrimidines as a new class of antileishmanial agents. Bioorg Med Chem 2005;13:6678-84.
3. Agarwal A, Srivastava K, Puri SK, Chauhan PM. Synthesis of 4-pyrido-6-aryl-2-substituted amino pyrimidines as a new class of antimalarial agents. Bioorg Med Chem 2005;13:6226-32.
4. Rahaman SA, Rajendra Pasad Y, Kumar P, Kumar B. Synthesis and anti-histaminic activity of some novel pyrimidines. Saudi Pharm J 2009;17:255-8.
5. Sushma D, Archana, Sukhjinder S, Munirajam S, Nitin K. Synthesis and biological evaluation of 2-[3-(4-methoxy phenyl)propan -3-one ]-5-(substituted phenyl)-1,3,4-oxadiazoles. Ind J Heterocycl Chem, 2008;17:265-6
6. Nimavat KS, Popat KH, Joshi H. Synthesis, anticancer, antitubercular and antimicrobial activity of some new pyrimidine derivatives. Ind J Heterocycl Chem 2003;12:217-20.
7. Karale BK, Gill CH. Synthesis of 3-methyl-4-[(chromon-3 yl) methylene]- 1-phenylpyrazolin-5(4H)-ones and their conversion into 2-thio-5-hydroxy-5H[1] benzopyrano [4,3-d]pyrimidines. Indian J Chem 2002;41B:1957-9.
8. Sharma GV, Reddy VM. Synthesis of 1,2 disubstituted- 4-[(chromon-3-yl) methylene]imidazolin-5(4H)-ones as potential pharmacological agents. Indian J Heterocycl Chem 1993;3:111-6.
9. Harshalata D, Dhongade HJ, Kavita C. Pharmacological potentials of pyrimidine derivatives: A review. Asian J Pharm Clin Res 2015;8:171 7.
10. Rana K, Kaur B, Kumar B. Synthesis and antihypertensive activity of some dihydropyrimidines. Indian J Chem B 2004;43:1553-7.
11. Sadagopan S, Nagaraja N, Sridhara AM, Peethamber SK. Synthesis and pharmacological evaluation of certain schiff base of octahydro-1H-pyro-[3, 4-B] pyridine derivative. Int J Pharm Pharm Sci 2015;7:412-9.
12. Kumara KS, Kirshnamurthy G, Sunil K. Synthesis, characterization, in-vitro antimicrobial, anthelmintic and docking studies of new 2-[(E)-{[4-(1H-1,2,4-traizole-1 ylmethyl)Phenyl]imino} methyl]phenol, and their complexes with 3D metal ions. Int J Pharm Pharm Sci 2016;8:134 9.
13. Pfoze NL, Kumar Y, Myrboh B, Bhagobaty RK, Joshi SR. In vitro antibacterial activity of alkaloid extract from stem bark of Mahonia manipurensis. Takeda. J Med Plants Res 2011;5:859-61.
14. Dabholkar VV, Gavande RP. Synthesis and antimicrobial activities of novel 1, 4-benzothiazine derivatives. Arab J Chem 2016;9:S225-9.
15. Ali P, Meshram J, Tiwari V, Dongre R, Sheikh J, Ahemad M. Bis-N-aryl-?-lactams: Vilsmeier reagent as an efficient entity for the synthesis via alternate cyclo-addition reaction and in vitro biology. Pharm Chem 2010;2:138-47.
16. Ali PS, Meshram JS, Raut RD. Theoretical and synthetic approach towards the biology of some novel monobactam induced sulphonamides: Assessing biology through coupling of active ingredients. Jordan J Chem 2011;6:153-64.
17. Husseein MD, Aljuboori S, Ammar MA. Synthesis, characterization and antibacterial evaluation with computational study of new schiff bases derived from 7-hydroxy-4-methyl coumarin. Orient J Chem 2017;33:768-82.
18. Husseein MD, Ammar MA, Aljuboori S. Synthesis, antibacterial and DFT study of derivatives derived from oxidation 7-hydroxy 4-methyl coumarin. Int J Pharm Sci Rev Res 2017;46:196-206.
19. Naama J, Alwan G, Obayes H, Al-Amiery A, Al-Temimi A, Kadhum A. Curcuminoids as antioxidants and theoretical study of stability of curcumin isomers in gaseous state. Res Chem Intermediates 2013;39:4040-7.
20. Vektariene A, Vektaris G, Svoboda J. A theoretical approach to the nucleophilic behavior of benzofused thieno[3,2-b]furans using DFT and HF based reactivity descriptors. ARKIVOC 2009;7:311-29.
21. Špirtovi?-Halilovi? S, Salihovi? MB, Veljovi? E, Osmanovi? A, Trifunovi? SC, Završnik D. Chemical reactivity and stability predictions of some coumarins by means of DFT calculations. Glas Hem Tehnol Bosne Herceg 2014;43:57-60.
22. Abbas AF, Turki AA, Hameed AJ. Synthesis, characterization and computational study of some new heterocyclic derived from 1-(biphenyl-4-yl)-3-(furan-2-yl)prop-2-en-1-one. J Mater Environ Sci 2012;6:1071-8.
23. Kumar S, Lim AM, Ramasamy K, Vasudevan M, Shah SA, Selvaraj M, et al. Synthesis, molecular docking and biological evaluation of bis pyrimidine schiff base deriv atives. Chem Cent J 2017;11:1-16.
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How to Cite
AL-JUBOORI, S. B., and A. A. R. MAHMOOD. “SYNTHESIS, ANTIMICROBIAL EVALUATION, DENSITY FUNCTIONAL THEORY, AND DOCKING STUDIES OF SOME NEW 2-MERCAPTO PYRIMIDINE SCHIFF BASES”. Asian Journal of Pharmaceutical and Clinical Research, Vol. 12, no. 2, Jan. 2019, pp. 496-02, doi:10.22159/ajpcr.2019.v12i2.30858.
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