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Synthesis and Pharmacological Properties of 1,3-Bis[(S)Phenylethyl]Imidazolidine-2-Thione

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Pharmaceutical Chemistry Journal Aims and scope

Enantiomerically and diastereomerically pure thiourea derivative (compound I) has been synthesized in two steps starting from (S)-1-phenylethanamine and 1,2-dibromoethane. Compound I was screened for various biochemical parameters including blood glucose level, serum total cholesterol level, serum bilirubin and triglyceride levels, serum glutamate pyruvate transaminase (SGPT) and alkaline phosphatase (ALP) activity in New Zealand White (NZW) rabbits. Compound I was also screened for brine shrimp cytotoxicity, antileishmanial and antioxidant activity. Acute toxicity tests in NZW rabbits were performed and the results showed that compound I was safe up to 2 mg/mL/kg rabbit body weight. For the blood parameters, it was found that compound I caused slightly reduced blood glucose level, increased blood serum bilirubin, ALP and SGPT levels, and caused no changes in cholesterol and triglyceride levels. Thus, results show that compound I possesses good cytotoxic, poor antileishmanial activity, and no prominent antioxidant activity.

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References

  1. K. Pourshamsian, N. Montazeri, and A. S. Khameneh, JACR, 16, 69 – 74 (2011).

    Google Scholar 

  2. R. A. Katritzky and F. M. Gordeev, J. Chem. Soc., Perkin Trans., 1, 9, 2199 – 2203 (1991).

  3. M. Struga, J. Kossakowski, E. Kedzierska, et al., Chem. Pharm. Bull., 5, 796 – 799 (2007).

    Article  Google Scholar 

  4. A. D. Desai, D. H. Mahajan, and K. H. Chikhalia, IJC, 7, 1169 – 1173 (2007).

    Google Scholar 

  5. B. R. Patel, H. K. Chikhalia, C. Pannecouque, et al., J. Braz. Chem. Soc., 2, 312 – 321 (2007).

    Google Scholar 

  6. G. Ayhan-Kilcigil and N. Altanlar, Turk. J. Chem., 30, 223 – 228(2006).

    CAS  Google Scholar 

  7. K. B. Sharma, K. S. Sharma, P. Singh, et al., J. Enzyme Inhib. Med. Chem., 23, 168 – 173 (2008).

    Article  CAS  PubMed  Google Scholar 

  8. A. Semwal, A. Nigam, and S. Gupta, AJPLS, 1, 149 – 155 (2011).

    CAS  Google Scholar 

  9. A. S. Khan, N. Singh, and K. Saleem, Eur. J. Med. Chem., 10, 2272 – 2277 (2008).

    Article  Google Scholar 

  10. A. Hakan, D. Nizami, B. Gulay, et al., Molecule, 14, 519 – 527 (2009).

    Article  Google Scholar 

  11. R. K. Venkata, S. Rasheed, G. Madhava, et al., J. Serb. Chem. Soc., 77, 1 – 14 (2012).

    Article  Google Scholar 

  12. G. Kavak, S. Ozbey, G. Binzet, et al., Turk J. Chem., 33, 857 – 868 (2009).

    CAS  Google Scholar 

  13. L. Wang and C. L. Weller, Trends Food Sci. Technol., 17, 300 – 312 (2006).

    Article  CAS  Google Scholar 

  14. I. Raskin, D. M. Ribnicky, S. Komarnytsky, et al., Trends Biotechnol., 20, 522 – 531 (2002).

    Article  CAS  PubMed  Google Scholar 

  15. R. Soliman, H. M. Faid?Allah, and S. K. El Sadany, J. Pharm. Sci., 76, 626 – 32 (1987).

  16. P. Zimmet, K. Alberti, and J. Shaw, Nature, 414,782 – 7 (2001).

    Article  CAS  PubMed  Google Scholar 

  17. M. Kumar and D. Verma, Pharmacol. Online, 2, 307 – 11 (2011).

    CAS  Google Scholar 

  18. S. Del Prato and N. Pulizzi, Metabolism, 55, S20 – S7 (2006).

    Article  PubMed  Google Scholar 

  19. S. Goyal, J. K. Rai, R. Narang, and K. Rajesh, Intl. J. Pharm. Pharm. Sci., 2, 1 – 6 (2010).

    CAS  Google Scholar 

  20. N. Hosseinzadeh, S. Seraj, M. E. Bakhshi-Dezffoli, et al., Iran. J. Pharm. Res., 12, 325 – 30 (2013).

    CAS  PubMed  PubMed Central  Google Scholar 

  21. H. M. Faidallah and K. A. Khan, J. Fluorine Chem., 142, 96 – 104 (2012).

    Article  CAS  Google Scholar 

  22. G. Mariappan, B. Saha, S. Datta, et al., J. Chem. Sci., 123, 335 – 41(2011).

    Article  CAS  Google Scholar 

  23. I. Ilahi, A. Asghar, S. Ali, et al., ISRN Pharmacol., 212, 478023 (2012).

    Google Scholar 

  24. N. Ali, G. Ahmed, S.W. A. Shah, et al., BMC Complem. Altern. Med., 11, 1 – 8 (2011).

    Article  Google Scholar 

  25. S. Nabi, N. Ahmed, M. J. Khan, et al., WAS J., 19, 1495 – 1500 (2012).

    CAS  Google Scholar 

  26. L. Zahi, M. Chen, J. Blom, et al., J. Antimicrob. Chemother., 6, 789 – 793 (1999).

    Google Scholar 

  27. L. I. Mensor, F. S. Menezes, G. G. Leitao, et al., Phytother. Res. 15, 127 – 130 (2001).

    Article  CAS  PubMed  Google Scholar 

  28. S. P. Roche and R. Kobos, Am. Fam. Physician, 69, 299 – 304 (2004).

    PubMed  Google Scholar 

  29. H. Himmerich, I. Anghelescu, C. Klawe, et al., Alc. Alcohol, 36, 26 – 28 (2001).

    Article  CAS  Google Scholar 

  30. P. L. Jansen and M. Muller, Gastroenterology, 116, 486 – 488 (1999).

    Article  CAS  PubMed  Google Scholar 

  31. R. H. Moseley, CLD 3, 465 – 475 (1999).

    CAS  Google Scholar 

  32. D. Agilandeswari, Int. J. Pharm. Ind. Res., 20(3), 195 – 201 (2012).

    Google Scholar 

  33. V. K. Sharma, S. Kumar, H. J. Patel, et al., Int. J. Pharm. Sci. Rev. Res., 1, 18 – 22 (2010).

    Google Scholar 

  34. T. Sundarrajan, R. T. Kumar, E. U. Kumar, et al., IJCPS, 1, 50 – 53 (2010).

    Google Scholar 

  35. K. Y. Ping, I. Darah, Y. Chen, et al., Asian Pac. J. Trop. Biomed., 3, 692 – 696 (2013).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  36. B. S. Patil and C. S. Magdum, Asian J. Res. Pharm. Sci., 1, 42 – 43 (2011).

    Google Scholar 

  37. I. U. Haq, A. Mannan, I. Ahmed, et al., PJB, 44, 1487 – 1490 (2012).

    Google Scholar 

  38. A. U. Rehman, A. Mannan, S. Inayatullah, et al., Pharm. Biol., 47, 628 – 633 (2009).

    Article  Google Scholar 

  39. R. Killick-Kendrick, Clin. Dermatol., 17, 279 – 289 (1999).

    Article  CAS  PubMed  Google Scholar 

  40. P. A. Onocha, G. K. OloyedeI, O. O. Dosumu, et al., Arch. Appl. Sci. Res., 3, 1 – 5 (2011).

    CAS  Google Scholar 

  41. L. Monzote, Open Antimicrob. Agents J., 1, 9 – 19 (2009).

    CAS  Google Scholar 

  42. P. Chakraborty, S. Kumar, D. Dutta, et al., RJPT, 2, 238 – 244 (2009).

    CAS  Google Scholar 

  43. E. Suhartono, E. Viani, M. A. Rahmadhan, et al., IJCEA, 3, 297 – 299 (2012).

    Article  CAS  Google Scholar 

  44. B. Mandana, A. R. Russly, S. T. Farah, et al., IFRJ, 19, 229 – 234 (2012).

    CAS  Google Scholar 

  45. P. N. R. Dekhuijzen, Eur. Respir. J., 23, 629 – 636 (2004).

    Article  CAS  PubMed  Google Scholar 

  46. D. K. Dash, V. C. Yeligar, S. S. Nayak, et al., Trop. J. Pharm. Res. 6, 755 – 765 (2007).

    Article  Google Scholar 

  47. M. Rai, G. Biswas, S. Chatterjee, et al., eJ Bio., 5, 292 – 302 (2009).

    Google Scholar 

  48. F. M. Areias, A. C. Rego, C. R. Oliveira, et al., Biochem. Pharmacol., 62, 111 – 118 (2001).

    Article  CAS  PubMed  Google Scholar 

  49. A. A. Hamid, O. O. Aiyelaagbe, L. A. Usman, et al., AJPAC, 4, 142 – 151 (2010).

    CAS  Google Scholar 

  50. T. B. Shyma, A. G. Deviprasad and M. P. Raghavendra, J. Chem. Pharm. Res., 4, 4501 – 4505 (2012).

    CAS  Google Scholar 

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Acknowledgments

The authors are grateful to the University of Malakand (Chakdara, Dir Lower KPK, Pakistan) for making the resources available to carry out the research work.

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Correspondence to Mohammad Shoaib.

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Umar, M.N., Shoaib, M., Sadiq, M. et al. Synthesis and Pharmacological Properties of 1,3-Bis[(S)Phenylethyl]Imidazolidine-2-Thione. Pharm Chem J 50, 382–387 (2016). https://doi.org/10.1007/s11094-016-1456-4

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  • DOI: https://doi.org/10.1007/s11094-016-1456-4

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