Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

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

Review Article

The Biological and Pharmacological Potentials of Indole-based Heterocycles

Author(s): Shivangi Sharma and Shivendra Singh*

Volume 20, Issue 8, 2023

Published on: 08 March, 2023

Page: [711 - 729] Pages: 19

DOI: 10.2174/1570178620666230215121808

Price: $65

Abstract

An important bioactive heterocycle having several uses in medicinal chemistry, synthetic organic chemistry, material chemistry, and natural product is indole along with its analogues. Many bioactive indole-based heterocycles have important antibacterial, anti-inflammatory, analgesic, antiviral, antimalarial, chemotherapeutic, antifungal, and anti-TB effects, as well as antioxidant capabilities. Several well-known medications, including tadalafil, rizatriptan, sumatriptan, and fluvastatin are indole- based potential bioactive compounds. Based on the existing and latest evidence, researchers have focused on developing indole-based compounds with novel biological and pharmacological properties for decades. Owing to useful bioactivities, we have described many bioactive indoles and their synthetic methods in this review article.

Keywords: Indole, pharmaceutical, heterocycles, biological activity, COX-1 & COX-2 (cyclooxygenase), agonistic effects, MCR technique.

Graphical Abstract
[1]
Arshad, M.; Bhat, A.R.; Hoi, K.K.; Choi, I.; Athar, F. Chin. Chem. Lett., 2017, 28(7), 1559-1565.
[http://dx.doi.org/10.1016/j.cclet.2016.12.037]
[2]
Lepri, S.; Buonerba, F.; Goracci, L.; Velilla, I.; Ruzziconi, R.; Schindler, B.D.; Seo, S.M.; Kaatz, G.W.; Cruciani, G. J. Med. Chem., 2016, 59(3), 867-891.
[http://dx.doi.org/10.1021/acs.jmedchem.5b01219] [PMID: 26757340]
[3]
Liu, Q.L.; Chen, A.H.; Tang, J.Y.; Ma, Y.L.; Jiang, Z.H.; Liu, Y.P.; Chen, G.Y.; Fu, Y.H.; Xu, W. Nat. Prod. Res., 2017, 31(18), 2107-2112.
[http://dx.doi.org/10.1080/14786419.2016.1277351] [PMID: 28067066]
[4]
Abadi, A.H.; Hegazy, G.H.; El-Zaher, A.A. Bioorg. Med. Chem., 2005, 13(20), 5759-5765.
[http://dx.doi.org/10.1016/j.bmc.2005.05.053] [PMID: 16002298]
[5]
Giampieri, M.; Balbi, A.; Mazzei, M.; La Colla, P.; Ibba, C.; Loddo, R. Antiviral Res., 2009, 83(2), 179-185.
[http://dx.doi.org/10.1016/j.antiviral.2009.05.001] [PMID: 19445965]
[6]
Li, J.Y.; Sun, X.F.; Li, J.J.; Yu, F.; Zhang, Y.; Huang, X.J.; Jiang, F.X. Arch. Pharm. (Weinheim), 2020, 353(11)2000131
[http://dx.doi.org/10.1002/ardp.202000131] [PMID: 32785974]
[7]
Mukhopadhyay, S.; Handy, G.A.; Funayama, S.; Cordell, G.A. J. Nat. Prod., 1981, 44(6), 696-700.
[http://dx.doi.org/10.1021/np50018a014] [PMID: 7334384]
[8]
Dekker, W.H.; Selling, H.A.; Overeem, J.C. J. Agric. Food Chem., 1975, 23(4), 785-791.
[http://dx.doi.org/10.1021/jf60200a041] [PMID: 1170225]
[9]
Desai, N.C.; Somani, H.; Trivedi, A.; Bhatt, K.; Nawale, L.; Khedkar, V.M.; Jha, P.C.; Sarkar, D. Bioorg. Med. Chem. Lett., 2016, 26(7), 1776-1783.
[http://dx.doi.org/10.1016/j.bmcl.2016.02.043] [PMID: 26920799]
[10]
Estevão, M.S.; Carvalho, L.C.; Ribeiro, D.; Couto, D.; Freitas, M.; Gomes, A.; Ferreira, L.M.; Fernandes, E.; Marques, M.M.B. Eur. J. Med. Chem., 2010, 45(11), 4869-4878.
[http://dx.doi.org/10.1016/j.ejmech.2010.07.059] [PMID: 20727623]
[11]
Evans, B.E.; Rittle, K.E.; Bock, M.G.; DiPardo, R.M.; Freidinger, R.M.; Whitter, W.L.; Lundell, G.F.; Veber, D.F.; Anderson, P.S.; Chang, R.S.L.; Lotti, V.J.; Cerino, D.J.; Chen, T.B.; Kling, P.J.; Kunkel, K.A.; Springer, J.P.; Hirshfield, J. J. Med. Chem., 1988, 31(12), 2235-2246.
[http://dx.doi.org/10.1021/jm00120a002] [PMID: 2848124]
[12]
Van Order, R.B.; Lindwall, H.G. Chem. Rev., 1942, 30(1), 69-96.
[http://dx.doi.org/10.1021/cr60095a004]
[13]
Horton, D.A.; Bourne, G.T.; Smythe, M.L. Chem. Rev., 2003, 103(3), 893-930.
[http://dx.doi.org/10.1021/cr020033s] [PMID: 12630855]
[14]
Sniady, A.; Morreale, M.S.; Wheeler, K.A.; Dembinski, R. Eur. J. Org. Chem., 2008, 2008(20), 3449-3452.
[http://dx.doi.org/10.1002/ejoc.200800397]
[15]
Cocuzza, A.J.; Chidester, D.R.; Culp, S.; Fitzgerald, L.; Gilligan, P. Bioorg. Med. Chem. Lett., 1999, 9(7), 1063-1066.
[http://dx.doi.org/10.1016/S0960-894X(99)00133-X] [PMID: 10230641]
[16]
Vitaku, E.; Smith, D.T.; Njardarson, J.T. J. Med. Chem., 2014, 57(24), 10257-10274.
[http://dx.doi.org/10.1021/jm501100b] [PMID: 25255204]
[17]
Vitaglione, P.; Fogliano, V. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 2004, 802(1), 189-199.
[http://dx.doi.org/10.1016/j.jchromb.2003.09.029] [PMID: 15036011]
[18]
Abdel-Wahab, B.F.; Awad, G.E.A.; Badria, F.A. Eur. J. Med. Chem., 2011, 46(5), 1505-1511.
[http://dx.doi.org/10.1016/j.ejmech.2011.01.062] [PMID: 21353349]
[19]
Talati, J.D.; Gandhi, D.K. Corros. Sci., 1983, 23(12), 1315-1332.
[http://dx.doi.org/10.1016/0010-938X(83)90081-1]
[20]
Raja, P.B.; Sethuraman, M.G. Mater. Lett., 2008, 62(1), 113-116.
[http://dx.doi.org/10.1016/j.matlet.2007.04.079]
[21]
Stead, C.V. Dyes Pigments, 1982, 3(2-3), 161-171.
[http://dx.doi.org/10.1016/0143-7208(82)80019-3]
[22]
Guo, L.; Zhang, D. J. Am. Chem. Soc., 2009, 131(50), 18072-18074.
[http://dx.doi.org/10.1021/ja907380d] [PMID: 19950948]
[23]
Butuc, E.; Gherasim, G.M. J. Polym. Sci. Polym. Chem. Ed., 1984, 22(2), 503-507.
[http://dx.doi.org/10.1002/pol.1984.170220220]
[24]
Sunderhaus, J.D.; Martin, S.F. Chemistry, 2009, 15(6), 1300-1308.
[http://dx.doi.org/10.1002/chem.200802140] [PMID: 19132705]
[25]
Zhu, J. Eur. J. Org. Chem., 2003, 2003(7), 1133-1144.
[http://dx.doi.org/10.1002/ejoc.200390167]
[26]
Jiang, B.; Rajale, T.; Wever, W.; Tu, S.J.; Li, G. Chem. Asian J., 2010, 5(11), 2318-2335.
[http://dx.doi.org/10.1002/asia.201000310] [PMID: 20922748]
[27]
Ugi, I.; Domling, A.; Werner, B. J. Heterocycl. Chem., 2000, 37(3), 647-658.
[http://dx.doi.org/10.1002/jhet.5570370322]
[28]
Kappe, C.O. Acc. Chem. Res., 2000, 33(12), 879-888.
[http://dx.doi.org/10.1021/ar000048h] [PMID: 11123887]
[29]
Orru, R.V.; de Greef, M. Synthesis, 2003, 10(10), 1471-1499.
[http://dx.doi.org/10.1055/s-2003-40507]
[30]
Ngouansavanh, T. Zhu. J. Angew. Chem. Int. Ed., 2006, 45(21), 3495-3497.
[http://dx.doi.org/10.1002/anie.200600588] [PMID: 16637095]
[31]
Ishikura, M.; Abe, T.; Choshi, T.; Hibino, S. Nat. Prod. Rep., 2015, 32(10), 1389-1471.
[http://dx.doi.org/10.1039/C5NP00032G] [PMID: 26151910]
[32]
Kinsman, A.C.; Kerr, M.A. J. Am. Chem. Soc., 2003, 125(46), 14120-14125.
[http://dx.doi.org/10.1021/ja036191y] [PMID: 14611249]
[33]
Chang-Fong, J.; Rangisetty, J.B.; Dukat, M.; Setola, V.; Raffay, T.; Roth, B.; Glennon, R.A. Bioorg. Med. Chem. Lett., 2004, 14(8), 1961-1964.
[http://dx.doi.org/10.1016/j.bmcl.2004.01.071] [PMID: 15050637]
[34]
Brock, W. Adolf von, Johann Friedrich Wilhelm eLS, 2001, 489-522.
[35]
Robinson, B. Chem. Rev., 1969, 69(2), 227-250.
[http://dx.doi.org/10.1021/cr60258a004]
[36]
Robinson, B. Chem. Rev., 1963, 63(4), 373-401.
[http://dx.doi.org/10.1021/cr60224a003]
[37]
Kumari, A.; Singh, R.K. Bioorg. Chem., 2019, 89(May)103021
[http://dx.doi.org/10.1016/j.bioorg.2019.103021] [PMID: 31176854]
[38]
Dolle, R.E.; Nelson, K.H., Jr J. Comb. Chem., 1999, 1(4), 235-282.
[http://dx.doi.org/10.1021/cc9900192] [PMID: 10748736]
[39]
Franzén, R.G. J. Comb. Chem., 2000, 2(3), 195-214.
[http://dx.doi.org/10.1021/cc000002f] [PMID: 10827923]
[40]
Dolle, R.E. J. Comb. Chem., 2001, 3(6), 477-517.
[http://dx.doi.org/10.1021/cc010049g] [PMID: 11703143]
[41]
Hanessian, S.; McNaughton-Smith, G.; Lombart, H.G.; Lubell, W.D. Tetrahedron, 1997, 53(38), 12789-12854.
[http://dx.doi.org/10.1016/S0040-4020(97)00476-6]
[42]
Chen, F.E. Huang. J. Chem. Rev., 2005, 105(12), 4671-4706.
[http://dx.doi.org/10.1021/cr050521a] [PMID: 16351058]
[43]
Berger, M.J.; Gray, A.; Roth, B.L. Annu. Rev. Med., 2009, 60(1), 355-366.
[44]
Almagro, L.; Fernández-Pérez, F.; Pedreño, M. Molecules, 2015, 20(2), 2973-3000.
[http://dx.doi.org/10.3390/molecules20022973] [PMID: 25685907]
[45]
Gul, W.; Hamann, M.T. Life Sci., 2005, 78(5), 442-453.
[http://dx.doi.org/10.1016/j.lfs.2005.09.007] [PMID: 16236327]
[46]
Lal, S.; Snape, T.J. Curr. Med. Chem., 2012, 19(28), 4828-4837.
[http://dx.doi.org/10.2174/092986712803341449] [PMID: 22830349]
[47]
DHHS panel Guidelines for the use of antiretroviral agents in HIV-1-infected adults and adolescents, 2006.
[48]
Xu, H.; Lv, M. Curr. Pharm. Des., 2009, 15(18), 2120-2148.
[49]
Ostojic, S.M. Res. Sports Med., 2006, 14(4), 289-299.
[http://dx.doi.org/10.1080/15438620600987106] [PMID: 17214405]
[50]
Rosengren, A.H.; Jokubka, R.; Tojjar, D.; Granhall, C.; Hansson, O.; Li, D.Q.; Nagaraj, V.; Reinbothe, T.M.; Tuncel, J.; Eliasson, L.; Groop, L.; Rorsman, P.; Salehi, A.; Lyssenko, V.; Luthman, H.; Renström, E. Science, 2010, 327(5962), 217-220.
[http://dx.doi.org/10.1126/science.1176827] [PMID: 19965390]
[51]
Isaac, M.T. Evid. Based Ment. Health, 2004, 7(4), 107-130.
[http://dx.doi.org/10.1136/ebmh.7.4.107] [PMID: 15504795]
[52]
Lednicer, D. Organic Chemistry of Drug Synthesis-A, John Wiley & Sons, NJ, USA., 2007, 7, 141-154.
[53]
Witjes, J.A.; Kolli, P.S. Expert Opin. Investig. Drugs, 2008, 17(7), 1085-1096.
[http://dx.doi.org/10.1517/13543784.17.7.1085] [PMID: 18549344]
[54]
Leneva, I.A.; Russell, R.J.; Boriskin, Y.S.; Hay, A.J. Antiviral Res., 2009, 81(2), 132-140.
[http://dx.doi.org/10.1016/j.antiviral.2008.10.009] [PMID: 19028526]
[55]
Brown, G.D.; Denning, D.W.; Gow, N.A.R.; Levitz, S.M.; Netea, M.G.; White, T.C. Sci. Transl. Med., 2012, 4(165)165rv13
[http://dx.doi.org/10.1126/scitranslmed.3004404] [PMID: 23253612]
[56]
Roberts, R.R.; Hota, B.; Ahmad, I.; Scott, R.D., II; Foster, S.D.; Abbasi, F.; Schabowski, S.; Kampe, L.M.; Ciavarella, G.G.; Supino, M.; Naples, J.; Cordell, R.; Levy, S.B.; Weinstein, R.A. Clin. Infect. Dis., 2009, 49(8), 1175-1184.
[http://dx.doi.org/10.1086/605630] [PMID: 19739972]
[57]
Zhang, F.F.; Gan, L.L.; Zhou, C.H. Bioorg. Med. Chem. Lett., 2010, 20(6), 1881-1884.
[http://dx.doi.org/10.1016/j.bmcl.2010.01.159] [PMID: 20176480]
[58]
Liu, C.; Bayer, A.; Cosgrove, S.E.; Daum, R.S.; Fridkin, S.K.; Gorwitz, R.J.; Kaplan, S.L.; Karchmer, A.W.; Levine, D.P.; Murray, B.E.; Rybak, M.J.; Talan, D.A.; Chambers, H.F. Clin. Infect. Dis., 2011, 52(3), e18-e55.
[http://dx.doi.org/10.1093/cid/ciq146] [PMID: 21208910]
[59]
Kaku, N.; Morinaga, Y.; Takeda, K.; Kosai, K.; Uno, N.; Hasegawa, H.; Miyazaki, T.; Izumikawa, K.; Mukae, H.; Yanagihara, K. Int. J. Med. Microbiol., 2016, 306(6), 421-428.
[http://dx.doi.org/10.1016/j.ijmm.2016.05.010] [PMID: 27259840]
[60]
O’Sullivan, D.A.; Lepkowski, W. Chem. Eng. News, 1990, 68(20), 42-61.
[http://dx.doi.org/10.1021/cen-v068n020.p042]
[61]
Berger, M.; Gray, J.A.; Roth, B.L. Annu. Rev. Med., 2009, 60(1), 355-366.
[http://dx.doi.org/10.1146/annurev.med.60.042307.110802] [PMID: 19630576]
[62]
Claudio, Viegas-Junior; Danuello, A.; da Silva Bolzani, V.; Barreiro, E.J.; Fraga, C.A. Curr. Med. Chem., 2007, 14(17), 1829-1852.
[http://dx.doi.org/10.2174/092986707781058805] [PMID: 17627520]
[63]
Shirinzadeh, H.; Süzen, S.; Altanlar, N.; Westwell, A.D. Turkish Journal of Pharmaceutical Sciences, 2018, 15(3), 291-297.
[http://dx.doi.org/10.4274/tjps.55707] [PMID: 32454672]
[64]
Mane, Y.D.; Sarnikar, Y.P.; Surwase, S.M.; Biradar, D.O.; Gorepatil, P.B.; Shinde, V.S.; Khade, B.C. Res. Chem. Intermed., 2017, 43(2), 1253-1275.
[http://dx.doi.org/10.1007/s11164-016-2696-3]
[65]
Schulze, B.; Schubert, U.S. Chem. Soc. Rev., 2014, 43(8), 2522-2571.
[http://dx.doi.org/10.1039/c3cs60386e] [PMID: 24492745]
[66]
Küçükgüzel, Ş.G.; Çıkla-Süzgün, P. Eur. J. Med. Chem., 2015, 97(1), 830-870.
[http://dx.doi.org/10.1016/j.ejmech.2014.11.033] [PMID: 25563511]
[67]
Akbari Dilmaghani, K.; Nasuhi Pur, F.; Hatami Nezhad, M. Iran. J. Pharm. Res., 2015, 14(3), 693-699.
[PMID: 26330857]
[68]
Radwan, M.A.A.; Ragab, E.A.; Sabry, N.M.; El-Shenawy, S.M. Bioorg. Med. Chem., 2007, 15(11), 3832-3841.
[http://dx.doi.org/10.1016/j.bmc.2007.03.024] [PMID: 17395469]
[69]
a) Bell, M.R. Eur. Patent 171037 1986.;
b) Brooks, C.D.W.; Craig, R.A.; Gunn, D.E.; Kolasa, T.; Moore, J.L.; Stewart, A.O.; Int, P.C.T.WO. Pat. 9741100 1998.
[70]
Özdemir, A.; Altıntop, M.D.; Turan-Zitouni, G.; Çiftçi, G.A.; Ertorun, İ.; Alataş, Ö.; Kaplancıklı, Z.A. Eur. J. Med. Chem., 2015, 89, 304-309.
[http://dx.doi.org/10.1016/j.ejmech.2014.10.056] [PMID: 25462246]
[71]
Torres, L.; Anderson, C.; Marro, P.; Mishra, O.P.; Delivoria-Papadopoulos, M. Neurochem. Res., 2004, 29(10), 1825-1830.
[http://dx.doi.org/10.1023/B:NERE.0000042208.20730.23] [PMID: 15532537]
[72]
Mayo, J.C.; Sainz, R.M.; Tan, D.X.; Hardeland, R.; Leon, J.; Rodriguez, C.; Reiter, R.J. J. Neuroimmunol., 2005, 165(1-2), 139-149.
[http://dx.doi.org/10.1016/j.jneuroim.2005.05.002] [PMID: 15975667]
[73]
Bhati, S.K.; Kumar, A. Eur. J. Med. Chem., 2008, 43(11), 2323-2330.
[http://dx.doi.org/10.1016/j.ejmech.2007.10.012] [PMID: 18063224]
[74]
a) Amir, M.; Javed, S.; Kumar, H. Acta Pharm., 2008, 58(4), 467-477.
[http://dx.doi.org/10.2478/v10007-008-0028-x] [PMID: 19103580];
b) Winter, C.A.; Risley, E.A.; Nuss, G.W. Exp. Biol. Med. (Maywood), 1962, 111(3), 544-547.
[http://dx.doi.org/10.3181/00379727-111-27849] [PMID: 14001233]
[75]
a) Shaveta, A.; Singh, A.; Kaur, M.; Sharma, S.; Bhatti, R.; Singh, P. Eur. J. Med. Chem., 2014, 77, 185-192.
[http://dx.doi.org/10.1016/j.ejmech.2014.03.003] [PMID: 24631898];
b) Sakurada, T.; Matsumura, T.; Moriyama, T.; Sakurada, C.; Ueno, S.; Sakurada, S. Pharmacology Biochemistry and Behavior, 2003, 75, 115-121.
[76]
Cohen, M.L. Commun. Dis. Rep. CDR Wkly., 1994, 4(43), 203.
[PMID: 7528603]
[77]
Rogers, T. R. Int. J. Infect. Dis., 2002, 6, SUPPL.1.
[78]
Nandakumar, A.; Thirumurugan, P.; Perumal, P.T.; Vembu, P.; Ponnuswamy, M.N.; Ramesh, P. Bioorg. Med. Chem. Lett., 2010, 20(14), 4252-4258.
[http://dx.doi.org/10.1016/j.bmcl.2010.05.025] [PMID: 20621732]
[79]
Singh, P.; Verma, P.; Yadav, B.; Komath, S.S. Bioorg. Med. Chem. Lett., 2011, 21(11), 3367-3372.
[http://dx.doi.org/10.1016/j.bmcl.2011.04.001] [PMID: 21524574]
[80]
Minvielle, M.J.; Eguren, K.; Melander, C. Chemistry, 2013, 19(51), 17595-17602.
[http://dx.doi.org/10.1002/chem.201303510] [PMID: 24243627]
[81]
Liou, J.P.; Hsu, K.S.; Kuo, C.C.; Chang, C.Y.; Chang, J.Y. J. Pharmacol. Exp. Ther., 2007, 323(1), 398-405.
[http://dx.doi.org/10.1124/jpet.107.126680] [PMID: 17660383]
[82]
Pathak, T.P.; Gligorich, K.M.; Welm, B.E.; Sigman, M.S. J. Am. Chem. Soc., 2010, 132(23), 7870-7871.
[http://dx.doi.org/10.1021/ja103472a] [PMID: 20486685]
[83]
Zhang, M.Z.; Chen, Q.; Yang, G.F. Eur. J. Med. Chem., 2015, 89, 421-441.
[http://dx.doi.org/10.1016/j.ejmech.2014.10.065] [PMID: 25462257]
[84]
Rossignol, J.F. Antiviral Res., 2014, 110(August), 94-103.
[http://dx.doi.org/10.1016/j.antiviral.2014.07.014] [PMID: 25108173]
[85]
Selvam, P.; Murugesh, N.; Chandramohan, M.; Sidwell, R.W.; Wandersee, M.K.; Smee, D.F. Antivir. Chem. Chemother., 2006, 17(5), 269-274.
[http://dx.doi.org/10.1177/095632020601700504] [PMID: 17176631]
[86]
Xue, S.; Ma, L.; Gao, R.; Li, Y.; Li, Z. Acta Pharm. Sin. B, 2014, 4(4), 313-321.
[http://dx.doi.org/10.1016/j.apsb.2014.06.003] [PMID: 26579401]
[87]
Fonseca, T.; Gigante, B.; Marques, M.M.; Gilchrist, T.L.; De Clercq, E. Bioorg. Med. Chem., 2004, 12(1), 103-112.
[http://dx.doi.org/10.1016/j.bmc.2003.10.013] [PMID: 14697775]
[88]
Luthra, T.; Nayak, A.K.; Bose, S.; Chakrabarti, S.; Gupta, A.; Sen, S. Eur. J. Med. Chem., 2019, 168, 11-27.
[http://dx.doi.org/10.1016/j.ejmech.2019.02.019] [PMID: 30798050]
[89]
Petersen, I.; Eastman, R.; Lanzer, M. FEBS Lett., 2011, 585(11), 1551-1562.
[http://dx.doi.org/10.1016/j.febslet.2011.04.042] [PMID: 21530510]
[90]
Frederich, M.; Tits, M.; Angenot, L. Trans. R. Soc. Trop. Med. Hyg., 2008, 102(1), 11-19.
[http://dx.doi.org/10.1016/j.trstmh.2007.10.002] [PMID: 18035385]
[91]
Kgokong, J.L.; Smith, P.P.; Ma, G.M. Bioorg. Med. Chem., 2005, 13(8), 2935-2942.
[http://dx.doi.org/10.1016/j.bmc.2005.02.017] [PMID: 15781403]
[92]
Fernandez, L.S.; Buchanan, M.S.; Carroll, A.R.; Feng, Y.J.; Quinn, R.J.; Avery, V.M.; Flinderoles, A-C. Org. Lett., 2009, 11(2), 329-332.
[http://dx.doi.org/10.1021/ol802506n] [PMID: 19090698]
[93]
Willson, T.M.; Cobb, J.E.; Cowan, D.J.; Wiethe, R.W.; Correa, I.D.; Prakash, S.R.; Beck, K.D.; Moore, L.B.; Kliewer, S.A.; Lehmann, J.M. J. Med. Chem., 1996, 39(3), 665-668.
[http://dx.doi.org/10.1021/jm950395a] [PMID: 8576907]
[94]
Nesto, R.W.; Bell, D.; Bonow, R.O.; Fonseca, V.; Grundy, S.M.; Horton, E.S.; Le Winter, M.; Porte, D.; Semenkovich, C.F.; Smith, S.; Young, L.H.; Kahn, R. Circulation, 2003, 108(23), 2941-2948.
[http://dx.doi.org/10.1161/01.CIR.0000103683.99399.7E] [PMID: 14662691]
[95]
Hoover, D.J.; Lefkowitz-Snow, S.; Burgess-Henry, J.L.; Martin, W.H.; Armento, S.J.; Stock, I.A.; McPherson, R.K.; Genereux, P.E.; Gibbs, E.M.; Treadway, J.L. J. Med. Chem., 1998, 41(16), 2934-2938.
[http://dx.doi.org/10.1021/jm980264k] [PMID: 9685232]
[96]
Li, Y.; Wu, H.; Tang, L.; Feng, C.; Yu, J.; Li, Y.; Yang, Y.; Yang, B.; He, Q. Pharmacol. Res., 2007, 56(4), 335-343.
[http://dx.doi.org/10.1016/j.phrs.2007.08.002] [PMID: 17889553]
[97]
Lamotte, Y.; Martres, P.; Faucher, N.; Laroze, A.; Grillot, D.; Ancellin, N.; Saintillan, Y.; Beneton, V.; Gampe, R.T., Jr Bioorg. Med. Chem. Lett., 2010, 20(4), 1399-1404.
[http://dx.doi.org/10.1016/j.bmcl.2009.12.107] [PMID: 20079636]
[98]
Gelb, M.H.; Hol, W.G. J. Science, 2002, 297(5580), 343-344.
[http://dx.doi.org/10.1126/science.1073126] [PMID: 12130767]
[99]
Khan, K.M.; Mughal, U.R. Samreen; Perveen, S.; Choudhary, M.I. Lett. Drug Des. Discov., 2008, 5(4), 243-249.
[http://dx.doi.org/10.2174/157018008784619915]
[100]
Lala, S.; Pramanick, S.; Mukhopadhyay, S.; Bandyopadhyay, S.; Basu, M.K. J. Drug Target., 2004, 12(3), 165-175.
[http://dx.doi.org/10.1080/10611860410001712696] [PMID: 15203896]
[101]
Cao, R.; Peng, W.; Chen, H.; Ma, Y.; Liu, X.; Hou, X.; Guan, H.; Xu, A. Biochem. Biophys. Res. Commun., 2005, 338(3), 1557-1563.
[http://dx.doi.org/10.1016/j.bbrc.2005.10.121] [PMID: 16288723]
[102]
Gupta, L.; Talwar, A.; Nishi, S.; Palne, S.; Gupta, S.; Chauhan, P.M.S. Bioorg. Med. Chem. Lett., 2007, 17(14), 4075-4079.
[http://dx.doi.org/10.1016/j.bmcl.2007.04.035] [PMID: 17548194]
[103]
Sharma, R.; Pandey, A.K.; Shivahare, R.; Srivastava, K.; Gupta, S.; Chauhan, P.M.S. Bioorg. Med. Chem. Lett., 2014, 24(1), 298-301.
[http://dx.doi.org/10.1016/j.bmcl.2013.11.018] [PMID: 24314395]
[104]
Dye, C.; Williams, B.G. Science, 2010, 328(5980), 856-861.
[http://dx.doi.org/10.1126/science.1185449] [PMID: 20466923]
[105]
Khan, G.A.; War, J.A.; Kumar, A.; Sheikh, I.A.; Saxena, A.; Das, R. J. Taibah Univ. Sci., 2017, 11(6), 910-921.
[http://dx.doi.org/10.1016/j.jtusci.2016.09.002]
[106]
Karthikeyan, S.V.; Perumal, S.; Shetty, K.A.; Yogeeswari, P.; Sriram, D. Bioorg. Med. Chem. Lett., 2009, 19(11), 3006-3009.
[http://dx.doi.org/10.1016/j.bmcl.2009.04.029] [PMID: 19403307]
[107]
Tehrani, K.H.M.E.; Mashayekhi, V.; Azerang, P.; Sardari, S.; Kobarfard, F.; Rostamizadeh, K. Chem. Biol. Drug Des., 2014, 83(2), 224-236.
[http://dx.doi.org/10.1111/cbdd.12230] [PMID: 24103309]
[108]
Tehrani, K.H.M.E.; Sardari, S.; Mashayekhi, V.; Esfahani Zadeh, M.; Azerang, P.; Kobarfard, F. Chem. Pharm. Bull. (Tokyo), 2013, 61(2), 160-166.
[http://dx.doi.org/10.1248/cpb.c12-00651] [PMID: 23183543]
[109]
Pajouhesh, H.; Parson, R.; Popp, F.D. J. Pharm. Sci., 1983, 72(3), 318-321.
[http://dx.doi.org/10.1002/jps.2600720330] [PMID: 6842387]
[110]
Kerzare, D.R.; Menghani, S.S.; Rarokar, N.R.; Khedekar, P.B. Arch. Pharm. (Weinheim), 2021, 354(1)2000100
[http://dx.doi.org/10.1002/ardp.202000100] [PMID: 32909304]
[111]
El-Gendy, A.A.; Said, M.M.; Ghareb, N.; Mostafa, Y.M.; El-Ashry, E.S.H. Arch. Pharm. (Weinheim), 2008, 341(5), 294-300.
[http://dx.doi.org/10.1002/ardp.200700161] [PMID: 18404776]
[112]
Gitto, R.; Luca, L.D.; Ferro, S.; Citraro, R.; Sarro, G.D.; Costa, L.; Ciranna, L.; Chimirri, A. Bioorg. Med. Chem., 2009, 17(4), 1640-1647.
[http://dx.doi.org/10.1016/j.bmc.2008.12.058] [PMID: 19157884]
[113]
Ahuja, P.; Siddiqui, N. Eur. J. Med. Chem., 2014, 80, 509-522.
[http://dx.doi.org/10.1016/j.ejmech.2014.04.043] [PMID: 24813879]
[114]
Jain, K.S.; Bariwal, J.B.; Kathiravan, M.K.; Phoujdar, M.S.; Sahne, R.S.; Chauhan, B.S.; Shah, A.K.; Yadav, M.R. Bioorg. Med. Chem., 2008, 16(9), 4759-4800.
[http://dx.doi.org/10.1016/j.bmc.2008.02.091] [PMID: 18378462]
[115]
El-Gendy, A.A.; El-Banna, H.A. Arch. Pharm. Res., 2001, 24(1), 21-26.
[http://dx.doi.org/10.1007/BF02976488] [PMID: 11235807]
[116]
Romeo, G.; Materia, L.; Manetti, F.; Cagnotto, A.; Mennini, T.; Nicoletti, F.; Botta, M.; Russo, F.; Minneman, K.P. J. Med. Chem., 2003, 46(14), 2877-2894.
[http://dx.doi.org/10.1021/jm0307741] [PMID: 12825930]
[117]
Romeo, G.; Materia, L.; Marucci, G.; Modica, M.; Pittalà, V.; Salerno, L.; Siracusa, M.A.; Buccioni, M.; Angeli, P.; Minneman, K.P. Bioorg. Med. Chem. Lett., 2006, 16(24), 6200-6203.
[http://dx.doi.org/10.1016/j.bmcl.2006.09.034] [PMID: 17027264]
[118]
Zhu, W.; Da, Y.; Wu, D.; Zheng, H.; Zhu, L.; Wang, L.; Yan, Y.; Chen, Z. Bioorg. Med. Chem., 2014, 22(7), 2294-2302.
[http://dx.doi.org/10.1016/j.bmc.2014.02.008] [PMID: 24613628]
[119]
Süzen, S. Top. Heterocycl. Chem., 2007, 11, 145-178.
[http://dx.doi.org/10.1007/7081_2007_074]
[120]
Aboul-Enein, H.Y.; Kruk, I.; Lichszteld, K.; Michalska, T.; Kladna, A.; Marczyński, S.; Ölgen, S. Luminescence, 2004, 19(1), 1-7.
[http://dx.doi.org/10.1002/bio.748] [PMID: 14981640]
[121]
Talaz, O.; Gülçin, İ.; Göksu, S.; Saracoglu, N. Bioorg. Med. Chem., 2009, 17(18), 6583-6589.
[http://dx.doi.org/10.1016/j.bmc.2009.07.077] [PMID: 19683932]
[122]
Andreadou, I.; Tasouli, A.; Bofilis, E.; Chrysselis, M.; Rekka, E.; Tsantili-Kakoulidou, A.; Iliodromitis, E.; Siatra, T.; Kremastinos, D.T. Chem. Pharm. Bull. (Tokyo), 2002, 50(2), 165-168.
[http://dx.doi.org/10.1248/cpb.50.165] [PMID: 11848203]
[123]
Barré-Sinoussi, F.; Chermann, J.C.; Rey, F.; Nugeyre, M.T.; Chamaret, S.; Gruest, J.; Dauguet, C.; Axler-Blin, C.; Vézinet-Brun, F.; Rouzioux, C.; Rozenbaum, W.; Montagnier, L. Rev. Invest. Clin., 2004, 56(2), 126-129.
[PMID: 15378805]
[124]
La Regina, G.; Coluccia, A.; Brancale, A.; Piscitelli, F.; Gatti, V.; Maga, G.; Samuele, A.; Pannecouque, C.; Schols, D.; Balzarini, J.; Novellino, E.; Silvestri, R. J. Med. Chem., 2011, 54(6), 1587-1598.
[http://dx.doi.org/10.1021/jm101614j] [PMID: 21366296]
[125]
La Regina, G.; Coluccia, A.; Brancale, A.; Piscitelli, F.; Famiglini, V.; Cosconati, S.; Maga, G.; Samuele, A.; Gonzalez, E.; Clotet, B.; Schols, D.; Esté, J.A.; Novellino, E.; Silvestri, R. J. Med. Chem., 2012, 55(14), 6634-6638.
[http://dx.doi.org/10.1021/jm300477h] [PMID: 22712652]
[126]
Alexandre, F.R.; Amador, A.; Bot, S.; Caillet, C.; Convard, T.; Jakubik, J.; Musiu, C.; Poddesu, B.; Vargiu, L.; Liuzzi, M.; Roland, A.; Seifer, M.; Standring, D.; Storer, R.; Dousson, C.B. J. Med. Chem., 2011, 54(1), 392-395.
[http://dx.doi.org/10.1021/jm101142k] [PMID: 21142105]
[127]
Wang, T.; Kadow, J.F.; Zhang, Z.; Yin, Z.; Gao, Q.; Wu, D.; Parker, D.D.; Yang, Z.; Zadjura, L.; Robinson, B.A.; Gong, Y.F.; Blair, W.S.; Shi, P-Y.; Yamanaka, G.; Lin, P-F.; Meanwell, N.A.; Meanwell, N.A. Bioorg. Med. Chem. Lett., 2009, 19(17), 5140-5145.
[http://dx.doi.org/10.1016/j.bmcl.2009.07.076] [PMID: 19664921]
[128]
Seigler, D.S. Plant secondary metabolism; Springer Science & Business Media, 1998.
[http://dx.doi.org/10.1007/978-1-4615-4913-0]
[129]
Hanson, J.R. Chemistry of fungi; Royal Society of Chemistry, 2008.
[130]
Wiemann, P.; Keller, N.P. J. Ind. Microbiol. Biotechnol., 2014, 41(2), 301-313.
[http://dx.doi.org/10.1007/s10295-013-1366-3] [PMID: 24146366]
[131]
Yaegashi, J.; Oakley, B.R.; Wang, C.C.C. J. Ind. Microbiol. Biotechnol., 2014, 41(2), 433-442.
[http://dx.doi.org/10.1007/s10295-013-1386-z] [PMID: 24342965]
[132]
Pullagurla, M.; Siripurapu, U.; Kolanos, R.; Bondarev, M.L.; Dukat, M.; Setola, V.; Roth, B.L.; Glennon, R.A. Bioorg. Med. Chem. Lett., 2005, 15(23), 5298-5302.
[http://dx.doi.org/10.1016/j.bmcl.2005.08.059] [PMID: 16183286]
[133]
Xu, H.; Wang, Q.; Yang, W.B. J. Biosci., 2010, 65(7-8), 437-439.
[134]
Na, Y.M. Bull. Korean Chem. Soc., 2010, 31(11), 3467-3470.
[http://dx.doi.org/10.5012/bkcs.2010.31.11.3467]
[135]
Tsuji, Y.; Kotachi, S.; Huh, K.T.; Watanabe, Y. J. Org. Chem., 1990, 55(2), 580-584.
[http://dx.doi.org/10.1021/jo00289a036]
[136]
Ryu, C.K.; Lee, J.Y.; Park, R.E.; Ma, M.Y.; Nho, J.H. Bioorg. Med. Chem. Lett., 2007, 17(1), 127-131.
[http://dx.doi.org/10.1016/j.bmcl.2006.09.076] [PMID: 17046257]
[137]
Rani, P.; Srivastava, V.K.; Kumar, A. Eur. J. Med. Chem., 2004, 39(5), 449-452.
[http://dx.doi.org/10.1016/j.ejmech.2003.11.002] [PMID: 15110970]
[138]
Leboho, T.C.; Michael, J.P.; van Otterlo, W.A.L.; van Vuuren, S.F.; de Koning, C.B. Bioorg. Med. Chem. Lett., 2009, 19(17), 4948-4951.
[http://dx.doi.org/10.1016/j.bmcl.2009.07.091] [PMID: 19660944]
[139]
Pourshab, M.; Asghari, S.; Mohseni, M. J. Heterocycl. Chem., 2018, 55(1), 173-180.
[http://dx.doi.org/10.1002/jhet.3021]
[140]
Dwivedi, G.R.; Gupta, S.; Maurya, A.; Tripathi, S.; Sharma, A.; Darokar, M.P.; Srivastava, S.K. Chem. Biol. Drug Des., 2015, 86(6), 1471-1481.
[http://dx.doi.org/10.1111/cbdd.12613] [PMID: 26132412]
[141]
Kokorekin, V.A.; Terent’ev, A.O.; Ramenskaya, G.V.; Grammatikova, N.É.; Rodionova, G.M.; Ilovaiskii, A.I. Pharm. Chem. J., 2013, 47(8), 422-425.
[http://dx.doi.org/10.1007/s11094-013-0973-7]
[142]
Sugiyama, H.; Yokokawa, F.; Aoyama, T.; Shioiri, T. Tetrahedron Lett., 2001, 42(41), 7277-7280.
[http://dx.doi.org/10.1016/S0040-4039(01)01492-7]
[143]
El-Sayed, N.S.; Shirazi, A.N.; El-Meligy, M.G.; El-Ziaty, A.K.; Rowley, D.; Sun, J.; Nagib, Z.A.; Parang, K. Tetrahedron Lett., 2014, 55(6), 1154-1158.
[http://dx.doi.org/10.1016/j.tetlet.2013.12.081] [PMID: 24678129]
[144]
Mahmoodi, N.O.; Ghavidast, A. Chem. Heterocycl. Compd., 2014, 49(10), 1451-1457.
[http://dx.doi.org/10.1007/s10593-014-1395-5]
[145]
Gali, R.; Banothu, J.; Porika, M.; Velpula, R.; Bavantula, R.; Abbagani, S. RSC Advances, 2014, 4(96), 53812-53819.
[http://dx.doi.org/10.1039/C4RA11428K]
[146]
Mahmoodi, N.O.; Khalili, B.; Rezaeianzade, O.; Ghavidast, A. Res. Chem. Intermed., 2016, 42(8), 6531-6542.
[http://dx.doi.org/10.1007/s11164-016-2478-y]
[147]
Bhattacharjee, S.; Das, D.K.; Khan, A.T. Synthesis, 2014, 46(1), 73-80.

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