Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

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

Review Article

Synthesis and Biological Properties of Coumarin Analogue: A Brief Review

Author(s): Diksha Chaudhary, Pooja Bedi, Soumava Santra and Tanay Pramanik*

Volume 19, Issue 5, 2022

Published on: 02 February, 2021

Page: [362 - 387] Pages: 26

DOI: 10.2174/1570178618666210202152452

Price: $65

Abstract

One of the most prominent aromatic organic chemical compound is Coumarin having formula C9H6O2 which is widely known for its benefits in drug industry. Colourless crystalline solid having sweet scent is coumarin’s physical identity. It serves various purposes such as in synthesis of medicines, laser dyes, perfumes and many more. Having enormous usages, it becomes important to synthesize such compound so various reactions were performed in order to obtain coumarins. This review explicates the preparation of coumarin by Pechmann Condensation and its biological characteristics.

Keywords: Coumarin, pechmann condensation, phenols, β-keto ester, biological properties, heterocycles.

Graphical Abstract
[1]
Madni, M.; Ahmed, M.N.; Hafeez, M.; Ashfaq, M.; Tahir, M.N.; Gil, D.M.; Galmés, B.; Hameed, S.; Frontera, A. Royal Society of Chemistry, 2013, 00, 1-3.
[2]
Naeem, M.; Ansar, K.; Ayub, K.; Mahmood, T.; Tahir, M.N.; Ahmad, B.; Hafeez, M.; Ahmed, M. J. Mol. Struct., 2016, 1106, 430-439.
[http://dx.doi.org/10.1016/j.molstruc.2015.11.010]
[3]
Hameed, S.; Mahmood, T.; Ayub, K.; Tahir, M.N.S.C. J. Mol. Struct., 2018, 1155, 403-413.
[http://dx.doi.org/10.1016/j.molstruc.2017.11.011]
[4]
Ahmed, M.N.; Yasin, K.A.; Aziz, S.; Khan, S.U.; Tahir, M.N.; Gil, D.M.; Frontera, A. Cryst. Eng. Comm., 2020, 22, 3567-3578.
[http://dx.doi.org/10.1039/D0CE00335B]
[5]
Monga, P.K.; Sharma, D.; Dubey, A. J. Chem. Pharm. Res., 2012, 4, 822-850.
[6]
Das, S.; Majee, A.; Hajra, A. Green Chem. Lett. Rev., 2011, 4, 349-353.
[http://dx.doi.org/10.1080/17518253.2011.572296]
[7]
Kumar, K.A.; Renuka, N.; Pavithra, G.; Kumar, G.V. J. Chem. Pharm. Res., 2015, 7, 67-81.
[8]
Thakur, A.; Singla, R.; Jaitak, V. Eur. J. Med. Chem., 2015, 101, 476-495.
[http://dx.doi.org/10.1016/j.ejmech.2015.07.010] [PMID: 26188907]
[9]
Bronikowska, J.; Szliszka, E.; Jaworska, D.; Czuba, Z.P.; Krol, W. Molecules, 2012, 17(6), 6449-6464.
[http://dx.doi.org/10.3390/molecules17066449] [PMID: 22643355]
[10]
Basanagouda, M.; Jambagi, V.B.; Barigidad, N.N.; Laxmeshwar, S.S.; Devaru, V. Eur. J. Med. Chem., 2014, 74, 225-233.
[http://dx.doi.org/10.1016/j.ejmech.2013.12.061] [PMID: 24463645]
[11]
Lacy, A.; O’Kennedy, R. Curr. Pharm. Des., 2004, 10(30), 3797-3811.
[http://dx.doi.org/10.2174/1381612043382693] [PMID: 15579072]
[12]
Grover, J.; Jachak, S.M. RSC Advances, 2015, 5, 38892-38905.
[http://dx.doi.org/10.1039/C5RA05643H]
[13]
Hadjipavlou-Litina, D.J.; Litinas, K.E.; Kontogiorgis, C. Antiinflamm. Antiallergy Agents Med. Chem., 2008, 6, 293-306.
[http://dx.doi.org/10.2174/187152307783219989]
[14]
Arora, R.K.; Kaur, N.; Bansal, Y.; Bansal, G. Acta Pharm. Sin. B, 2014, 4(5), 368-375.
[http://dx.doi.org/10.1016/j.apsb.2014.07.001] [PMID: 26579406]
[15]
Kawase, M.; Varu, B.; Shah, A.; Motohashi, N.; Tani, S.; Saito, S.; Debnath, S.; Mahapatra, S.; Dastidar, S.G.; Chakrabarty, A.N. Arzneimittelforschung, 2001, 51(1), 67-71.
[PMID: 11215328]
[16]
Shi, Y.; Zhou, C.H. Bioorg. Med. Chem. Lett., 2011, 21(3), 956-960.
[http://dx.doi.org/10.1016/j.bmcl.2010.12.059] [PMID: 21215620]
[17]
Zaki, R.M.; Elossaily, Y.A.; Kamal El-Dean, A.M. Russ. J. Bioorganic Chem., 2012, 38, 639-646.
[http://dx.doi.org/10.1134/S1068162012040152]
[18]
Govori, S.; Spahiu, S.; Haziri, A.; Ibrahimi, H. Eur. J. Exp. Biol., 2013, 3, 515-519.
[19]
Guíñez, R.F.; Matos, M.J.; Vazquez-Rodriguez, S.; Santana, L.; Uriarte, E.; Olea-Azar, C.; Maya, J.D. Future Med. Chem., 2013, 5(16), 1911-1922.
[http://dx.doi.org/10.4155/fmc.13.147] [PMID: 24175743]
[20]
Bansal, Y.; Setha, P.; Bansal, G. Med. Chem. Res., 2013, 22, 3049-3060.
[http://dx.doi.org/10.1007/s00044-012-0321-6]
[21]
Zhang, K.; Ding, W.; Sun, J.; Zhang, B.; Lu, F.; Lai, R.; Zou, Y.; Yedid, G. Biochimie, 2014, 107(Pt B), 203-210.
[http://dx.doi.org/10.1016/j.biochi.2014.03.014] [PMID: 24721580]
[22]
Foti, M.; Piattelli, M.; Baratta, M.T.; Ruberto, G. J. Agric. Food Chem., 1996, 44, 497-501.
[http://dx.doi.org/10.1021/jf950378u]
[23]
Kostova, I. Mini Rev. Med. Chem., 2006, 6(4), 365-374.
[http://dx.doi.org/10.2174/138955706776361457] [PMID: 16613573]
[24]
Imenshahidi, M.; Eghbal, M.; Sahebkar, A.; Iranshahi, M. Pharm. Biol., 2013, 51(5), 545-549.
[http://dx.doi.org/10.3109/13880209.2012.747546] [PMID: 23368941]
[25]
Chavhan, J.V.; Patil, S.S. Int. J. Pharm. Chem. Biol. Sci., 2017, 7, 352-356.
[26]
Neyts, J.; De Clercq, E.; Singha, R.; Chang, Y.H.; Das, A.R.; Chakraborty, S.K.; Hong, S.C.; Tsay, S.C.; Hsu, M.H.; Hwu, J.R. J. Med. Chem., 2009, 52(5), 1486-1490.
[http://dx.doi.org/10.1021/jm801240d] [PMID: 19193060]
[27]
Yu, D.; Suzuki, M.; Xie, L.; Morris-Natschke, S.L.; Lee, K.H. Med. Res. Rev., 2003, 23(3), 322-345.
[http://dx.doi.org/10.1002/med.10034] [PMID: 12647313]
[28]
Verhoef, T.I.; Pirmohamed, M.; Barallon, R.; Daly, A.K.; Kamali, F.; Wadelius, M.; van Schie, R.M.; Haschke-Becher, E.; Kirchheiner, J.; Briz, M. Pharmacogenomics, 2009, 10, 1687-1695.
[http://dx.doi.org/10.2217/pgs.09.125] [PMID: 19842940]
[29]
Jiao, C.X.; Niu, C.G.; Chen, L.X.; Shen, G.L.; Yu, R.Q. Anal. Bioanal. Chem., 2003, 376(3), 392-398.
[http://dx.doi.org/10.1007/s00216-003-1909-y] [PMID: 12712312]
[30]
Fan, G. Bioorg. Med. Chem. Lett., 2001, 11, 2361-2363.
[http://dx.doi.org/10.1016/S0960-894X(01)00429-2] [PMID: 11527731]
[31]
Al-Amiery, A.A.; Musa, A.Y.; Kadhum, A.A.H.; Mohamad, A.B. Molecules, 2011, 16(8), 6833-6843.
[http://dx.doi.org/10.3390/molecules16086833] [PMID: 21832973]
[32]
Ramesh, B.; Viswanathan, P.; Pugalendi, K.V. Eur. J. Pharmacol., 2007, 566(1-3), 231-239.
[http://dx.doi.org/10.1016/j.ejphar.2007.03.045] [PMID: 17477917]
[33]
Abdel Hafez, O.M.; Amin, K.M.; Abdel-Latif, N.A.; Mohamed, T.K.; Ahmed, E.Y.; Maher, T. Eur. J. Med. Chem., 2009, 44(7), 2967-2974.
[http://dx.doi.org/10.1016/j.ejmech.2009.01.006] [PMID: 19217697]
[34]
Wulff, W.D.; McCallum, J.S.; Kunng, F.A. J. Am. Chem. Soc., 1988, 110, 7419-7434.
[http://dx.doi.org/10.1021/ja00230a023]
[35]
Magiatis, P.; Melliou, E.; Skaltsounis, A.L.; Mitaku, S.; Léonce, S.; Renard, P.; Pierré, A.; Atassi, G. J. Nat. Prod., 1998, 61(8), 982-986.
[http://dx.doi.org/10.1021/np9800295] [PMID: 9722480]
[36]
Dong, J.; Du, D.M. Org. Biomol. Chem., 2012, 10(40), 8125-8131.
[http://dx.doi.org/10.1039/c2ob26334c] [PMID: 22956019]
[37]
Bell, R.G.; Caldwell, P.T. Biochemistry, 1973, 12(9), 1759-1762.
[http://dx.doi.org/10.1021/bi00733a015] [PMID: 4699235]
[38]
Harishkumar, H.N.; Mahadevan, K.M.; Kiran Kumar, H.C.; Satya-narayan, N.D. Orga. Commun., 2011, 4, 26-32.
[39]
Aslam, K.; Khosa, M.K.; Jahan, N.; Nosheen, S. Pak. J. Pharm. Sci., 2010, 23, 449-454.
[PMID: 20884461]
[40]
Yavari, I.; Hekmat-Shoar, R.; Zonouzi, A. Tetrahedron Lett., 1998, 39, 2391-2392.
[http://dx.doi.org/10.1016/S0040-4039(98)00206-8]
[41]
Desai, V.G.; Shet, J.B.; Tilve, S.G.; Mali, R.S. J. Chem. Res., 2009, 2003, 628-629.
[http://dx.doi.org/10.3184/030823403322655888]
[42]
Dutta, L.N.; Bhattacharyya, M.; Sarkar, A.K. Can. J. Chem., 2006, 73, 1556-1562.
[http://dx.doi.org/10.1139/v95-193]
[43]
Smitha, G.; Reddy, C.S. Synth. Commun., 2004, 34, 3997-4003.
[http://dx.doi.org/10.1081/SCC-200034821]
[44]
Hegedüs, A. Hell. Z. Catal. Lett., 2006, 112, 105-108.
[http://dx.doi.org/10.1007/s10562-006-0171-2]
[45]
Reddy, B.M.; Reddy, V.R.; Giridhar, D. Synth. Commun., 2001, 31, 3603-3607.
[http://dx.doi.org/10.1081/SCC-100107007]
[46]
Romanelli, G.P.; Bennardi, D.; Ruiz, D.M.; Baronetti, G.; Thomas, H.J.; Autino, J.C. Tetrahedron Lett., 2004, 45, 8935-8939.
[http://dx.doi.org/10.1016/j.tetlet.2004.09.183]
[47]
Holden, M.S.; Crouch, R.D. J. Chem. Educ., 2009, 75, 1631.
[http://dx.doi.org/10.1021/ed075p1631]
[48]
Woods, L.L.; Sapp, J. J. Org. Chem., 1962, 27, 3703-3705.
[http://dx.doi.org/10.1021/jo01057a519]
[49]
Singh, P.R.; Singh, D.U.; Samant, S.D. Synlett, 2004, 11, 1909-1912.
[50]
Sugino, T.; Tanaka, K. Chem. Lett., 2002, 30, 110-111.
[http://dx.doi.org/10.1246/cl.2001.110]
[51]
Wang, H. Monatsh. Chem., 2013, 144, 411-414.
[http://dx.doi.org/10.1007/s00706-012-0823-4]
[52]
Datta, B.; Pasha, M.A. ISRN Org. Chem., 2013, 2013, 1-5.
[http://dx.doi.org/10.1155/2013/132794]
[53]
Simonetti, R.B. Asian J. Chem., 2014, 26, 6097-6100.
[http://dx.doi.org/10.14233/ajchem.2014.16733]
[54]
De, S.K.; Gibbs, R.A. Synthesis, 2005, 8, 1231-1233.
[http://dx.doi.org/10.1055/s-2005-865282]
[55]
Montazeri, N.; Khaksar, S.; Nazari, A.; Alavi, S.S.; Vahdat, S.M.; Tajbakhsh, M. J. Fluor. Chem., 2011, 132, 450-452.
[http://dx.doi.org/10.1016/j.jfluchem.2011.04.016]
[56]
Stoyanov, E.V.; Mezger, J. Molecules, 2005, 10(7), 762-766.
[http://dx.doi.org/10.3390/10070762] [PMID: 18007344]
[57]
Mirosanloo, A.; Zareyee, D.; Khalilzadeh, M.A. Appl. Organomet. Chem., 2018, 32, 1-9.
[http://dx.doi.org/10.1002/aoc.4546]
[58]
Sun, H.; Zhang, Y.; Guo, F.; Yan, Y.; Wan, C.; Zha, Z.; Wang, Z. Eur. J. Org. Chem., 2012, 3, 480-483.
[http://dx.doi.org/10.1002/ejoc.201101578]
[59]
Gao, S.T.; Li, C.; Wang, Y.; Ma, J.J.; Wang, C.; Zhang, J.W. Synth. Commun., 2011, 41, 1486-1491.
[http://dx.doi.org/10.1080/00397911.2010.486514]
[60]
Hosseini-Sarvari, M.; Najafvand-Derikvandi, S. J. Catal., 2016, 6, 423-430.
[61]
Laufer, M.C.; Hausmann, H.; Hölderich, W.F. J. Catal., 2003, 218, 315-320.
[http://dx.doi.org/10.1016/S0021-9517(03)00073-3]
[62]
Li, T.S.; Zhang, Z.H.; Yang, F.; Fu, C.G. J. Chem. Res.-Part S, 1998, 1, 38-39.
[http://dx.doi.org/10.1039/a703694i]
[63]
Kumar, S.; Saini, A.; Sandhu, J.S. ARKIVOC, 2007, 2007, 18-23.
[http://dx.doi.org/10.3998/ark.5550190.0008.f03]
[64]
Subhas Bose, D.; Rudradas, A.P.; Babu, H. Tetrahedron Lett., 2002, 43, 9195-9197.
[http://dx.doi.org/10.1016/S0040-4039(02)02266-9]
[65]
Karami, B.; Kiani, M.; Hoseini, M.A. Chin. J. Catal., 2014, 35, 1206-1211.
[http://dx.doi.org/10.1016/S1872-2067(14)60090-5]
[66]
Young, D.M.; Welker, J.J.C.; Doxsee, K.M. J. Chem. Educ., 2011, 88, 319-321.
[http://dx.doi.org/10.1021/ed1004883]
[67]
Abbasi, Z.; Rezayati, S.; Bagheri, M.; Hajinasiri, R. Chin. Chem. Lett., 2017, 28, 75-82.
[http://dx.doi.org/10.1016/j.cclet.2016.06.022]
[68]
Gunnewegh, E.A.; Hoefnagel, A.J.; Downing, R.S.; van Bekkum, H. Recl. Trav. Chim. Pays Bas, 1996, 115, 226-230.
[http://dx.doi.org/10.1002/recl.19961150407]
[69]
Amoozadeh, A.; Ahmadzadeh, M.; Kolvari, E. J. Chem., 2013, 2013, 1-7.
[http://dx.doi.org/10.1155/2013/767825]
[70]
Rezaei, R.; Farjam, M.H.; Farasat, M. Org. Chem., 2006, 10, 73-78.
[71]
Zhang, Y.; Zhu, A.; Li, Q.; Li, L.; Zhao, Y.; Wang, J. RSC Advances, 2014, 4, 22946-22950.
[http://dx.doi.org/10.1039/C4RA02227K]
[72]
Reddy, Y.T.; Sonar, V.N. Synth. Commun., 2008, 38, 2082-2088.
[http://dx.doi.org/10.1080/00397910802029091]
[73]
Khodabakhshi, S. Org. Chem. Int., 2012, 2012, 1-5.
[http://dx.doi.org/10.1155/2012/306162]
[74]
Bhatia, R.; Pathania, S.; Singh, V.; Rawal, R.K. Chem. Heterocycl. Compd., 2018, 54, 280-291.
[http://dx.doi.org/10.1007/s10593-018-2262-6]
[75]
Bulut, M.; Erk, Ç. Dyes Pigments, 1996, 30, 99-104.
[http://dx.doi.org/10.1016/0143-7208(95)00060-7]
[76]
Wang, L.; Xia, J.; Tian, H.; Qian, C.; Ma, Y. Indian J. Chem., 2003, 42, 2097-2099.
[77]
Selvakumar, S.; Chidambaram, M.; Singh, A.P. Catal. Commun., 2007, 8, 777-783.
[http://dx.doi.org/10.1016/j.catcom.2006.08.039]
[78]
Rajitha, B.; Kumar, V.N.; Someshwar, P.; Madhav, J.V.; Reddy, P.N. Arkivoc, 2012, 2006, 23-27.
[http://dx.doi.org/10.3998/ark.5550190.0007.c02]
[79]
Moradi, L.; Rabiei, K.; Belali, F. Synth. Commun., 2016, 46, 1283-1291.
[http://dx.doi.org/10.1080/00397911.2016.1201512]
[80]
Sinhamahapatra, A.; Sutradhar, N.; Pahari, S.; Bajaj, H.C.; Panda, A.B. Appl. Catal. A Gen., 2011, 394, 93-100.
[http://dx.doi.org/10.1016/j.apcata.2010.12.027]
[81]
Esfahani, F.K.; Zareyee, D.; Yousefi, R. ChemCatChem, 2014, 6, 1-6.
[http://dx.doi.org/10.1002/cctc.201402547]
[82]
Yaghoobi, M.; Zareyee, D.; Khalilzadeh, M.A. Appl. Organomet. Chem., 2020, 34, 1-10.
[http://dx.doi.org/10.1002/aoc.5787]
[83]
Zareyee, D.; Serehneh, M. J. Mol. Catal. Chem., 2014, 391, 88-91.
[http://dx.doi.org/10.1016/j.molcata.2014.04.013]
[84]
Albadi, J.; Shirini, F.; Abasi, J.; Armand, N.; Motaharizadeh, T. C. R. Chim., 2013, 16, 407-411.
[http://dx.doi.org/10.1016/j.crci.2012.10.002]
[85]
Prousis, K.C.; Avlonitis, N.; Heropoulos, G.A.; Calogeropoulou, T. Ultrason. Sonochem., 2014, 21(3), 937-942.
[http://dx.doi.org/10.1016/j.ultsonch.2013.10.018] [PMID: 24262761]
[86]
Patil, S.B.; Bhat, R.P.; Raje, V.P.; Samant, S.D. Synth. Commun., 2006, 36, 525-531.
[http://dx.doi.org/10.1080/00397910500385241]
[87]
Hari Krishna, M.; Thriveni, P. Pharma Chem., 2016, 8, 94-98.
[88]
Krishna, M.H.; Thriveni, P. Pharma Chem., 2016, 8, 18-22.
[89]
Tyagi, B.; Mishra, M.K. J. Mol. Catal. Chem., 2008, 286, 41-46.
[http://dx.doi.org/10.1016/j.molcata.2008.01.035]
[90]
Chavan, O.S.; Jadhav, S.A.; Shioorkar, M.G.; Chavan, S.B.; Baseer, M.A.; Shinde, D.B. Rasayan J. Chem., 2015, 8, 194-197.
[91]
Bouasla, S.; Amaro-Gahete, J.; Esquivel, D.; López, M.I.; Jiménez-Sanchidrián, C.; Teguiche, M.; Romero-Salguero, F.J. Molecules, 2017, 22, 1-8.
[92]
Valizadeh, H.; Kordi, F.M.; Gholipur, H. Phosphorus Sulfur Silicon Relat. Elem., 2009, 184, 3075-3081.
[http://dx.doi.org/10.1080/10426500802667125]
[93]
Vahabi, V.; Hatamjafari, F. Molecules, 2014, 19(9), 13093-13103.
[http://dx.doi.org/10.3390/molecules190913093] [PMID: 25255747]
[94]
Singh, V.; Kaur, S.; Sapehiyia, V.; Singh, J.; Kad, G.L. Catal. Commun., 2005, 6, 57-60.
[http://dx.doi.org/10.1016/j.catcom.2004.10.011]
[95]
Frère, S.; Thiéry, V.; Besson, T. Tetrahedron Lett., 2001, 42, 2791-2794.
[http://dx.doi.org/10.1016/S0040-4039(01)00295-7]
[96]
Chavan, O.S.; Shioorkar, M.G.; Jadhav, S.A.; Sakhare, M.A.; Pawar, Y.M.; Chavan, S.B.; Baseer, M.A. Heterocyclic Letters, 2017, 7, 377-380.
[97]
Prajapati, D.; Gohain, M. Catal. Lett., 2007, 119, 59-63.
[http://dx.doi.org/10.1007/s10562-007-9186-6]
[98]
Joshi, R.; Mandhane, P.; Nagargoje, D. Short communication, 2008, 8, 7-10.
[99]
Valizadeh, H.; Shockravi, A. Tetrahedron Lett., 2005, 46, 3501-3503.
[http://dx.doi.org/10.1016/j.tetlet.2005.03.124]
[100]
Kuarm, B.S.; Madhav, J.V.; Rajitha, B. Synth. Commun., 2012, 42, 1770-1777.
[http://dx.doi.org/10.1080/00397911.2010.543964]
[101]
Bavantula, R. Banothu. J. Adv. Appl. Sci. Res., 2013, 4, 74-78.
[102]
Kotharkar, S.A.; Bahekar, S.S.; Shinde, D.B. Mendeleev Commun., 2006, 16, 241-242.
[http://dx.doi.org/10.1070/MC2006v016n04ABEH002256]
[103]
Sharma, D.; Kumar, S.; Makrandi, J.K. Green Chem. Lett. Rev., 2011, 4, 127-129.
[http://dx.doi.org/10.1080/17518253.2010.517785]
[104]
Narwal, J.K.; Malik, R.K.; Kumari, N. Chem. Sci. Trans., 2015, 4, 1092-1094.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy