Synthetic Study on Chalcone and their Dihydropyrimidinone and Dihydropyrimidinethione Derivatives

Authors

  • Basavaiah Umesha  Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru, Karnataka, India
  • Sowbhagya  Department of Studies in Organic Chemistry, University of Mysore, Manasagangotri, Mysuru, Karnataka, India
  • Yeriyur Basavaiah Basavaraju  Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru, Karnataka, India

Keywords:

Chalcone, Urea, Thiourea, Dihydropyrimidinone, Dihydropyrimidinethione.

Abstract

A series of chalcones, dihydropyrimidinone and dihydropyrimidinethione derivatives were synthesized in good yields by Claisen Schmidt reaction of acetophenones with substituted aldehydes in the presence of sodium hydroxide in water-ethanol mixture followed by the condensation reaction of chalcones with urea and thiourea in ethanol respectively. The structures of the synthesized compounds were elucidated based on spectroscopic evidence.

References

  1. Brogna A, Ferrara R, Bucceri AM, Catalano F, Natoli G, Locata V (1998) Gastric emptying rates of solid food in relation to body mass index: an ultrasonographic and scintigraphic study. Euro J adiology 27:258-263
  2. Sahi Y, Sun B (2005) The effects of ultrasonic wave on oil adsorption of alcohol precipitated soy protein concentrate. Shipin Gongye Keji 26:84-86
  3. Burstein M, Lewi S (1952) The physical properties of the plasma clot; compressibility and retraction by ultrasonics. Soc Biol Fil 146:1544-1546
  4. Shung KK, Reid JM (1978) Ultrasound velocity in major bovine blood vessel walls. J Acoust Soc 64:692-694
  5. Nikoonahad M, Iravani MV (1989) Focusing ultrasound in biological media. IEEE 36:209-215
  6. Halstenberg S, Heimburg T, Hianik T, Kaatze U, Krivanek R (1998) Cholesterol induced variations in the volume and enthalpy fluctuations of lipid bilayers. J Biophys 75, 264-271
  7. Achiron A, Edelstein S, Ziev-Ner Y, Givon U, Rotstein Z, Barak Y (2004) Bone strength in multiple sclerosis: cortical midtibial speed-of-sound assessment. Mult Scler 10:488-493
  8. Fahey M, Ko HH, Srivastava S, Lai WW, Chatterjee S, Parness IA, Lytrivi ID (2009) A comparison of echocardiographic techniques in determination of arterial elasticity in the pediatric population. Echocardiography 26:567-573
  9. Fuller ER., Granato AV, Holder J, Naimon ER (1974) Ultrasonic studies of the properties of solids. Methods Exp Phy 11:371-441
  10. Baud JM, Lemasle P, Gras C, De CB, Tricot JF (1988) Doppler ultrasonic evaluation of the embolism-causing potential of carotid artery plaques apropos of 113 macroscopic findings. J des maladies vasculaires 13:33-40
  11. Kappe CO (2000) Recent advances in the Biginelli dihydropyrimidine synthesis, new tricks from an old dog. Acco Chemi Res 33:879-888
  12. Champaneri HR, Modi SR, Naik HB (1994) Synthesis and antibacterial activity of 6-(2'-hydroxy-5'-methylphen-1'-yl)-3-acetyl-4-substitutedphenyl-3,4-dihydropyrimidine-2-thiols. Asi J Chem 6:1057-1058
  13. Wiebe LI, Knaus EE, Cheraghali AM, Kumar R, Morin KW, Wang L (1995) 5-Halo-6-alkoxy-5,6-dihydro-pyrimidine nucleosides, antiviral nucleosides or nucleoside prodrugs. Nucleo Nucleotides 14:501-505
  14. Goldmann S, Stoltefuss J, Paessens A, Graef E, Lottmann S (1999) New 2-heterocyclic substituted dihydropyrimidines. Ger Offen 16pp.
  15. Hanna MA, Girges MM, Moawad EB, Hassan HM (1989) Novel anchored nitrogen-containing heterocycles of potential biological activity from 2,3-dioxobutanethioanilide 2-arylhydrazone. Chemi Pap 43:651-659
  16. Sondhi SM, Magan A, Sahu R, Mahesh VK, Shukla R, Patnaik GK (1994) Evaluation of some anti-inflammatory pyrimidobenzimidazoles synthesized via novel tin(II) chloride-hydrochloric acid assisted water addition and reduction of 4,4,6-trimethyl-1-(2-nitroaryl)-1,4- dihydropyrimidine-2(3H)-thiones. Synthesis. 11:1175-1180
  17. Modha J, Datta N, Parekh H (2001) Synthesis and biological evaluation of some new 3,4- dihydropyrimidin-2-thiols. Farmaco 56:641-646
  18. Rovnyak GC, Atwal KS, Hedberg A, Kimball SD, Moreland S, Gougoutas JZ, O'Reilly BC, Schwartz J, Malley MF (1992) Basic 3-substituted-4-aryl-1,4-dihydropyrimidi ne -5-carboxylic acid esters, potent antihypertensive agents. J Medi Chem 35:3254-3263
  19. Sondhi SM, Verma RP, Singhal N, Sharma VK, Husiu C, Vargiu L, Longu S, La Colla P (2000) Anti-HIV, antibacterial and antifungal potential of a variety of heterocyclic compounds containing nitrogen and/or sulphur Ind J Pharma Sci 62:71-76
  20. Sidler DR, Barta N, Li W, Hu E, Matty L, Ikemoto N, Campbell JS, Chartrain M, Gbewonyo K, Boyd R, Corley E, Ball RG (2002) Efficient synthesis of the optically active dihydropyrimidinone of a potent α1a 1A-selective adrenoceptor antagonist. Cana J Chem 80:646-652
  21. Takahashi D, Izawa K (2005) Method for the production of 5-protected aminopyrimidine compounds and intermediates thereof with NK1 antagonistic activity. Eur Pat Appl 16pp.
  22. Bruce MA, Poindexter GS, Johnson G (1999) Dihydropyrimidinone derivatives as neuropeptide Y antagonists. Expert Opinion on Therapeutic Patents.9:321-325
  23. Fujita K, Nakayama H, Ichikawa W, Yamamoto W, Endo H, Nagashima F, Tanaka R, Miya T, Sunakawa Y, Yamashita K, Mizuno K, Ishida H, Araki K (2009) Pharmacokinetics of 5-fluorouracil in elderly Japanese patients with cancer treated with S-1 (a combination of tegafur and dihydropyrimidine dehydrogenase inhibitor 5-chloro-2,4-dihydroxypyridine) Drug Meta Dispo 37:1375-1377
  24. Gonzalez-Rosende M, Olivar T, Castillo E, Sepulveda-Arques J (2008) 2-sulfonyliminodi hydropyrimidinethines, a novel class of analgesic compounds. Archivder Pharma 341:690-695
  25. Van K, Andre BP, Van L, Blom M, Mul E, Van G, Albert H (1998) The activity of dihydropyrimidinthiones dehydrogenase in human blood cells. Adva Experi Medi Bio 431:823-826
  26. Ranise A, Bruno O, Schenone S, Bondavalli F, Falcone G, Filippelli W, Sorrentino S (1997) Synthesis of 6-thiosubstituted 5-ethoxycarbonyl-1,3-diphenyl-2-thioxo-2,3-dihydropyrimidin -4(1H)-ones, 6-substituted 5-hydroxy-1,3-diphenyl-2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-ones and their esters with local anesthetic, antiarrhythmic, antiinflammatory and analgesic activities. Farmaco 52:547-555
  27. Mohan KC, Ravikumar K, Shetty MM, Velmurugan D (2003) Crystal and molecular structures of 4-aryl-1,4- dihydropyrimidines: Novel calcium channel antagonists. Zeit Fuer Krista 218:46-55

International Journal of Scientific Research in Science and Technology

Downloads

Published

2017-12-31

Issue

Volume 2, Issue 3, May-June-2016

Section

Research Articles

License

Copyright (c) IJSRST

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

[1]
Basavaiah Umesha, Sowbhagya, Yeriyur Basavaiah Basavaraju, " Synthetic Study on Chalcone and their Dihydropyrimidinone and Dihydropyrimidinethione Derivatives, International Journal of Scientific Research in Science and Technology(IJSRST), Online ISSN : 2395-602X, Print ISSN : 2395-6011, Volume 2, Issue 3, pp.340-343, May-June-2016.