[01] C. E. Sokwaibe, Department of Chemistry, Michael Okpara University of Agriculture, Umudike, Nigeria. [02] I. E. Otuokere, Department of Chemistry, Michael Okpara University of Agriculture, Umudike, Nigeria.

Novel ligand, 1-(5-hydroxy-3-methyl-1-phenyl-1h-pyrazol-4-yl) octadecan-1-one (HMPPO) was synthesized by the reaction between 3-methyl-1-phenylpyrazol-5-one and octadecanoyl. HMPPO was characterized based on elemental analysis, IR, ¹HNMR and ¹³CNMR spectroscopy. Physical properties such as colour, melting points and solubility profile were also determined for HMPPO. Spectroscopic analysis showed that HMPPO existed in the enol form. The solubility data showed that HMPPO was hydrophobic. Furthermore the biological activities of the HMPPO against benign Prostatic Hyperplasia (BPH) cells were studied. HMPPO reduced prostate specific antigen (PSA) significantly (P<0.05) relative to the hormone control ‘HC’ group. The reduction in PSA concentration may have been as a result of decrease in proliferation of prostatic cells in the test groups since PSA level is known to elevate in prostatic lesion due to cellular proliferation. HMPPO arrested growth of prostatic cells in the test groups leading to decreased secretion of prostatic acid phosphatase in the prostatic cells. There was significant increase (P<0.05) in relative prostate weight of ‘HC’ group compared to the test group HMPPO and Finasteride group. The result of this study showed that HMPPO have inhibitory effect on the development of benign prostatic hyperplasia.

1-(5-hydroxy-3-methyl-1-phenyl-1h-pyrazol-4-yl) octadecan-1-one, Spectroscopy, Benign Prostatic Hyperplasia, Pyrazolone

[01] Jensen, B. S. (1959). The Synthesis of 1-phenyl-3-methyl-4-acylpyrazolones-5, ActaChemica Scandinavia, 13, 1668–1670. [02] Sarbani, P., Jyoti, M. and Nalla, S. D. (2008). High Speed Synthesis of Pyrazolones using Microwave assisted Neat Reaction Technology, J. Braz. Chem. Soc., 19, 1590. [03] Eller, G. A. and Holzer, W. (2006). A One-step synthesis of pyrazolone, Molbank, 33: 464. [04] Poonam, G., Jitendra, k., Gupta and halve A. k. (2015). Synthesis and biological significance of pyrazolones: a review. International journal of pharmaceutical science and research. Vol. 6(6): 2291-2310. [05] Okafor, E. C., Uzoukwu, A. B., Hitchoock, P. B. and Smith, J. D. (1990). Crystal Structure of bisoxo-bis (1-phenyl-3-methyl-4-acetylpyrazolone-5- O ketoaquouranium (VI), Inorg. Chim. Acta., 172: 97. [06] Ogwuegbu, M. O. C. and Maseka, K. K. (1998). Studies on the coordination complexes of Ca (II), Cd (II) and In (IV) with p-nitrobenzoyl-oxo-pyrazole, Bull. Chem. Soc. Ethiop., 12 (1), 27–33. [07] Arinze, J. C., Daniel, N. E. and Ogwuegbu, M. O. C. (2012). Synthesis and Characterization of p-nitrobenzoylpyrazolone-5 and its complexes of Mn (II), Fe (III), Rh (III), W (VI) and U (VI), Journal of Emerging Trends in Engineering and Applied Sciences, (JETEAS), 3(1), 61–68. [08] Ogwuegbu, M. O. C. (1999). Synthesis and Characterization of Nitroacyl-5-oxo-pyrazole and its Vanadium (V), Iron (III) and Cobalt (II) complexes, Bull. Chem. Soc. Ethiop., 13 (2), 113—120. [09] Okafor, E. C. (1984). 1H and 13C NMR Spectral studies of 1-phenyl-3-methyl-4-acylpyrazol-5-ones in chloroform, SpectrochimicaActa., 40(5): 397-401. [10] Ahaiwe, U. (2012). The effect of oral administration of leaf extract of VernoniaAmygdalina on benign prostatic hyperplasia in rats. A Thesis of Biochemistry Dept. MOUAU. [11] David, A. A. (1993). Prostate – Specific Antigen: Biochemistry Analytical methods and clinical Application. Clin. Chem. 39(2):181–195 [12] Shina, A. A., Wilson, M. J. and Glesson D. F. (1987). Immunoelectron microscopic localization of prostate specific antigen in human prostate by a protein gold complex. J. Natl. Cancer Inst. Monogr Cancer. 60: 1288–1293. [13] Wang, M. C., Valenzuela, L. A., Murphy, G. P. and Chu, T. M. (1981). Purification of a human prostate specific antigen. Invest Urol. 17: 159–163. [14] Lilja, H. A. (1980). A killikrein – like serine protease in prostatic fluid cleaves the predominant seminal vesicle protein. J Clin. Invest. 76: 1898–1903. [15] De La Rosette, J., Alivizatos, G., Madersbacher, S., Rioja, S. C., Nordling, J., Emberton, M., Gravas, S., Michelm M. C and Oelke, M. (2006). Guidelines on benign prostatic hyperplasia. European Association of Urology. 40: 672–676. [16] Joshua, P. E., Obidoa, O. and Nwodo, F. C. (2010). Biochemical responses of rat prostate to coconut (cocosnucifera) milk ingestion/treatment. NJBM. 25(1): 1-8. [17] Jeyaraj, D. A., Uduyakumar, T. S., Rajalakshmi, M., Pal, P. C. and Sharma, R.s. (2000). Effect of long administration of androgens and estrogen on rhesus monkey prostate: possible induction of benign prostatic hyperplasia. J. Androl. 21: 833–841. [18] Rani, V. E. and Ravindranath, L. K. (2016). Synthesis and antimicrobial activity of Novel pyrazolo-5-one containing 1,3,4-oxadiazole Sulfonyl Phosphonates, American Journal of organic Chemistry, 6(1): 1–7. [19] Prajuli, R. Banerjee, J., Khanal, H. (2015). Synthesis of some pyrazolonederivaties and evaluation of its antibacterial and cytotoxic activity, Orient J. Chem, 31(4): 2099-2106. [20] Naim, M. J., Alam, O., Nawaz, F., Alam, A. J. and Alam P. (2016). Current status of pyrazole and its biological activities. J. Pharm Bioallied Sci. 2016, 8(1): 2-17.