Modern Organic Chemistry Research

Download PDF (451.1 KB) PP. 25 - 32 Pub. Date: February 14, 2017

DOI: 10.22606/mocr.2017.21005

• Shipra Baluja^*
  Physical Chemistry Laboratory, Department of Chemistry, Saurashtra University, Rajkot-360005 (Gujarat), India.
• Kapil D. Bhesaniya
  
  Physical Chemistry Laboratory, Department of Chemistry, Saurashtra University, Rajkot-360005 (Gujarat), India.
• Ashish B. Patel
  
  Physical Chemistry Laboratory, Department of Chemistry, Saurashtra University, Rajkot-360005 (Gujarat), India.

Some tetrahydropyrimidine derivatives have been synthesized and their structures have been confirmed by IR, ¹H NMR, ¹³C NMR and mass spectral data. The dissociation constants of these derivatives of tetrahydropyrimidine have been measured by Calvin Bjerrum pH titration method in DMF-water (60: 40 v/v) system at 303.15 K. It is observed that dissociation constant depends on substituent groups present in the compounds.

Tetrahydropyrimidine derivatives, dissociation constant, DMF-water system, Calvin Bjerrum pH titration method

[1] R. Kumar, A. Mittal and U. Ramachandran, “Design and synthesis of 6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine- 5- carboxylic acid derivatives as PPARγ activators”, Bioorg. Med. Chem. Lett., 2007, 17, 4613-4618.

[2] R. L. Sawant and M. S. Bhatia, “Synthesis, screening and qsar studies of 3-formyl-2-oxo-1, 2, 3, 4-tetra hydropyrimidine analogues as antibacterial agents”, Bull. Chem. Soc. Ethiopia, 2008, 22, 391-402.

[3] M. K. Manal, M. R. Sameha, A. A. Mohamed, K. A. Eman and F. L. Phoebe, “Design, synthesis and cytotoxic activity of some novel compounds containing pyrazolo[3,4-d ]pyrimidine nucleus”, Der Pharma Chem., 2013, 5, 109-124.

[4] K. Weinhardt, M. B. Wallach and M. Marx, “Synthesis and antidepressant profiles of phenyl-substituted 2- amino- and 2-[(alkoxycarbonyl)amino]-1,4,5,6-tetrahydro pyrimidines,” J. Med. Chem., 1985, 28, 694-698.

[5] A. Balkan, B. Tozkoparan, M. Ertan, Y. Sara and N. Ertekin, “New thiazolo [3, 2-a]pyrimidine derivatives, synthesis and calcium antagonistic activities,” Boll. Chim. Farma., 1996, 135, 648-652.

[6] K. Kaur and E. Knaus, “Synthesis of alkyl 6-methyl-4-(2-pyridyl)-1,2,3,4-tetrahydro-2H-pyrimidine-2-one-5- carboxylates for evaluation as calcium channel antagonists,” J. Heterocycl. Chem., 2007, 44, 745-747.

[7] Y. Ji-Xin, C. Xiao-Qing, C. Di-Mei and H. Mao-Lin, “Synthesis, structure analysis, and antitumor activity of (R)-2,4-dioxo-5-fluoro-1(methoxycarbonyl) ethylamino carbonyl methyl] 1,2,3,4 tetrahydro pyrimidine,” Chin. J. Chem., 2007, 25, 417-421.

[8] V. Virsodia, R. R. S. Pissurlenkar, D. Manvar, C. Dholakia, P. Adlakha, A. Shah and E. V. Coutinho, “Synthesis, screening for antitubercular activity and 3D-QSAR studies of substituted N-phenyl-6-methyl-2-oxo-4- phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxamides’’ Eur. J. Med. Chem., 2008, 43, 2103–2115.

[9] S. Mokale, S. Shinde, R. Elgire, J. Sangshetti and D. Shinde, “Synthesis and anti-inflammatory activity of some 3-(4,6-disubtituted 2 thioxo1,2,3,4 tetrahydro pyrimidin-5-yl)propanoic acid derivatives,” Bioorg. Med. Chem. Lett., 2010, 20, 4424-4426.

[10] R. Dhankar, A. M. Rahatgaonkar, R. Shukla, M. Chorghade and A. Tiwari, “Computer simulation of the in vitro and in vivo anti- inflammatory activities of dihydropyrimidines acid derivatives through the inhibition of cyclooxygenase-2”, Med. Chem. Res., 2013, 22, 2493–2504.

[11] K. Satyavathi, K. T. Naga Ravi, R. P. Bhoja and M. Sharmila, “Synthesis and screening of 3-formyl-2-thio- 1,2,3,4-tetrahydro pyrimidine analogues as antibacterial agents,” Asian J. Chem., 2010, 22, 5182-5186.

[12] S. N. Darandale, D. N. Pansare, N. A. Mulla and D. B. Shinde, “Green synthesis of tetrahydropyrimidine analogues and evaluation of their antimicrobial activity”, Bioorg. Med. Chem. Lett., 2013, 23, 2632-2635.

[13] N. Arora and S. Pandeya, “Synthesis and analgesic activity of novel pyrimidine derivatives,” Int. J. Pharma. Sci. Rev. Res., 2011, 11, 48-52.

[14] H. S. Basavaraja, P. Basavaraj, M. Vijaykumar, M. M. Hussain and B. N. Chidananda, “Synthesis and antimicrobial screening of some substituted INH- and THPHM-linked pyrimidines,” Ind. J. Heterocycl. Chem., 2011, 20, 237-240.

[15] M. Mansouri, A. Movahedian, M. Rostami and A. Fassihi, “Synthesis and antioxidant evaluation of 4-(furan-2- yl)-6-methyl-2-thioxo-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylate esters”, Res. Pharma. Sci., 2012, 7, 257-264.

[16] M. Andrasi, P. Buglyo L. Zekany and A. Gaspar, “A comparative study of capillary zone electrophoresis and pH-potentiometry for determination of dissociation constants,” J. Pharma. Biomed. Ana., 2007, 44, 1040-1047.

[17] T. Fengxiang, G. Zhongli, L. Daqiang, C. Haoyu and Z. Suying, “Dissociation constant and solubility of (S)-2- Hydroxy-4-phenylbutyric Acid,” J. Chem. Eng. Data, 2013, 58, 1265-1270.

[18] A. Ahmed, B. Ahmed and I. T. Ahmed, “Acid dissociation constants mercapto benzazoles in aqueous-organic solvent mixtures,” J. Chem. Eng. Data, 1996, 41, 787-790.

[19] J. A. Riddick, W. B. Bunger and T. Sakano, “Organic Solvents: Physical Properties and Methods of Purification”, 4th edition, John Wiley & Sons Inc., USA , 1986.

[20] M. Calvin and K. W. Wilson, ‘‘Stability of Chelate Compounds’’. J. Am. Chem. Soc., 1947, 67, 2003-2007.

[21] J. Bjerrum, ‘‘Metal amine formation in aqueous solution’’. P Hasse and Son, Coppehagen, 1941.

[22] L. G. Van Uitert and G. G. Hass, “Studies on coordination compounds. I. A method for determining thermodynamic equilibrium constants in mixed so1vent,” J. Am. Chem. Soc., 1953, 75, 451-454.

[23] H. Irving and H. S. Rossoti, “The calculation of formation curves of metal complexes from pH titration curves in mixed solvents,” J. Chem. Soc., 1954, 12, 2094-2010.

[24] J. Ephraim, S. Alegret, A. Mathuthu, M. Bicking, R. Malcolm and J. Marinsky, “A unified physicochemical description of the protonation and metal ion complexation equilibria of natural organic acids (humic and fulvic acids). 2. Influence of polyelectrolyte properties and functional group heterogeneity on the protonation equilibria of fulvic acid,” Environ. Sci. Tech., 1986, 20, 354-366.

[25] A. Yoda,“Structure-Activity relationships of cardiotonic steroids for the inhibition of sodium- and potassiumdependent adenosine triphosphatase I. Dissociation rate constants of various enzyme-cardiac glycoside complexes formed in the presence of magnesium and phosphate,” Mol. Pharmaco., 1973, 9, 51-60.

[26] A. El-Sonbati, A. El-Bindary, A. Shoair and R. Younes, “Stereochemistry of new nitrogen containing heterocyclic aldehyde. vii. Potentiometric, conductometric and thermodynamic studies of novel quinolineazodyes and their metal complexes with some transition metals,” Chem. Pharma. Bull., 2001, 49, 1308-1313.

[27] Y. M. Issa, O. E. Sherif and S. M., Abbas, “Chelation behavior of Ce(III), Th(IV), and UO 2 (VI) with 5,7- dihydroxy-6-formyl-2-methylbenzopyran-4-one Schiff bases,” Monat. Chem., 1998, 129, 985-998.