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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Review Article

Chemistry and Pharmacology of Acetanilide Derivatives: A Mini Review

Author(s): Rajib K. Singh, Arvind Kumar and Arun K. Mishra*

Volume 16, Issue 1, 2019

Page: [6 - 15] Pages: 10

DOI: 10.2174/1570178615666180808120658

Price: $65

Abstract

Acetanilide or N-phenylacetamide is an aromatic compound having phenyl ring attached to an acetamido group (–NHCOCH3). In 1886, acetanilide was introduced as an analgesic and antipyretic drug into medical practice by A. Cahn and P. Hepp. Since then, many acetanilide derivatives have been found to have antimicrobial, analgesic, anti-inflammatory, antipyretic, antioxidant, anticonvulsant, anti- cancer, antihyperglycaemic and antimalarial activities. Acetanilide also plays an important role in the synthesis of a number of chemicals as intermediates and precursors. The chief objective of the present article is to highlight the chemistry and pharmacological aspects of various derivatives of acetanilide and their pharmacological activities to assist the future discovery of more efficacious derivatives with less toxicity.

Keywords: Acetanilide, analgesic, antipyretic, anticonvulsant, anticancer, antimalarial.

Graphical Abstract

[1]
Bbenista, M.J.; Nowak, J.Z. Acta Poloniae Pharm. Drug Res., 2014, 71, 11-23.
[2]
Chan, A.; Hepp, P. Centralbl Klein Med, 1886, 7, 561-564.
[3]
Coppock, P.; Park, S.H.; Paredes, J.; Pennington, R.; Pursell, D.P.; Rudd, G.; Sloop, J.C.; Tsoi, M.Y. J. Laborat. Chem. Edu., 2017, 5, 41-47.
[4]
Phukan, K.; Ganguly, M.; Devi, N. Synth. Commun., 2009, 39, 2694-2701.
[5]
Redasani, V.K.; Kumawat, V.S.; Kabra, R.P.; Kansagara, P.; Surana, S.J. Int. J. Chemtech Res., 2010, 2, 856-1859.
[6]
Fernandez, A.B.; Lezcano-Gonzalez, I.; Boronat, M.; Blasco, T.; Corma, A. Phys. Chem. Chem. Phys., 2009, 11, 5134-5141.
[7]
Francis, A.C. Organic Chemistry.6th ed.; McGrawYHill: New York; , 2006.
[8]
Gilbert, E.E. The Chem. Rev., 1962, 62, 549-589.
[9]
Schatz, P.F. J. Chem. Educ., 1996, 73, 267.
[10]
Merrill, D.R.; Adamas, E.Q. J. Am. Chem. Soc., 1917, 39, 1588-1598.
[11]
Liu, G.; Gelboin, H.V.; Myers, M.J. Arch. Biochem. Biophys., 1991, 284, 400-406.
[12]
Brodie, B.B.; Axelrod, J.; Shore, P.A.; Udenfriend, S. J. Biol. Chem., 1954, 208, 741-750.
[13]
Mohan, H. Text book of Pathology, 4th ed; J.P. Publisher, 2000.
[14]
Quartarone, G.; Rancan, E.; Ronchin, L.; Vavasori, A. Appl. Catal. A Gen., 2014, 472, 167-177.
[15]
Keerthi, D.S.; Shashikala, P. Asian. J. Pharmceutics., 2017, 11, S121-S128.
[16]
Adeyeye, C.M.; Li, P.K. Anal. Prof. Drug Subst, 1990, 19, 123-144.
[17]
Graham, G.G.; Scott, K.F. Am. J. Ther., 2005, 12, 46-55.
[18]
Zhou, Y.; Plowman, S.J.; Lichtenberger, L.M.; Hancock, J.F. J. Biol. Chem., 2010, 285, 35188-35195.
[19]
Clissold, S.P. Drugs, 1986, 32, 46-59.
[20]
Aarbakke, J. Clin. Pharmacol., 1978, 3, 369-380.
[21]
Sim, E.; Stanley, L.; Gill, E.W.; Jones, A. Biochem. J., 1988, 251, 323-326.
[22]
Grewal, M.S.; Sanan, S.; Mittal, G.C. Indian J. Physiol. Pharmacol., 1975, 19(2), 76-80.
[23]
Robarts, L.J.; Morrow, J.D. Analgesic – Antipyretic and Antiinflammatory agents and Drugs employed in the treatmaent of Gout.In: Goodman & Gilman’s the Pharmacological Basis of Therapeutics.Gilman, G.A., Ed.; Mcgraw-Hill: NewYork,; pp. 687-696.
[24]
Pandeya, S.N. A text book of Medicinal Chemistry; S.G. Publisher, 2001.
[25]
John, H.B.; John, M.B. Wilson and Grisvold’s Text book of Organic Medicinal and Pharmaceutical Chemistry, 11th ed; Lippincott Williams and Wilkin Publication: Philadelphia, 1991.
[26]
Abraham, D.J. Burger’s Medicinal Chemistry and Drug Discovery, 6th ed; John Willey Publication: New Jersey, 1996.
[27]
Tripathi, K.D. Essential of Medicinal Pharmacology, 5th ed; , 2006.
[28]
Pattan, S.R.; Ali, M.S.; Pattan, J.S.; Purohit, S.S.; Reddy, V.V.K.; Nataraj, B.R. Indian J. Chem., 2006, 54B, 1929-1932.
[29]
Crumplin, G.C.; Kenwright, M.; Hirst, T. J. Antimicrob. Chemother., 1984, 13, 9-23.
[30]
Konda, R.K.; Nuthakki, V.K.; Nagarjuna, R. Sch. Acad. J. Pharm., 2014, 3, 344-349.
[31]
Baena, Y.; Pinzon, J.A.; Barbosa, H.J.; Martinez, F. Acta Pharm., 2005, 55, 195-205.
[32]
Verma, A.K.; Martin, A.; Singh, A.K. Ind. J. Pharm. Biol. Res., 2014, 2, 84-89.
[33]
Vane, J.R.; Botting, R.M. Thromb. Res., 2003, 110, 255-258.
[34]
Kumar, R.; Jain, S.; Jain, N. Pharma Chem., 2013, 5, 73-78.
[35]
Graham, G.G.; Scott, K.F. Am. J. Ther., 2005, 12, 46-55.
[36]
Srikanth, J.; Sandeep, T.; Divya, K.; Govindarajan, R. Int. J. Res. Pharm. Chem., 2013, 3, 213-220.
[37]
Roy, A.; Dumbare, D.R.; Harak, S.S.; Najeeb, M.Z.M.; Deshmukh, R.D. Int. Res. J. Pharm, 2013, 4, 151-157.
[38]
Luzi, L.; Pozza, G. Acta Diabetol., 1997, 34, 239-244.
[39]
Karata, F.; Cansiz, A.; Kara, H.; Karatepe, M.; Koparir, M. Russ. J. Bioorganic Chem., 2005, 31, 499-501.
[40]
Phadnis, P.P.; Hodage, A.S.; Priyadarshni, K.I.; Jain, V.K. Indian J. Chem., 2014, 53A, 34-40.
[41]
Johri, A.; Beal, M.F. Biochim. Biophys. Acta, 2012, 1822, 664-674.
[42]
Malki, F.; Touati, A.; Moulay, S. J. Anal. Pharm. Res., 2017, 5, 00143-00146.
[43]
Suresh, C.; Venkateshwar, R.J.; Jayaveera, K.N.; Reddy, G.J. Int. J. Biol. Sci., 2011, 1, 409-413.
[44]
Yurttaş, L.; Özkay, Y.; Akalın-Çiftçi, G.; Ulusoylar-Yıldırım, S. J. Enzyme Inhib. Med. Chem., 2014, 29, 175-184.
[45]
Mashelkar, U.C.; Jha, M.; Mashelkar, B.U. J. Serb. Chem. Soc., 2013, 78, 621-625.
[46]
Foley, M.; Tilley, L. Pharmacol. Ther., 1998, 79, 55-87.
[47]
Singh, A.; Rana, A.C. J. Chem. Pharm. Res., 2010, 2, 505-511.
[48]
Ski, P.C.; Blaszczyk, B.; Czuczwar, S.J. Curr. Top. Med. Chem., 2005, 5, 3-14.
[49]
Takeda, Y.; Kawagoe, K.; Yokomizo, A.; Yokomizo, Y.; Hosokami, T.; Shimoto, Y.; Tabuchi, Y.; Ogihara, Y.; Otsubo, R.; Honda, Y.; Yokohama, S. Chem. Pharm. Bull. (Tokyo), 1998, 46, 951-961.
[50]
Takeda, Y.; Kawagoe, K.; Yokomizo, A.; Yokomizo, Y.; Hosokami, T.; Shimoto, Y.; Tabuchi, Y.; Ogihara, Y.; Otsubo, R.; Honda, Y.; Kawarabayashi, K.; Iseri, M.; Yokohama, S. Chem. Pharm. Bull. (Tokyo), 1999, 47, 755-771.
[51]
Shimizu, K.; Maruyama, M.; Yasui, Y.; Minegishi, H.; Ban, H.S. Nakamura, H. Bioorg. Med. Chem. Lett., 2010, 20, 1453-1456.
[52]
Baker, B.R.; Jeffrey, A.H. Proteolytic Enzy., 1968, 11, 1054-1057.

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