European Journal of Chemistry

Synthesis and antimicrobial activity of novel oxime derivatives of phenothiazine



Main Article Content

Ashutosh Barve
Malleshappa Noolvi
Niharika Subhedar
Vishnu Dev Gupta
Gaurav Bhatia

Abstract

A series of 4-methyl-2-oxo-pyranyl-phenothiazines (IIIa-j) followed by 4-methylpyrano-(2, 3-β)-phenothiazine-2(11H)-one oxime (IVa-j) were synthesized by using 7-hydroxy-4-methylcoumarin (I). Further reaction of (I) was carried out with substituted aromatic amines (a-j) to convert into 7-arylamino-4-methyl-coumarin (IIa-j). Additionally (IIa-j) was treated with sulphur in presence of iodine to obtain a series of novel 4-methyl-2-oxo-pyranyl-phenothiazine (IIIa-j) derivatives, which on treatment with hydroxylamine hydrochloride afforded the title compounds i.e. 4-methylpyrano-(2,3-β)-phenothiazine-2(11H)-one oxime (IVa-j). The structures of these compounds were confirmed by IR, NMR and Mass spectral analysis. The newly synthesized compounds were evaluated for antibacterial and antifungal activity. The results show that compound IIIa, IIIe, IIIh, IIIj, IVa, IVi and IVj exhibited moderate to good antibacterial and antifungal activity at 5-100 mcg/mL.

2_3_388_393_800


icon graph This Abstract was viewed 2203 times | icon graph Article PDF downloaded 907 times

How to Cite
(1)
Barve, A.; Noolvi, M.; Subhedar, N.; Gupta, V. D.; Bhatia, G. Synthesis and Antimicrobial Activity of Novel Oxime Derivatives of Phenothiazine. Eur. J. Chem. 2011, 2, 388-393.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Bisignano, G.; Sanogo, R.; Marino, A.; Aquino, R.; Dangelo, V.; Germano, M.P.; De Pasquale, R.; Pizza, C. Lett. Appl. Microbiol. 2000, 30, 105-108.
http://dx.doi.org/10.1046/j.1472-765x.2000.00692.x
PMid:10736009

[2]. Kayser, O.; Kolodziej, H. Planta Med. 1997, 63, 508-510.
http://dx.doi.org/10.1055/s-2006-957752
PMid:9434601

[3]. Sardari, S.; Mori, Y.; Horita, K.; Micetich, R.G.; Nishibe, S.; Daneshtalab, M. Bioorg. Med. Chem. 1999, 7, 1933-1940.
http://dx.doi.org/10.1016/S0968-0896(99)00138-8

[4]. Jurd, D. L.; Corse, J.; King, A.; Bayne, H.; Mihara, K. Phytochemistry 1971, 10, 2971-2974.
http://dx.doi.org/10.1016/S0031-9422(00)97334-5

[5]. Jurd, D. L.; King, J. R.; Mihara, K. Experientia. 1970, 26, 1281-1283.
http://dx.doi.org/10.1007/BF01898019
PMid:4991933

[6]. Shukla, Y.; Srivastava, A.; Kumar, S.; Kumar, S. J. Ethnopharm. 1999, 67, 241-245.
http://dx.doi.org/10.1016/S0378-8741(99)00017-3

[7]. Kwon, Y. S.; Kobayashi, A.; Kajiyama, S. I.; Kawazu, K.; Kanzaki, H.; Kim, C. M. Phytochemistry 1997, 44, 887-889.
http://dx.doi.org/10.1016/S0031-9422(96)00634-6

[8]. Marston, A.; Hostettmann, K.; Msonthi, J. D. J. Nat. Prod. 1995, 58, 128-130.
http://dx.doi.org/10.1021/np50115a019
PMid:7760070

[9]. Fuller, R. W.; Bokesch, H. R.; Gustafson, K. R.; Mckee, T. C.; Cardellina, J. H.; Mcmahon, J. B.; Cragg, G. M.; Sojaerto, D. D.; Boyd, M. R. Bioorg. Med. Chem. Lettr. 1994, 4, 1961-1964
http://dx.doi.org/10.1016/S0960-894X(01)80543-6

[10]. Yang, Y. Z.; Ranz, A.; Pan, H. Z.; Zhang, Z. N.; Lin, X. B.; Meshnick, S. R. Am. J. Trop. Med. Hyg. 1992, 46, 15-20.
PMid:1311154

[11]. Ehlich, P. Chemotherapeutics: scientific principles, methods, and results. Lancet. 1913, Ed. 2, pp. 445-451.

[12]. Leonard, A.; Jette, E. K. Int. J. Antimicrob. Agent. 2001, 18, 411-417.
http://dx.doi.org/10.1016/S0924-8579(01)00432-0

[13]. Amaral, L.; Kristiansen, J.; Thomsen, V.; Markowich, B. Int. J. Antimicrob. Agents. 2000, 14, 225-229.
http://dx.doi.org/10.1016/S0924-8579(00)00136-9

[14]. Ratnakar, P.; Rao, S. P.; Sriramarao, P. Int. Clin. Psychopharmocol. 1995, 10, 39-43.
http://dx.doi.org/10.1097/00004850-199503000-00005
PMid:7622803

[15]. Kristiansen, J. E.; Justesen, T.; Hvidberg, E. F.; Andersen, L. P. Pharmacol Toxicol. 1989, 64, 386-388.
http://dx.doi.org/10.1111/j.1600-0773.1989.tb00672.x

[16]. Chakrabarty, A. N.; Bhattacharya, C. P.; Dasdidar, S. G. Acta Path et Microbiol Scand. 1993, 101, 449-454.

[17]. Amaral, L.; Kristiansen, J. E.; Lorian, V. J. Antimicrob. Chemother. 1992, 30, 556-558.
http://dx.doi.org/10.1093/jac/30.4.556
PMid:1490927

[18]. Bettencourt, V. M.; Amaral, L. Int. J. Antimicrob. Agents. 2001, 17, 225-228.
http://dx.doi.org/10.1016/S0924-8579(00)00343-5

[19]. Kristiansen, J. E.; Vergann, B. Acta Path. Micro. 1986, 94, 393-398.

[20]. Molnar, J.; Beladi, I.; Foldes, I. Zbl. Bakt. Mik. Hyg. 1977, 239, 521-526.

[21]. Deeds, F.; Stockton, A. B.; Thomas, J. O. Pharmaco. Exp. Therapy 1939, 65, 353-371.

[22]. Chan, Y.; Ong, Y.; Chua, K. L. Antimicrob. Agents. Ch. 2007, 51, 623-630.
http://dx.doi.org/10.1128/AAC.01033-06
PMid:17145801 PMCid:1797753

[23]. Desai, J. J.; Desai, P. G.; Mehta, A. G. Asian J. Chem. 1999, 11, 519-522.

[24]. Desai, J. J.; Desai, P. G.; Mehta, A. G. Asian J. Chem. 2000, 12, 1067.

[25]. Hania, M. M. Asian J. Chem. 2002, 14, 1074-1079.

[26]. Rai, B. K. Asian J. Chem., 2002, 14, 1595-1599.

[27]. Rai, B. K., Asian J. Chem. 2002, 14, 312-316.

[28]. Hania, M. M. Asian J. Chem. 2005, 17, 439-442.

[29]. Dobeck, A. S.; Klayman, D. Antimicrob Agents Chemother. 1980, 18, 27-30.
PMid:7416748 PMCid:283934

[30]. Wagner, W. H.; Winkelman. E. Arzneim Forschi. 1972, 22, 1713-1721.

[31]. Hania, M. M. Asian J. Chem. 2007, 17, 439-443.

[32]. Morrison, N. E.; Collins, F. M. Int. J. Leprosy. 1981, 49, 180-188.

[33]. Jones, D. H.; Slack, R.; Squires, S. J. Med. Chem. 1965, 2, 676-681.
http://dx.doi.org/10.1021/jm00329a026

[34]. Klayman, D. L.; Joseph, F. J. Med. Chem. 1979, 22, 855-860.
http://dx.doi.org/10.1021/jm00193a020
PMid:376848

[35]. Mann, F. G.; Saunders, B. C. Practical Organic Chemistry, Longan Inc., New York, 1960, 6th Edn. pp 307-308.

[36]. Pandey, V. K.; Saxena, S. K.; Joshi, M. N. Indian J. Chem. 2004, 43, 1015-1017.

[37]. Li, J. J.; Limberakis, C.; Pflum, D. A. Modern Organic Synthesis in the Laboratory A Collection of Standard Experimental Procedures, Pfizer Global Research & Development, Oxford University press, 2007, 2nd Edn., pp 42-44.

[38]. Hart, D. J.; Magomedov, N. A. J. Am. Chem. Soc. 2001, 123, 5892-5899.
http://dx.doi.org/10.1021/ja010066+
PMid:11414821

[39]. Coleman, K. Drug Discov. Today, Therapeutic Strategies 2004, 1st Edn. pp 455-460.

[40]. Smyth, R. D. Clinical analysis, Microbiology, Remingtonâs Pharmaceutical sciences 18th Edition, Mack Publishing Company Peninisilvenia, 1991, pp. 524-27

[41]. Biological assay, Indian Pharmacopoeia published by Govt. of India 1996 (2): A-88.

[42]. Pellczar, M. J. R.; Chan, E. C. S. Antibiotics and other chemotherapeutic agent Microbiology, TMH Edition, TATA-McGraw-Hill Publishing Houses, 1989, pp. 466-493

[43]. Harry, W. Antiseptic and Disinfectant action, Microbes in Action, A Laboratory manual in Microbiology 1982, pp. 75-76.

[44]. Davis, W. W.; Stout, T. R. Appl. Environ. Microbiol. 1971, 22(4), 666-670.

[45]. Lalitha, M. K. Manual on Antimicrobial Susceptibility Testing (Under the auspices of Indian Association of Medical Microbiologists) http://www.ijmm.org/documents/Antimicrobial.doc.

[46]. Gaud, S. R. Microbial Assays, In Practical Microbiology, Nirali Publication, 2006, 2nd Edn. Pp. 111-116.

[47]. Carter, S. J. Basics of Microbiology, Cooper and Gunnâs Tutorial Pharmacy, CBS Publishers and Distributors, 2005, pp. 289-366.

[48]. Andrews, J. M. J. Antimicrob. Chemoth. 2001, 48, 5-11.

[49]. Phair, J. P.; Watanakunakorn, C.; bannister, T. Am. Soc. Microb. 1969, 18(3), 303-306.

[50]. Therese, K. L.; Bagyalakshmi, R.; Madhavan, H. N.; Deepa, P. Indian J. Med. Microbio. 2006, 24(4), 273-279.
http://dx.doi.org/10.4103/0255-0857.29386
PMid:17185846

Supporting Agencies

Bhanwar Nahata College of Pharmacy, Mandsaur (Madhya Pradesh), India
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).