Synthesis and Antibacterial Activity of Urea and Thiourea Derivatives of Anacardic Acid Mixture Isolated from A Natural Product Cashew Nut Shell Liquid (CNSL)

N. Subhakara Reddy, A. Srinivas Rao, M. Adharvana Chari, V. Ravi kumar, V. Jyothy, V. Himabindu

Bio-Pharma Pvt. Ltd., Westren Hills, Hyderabad, India.
Centre for Environment, Institute of Science and Technology, JNT University, Hyderabad, India.
Medicinal Chemistry Laboratory, GVK Biosciences Pvt. Ltd., Hyderabad, India.

DOI: 10.4236/ijoc.2012.23036                

Abstract

Synthesis and antibacterial activity of some novel urea and thiourea derivatives (8a - 8k, 9a - 9f) of anacardic acid prepared from commercially available anacardic acid which is obtained from natural product Cashew Nut Shell Liquid (CNSL). Compounds (8a - 8k, 9a - 9f) were tested for Gram positive and Gram negative bacterial cultures. Most of the compounds were showed active compared with standard drug ampicilline.

Keywords

Synthesis; Urea and Thiourea Derivatives; Anacardic Acid; Anti-Bacterial Activity

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	J. H. P. Tyman, “Non-Isoprenoid Long Chain Phenols,” Chemical Society Reviews, Vol. 8, No. 4, 1979, pp. 499- 537. doi:10.1039/cs9790800499
[2]	I. Kubo, M. Ochi, P. C. Viera and S. Komatsu, “Antitumor Agents from the Cashew (Ana-cardium occidentale) apple juice,” Journal of Agricultural and Food Chemistry, Vol. 41, No. 6, 1993, pp. 1012-1015. doi:10.1021/jf00030a035
[3]	M. J. Rybak and R. L. Akins, “Emergence of Methicillin-Resistant Staphylococcus Aureus with Intermediate Glycopeptide Resistance: Clinical Signifi-cance and Treatment Options,” Drugs, Vol. 61, No. 1, 2001, pp. 1-7. doi:10.2165/00003495-200161010-00001
[4]	M. Lipsitch, “The Rise and Fall of Antimicrobial Resistance,” Trends Mi-crobiology, Vol. 9, No. 9, 2001, pp. 438-444. doi:10.1016/S0966-842X(01)02130-8
[5]	B. A. Cunha, Drugs Today, Vol. 34, 1998, pp. 691-698.
[6]	A. Marchese, G. C. Schito and E. A. Debbia, “Evolution of Antibiotic Resis-tance in Gram-Positive Pathogens,” Journal of Chemotherapy, Vol. 12, No. 6, 2000, pp. 459- 462.
[7]	Y. Cetinkaya, P. Falk and C. G. Mayhall, “Vancomy- cin-Resistant Enterococci,” Clinical Microbiology Reviews, Vol. 13, No. 4, 2000, pp. 686-707. doi:10.1128/CMR.13.4.686-707.2000
[8]	G. H. Cassell and J. Mekalanos, “Development of An- timicrobial Agents in the Era of New and Reemerging Infectious Diseases and Increasing Antibiotic Resis- tance,” Journal of the American Medical Association, Vol 285, No. 5, 2001, pp. 601-605. doi:10.1001/jama.285.5.601
[9]	D. T. W. Chu, J. J. Plattner and L. Katz, “New Directions in Antibacterial Research,” Journal of Medicinal Chemistry, Vol. 39, No. 20, 1996, pp. 3853-3874. doi:10.1021/jm960294s
[10]	I. Kubo, H. Muroi and M. Himejima, “Structure-Anti Bacterial Activity Relationships of Anacardic Acids,” Journal of Agricultural and Food Chemistry, Vol. 41, No. 6, 1993, pp. 1016-1019. doi:10.1021/jf00030a036
[11]	J. L. Gillerman, N. J. Walsh, N. K. Werner and H. Schlenk, “Antimicrobial Effects of Ana-cardic Acids,” Canadian Journal of Microbiology, Vol. 15, No. 10, 1969, pp. 1219- 1223. doi:10.1139/m69-220
[12]	A. S. Gulati and B. C. Subba Rao, Indian Journal of Chemistry, Vol. 2, 1964, pp.337.
[13]	M. A. EIShol, P. D. Adawadkar, D. A. Benign, E. S. Watson and T. L. Little Jr., “6-(Alkylamino)-9-benzyl- 9H-purines. A New Class of Anti-convulsant Agents,” Journal of Medicinal Chemistry, Vol. 29, 1986, pp. 606- 612.
[14]	S. V. Shoba, C. S. Ramadoss and B. Ravindranath, “Inhibition of Soybene Lipoxygenase-1 by Ana-cardic Acids, Cardol, and Cardanols,” Journal of Natural Products, Vol. 57, No. 12, 1994, pp. 1755-1757. doi:10.1021/np50114a025
[15]	T. J. Ha and I. Kubo, “Li-poxygenase Inhibitory Activity of Anacardic Acids,” Journal of Agricultural and Food Chemistry, Vol. 53, No. 11, 2005, pp.4350-4354. doi:10.1021/jf048184e
[16]	V. Chandregowda, A. Kush and G. C. Reddy, “Synthesis of Benzamide Derivatives of Anacardic Acid and Their Cytotoxic Activity,” European Journal of Medicinal Chemistry, Vol. 44, No. 6, 2009, pp. 2711-2719. doi:10.1016/j.ejmech.2009.01.033
[17]	R. Paramashivappa, P. Phanikumar, P. V. Subba Rao and A. Srinivasa Rao, “Synthesis of Sildenafil Analogues from Anacardic Acid and Their Phos-phodiesterase-5 Inhibition,” Journal of Agricultural and Food Chemistry, Vol. 50, No. 26, 2002, pp. 7709-7713. doi:10.1021/jf0258050
[18]	P. Phanikumar, S. C. Stotz, R. Paramashivappa, M. Beedle, G. W. Zamponi and A. Srinivasa Rao, “Synthesis and Evaluation of a New Class of Nifedipine Analogs with T-Type Calcium Channel Blocking Activity,” Molecular Pharmacology, Vol. 61, No. 3, 2002, pp. 649-658. doi:10.1124/mol.61.3
[19]	B. Narayana Swamy, T. K. Suma, G. Venkateswara Rao and G. Chandrasekara Reddy, European Journal of Medicinal Chemistry, Vol. 42, 2007, pp. 422-424.
[20]	K. Mantelingu, A. H. Kishore, K. Balasubra-manyam, G. V. Kumar, M. Altaf, S. N. Swamy, R. Selvi, C. Das, C. Narayana, K. S. Rangappa and T. K. Kundu, “Activation of p300 Histone Acetyltransferase by Small Molecules Altering Enzyme Structure: Probed by Surface-Enhanced Raman Spectroscopy,” Journal of Physical Chemistry B, Vol. 111, No. 17, 2007, pp. 4527-4534. doi:10.1021/jp067655s
[21]	A. Hari Kishore, B. M. Veda-murth, K. Mantelingu, S. Agrawal, B. A. Ashok Redd, S. Roy, K. S. Rangappa and T. K. Kundu, “Specific Small-Molecule Activator of Aurora Kinase A Induces Autophosphorylation in a Cell- Free System,” Journal of Medicinal Chemistry, Vol. 51, No. 4, 2008, pp. 792-797. doi:10.1021/jm700954w
[22]	B. Sung, M. K. Pande, K. S. Ahn, T. Yi, M. M. Chaturved, M. Liu and B. B. Aggarwal, “Anacardic Acid (6-Nonadecyl Salicylic Acid), an Inhibitor of Histone Acetyltransferase, Suppresses Expression of Nuclear Factor-κB-Regulated Gene Products Involved in Cell Survival, Proliferation, Invasion, and Inflammation through Inhibition of the Inhibitory Subunit of Nuclear Factor- κBα Kinase, Leading to Potentiation of Apoptosis,” Blood, Vol. 111, No. 10, 2008, pp. 4880-4891. doi:10.1182/blood-2007-10-117994
[23]	L. Cui, J. Miao, T. Furuya, Q. Fan, X. Li, P. K. Rathod, X. Z. Su and L. Cui, “Histone Acetyltransferase Inhibitor Anacardic Acid Causes Changes in Global Gene Expres- sion during in Vitro Plasmo-dium Falciparum Development,” Eukaryotic Cell, Vol.7, No. 7, 2008, pp. 1200- 1210. doi:10.1128/EC.00063-08
[24]	G. Sbardella, S. Castellano, C. Vicidomini, D. Rotili, A. Nebbioso, M. Miceli, L. Altucci and A. Mai, “Identification of Long Chain Alkylidenemalonates as Novel Small Molecule Modulators of Histone Acetyl-Transferases,” Bioorganic & Medicinal Chemistry Letters, Vol. 18, No. 9, 2008, pp. 2788-2792. doi:10.1016/j.bmcl.2008.04.017
[25]	R. Paramashivappa, P. Phanikumar, P. J. Vithayathil and A. Srinivasa Rao, “Novel Method for Isolation of Major Phenolic Constituents from Cashew (Anacardium occidentale L.) Nut Shell Liquid,” Journal of Agricultural and Food Chemistry, Vol. 49, No. 5, 2001, pp. 2548-2551. doi:10.1021/jf001222j
[26]	A. Rahman, M. L. Choudhary and W. J. Thomson, “Bioassay Techniques for Drug Develop-ment,” Harwood Academic Publishers, The Netherlands, 2001. doi:10.4324/9780203304532