Synthesis and Antibacterial Activity of PCMX Derivative

Abstract

Para Chloro Meta Xylenol (PCMX) is an exceptionally broad spectrum bactericide and preservative with a long established and proven use in controlling bacteria, mildew and fungal growth in a wide range of applications (medical, domestic and industrial). Chloroxylenol, also known as para chloro meta xylenol, is an antiseptic and disinfectant which is used for skin disinfection and cleaning surgical instruments. It is also used within a number of household disinfectants and wound cleaners. Their analogues viz. hybrid / ester molecules also possess various biological activities which prompted us to synthesize a novel analogue for their future application as bioactive molecule. The synthesized compound was characterized by IR, 1HNMR, mass spectral data, elemental analysis and screened for its potential antibacterial activity against Gram positive and Gram negative bacteria. It shows a promising antibacterial activity.

Introduction

I. INTRODUCTION

Phenolic phytochemicals are known to exhibit anti-inflammatory, antioxidant, anti-carcinogenic, anti-diabetic, anti-atherosclerosis and immunomodulatory activities in animals1,2. These are mostly polyphenols known as secondary plant metabolites3 present in plant and trees. One of such compound PCMX which is used as antiseptic, disinfectant and antimicrobial agent4,5. Chloroxylenol is an antimicrobial used to control bacteria, algae and fungi in adhesives, emulsions, paints and wash tanks. It also is used to sanitize bathroom premises, diaper pails, laundry equipment, human bedding and pet living quarters in households, hospitals and other institutions. Since it possesses various biological activity and in continuation to our earlier work6, we decided to make a library of compounds using various permutations and combinations to come up with a novel ester derivative of PCMX using conventional method. The objective of this study is to condense two molecules of the same disease domain to produce a more potent candidate in the same disease domain or to condense two molecules of different disease domain to produce mixed variety of those disease domains or to have drug candidate with entirely different disease domains. In the present work, in continuation to our earlier work7, we are condensing para chloro meta xylenol with 4-bromo benzoic acid under DCC / DMAP/ Pyridine reaction condition in dichloromethane as solvent at room temperature to yield desired ester derivative in 80 % yield. The resultant ester derivative evaluated for its potential antimicrobial activity.

II. RESULTS   AND DISCUSSION

1) Preparation of PCMX: It was prepared by passing chlorine gas through meta xylenol in xylene at ambient temperature to yield a mixture of para chloro meta xylenol (80 %, major) and dichloro meta xylenol (20 %, minor) since –OH group was activating and ortho, para directing. The PCMX was purified by crystallization and the mother liquor which was enriched in DCMX was used to prepare DCMX commercially.

References

[1] Wattenberg L. W., Coccia J. B.,Lam L. K. Inhibitory effects of phenolic compounds on benzo(a)pyrene-induced neoplasia. Cancer Res., 1980, 40, pp. 2820 – 2823. [2] Talalay P., De Long M. U., Prochaska H. J. Identification of a common chemical signal regulating the induction of enzymes that protects against chemical carcinogenesis. Proc. Natl. Acad. Sci. USA. [3] Macheix JJ., Fleuriet A.;Billot J. Fruit phenolics. Boca Raton, FL; CTC; 1990. [4] World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization .p. 324. hdl:10665/44053. ISBN 9789241547659. [5] Griffiths, Christopher; Barker, Jonathan; Bleiker, Tanya; Chalmers, Robert; Creamer, Daniel (2016-02-29). Rook\'s Textbook of Dermatology, 4 Volume Set. John Wiley & Sons. p. 128.38. ISBN 9781118441176. Archived from the original on 2017-01-13. [6] Gangan V. D., Yadav U, Mewada K., Khandait S. A., Parulekar T. P., Singh A., Raddi K. Ester Derivatives of eugenol as potential Antibacterial agent. International journal of food and nutritional sciences, 2022, UGC Care listed Journal (Group I), Vol. 11 (10), pp. 2818 – 2825. [7] Parulekar T. P., Gangan V. D., Nair A. S., Mathew A. and Raddi K. International Journal of Scientific Research in Science & Technology, November – December 2023, 10 (6), pp. 65 – 70. [8] a) Finn R. K. Theory of Agar Diffussion Methods for Bioassay. Anal. Chem., 1959, 31 (6), pp 975 – 977. b ) Al lafi T et. al.. The effect of miswak used in Jordan and Middle East on oral bacteria. International Dental Journal, 1995, 45 (3), pp. 218 – 222.

Copyright

Copyright © 2024 Tanuja P. Parulekar, Vijay D. Gangan, Kundan Mewada, Mangesh Kulkarni, Karuna Raddi. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.