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Letters in Organic Chemistry

Editor-in-Chief

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

Research Article

Acemannan from Aloe vera Extract: A Catalyst-Free, Approach for the Access of Imidazole-Fused Nitrogen-Bridgehead Heterocycles

Author(s): Jyoti Baranwal, Swastika Singh, Smriti Kushwaha and Archana Jyoti*

Volume 20, Issue 5, 2023

Published on: 26 December, 2022

Page: [446 - 456] Pages: 11

DOI: 10.2174/1570178620666221116093457

Price: $65

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Abstract

A series of 2-phenyl substituted imidazo-pyridines, pyrazines and pyrimidines were synthesized through an efficient one-pot, environmentally benign, and regioselective strategy which involves the reaction between 2-bromocarbonyl compounds and 2-aminopyridines, 2-aminopyrazines, 2- aminopyrimidines, respectively using A Aloe vera loe vera/water (3:2) as a green promoting media. To the best of our knowledge, this is the first Aloe vera promoted protocol for the synthesis of this important scaffold having potential applications in medicinal and materials chemistry. The use of Aloe vera as a bio-renewable and biodegradable reaction medium-cum-promoter, operational simplicity, use of readily available substrates, mild reaction conditions, broad substrate scope, short reaction time, easy workup, and high yields, makes the disclosed protocol a superior alternative to existing methods. Substituted imidazo-pyridines, pyrazines and pyrimidines were obtained with 95%, 76% and 84% yields, respectively.

Graphical Abstract

[1]
a) Al-Mulla, A. Pharma Chem., 2017, 9(13), 141-147.;
b) El Aadad, H.; Benzekri, Z.; Boukhris, S.; Chahine, A. J. Chem. Sci., 2020, 132(1), 87. http://dx.doi.org/10.1007/s12039-020-01798-x;
c) Benzekri, Z.; Sibous, S.; Serrar, H.; Boukhris, S.; Hassikou, A.; Ghailane, R. Org. Prep. Proced. Int., 2019, 51(6), 566-575. http://dx.doi.org/10.1080/00304948.2019.1677991;
d) Serrar, H.; Marmouzi, I.; Benzekri, Z.; Boukhris, S.; Hassikou, A.; Faouzi, M.E.A.; Souizi, A. Lett. Org. Chem., 2017, 14(4), 267-277. http://dx.doi.org/10.2174/1570178614666170227124523;
e) Ouakki, M.; Galai, M.; Benzekri, Z.; Aribou, Z.; Ech-chihbi, E.; Guo, L.; Dahmani, K.; Nouneh, K.; Briche, S.; Boukhris, S.; Cherkaoui, M. J. Mol. Liq., 2021, 344, 117777. http://dx.doi.org/10.1016/j.molliq.2021.117777;
f) Li, S.; Li, W.J.; Yang, X.; Sun, R.; Tang, J.; Zheng, X.L.; Yuan, M.L.; Li, R.X.; Chen, H.; Fu, H.Y. Org. Chem. Front., 2020, 7(23), 3887-3895.
[http://dx.doi.org/10.1039/D0QO00923G]
[2]
Taylor, A.P.; Robinson, R.P.; Fobian, Y.M.; Blakemore, D.C.; Jones, L.H.; Fadeyi, O. Org. Biomol. Chem., 2016, 14(28), 6611-6637.
[http://dx.doi.org/10.1039/C6OB00936K] [PMID: 27282396]
[3]
Tandon, R.; Singh, I.; Luxami, V.; Tandon, N.; Paul, K. Chem. Rec., 2019, 19(2-3), 362-393.
[http://dx.doi.org/10.1002/tcr.201800024] [PMID: 29943894]
[4]
Enguehard-Gueiffier, C.; Gueiffier, A. Mini Rev. Med. Chem., 2007, 7(9), 888-899.
[http://dx.doi.org/10.2174/138955707781662645] [PMID: 17897079]
[5]
a) Wan, J.; Zheng, C.J.; Fung, M.K.; Liu, X.K.; Lee, C.S.; Zhang, X.H. J. Mater. Chem., 2012, 22(10), 4502-4510. http://dx.doi.org/10.1039/c2jm14904d;
b) Song, G.; Zhang, Y.; Li, X. Organometallics, 2008, 27(8), 1936-1943. http://dx.doi.org/10.1021/om800109a;
c) John, A.; Shaikh, M.M.; Ghosh, P. Dalton Trans., 2009, 47(47), 10581-10591.
[http://dx.doi.org/10.1039/b913068c] [PMID: 20023883]
[6]
Pericherla, K.; Kaswan, P.; Pandey, K.; Kumar, A. Synthesis, 2015, 47(07), 887-912.
[http://dx.doi.org/10.1055/s-0034-1380182]
[7]
Goel, R.; Luxami, V.; Paul, K. RSC Advances, 2015, 5(99), 81608-81637.
[http://dx.doi.org/10.1039/C5RA14795F]
[8]
Bagdi, A.K.; Santra, S.; Monir, K.; Hajra, A. Chem. Commun. (Camb.), 2015, 51(9), 1555-1575.
[http://dx.doi.org/10.1039/C4CC08495K]
[9]
Goel, R.; Luxami, V.; Paul, K. Org. Biomol. Chem., 2015, 13(12), 3525-3555.
[http://dx.doi.org/10.1039/C4OB01380H] [PMID: 25563506]
[10]
Boerner, R.J.; Moller, H.J. Psychopharmakotherapie, 1997, 4(4), 145-148.
[11]
Sanger, D.J.; Zivkovic, B. Psychopharmacology (Berl.), 1994, 113(3-4), 395-403.
[http://dx.doi.org/10.1007/BF02245215] [PMID: 7862851]
[12]
Belohlavek, D.; Malfertheiner, P. Supplement, 1979, 54, 44-44.
[13]
Rosenberg, R.P. Ann. Clin. Psychiatry, 2006, 18(1), 49-56.
[http://dx.doi.org/10.1080/10401230500464711] [PMID: 16517453]
[14]
Boggs, S.; Elitzin, V.I.; Gudmundsson, K.; Martin, M.T.; Sharp, M.J. Org. Process Res. Dev., 2009, 13(4), 781-785.
[http://dx.doi.org/10.1021/op9000675]
[15]
Gerard, L.; Garey, K.W.; DuPont, H.L. Expert Rev. Anti Infect. Ther., 2005, 3(2), 201-211.
[http://dx.doi.org/10.1586/14787210.3.2.201] [PMID: 15918778]
[16]
Mizushige, K.; Ueda, T.; Yukiiri, K.; Suzuki, H. Cardiovasc. Drug Rev., 2002, 20(3), 163-174.
[http://dx.doi.org/10.1111/j.1527-3466.2002.tb00085.x] [PMID: 12397365]
[17]
Cheng, Y.; Moraski, G.C.; Cramer, J.; Miller, M.J.; Schorey, J.S. PLoS One, 2014, 9(1), e87483.
[http://dx.doi.org/10.1371/journal.pone.0087483] [PMID: 24498115]
[18]
Gudmundsson, K.S.; Williams, J.D.; Drach, J.C.; Townsend, L.B. J. Med. Chem., 2003, 46(8), 1449-1455.
[http://dx.doi.org/10.1021/jm020339r] [PMID: 12672244]
[19]
a) Ismail, M.A.; Brun, R.; Wenzler, T.; Tanious, F.A.; Wilson, W.D.; Boykin, D.W. J. Med. Chem., 2004, 47(14), 3658-3664.
[http://dx.doi.org/10.1021/jm0400092] [PMID: 15214792];
b) Kaminski, J.J.; Bristol, J.A.; Puchalski, C.; Lovey, R.G.; Elliott, A.J.; Guzik, H.; Solomon, D.M.; Conn, D.J.; Domalski, M.S.; Wong, S.C. J. Med. Chem., 1985, 28(7), 876-892.
[http://dx.doi.org/10.1021/jm00145a006] [PMID: 4009611]
[20]
a) Ulloora, S.; Shabaraya, R.; Adhikari, A.V. Bioorg. Med. Chem. Lett., 2013, 23(11), 3368-3372.
[http://dx.doi.org/10.1016/j.bmcl.2013.03.086] [PMID: 23623419];
b) Hieke, M.; Rödl, C.B.; Wisniewska, J.M.; la Buscató, E.; Stark, H.; Schubert-Zsilavecz, M.; Steinhilber, D.; Hofmann, B.; Proschak, E. Bioorg. Med. Chem. Lett., 2012, 22(5), 1969-1975.
[http://dx.doi.org/10.1016/j.bmcl.2012.01.038] [PMID: 22326163]
[21]
Accounts in Drug Discovery: Case Studies in Medicinal Chemistry; Barrish, J.; Carter, P.; Cheng, P.; Zahler, R., Eds.; Royal Society of Chemistry: London, 2010.
[http://dx.doi.org/10.1039/9781849731980]
[22]
Sanfilippo, P.J.; Urbanski, M.; Press, J.B.; Dubinsky, B.; Moore, J.B., Jr J. Med. Chem., 1988, 31(11), 2221-2227.
[http://dx.doi.org/10.1021/jm00119a026] [PMID: 3184128]
[23]
Guo, C.; Linton, A.; Kephart, S.; Ornelas, M.; Pairish, M.; Gonzalez, J.; Greasley, S.; Nagata, A.; Burke, J. J. Med. Chem., 2011, 54(21), 7693-7704.
[http://dx.doi.org/10.1021/jm201059s] [PMID: 21936524]
[24]
a) Lumma, W.C., Jr; Randall, W.C.; Cresson, E.L.; Huff, J.R.; Hartman, R.D.; Lyon, T.F. J. Med. Chem., 1983, 26(3), 357-363.
[http://dx.doi.org/10.1021/jm00357a009] [PMID: 6298426];
b) Bonnet, P.A.; Michel, A.; Laurent, F.; Sablayrolles, C.; Rechencq, E.; Mani, J.C.; Boucard, M.; Chapat, J.P. J. Med. Chem., 1992, 35(18), 3353-3358.
[http://dx.doi.org/10.1021/jm00096a008] [PMID: 1527785]
[25]
Kaminski, J.J.; Perkins, D.G.; Frantz, J.D.; Solomon, D.M.; Elliott, A.J.; Chiu, P.J.S.; Long, J.F. J. Med. Chem., 1987, 30(11), 2047-2051.
[http://dx.doi.org/10.1021/jm00394a019] [PMID: 3669012]
[26]
Belanger, D.B.; Williams, M.J.; Curran, P.J.; Mandal, A.K.; Meng, Z.; Rainka, M.P.; Yu, T.; Shih, N.Y.; Siddiqui, M.A.; Liu, M.; Tevar, S.; Lee, S.; Liang, L.; Gray, K.; Yaremko, B.; Jones, J.; Smith, E.B.; Prelusky, D.B.; Basso, A.D. Bioorg. Med. Chem. Lett., 2010, 20(22), 6739-6743.
[http://dx.doi.org/10.1016/j.bmcl.2010.08.140] [PMID: 20855207]
[27]
Zou, B.; Nagle, A.; Chatterjee, A.K.; Leong, S.Y.; Tan, L.J.; Sim, W.L.S.; Mishra, P.; Guntapalli, P.; Tully, D.C.; Lakshminarayana, S.B.; Lim, C.S.; Tan, Y.C.; Abas, S.N.; Bodenreider, C.; Kuhen, K.L.; Gagaring, K.; Borboa, R.; Chang, J.; Li, C.; Hollenbeck, T.; Tuntland, T.; Zeeman, A.M.; Kocken, C.H.M.; McNamara, C.; Kato, N.; Winzeler, E.A.; Yeung, B.K.S.; Diagana, T.T.; Smith, P.W.; Roland, J. ACS Med. Chem. Lett., 2014, 5(8), 947-950.
[http://dx.doi.org/10.1021/ml500244m] [PMID: 25147620]
[28]
Zeeman, A.M.; van Amsterdam, S.M.; McNamara, C.W.; Voorberg-van der Wel, A.; Klooster, E.J.; van den Berg, A.; Remarque, E.J.; Plouffe, D.M.; van Gemert, G.J.; Luty, A.; Sauerwein, R.; Gagaring, K.; Borboa, R.; Chen, Z.; Kuhen, K.; Glynne, R.J.; Chatterjee, A.K.; Nagle, A.; Roland, J.; Winzeler, E.A.; Leroy, D.; Campo, B.; Diagana, T.T.; Yeung, B.K.S.; Thomas, A.W.; Kocken, C.H.M. Antimicrob. Agents Chemother., 2014, 58(3), 1586-1595.
[http://dx.doi.org/10.1128/AAC.01927-13] [PMID: 24366744]
[29]
McNamara, C.W.; Lee, M.C.S.; Lim, C.S.; Lim, S.H.; Roland, J.; Nagle, A.; Simon, O.; Yeung, B.K.S.; Chatterjee, A.K.; McCormack, S.L.; Manary, M.J.; Zeeman, A-M.; Dechering, K.J.; Kumar, T.R.S.; Henrich, P.P.; Gagaring, K.; Ibanez, M.; Kato, N.; Kuhen, K.L.; Fischli, C.; Rottmann, M.; Plouffe, D.M.; Bursulaya, B.; Meister, S.; Rameh, L.; Trappe, J.; Haasen, D.; Timmerman, M.; Sauerwein, R.W.; Suwanarusk, R.; Russell, B.; Renia, L.; Nosten, F.; Tully, D.C.; Kocken, C.H.M.; Glynne, R.J.; Bodenreider, C.; Fidock, D.A.; Diagana, T.T.; Winzeler, E.A. Nature, 2013, 504(7479), 248-253.
[http://dx.doi.org/10.1038/nature12782] [PMID: 24284631]
[30]
a) Chapman, M.R.; Kwan, M.H.T.; King, G.E.; Kyffin, B.A.; Blacker, A.J.; Willans, C.E.; Nguyen, B.N. Green Chem., 2016, 18(17), 4623-4627.
[http://dx.doi.org/10.1039/C6GC01601D];
b) Zali-Boeini, H.; Norastehfar, N.; Amiri Rudbari, H. RSC Advances, 2016, 6(85), 81943-81949.
[http://dx.doi.org/10.1039/C6RA17065J]
[31]
a) Yu, J.; Jin, Y.; Zhang, H.; Yang, X.; Fu, H. Chemistry, 2013, 19(49), 16804-16808.
[http://dx.doi.org/10.1002/chem.201302737] [PMID: 24151176];
b) Karamthulla, S.; Khan, M.N.; Choudhury, L.H. RSC Advances, 2015, 5(25), 19724-19733.
[http://dx.doi.org/10.1039/C4RA16298F]
[32]
a) Fisher, M.H.; Lusi, A. J. Med. Chem., 1972, 15(9), 982-985.
[http://dx.doi.org/10.1021/jm00279a026] [PMID: 5065787];
b) Tomoda, H.; Hirano, T.; Saito, S.; Mutai, T.; Araki, K. Bull. Chem. Soc. Jpn., 1999, 72(6), 1327-1334. http://dx.doi.org/10.1246/bcsj.72.1327;
c) Ponnala, S.; Kiran Kumar, S.T.V.S.; Bhat, B.A.; Prasad Sahu, D. Synth. Commun., 2005, 35(7), 901-906. http://dx.doi.org/10.1081/SCC-200051674;
d) Zhu, D.J.; Chen, J.X.; Liu, M.C.; Ding, J.C.; Wu, H.Y. J. Braz. Chem. Soc., 2009, 20(3), 482-487. http://dx.doi.org/10.1590/S0103-50532009000300012;
e) Patil, S.V.; Gaikwad, N.D.; Bobade, V.D. Arab. J. Chem., 2016, 9, S1649-S1653. http://dx.doi.org/10.1016/j.arabjc.2012.04.017;
f) Tufail, F.; Singh, S.; Saquib, M.; Tiwari, J.; Singh, J.; Singh, J. ChemistrySelect, 2017, 2(21), 6082-6089. http://dx.doi.org/10.1002/slct.201700557;
g) Veer, B.; Singh, R. Proc. R. Soc. Lond. A, 2019, 475(2230), 20190238.;
h) Dhas, A.; Deshmukh, S.; Pansare, D.; Pawar, R.; Kakade, G. Letters in Applied NanoBioScience, 2020, 10, 2565-2570.;
i) Al-lami, N.; Salom, K.J. J. Pharm. Sci. Res., 2019, 11(1), 125-130.
[33]
a) Kumar, S.; Sahu, D.P. ARKIVOC, 2008, 2008(15), 88-98. http://dx.doi.org/10.3998/ark.5550190.0009.f11;
b) Stasyuk, A.J.; Banasiewicz, M. Cyrański, M.K.; Gryko, D.T. J. Org. Chem., 2012, 77(13), 5552-5558.
[http://dx.doi.org/10.1021/jo300643w] [PMID: 22662878];
c) Ermolat’ev, D.S.; Savaliya, B.; Shah, A.; Van der Eycken, E. Mol. Divers., 2011, 15(2), 491-496.
[http://dx.doi.org/10.1007/s11030-010-9270-5] [PMID: 20740313];
d) Vara, Y.; Aldaba, E.; Arrieta, A.; Pizarro, J.L.; Arriortua, M.I.; Cossío, F.P. Org. Biomol. Chem., 2008, 6(10), 1763-1772.
[http://dx.doi.org/10.1039/b719641e] [PMID: 18452011];
e) Myadaraboina, S.; Alla, M.; Saddanapu, V.; Bommena, V.R.; Addlagatta, A. Eur. J. Med. Chem., 2010, 45(11), 5208-5216.
[http://dx.doi.org/10.1016/j.ejmech.2010.08.035] [PMID: 20832916];
f) Feng, M.L.; Li, S.Q.; He, H.Z.; Xi, L.Y.; Chen, S.Y.; Yu, X.Q. Green Chem., 2019, 21(7), 1619-1624.
[http://dx.doi.org/10.1039/C8GC03622E]
[34]
a) Tufail, F.; Saquib, M.; Singh, S.; Tiwari, J.; Singh, M.; Singh, J.; Singh, J. New J. Chem., 2017, 41(4), 1618-1624. http://dx.doi.org/10.1039/C6NJ03907C;
b) Tiwari, J.; Saquib, M.; Singh, S.; Tufail, F.; Singh, M.; Singh, J.; Singh, J. Green Chem., 2016, 18(11), 3221-3231. http://dx.doi.org/10.1039/C5GC02855H;
c) Singh, S.; Saquib, M.; Singh, M.; Tiwari, J.; Tufail, F.; Singh, J.; Singh, J. New J. Chem., 2016, 40(1), 63-67. http://dx.doi.org/10.1039/C5NJ01938A;
d) Singh, M.; Saquib, M.; Singh, S.B.; Singh, S.; Ankit, P.; Fatma, S.; Singh, J. Tetrahedron Lett., 2014, 55(45), 6175-6179. http://dx.doi.org/10.1016/j.tetlet.2014.09.030;
e) Tufail, F.; Saquib, M.; Singh, S.; Tiwari, J.; Dixit, P.; Singh, J.; Singh, J. New J. Chem., 2018, 42(21), 17279-17290. http://dx.doi.org/10.1039/C8NJ03028F;
f) Tiwari, J.; Singh, S.; Tufail, F.; Jaiswal, D.; Singh, J.; Singh, J. ChemistrySelect, 2018, 3(41), 11634-11642. http://dx.doi.org/10.1002/slct.201802511;
g) Tiwari, J.; Singh, S.; Saquib, M.; Tufail, F.; Sharma, A.K.; Singh, S.; Singh, J. Singh. J. Synth. Commun., 2018, 48(2), 188-196. http://dx.doi.org/10.1080/00397911.2017.1393087;
h) Tiwari, J.; Singh, S.; Jaiswal, D.; Sharma, A.K.; Singh, S.; Singh, J. Singh. J. Curr. Catal., 2021, 9(2), 92-101.
[http://dx.doi.org/10.2174/2211544709999200614165508];
i) Singh, A.; Singh, K.; Singh, S. Green Chemistry for the Development of Eco-Friendly Products, 2022, 104(28);
j) Baranwal, J.; Kushwaha, S.; Singh, S.; Jyoti, A. Heterocyclic Letters, 2022, 12, 621-630.
[35]
a) Rajasekaran, S.; Ravi, K.; Sivagnanam, K.; Subramanian, S. Clin. Exp. Pharmacol. Physiol., 2006, 33(3), 232-237.
[http://dx.doi.org/10.1111/j.1440-1681.2006.04351.x] [PMID: 16487267];
b) Maharjan, R. Bio-prospecting of Aloe vera Gel for the Treatment of Female Infertility, 2016.
[36]
a) Shanmugavel, S.; Reddy, V.J.; Ramakrishna, S.; Lakshmi, B.S.; Dev, V.R.G. J. Biomater. Appl., 2014, 29(1), 46-58.
[http://dx.doi.org/10.1177/0885328213513934] [PMID: 24287981];
b) Chithra, P.; Sajithlal, G.B.; Chandrakasan, G. Doctoral dissertation, Maharaja Sayajirao University of Baroda, India. Mol. Cell. Biochem., 1998, 181(1/2), 71-76.
[http://dx.doi.org/10.1023/A:1006813510959] [PMID: 9562243]
[37]
a) Ozsoy, N.; Candoken, E.; Akev, N. Oxid. Med. Cell. Longev., 2009, 2(2), 99-106.
[http://dx.doi.org/10.4161/oxim.2.2.8493] [PMID: 20357932];
b) Bala, S.; Chugh, N.A.; Bansal, S.C.; Garg, M.L.; Koul, A. Andrologia, 2017, 49(7), e12697.
[http://dx.doi.org/10.1111/and.12697] [PMID: 27620003]
[38]
Hamman, J. Molecules, 2008, 13(8), 1599-1616.
[http://dx.doi.org/10.3390/molecules13081599] [PMID: 18794775]
[39]
Chow, J.; Williamson, T.; Yates, K. Carbohydr. Res., 2005, 340, 1131-1147.
[http://dx.doi.org/10.1016/j.carres.2005.02.016] [PMID: 15797128]
[40]
Chun-hui, L.; Chang-hai, W.; Zhi-liang, X.; Yi, W. Process Biochem., 2007, 42(6), 961-970.
[http://dx.doi.org/10.1016/j.procbio.2007.03.004]
[41]
Anju, T.R.; Parvathy, S.; Valiya Veettil, M.; Rosemary, J.; Ansalna, T.H.; Shahzabanu, M.M.; Devika, S. Mater. Today Proc., 2021, 43, 3956-3960.
[http://dx.doi.org/10.1016/j.matpr.2021.02.665]
[42]
a) Chandrababu, P.; Cheriyan, S.; Raghavan, R. J. Therm. Anal. Calorim., 2020, 139(1), 89-99.
[http://dx.doi.org/10.1007/s10973-019-08376-5];
b) Ramkumar, R.; Sapru, S.; Archana, P. P. 2020.
[43]
Tummalapalli, M.; Berthet, M.; Verrier, B.; Deopura, B.L.; Alam, M.S.; Gupta, B. Int. J. Biol. Macromol., 2016, 82, 104-113.
[http://dx.doi.org/10.1016/j.ijbiomac.2015.10.087] [PMID: 26529192]
[44]
Liu, C.; Cui, Y.; Pi, F.; Cheng, Y.; Guo, Y.; Qian, H. Molecules, 2019, 24(8), 1554.
[http://dx.doi.org/10.3390/molecules24081554]
[45]
Pinzon, M.I.; Garcia, O.R.; Villa, C.C. J. Sci. Food Agric., 2018, 98(11), 4042-4049.
[http://dx.doi.org/10.1002/jsfa.8915] [PMID: 29377147]
[46]
Boudreau, M.D.; Beland, F.A. J. Environ. Sci. Health Part C Environ. Carcinog. Ecotoxicol. Rev., 2006, 24(1), 103-154.
[http://dx.doi.org/10.1080/10590500600614303]
[47]
Escobedo-Lozano, A.Y.; Domard, A.; Velázquez, C.A.; Goycoolea, F.M.; Argüelles-Monal, W.M. Carbohydr. Polym., 2015, 115, 707-714.
[http://dx.doi.org/10.1016/j.carbpol.2014.07.064] [PMID: 25439952]
[48]
Day, M.J. Glucocorticosteroids and antihistamines. Small Animal Clinical Pharmacology; Saunders Elsevier: Philadelphia, PA, 2008, 261-269.
[http://dx.doi.org/10.1016/B978-070202858-8.50013-0];
b) Sykes, J. E.; Papich, M. G. Canine and feline infectious diseases,, 2014, 54-65.;
c) Rush, B.R.; Davis, E.G. Pharmacology and therapeutics of pulmonary medications; Equine Respiratory Medicine and Surgery 2007, 83-99.;
d) Wynn, S. G.; Fougère, B. J. Veterinary herbal medicine, 2007, 291-409.;
e) Theoret, C.L.; Stashak, T.S. Equine Emergencies, 2014, 238-267.
[http://dx.doi.org/10.1016/B978-1-4557-0892-5.00019-2];
f) Kennewell, P.D.; Taylor, J.B.; Triggle, D.J. Comprehensive Medicinal Chemistry II., 2007, 1, 97-249.
[http://dx.doi.org/10.1016/B0-08-045044-X/00003-1];
g) Sharrif Moghaddasi, M.; Verma, S.K. Int. J. Biol. Med. Res., 2011, 2(1), 467.
[49]
a) Darabighane, B.; Nahashon, S.N. Ann. Anim. Sci., 2014, 14(3), 491-500. http://dx.doi.org/10.2478/aoas-2014-0026;
b) Peng, S.Y.; Norman, J.; Curtin, G.; Corrier, D.; McDaniel, H.R.; Busbee, D. Mol. Biother., 1991, 3(2), 79-87.
[PMID: 1910624]
[50]
a) Womble, D.; Helderman, J.H. Immunopharmacol. Immunotoxicol., 1992, 14(1-2), 63-77.
[http://dx.doi.org/10.3109/08923979209009213] [PMID: 1597661];
b) Womble, D.; Helderman, J.H. Int. J. Immunopharmacol., 1988, 10(8), 967-974.
[http://dx.doi.org/10.1016/0192-0561(88)90043-4] [PMID: 2975271];
c) Lee, J.K.; Lee, M.K.; Yun, Y.P.; Kim, Y.; Kim, J.S.; Kim, Y.S.; Kim, K.; Han, S.S.; Lee, C.K. Int. Immunopharmacol., 2001, 1(7), 1275-1284.
[http://dx.doi.org/10.1016/S1567-5769(01)00052-2] [PMID: 11460308]
[51]
Stuart, R.W.; Lefkowitz, D.L.; Lincoln, J.A.; Howard, K.; Gelderman, M.P.; Lefkowitz, S.S. Int. J. Immunopharmacol., 1997, 19(2), 75-82.
[http://dx.doi.org/10.1016/S0192-0561(97)00010-6] [PMID: 9278177]
[52]
Gangadharan, C.; Arthanareeswari, M.; Pandiyan, R.; Ilango, K. MohanKumar. R. Mater. Today Proc., 2019, 14, 296-301.
[http://dx.doi.org/10.1016/j.matpr.2019.04.150]
[53]
a) Deep, A.; Bhatia, R.; Kaur, R.; Kumar, S.; Jain, U.; Singh, H.; Batra, S.; Kaushik, D.; Deb, P. Curr. Top. Med. Chem., 2016, 17(2), 238-250.
[http://dx.doi.org/10.2174/1568026616666160530153233] [PMID: 27237332];
b) Aziz, J.; Piguel, S. Synthesis, 2017, 49(20), 4562-4585. http://dx.doi.org/10.1055/s-0036-1590859;
c) Abdel-Mohsen, H.T.; Abood, A.; Flanagan, K.J.; Meindl, A.; Senge, M.O.; El Diwani, H.I. Arch. Pharm. (Weinheim), 2020, 353(3), 1900271.
[http://dx.doi.org/10.1002/ardp.201900271] [PMID: 31989670];
d) Reddy, K.T.; Sreenivasulu, R.; Raju, R.R. J. Indian Chem. Soc., 2019, 96, 1085-1090.
[54]
a) Patel, O.P.S.; Nandwana, N.K.; Legoabe, L.J.; Das, B.C.; Kumar, A. Adv. Synth. Catal., 2020, 362(20), 4226-4255. http://dx.doi.org/10.1002/adsc.202000633;
b) Aeluri, R.; Alla, M.; Polepalli, S.; Jain, N. Eur. J. Med. Chem., 2015, 100, 18-23.
[http://dx.doi.org/10.1016/j.ejmech.2015.05.037] [PMID: 26067381]
[55]
a) Altaher, A.; Adris, M.A.; Aliwaini, S. Systematic Reviews in Pharmacy, 2021, 12, 79-86.;
b) Bagdi, A.K.; Hajra, A. Org. Biomol. Chem., 2020, 18(14), 2611-2631.
[http://dx.doi.org/10.1039/D0OB00246A] [PMID: 32215443]
[56]
Ma, C.H.; Chen, M.; Feng, Z.W.; Zhang, Y.; Wang, J.; Jiang, Y.Q.; Yu, B. New J. Chem., 2021, 45(21), 9302-9314.
[http://dx.doi.org/10.1039/D1NJ00704A]
[57]
Tashrifi, Z.; Mohammadi-Khanaposhtani, M.; Larijani, B.; Mahdavi, M. Eur. J. Org. Chem., 2020, 2020(3), 269-284.
[http://dx.doi.org/10.1002/ejoc.201901491]
[58]
Hand, E.S.; Paudler, W.W. Tetrahedron, 1982, 38(1), 49-55.
[http://dx.doi.org/10.1016/0040-4020(82)85044-8]

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