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Mini-Reviews in Organic Chemistry

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ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

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Review Article

para-Aminobenzoic Acid-A Substrate of Immense Significance

Author(s): Zaib Un Nisa and Tashfeen Akhtar*

Volume 17, Issue 6, 2020

Page: [686 - 700] Pages: 15

DOI: 10.2174/1570193X16666190828201234

Price: $65

Abstract

PABA (p-aminobenzoic acid) is an important substrate for the synthesis of various biological scaffolds. Its pharmacological significance is apparent form the drugs like folic acid and benzocaine, which are used for certain biological disorders. Although, it is not a vitamin but still it is referred as a member of vitamin B. The deficiency of PABA leads to several disorders like erratic white areas of skin, grey hair, fatigue, depression and irritability. Besides its medicinal importance, PABA has been used in the synthesis of various biologically active heterocyclic nuclei like benzimidazoles, azitidinones, thiazolidinones, pyrazoline, etc. This review will describe the applications of PABA in the synthesis of these biologically active nuclei and hence emphasizing its importance as a versatile substrate.

Keywords: Amino benzoic acid, azetidinone, diazoles, folic acid, natural products, imidazoles.

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[1]
Crisan, M.E.; Bourosh, P.; Maffei, M.E.; Forni, A.; Pieraccini, S.; Sironi, M.; Chumakov, Y.M. Synthesis, crystal structure and biological activity of 2-hydroxyethylammonium salt of p-aminobenzoic acid. PLoS One, 2014, 9(7), e101892.
[http://dx.doi.org/10.1371/journal.pone.0101892] [PMID: 25054237]
[2]
Samsonowicz, M.; Hrynaszkiewicz, T.; Swislocka, R.; Regulska, E.; Lewandowski, W. Experimental and theoretical IR, Raman, NMR spectra of 2, 3- and 4-aminobenzoic acids. J. Mol. Struct., 2005, 744-747, 345-352.
[http://dx.doi.org/10.1016/j.molstruc.2004.11.063]
[3]
He, Y.; Wu, C.; Kong, W. A theoretical and experimental study of water complexes of m-aminobenzoic acid MABA.(H2O)n (n = 1 and 2). J. Phys. Chem. A, 2005, 109(5), 748-753.
[http://dx.doi.org/10.1021/jp0460644] [PMID: 16838942]
[4]
Akberova, S.I. New biological properties of p-aminobenzoic acid. Izv. Akad. Nauk Ser. Biol., 2002, 29(4), 477-481.
[PMID: 12180014]
[5]
o'Neil, M.J. The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals; The Royal Society of Chemistry: Cambridge, 2013.
[6]
Parimoo, P. Textbook of Medicinal Chemistry; Oxford and IBH Publishers: Devon, 2006.
[7]
Yurttaş, L.; Tay, F.; Demirayak, Ş. Synthesis and antitumor activity evaluation of new 2-(4-aminophenyl)benzothiazole derivatives bearing different heterocyclic rings. J. Enzyme Inhib. Med. Chem., 2015, 30(3), 458-465.
[http://dx.doi.org/10.3109/14756366.2014.945168] [PMID: 25198890]
[8]
Dahiya, R.; Kumar, A. Synthesis, spectral and anthelmintic activity studies on some novel imidazole derivatives. E-J. Chem., 2008, 5, 1133-1143.
[http://dx.doi.org/10.1155/2008/161783]
[9]
Sugumaran, M.; Sethuvani, S.; Poornima, M. Synthesis, characterization and antimicrobial evaluation of 2-azetidinone and 4-thiazolidinone derivatives. Res. J. Pharma. Biol. Chem. Sci., 2012, 3(2), 625-631.
[10]
Michael, R.; Richards, E.; Xing, D.L.K. Investigation of the antibacterial activity of p-Aminobenzoic acid against P. aeruginosa and E. cloacae. Int. J. Pharm., 1992, 87, 195-201.
[http://dx.doi.org/10.1016/0378-5173(92)90243-U]
[11]
Chhonker, Y.S.; Veenu, B.; Hasim, S.R.; Kaushik, N.; Kumar, D.; Kumar, P. Synthesis and pharmacological evaluation of some new 2-Phenyl benzimidazoles derivatives and their Schiff’s bases. E-J. Chem., 2009, 6, 342-346.
[http://dx.doi.org/10.1155/2009/604203]
[12]
Sreena, K.; Ratheesh, R.; Rachana, M.; Mongolla, P.; Shyni, C. Synthesis and anthelmintic activity of benzimidazole derivatives. Hygeia, 2009, 1, 21-22.
[13]
Shahare, M.B.; Kadam, V.J.; Jagdale, D.M.; Gandhi, P.S.; Gaikwad, P.L. Synthesis and evaluation of novel anthelmentic benzimidazole derivatives. Int. J. Res. Pharm. Chem., 2012, 2(1), 132-136.
[14]
Baviskar, B.; Chuadhary, S.; Parwani, K.; Balani, P.; Salode, V.; Patil, S.; Khadabadi, S.S. Synthesis of novel benzimidazole derivatives as potent antimicrobial agent. Rasayan J. Chem., 2009, 2(1), 186-190.
[15]
Abd El-All, A.S.; Ragab, F.A.; Magd El-Din, A.A.; Abdalla, M.M.; El-Hefnawi, M.M.; El-Rashedy, A.A. Design, synthesis and anticancer evaluation of some selected Schiff bases derived from benzimidazole derivative. Glob. J. Pharmacol., 2013, 7(2), 143-152.
[16]
Prabhu, M.; Radha, R. Synthesis, characterization and evaluation of anti-bacterial and antihelmintic activity of some novel aryl imidazole derivatives. Asian J. Pharm. Clin. Res., 2012, 5, 154-159.
[17]
Muthukumar, V.A.; Verma, A.K.; Sujatha, R.; Raj, K. Synthesis and characterization of novel Mannich bases of benzimidazole derivatives for antibacterial and antifungal activity. Int. J. Pharm. Pharm. Sci., 2013, 5(2), 295-297.
[18]
Verma, A.K.; Kumari, R.; Singh, A.K.; Maurya, R.; Sharma, M.C. Synthesis, characterization and biological evaluation of novel 2-substituted benzimidazole Schiff bases and azetidinone and thiazolidinone derivatives. World J. Pharm. Pharm. Sci., 2014, 3, 1417-1429.
[19]
Pawar, P.Y.; Kalure, S.U.; Kulkarni, R.B. Synthesis and pharmacological screening of some new azetidinone derivatives. Int. J. Pharm. Pharm. Sci., 2012, 4, 464-467.
[20]
Selvam, T.P.; Radhika, P.P.; Janagaraj, S.; Kumar, A.S. Synthesis of novel 2-substituted benzimidazole derivatives as potential antimicrobial agents. Res. Biotech., 2011, 2, 50-57.
[21]
Parmar, K.; Modi, V.; Prajapati, S.; Patel, R. A facile and expeditious approach for the synthesis of 2-Azetidinone derivatives with microbial activity. Asian J. Biochem. Pharm. Res., 2011, 1, 612-620.
[22]
Belwal, C.K.; Joshi, K.A. Synthesis and antifungal activity of some novel thiazolidinone derivatives of 4-(4-oxo-2-phenylthiazolidin-3-yl) benzoic acid. Int. J. Chemtech Res., 2012, 4, 1758-1764.
[23]
Sugumaran, M.; Sethuvani, S.; Poornima, M. Synthesis, characterization and biological evaluation of 4-thiazolidinone derivatives. J. Pharm. Biomed. Sci., 2012, 16, 1-5.
[24]
Swaraj, P.; Hipparagi, S.M.; Meharoon, D.; Sharma, R.K.; Sandeep, D. Microwave assisted synthesis of flouro chloro benzimidazolo substituted thiazolidinone derivatives for antimicrobial activities. Int. J. Res. Pharm. Sci., 2011, 1(2), 77-90.
[25]
Raja, P.P.; Riyazulah, M.S.; Kumar, V.S. Synthesis and biological evaluation of some chalcone derivatives. Int. J. Chemtech Res., 2010, 2, 1998-2004.
[26]
Gupta, M.; Upmanyu, N.; Pramanik, S.; Tyagi, C.K.; Chandekar, A. Synthesis and antimicrobial evaluation of 3,5-pyrazolidinedione substituted 4-quinolone derivatives. Int. J. Drug Dev. Res., 2011, 3, 233-239.
[27]
Patel, B.P.; Patel, H.S.; Shah, P.J. Synthesis and antibacterial activity of some new azopyrazoles. Izv. Him., 2010, 42, 274-278.
[28]
Shah, P.J.; Patel, H.S.; Patel, B.P. Synthesis, characterization and antimicrobial activity of novel sulphapiperazine containing arylazopyrazoles. J. Saudi Chem. Soc., 2013, 17, 307-313.
[http://dx.doi.org/10.1016/j.jscs.2011.04.016]
[29]
Jagrut, V.B.; Netankar, P.D.; Jawale, D.V.; Mane, R.A.; Jadhav, W.N. An efficient synthetic route for new 1,3,4-oxadiazoles having sulphonamido pharmacophore. Bull. Korean Chem. Soc., 2009, 30, 2812-2814.
[http://dx.doi.org/10.5012/bkcs.2009.30.11.2812]
[30]
Al-Azzawi, A.M.; Hassan, A.S. Synthesis and antimicrobial activity of new succinimides bearing different heterocycles. Int. J. Res. Pharm. Chem., 2014, 4(4), 755-762.
[31]
Naif, O.A. Synthesis of new benzoxadiazole compounds derived from ethyl 4-(7- nitro-2.1,3,- benzoxadiazole -4-yl) amino benzoate. J. Al-Nahrain Uni., 2012, 15, 1-12.
[32]
Bercean, V.N.; Creanga, A.A.; Badea, V.; Deleanu, C.; Csunderlik, C. (New) 5-substituted-4H-4-amino-3-mercapto-1,2,4-triazoles with increased complexing capabilities. Rev. Chim. (Bucharest), 2011, 62, 47-50.
[33]
Harkala, K.J.; Eppakayala, L.; Maringanti, T.C. Synthesis and biological evaluation of benzimidazole-linked 1,2,3-triazole congeners as agents. Org. Med. Chem. Lett., 2014, 4(1), 14.
[http://dx.doi.org/10.1186/s13588-014-0014-x] [PMID: 26548990]
[34]
Arief, M.M. H.; Aly, A, A.; Khalil, A, A.; Mohamed, H, I. Utility of 4-(isatin-3-ylideneamino)benzohydrazide in the synthesis of bioactive N-heterocyclic compounds. J. Chem. Pharm. Res., 2014, 6(2), 327-335.
[35]
Amir, M.; Khan, M.S.; Zaman, M.S. Synthesis, characterization and biological activities of substituted oxadiazole, triazole, thiadiazole and thiazolidinone derivatives. Indian J. Chem., 2004, 43, 2189-2194.
[36]
Prasad, S.R.; Saraswathy, T.; Niraimathi, V.; Indhumathi, B. Synthesis, characterization and antimicrobial activity of some hetero benzocaine derivatives. Int. J. Pharm. Pharm. Sci., 2012, 4(5), 285-287.
[37]
Dhani, R. Synthesis, characterization and anthelmintic activity of 4-[2′-(5′-nitro) imidazolyl] benzoyl (n-methyl) amino acid derivatives. Int. J. Pharm. Life Sci., 2012, 3, 2120-2125.
[38]
Himaja, M. Archana; Asif, K. Synthesis and biological evaluation of 4-[2-(5-nitroimidazolyl]benzoylamino acids and peptides. Uni. Rey Juan Carlos., 2013, 1, 30-34.
[39]
Bhatt, S.; Kumar, S.; Ahmad, Z.; Kumar, D.; Singh, C.P. Synthesis of novel N1-(4-aminobenzoyl)-3-methyl-5-phenyl-4(N-4-sulfamoylphenylazo)-1,2-diazole. IOSR J. Pharm., 2012, 5, 60-64.
[40]
Racanè, L.; Tralić-Kulenović, V.; Boykin, D.W.; Zamola, G.K. Synthesis of new cyano-substituted bis-benzothiazolyl arylfurans and arylthiophenes. Molecules, 2003, 8, 342-349.
[http://dx.doi.org/10.3390/80300342]
[41]
Banurekha, J.; Babu, K.A.; Jayakar, B. Synthesis, characterization and anti inflammatory activity of 4[(phenyl substituted) (2-methyl-3a, 7a-dihydro-1h-indol-1-yl)benzyl] amino benzoic acid. Res. J. Pharm. Biol. Chem. Sci., 2011, 2, 863-868.
[42]
Ashraf, M.S.; Pathak, D.P. Synthesis of 7-azaindole derivatives and their evaluation for analgesic activity. Int. J. Pharm. Fron. Res., 2012, 2, 1-8.
[43]
Kiruthiga, B.; Ilango, K.; Valentina, P.; Umarani, N.; Patel, R. Synthesis of some new 2-substituted quinazoli-4-one derivatives and their biological activities. Int. J. Pharm. Tech. Res., 2009, 1, 1503-1506.
[44]
Kumar, A.; Jakhar, A.; Makrandi, J.K. A Highly efficient solvent free synthesis of hydrazide using grinding technique. Heterocycl. Lett., 2012, 2, 401-404.
[45]
Küçükgüzela, S.G.; Rollasa, S.; Küçükgüzela, I.; Kiraz, M. Synthesis and antimycobacterial activity of some coupling products from 4-aminobenzoic acid hydrazones. Eur. J. Med. Chem., 1999, 34, 1093-1100.
[http://dx.doi.org/10.1016/S0223-5234(99)00129-4]
[46]
Rezaee Zavareh, E.; Hedayati, M.; Hoghooghi Rad, L.; Shahhosseini, S.; Faizi, M.; Tabatabai, S.A. Design, synthesis and biological evaluation of 4-benzamidobenzoic acid hydrazide derivatives as novel soluble epoxide hydrolase inhibitors. Iran. J. Pharm. Res., 2014, 13(Suppl.), 51-59.
[PMID: 24711829]
[47]
Siddique, M.; Saeed, A.B.; Shahzad, S.A.; Shahid, B. Synthesis and biological evaluation of hydrazide based formamides derivatives. J. Sci. Innov. Res., 2013, 2, 772-776.
[48]
Xaiver, J.J.; Krishnasamy, K.; Sankar, C. Synthesis and antibacterial, antifungal activities of some 2r, 4c-diaryl-3-azabicyclo[3.3.1] nonan-9-one-4-aminobenzoylhydrazones. Med. Chem. Res., 2012, 21, 345-350.
[http://dx.doi.org/10.1007/s00044-010-9528-6]
[49]
Nagalakshmi, G. Synthesis and characterization of aryl alkanoic acids as potential antimicrobial agents. Asian J. Chem., 2008, 20, 3617-3622.
[50]
Parekh, J.; Inamdhar, P.; Nair, R.; Baluja, S.; Chanda, S. Synthesis and antibacterial activity of some Schiff bases derived from 4-aminobenzoic acid. J. Serb. Chem. Soc., 2005, 70, 1155-1161.
[http://dx.doi.org/10.2298/JSC0510155P]
[51]
Ejiah, F.N.; Fasina, T.M.; Familoni, O.B.; Ogunsola, F.T. Substituent effect on spectral and antimicrobial activity of Schiff bases derived from aminobenzoic acids. Adv. Biol. Chem., 2013, 3, 475-479.
[http://dx.doi.org/10.4236/abc.2013.35051]
[52]
Jha, A.; Yashmeen, S.; Kumar, D.N. An innovative green synthesis of some Schiff bases and their antimicrobial activity. Int. J. Pharma Bio Sci., 2013, 4, 197-204.
[53]
Meeta.; Kumar, P.; Narasimhan, B. Synthesis, antimicrobial evaluation and QSAR studies of p-amino benzoic acid derivatives. J. Pharm. Tech. Res. Manag., 2014, 2, 339-356.
[54]
Kulkarni, S.S.; Mehere, A.P.; Shenoy, P.A. Synthesis and in-vitro antimicrobial activity of 4-(Piperazin-1-ylcarbonyl) aniline – An amide derivative of p-aminobenzoic Acid. Asian J. Res. Chem, 2009, 2, 300-303.
[55]
Faghihi, K. New polyamides based on Bis(p-amidobenzoic acid)-pphenylene diacrylic acid and hydantoin derivatives: Synthesis and characterization. Turk. J. Chem., 2008, 32, 75-86.
[56]
Dahiya, R. Synthesis, characterization and antimicrobial studies on some newer imidazole analogs. Sci. Pharm., 2008, 76, 217-239.
[http://dx.doi.org/10.3797/scipharm.0803-04]
[57]
Adnan, S.; Hassan, K.; Thamer, H. Synthesis and identification some of heterocyclic compounds from imidazole derivatives. Iraqi Nat. J. Chem., 2013, 51, 327-337.
[58]
El-Faham, A.; Al Marhoon, Z.; Abdel-Megeed, A.; Albericio, F. OxymaPure/DIC: an efficient reagent for the synthesis of a novel series of 4-[2-(2-acetylaminophenyl)-2-oxo-acetylamino] benzoyl amino acid ester derivatives. Molecules, 2013, 18(12), 14747-14759.
[http://dx.doi.org/10.3390/molecules181214747] [PMID: 24288002]
[59]
El-Faham, A.; Marhoon, Z.A.; Abdel-Megeed, A.A.; Siddiqui, M. An efficient and mild method for the synthesis and hydrazinolysis of N-glyoxylamino acid esters. J. Chem., 2013, 2013 article id 901745.
[http://dx.doi.org/10.1155/2013/901745]
[60]
Kirkan, B.; Gup, R. Synthesis of new azo dyes and Copper (II) complexes derived from barbituric acid and 4-aminobenzoylhydrazone. Turk. J. Chem., 2008, 32, 9-17.
[61]
Gaikwad, P.D.; Bankar, V.H.; Bodele, S.B.; Mehere, A.P. Synthesis of new anthranilic acid dyes and evaluation for their antimicrobial and anti-inflammatory activities. Int. J. Pharm. Tech., 2010, 2, 541-548.
[62]
Jber, N.R.; Abood, R.S.; Al-Dhaief, Y.A. Synthesis and spectral study of new azo-azomethine dyes and its copper (II) complexes derived from resorcinol, 4-aminobenzoylhydrazone and 4-amino antipyrine. J. Al-Nahrain Uni., 2011, 14, 50-56.
[http://dx.doi.org/10.22401/JNUS.14.4.07]
[63]
Vashi, D.M.; Vashi, P.D.; Desai, K.R.; Kapadiya, K.K. Synthesis of various acid dyes from benzthiazole derivative. Arch. Appl. Sci. Res., 2014, 6, 89-93.
[64]
Mukhlus, A.A.; Al-Rawi, M.S.; Tomma, J.H.; Al-Dujaili, A.H. Synthesis and characterization of new oxazepines derived from Derythroascorbic acid. Ibn Al-Haitham J. Pure Appl. Sci., 2012, 25, 293-307.
[65]
Muresan-Pop, M.; Kacso, I.; Martin, F.; Simon, S.; Stefan, R.; Bratu, I. Ambazone salt with p-aminobenzoic acid. J. Therm. Anal. Calorim., 2015, 120, 905-912.
[http://dx.doi.org/10.1007/s10973-015-4452-0]
[66]
Jarad, A.J. Synthesis and characterization of 3-(4-antipyrene azo)-4-amino benzoic acid complexes with selected metal ions. Diyala J. Pure Sci., 2012, 8, 1-13.
[67]
Gup, R.; Koc, Z, E. Synthesis and investigation extraction properties of 4-methylacetophenone, 4-chloroacetophenone and isonitrosoacetephenone 4-aminobenzoylhydrazones. S U Fen Ed Fak Fen Derg., 2004, 23, 15-19.
[68]
Acharya, S.; Soni, R. Interaction of p-Amino Benzoic Acid (PABA) with ionic and nonionic micelles by fluorescence. Rasayan J. Chem., 2013, 6(1), 24-28.
[69]
Salvador, A.; Chisvert, A.; Rodriguez, A.; March, J.G. Indirect spectrophotometric determination of p-aminobenzoic acid in sunscreen formulations by sequential injection analysis. Anal. Chim. Acta, 2003, 493, 233-239.
[http://dx.doi.org/10.1016/S0003-2670(03)00873-0]

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