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Letters in Organic Chemistry

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Review Article

Insights Into the Synthetic Strategies, Biological Activity, and Structure- Activity Relationship of Pyridine and Analogs: A Review

Author(s): Aprajita Matthew, Rajnish Kumar*, Avijit Mazumder, Salahuddin and Harshita Bhadauria

Volume 20, Issue 11, 2023

Published on: 05 July, 2023

Page: [1025 - 1054] Pages: 30

DOI: 10.2174/1570178620666230525142927

Price: $65

Abstract

Based on various research reports, pyridine possesses a wide range of pharmacological activities along with many other industrial applications. Because of its diverse applications, pyridine moiety is the center of attraction for researchers, and many patents have been granted focusing on it. Several synthetic protocols, such as cyclo-condensation, cyclization, cycloaddition, electrolysis, etc., were used by researchers to synthesize pyridine and analogs. Each synthetic protocol has merits and demerits and requires several types of reagents, catalysts, and reaction conditions. So, there is always a need for careful analysis of reported synthetic protocols whenever researchers like to initiate research on synthesizing pyridine and its analogs. The therapeutic activity of successfully marketed drugs might be possible because of the presence of pyridine in their structure. Any small alteration in the structure of the medicinal compounds may produce a major change in their pharmacological action. So, the correlation between the structure of its analogs with biological activity is also important. The proposed article also includes recently reported pharmacological activities and the structureactivity relationship of pyridine and its analogs. This article aims to help the researchers by highlighting recently reported methods for synthesizing pharmacologically useful pyridine analogs and their merits.

Keywords: Pyridine, pharmacological activities, patents, synthetic strategies, marketed drugs, structure-activity relationship.

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[1]
El Azab, I.H.; Bakr, R.B.; Elkanzi, N.A.A. Molecules, 2021, 26(11), 3103.
[http://dx.doi.org/10.3390/molecules26113103] [PMID: 34067399]
[2]
Pal, S. Pyridine: A useful ligand in transition metal complexes; Pyridine, 2018, p. 57.
[3]
Marinescu, M.; Popa, C.V. Int. J. Mol. Sci., 2022, 23(10), 5659.
[http://dx.doi.org/10.3390/ijms23105659] [PMID: 35628466]
[4]
Mahmood, R.M.U.; Aljamali, N.M. Eur. J. Mol. Clin. Med., 2020, 7, 4444-4453.
[5]
Shankaraiah, N.; Sharma, P.; Pedapati, S.; Nekkanti, S.; Srinivasulu, V.; Praveen Kumar, N.; Kamal, A. Lett. Drug Des. Discov., 2016, 13(4), 335-342.
[http://dx.doi.org/10.2174/157018081304160303180050]
[6]
Eissa, I.H.; El-Naggar, A.M.; El-Hashash, M.A. Bioorg. Chem., 2016, 67, 43-56.
[http://dx.doi.org/10.1016/j.bioorg.2016.05.006] [PMID: 27253830]
[7]
Grover, G.; Nath, R.; Bhatia, R.; Akhtar, M.J. Bioorg. Med. Chem., 2020, 28(15)115585
[http://dx.doi.org/10.1016/j.bmc.2020.115585] [PMID: 32631563]
[8]
Malani, A.; Makwana, A.; Monapara, J.; Ahmad, I.; Patel, H.; Desai, N. J. Biochem. Mol. Toxicol., 2021, 35(11)e22903
[http://dx.doi.org/10.1002/jbt.22903] [PMID: 34459052]
[9]
Jain, S.; Sen, D.J. Indian J. Chem., 2022, 61(3), 305-312.
[10]
Pawar, S.D.; Gosavi, D.H.; Pawar, S.D. World J. Pharm. Res., 2021, 10, 296-309.
[11]
Jwaid, M.M. Int. J. Drug Deliv. Technol., 2022, 12(2), 705-710.
[12]
Ali, E.M.H.; Abdel-Maksoud, M.S.; Hassan, R.M.; Mersal, K.I.; Ammar, U.M.; Se-In, C.; He-Soo, H.; Kim, H.K.; Lee, A.; Lee, K.T.; Oh, C.H. Bioorg. Med. Chem., 2021, 31115969
[http://dx.doi.org/10.1016/j.bmc.2020.115969] [PMID: 33422910]
[13]
Sadawarte, G.; Jagatap, S.; Patil, M.; Jagrut, V.; Rajput, J.D. Eur. J. Chem., 2021, 12(3), 279-283.
[http://dx.doi.org/10.5155/eurjchem.12.3.279-283.2118]
[14]
Abdpour, S.; Jalili-Baleh, L.; Nadri, H.; Forootanfar, H.; Bukhari, S.N.A.; Ramazani, A.; Ebrahimi, S.E.S.; Foroumadi, A.; Khoobi, M. Bioorg. Chem., 2021, 110104750
[http://dx.doi.org/10.1016/j.bioorg.2021.104750] [PMID: 33691251]
[15]
Pham, H.T.; Martin, J.P.; Le, T.G. Synth. Commun., 2020, 50(12), 1845-1853.
[http://dx.doi.org/10.1080/00397911.2020.1757717]
[16]
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]
[17]
Higasio, Y.S.; Shoji, T. Appl. Catal. A Gen., 2001, 221(1-2), 197-207.
[http://dx.doi.org/10.1016/S0926-860X(01)00815-8]
[18]
Altaf, A.A.; Shahzad, A.; Gul, Z.; Rasool, N.; Badshah, A.; Lal, B.; Khan, E.J. Drug Des. Med. Chem., 2015, 1(1), 1-11.
[19]
Patil, P.; Sethy, S.P.; Sameena, T.; Shailaja, K. Asian J. Chem., 2013, 10, 888.
[20]
Agranat, I.; Marom, H. ACS Med. Chem. Lett., 2020, 11(2), 91-98.
[http://dx.doi.org/10.1021/acsmedchemlett.9b00497] [PMID: 32280427]
[21]
Baumann, M.; Baxendale, I.R. Beilstein J. Org. Chem., 2013, 9, 2265-2319.
[22]
Goetz, A.E.; Garg, N.K. Nat. Chem., 2013, 5(1), 54-60.
[http://dx.doi.org/10.1038/nchem.1504] [PMID: 23247178]
[23]
Ling, Y.; Hao, Z.Y.; Liang, D.; Zhang, C.L.; Liu, Y.F.; Wang, Y. Drug Des. Devel. Ther., 2021, 15, 4289-4338.
[http://dx.doi.org/10.2147/DDDT.S329547] [PMID: 34675489]
[24]
Lopez-Salazar, M.B.; Gonzalez, A.; Hermida, N.; Laviades, C.; Diez-Martinez, J. Kidney Int. Suppl., 2008, (111), S19-S23.
[25]
Shore, S.N.; Britnell, S.R.; Brown, J.N. J. Oncol. Pharm. Pract., 2020, 26(2), 306-311.
[http://dx.doi.org/10.1177/1078155219842646] [PMID: 31006341]
[26]
Roger, C.; Roberts, J.A.; Muller, L. Clin. Pharmacokinet., 2018, 57(5), 559-575.
[http://dx.doi.org/10.1007/s40262-017-0601-x] [PMID: 29063519]
[27]
Konstantinopoulos, P.A.; Barry, W.T.; Birrer, M.; Westin, S.N.; Cadoo, K.A.; Shapiro, G.I.; Mayer, E.L.; O’Cearbhaill, R.E.; Coleman, R.L.; Kochupurakkal, B.; Whalen, C.; Curtis, J.; Farooq, S.; Luo, W.; Eismann, J.; Buss, M.K.; Aghajanian, C.; Mills, G.B.; Palakurthi, S.; Kirschmeier, P.; Liu, J.; Cantley, L.C.; Kaufmann, S.H.; Swisher, E.M.; D’Andrea, A.D.; Winer, E.; Wulf, G.M.; Matulonis, U.A. Lancet Oncol., 2019, 20(4), 570-580.
[http://dx.doi.org/10.1016/S1470-2045(18)30905-7] [PMID: 30880072]
[28]
Andrew, A.K.; Charles, A.E. Attribute combination discovery for predisposition determination of health conditions. US20220359090A1, 2022.
[29]
Kenedy, A.A.; Eldering, C.A. Attribute combination discovery for predisposition determination of health condition. US11482340B1, 2022.
[30]
Sarnik, A.A.; Weber, J.S.; Thomas, S.P.; Radvanyi, L.G.; Chacon, J.A.; Mule, J.J.; Hall, M.S. Enhanced expansion of tumorinfiltrating lympocytes for adoptive cell therapy. US202203408 74A1, 2022.
[31]
Karp, J.M.; Langer, R.S.; Yin, X.; Joshi, N. Compositions, systems and methods for generating inner ear hair cells for treatment of hearing loss. US20220339154A1, 2022.
[32]
Cleeman, F.; Hersel, U.; Kaden, S.; Rau, H.; Wegge, T. Prodrug comprising a drug-linker conjugate. US20220331334A1, 2022.
[33]
Feng, L.; Godtfredsen, E.; Sutton, P.A.; Prashad, M.; Girgis, M.J.; Hu, B.; Liu, Y.; Blacklock, T.J.; Karpinski, P.H. Amorphous solid form of compounds containing S.-N. Valeryl -N-{[2′-1H - Tetrazole-5-yl)-Biphenyl-4-yl]-Methyl}-Valine and (2R, 4S)-5- Biphenyl-4-yl-4-(3-Carboxy-Propionylamino)-2-Methyl pentanoic acid ethyl ester moieties and sodium cations. US20220331282A1, 2022.
[34]
Swanson, K.; Carfi, A. Pre-fusion RSV F antigens. US20220332767A1, 2022.
[35]
Swanson, K.; Dormitzer, P.R. Protein compositions and methods for making same. US20220340645A1, 2022.
[36]
Jiang, X.; Reddy, S.; Brandacher, G.; Mao, H.Q.; Sacks, J.; Li, X.; Feng, K.; Martin, R.; Yalanis, G.C.; Choi, J.S. Composite material for tissue restoration. US20220339321A1, 2022.
[37]
Ni, Y.; Parikh, B.; Yeleswaram, K.; Viitanen, S.E.; Williams, W.V. Sustained-release dosage forms of Ruxolitinib. US20220323363A1, 2022.
[38]
Sentman, C.L. T-cells receptor-deficient T-cell compositions. US20220333075A1, 2022.
[39]
Burns, T.W.; Heitzmann, H.A.; Curry, K.M.; Haffner, D.S.; Applegate, D.; Nogales, B. Intraocular physiological sensor. US20220330819A1, 2022.
[40]
Behenna, D.C.; Chen, P.; Freeman-Cook, K.D.; Hoffman, R.L.; Jalaie, M.; Nagata, A.; Nair, S.K.; Ninkovic, S.; Ornelas, M.A.; Palmer, C.L.; Rui, E.Y. CDK2/4/6 inhibitors. US20220324872A1, 2022.
[41]
Mortimer, S.A.W.; Talasaz, A.A.; Chudova, D.; Eltoukhy, H. Methods for computer processing sequence reads to detect molecular residual disease. US20220325360A1, 2022.
[42]
Florence, T.; Gan, D.; Hines, M. Topical skin care formulations comprising plant extracts. US20220296496A1, 2022.
[43]
Kim, S.J.; Kim, K.H.; Lee, K.Y.; Koh, S.H.; Park, H.H.; Huh, S.J.; Lee, W.J.; Kim, B.J. Anti-inflammatory peptides and composition comprising the same. US20220331407A1, 2022.
[44]
Brisander, M.; Demirbuker, M.; Jesson, G.; Malmsten, M.; Derand, H. Pharmaceutical compositions. US20220296575A1, 2022.
[45]
Wang, L. Drug releasing coatings for medical devices. US20220296863A1, 2022.
[46]
Keilhack, H.; Knutson, S.K.; Kuntz, K.W. Combination therapy for treating cancer. US20220281854A1, 2022.
[47]
Bilodeau, M.T.; Kadiyala, S.; Shinde, R.R.; White, B.H.; Wooster, R.; Moreau, B. Targeted conjugates encapsulated in particles and formulations thereof. US20220288229A1, 2022.
[48]
Olschewski, H.; Roscigno, R.; Rubin, L.J.; Schmehl, T.; Seeger, W.; Sterritt, C.; Voswinckel, R. Treprostinil administration by inhalation. US20220323459A1, 2022.
[49]
Cunningham, S.; Mulligan, S.; Myers, M. Sustained release aminopyridine composition. US20220265624A1, 2022.
[50]
Zhang, X.; Terao, K. Subcutaneously administered anti-IL-6 receptor antibody. US20220280532A1, 2022.
[51]
Vlahov, I.R.; Reddy, J.A.; Bloomfield, A.; Dorton, R.; Nelson, M.; Vetzel, M.; Leamon, C.P. Conjugates for treating diseases caused by PSMA expressing cells. US20220265841A1, 2022.
[52]
Chapman, P.S.; Turfler, D.T. Capsule-containing pouched product for oral use. US20220264931A1, 2022.
[53]
Borody, T.J. Compositions for fecal floral transplantation and methods for making and using them and devices for delivering them. US20220257672A1, 2022.
[54]
Poltorak, A. Methods and apparatus for neuroenhancement to enhance emotional response. US20220273908A1, 2022.
[55]
Hariri, R.J.; Heidaran, M.A.; Jasko, S.; Kang, L.; Law, E.; Pal, A.; Stout, B.; Berse, V.V.; Zeitlin, A.; Zhang, X. Methods for generating natural killer cells. U.S Patent 0259563, 2022.
[56]
Fritsche, J.; Weinschenk, T.; Walter, S.; Lewandrowski, P.; Singh, H. Novel immunotherapy against several tumors including gastrointestinal and gastric cancer. U.S Patent 0265764, 2022.
[57]
Gedulin, B.; Grey, M.; O’Donnell, N. Bile acid recycling inhibitors for treatment of pediatric cholestatic liver diseases. U.S Patent 0265649, 2022.
[58]
Shimizu, S.; Watanabe, N.; Kataoka, T.; Shoji, T.; Abe, N.; Morishita, S.; Ichimura, H. Pyridine and pyridine derivatives. In: Ullmann’s encyclopedia of industrial chemistry;
[http://dx.doi.org/10.1002/14356007.a22_399]
[59]
Raja, V.P.A.; Tenti, G.; Perumal, S.; Menéndez, J.C. Chem. Commun. (Camb.), 2014, 50(82), 12270-12272.
[http://dx.doi.org/10.1039/C4CC01791A] [PMID: 24776752]
[60]
Adib, M.; Tahermansouri, H.; Koloogani, S.A.; Mohammadi, B.; Bijanzadeh, H.R. Tetrahedron Lett., 2006, 47(33), 5957-5960.
[http://dx.doi.org/10.1016/j.tetlet.2006.01.162]
[61]
Siddiqui, N.; Ahsan, W.; Alam, M.S.; Azad, B.; Akhtar, M.J. Res. J. Pharm. Technol., 2011, 4(12), 1918-1932.
[62]
Saranya, S.; Radhika, S.; Afsina Abdulla, C.M.; Anilkumar, G. J. Heterocycl. Chem., 2021, 58(8), 1570-1580.
[http://dx.doi.org/10.1002/jhet.4261]
[63]
Biswas, S.; Majee, D.; Guin, S.; Samanta, S. J. Org. Chem., 2017, 82(20), 10928-10938.
[http://dx.doi.org/10.1021/acs.joc.7b01792] [PMID: 28933552]
[64]
Raja, R.; Sivasubramaniyan, A.; Murugan, D.; Subbaiah, N.; George, J.; Poovan, S.; Sangaraiah, N.; Alagusundaram, P.; Shanmugam, K.; Manivachagam, C. Res. Chem. Intermed., 2016, 42(12), 8005-8021.
[http://dx.doi.org/10.1007/s11164-016-2575-y]
[65]
Sotnik, S.O.; Subota, A.I.; Kliuchynskyi, A.Y.; Yehorov, D.V.; Lytvynenko, A.S.; Rozhenko, A.B.; Kolotilov, S.V.; Ryabukhin, S.V.; Volochnyuk, D.M. J. Org. Chem., 2021, 86(11), 7315-7325.
[http://dx.doi.org/10.1021/acs.joc.0c03038] [PMID: 33977713]
[66]
Xi, L.Y.; Zhang, R.Y.; Liang, S.; Chen, S.Y.; Yu, X.Q. Org. Lett., 2014, 16(20), 5269-5271.
[http://dx.doi.org/10.1021/ol5023596] [PMID: 25285847]
[67]
Chen, G.; Wang, Z.; Zhang, X.; Fan, X. J. Org. Chem., 2017, 82(20), 11230-11237.
[http://dx.doi.org/10.1021/acs.joc.7b01901] [PMID: 28990782]
[68]
Chen, S.; Bergman, R.G.; Ellman, J.A. Org. Lett., 2015, 17(11), 2567-2569.
[http://dx.doi.org/10.1021/acs.orglett.5b00979] [PMID: 25992591]
[69]
Ghodse, S.M.; Telvekar, V.N. Tetrahedron Lett., 2017, 58(6), 524-526.
[http://dx.doi.org/10.1016/j.tetlet.2016.12.075]
[70]
Albratty, M.; El-Sharkawy, K.A.; Alhazmi, H.A. Acta Pharm., 2019, 69(2), 261-276.
[http://dx.doi.org/10.2478/acph-2019-0015] [PMID: 31259726]
[71]
Karadeniz, E.; Zora, M. Kılıçaslan. N.Z. Tetrahedron, 2015, 71(47), 8943-8952.
[http://dx.doi.org/10.1016/j.tet.2015.09.063]
[72]
Gao, P.; Chen, H.J.; Bai, Z.J.; Zhao, M.N.; Yang, D.; Wang, J.; Wang, N.; Du, L.; Guan, Z.H. J. Org. Chem., 2020, 85(12), 7939-7951.
[http://dx.doi.org/10.1021/acs.joc.0c00625] [PMID: 32441101]
[73]
Cheng, G.; Xue, L.; Weng, Y.; Cui, X. J. Org. Chem., 2017, 82(18), 9515-9524.
[http://dx.doi.org/10.1021/acs.joc.7b01541] [PMID: 28825296]
[74]
Huang, H.; Cai, J.; Tang, L.; Wang, Z.; Li, F.; Deng, G.J. J. Org. Chem., 2016, 81(4), 1499-1505.
[http://dx.doi.org/10.1021/acs.joc.5b02624] [PMID: 26788938]
[75]
Zhang, X.; Wang, P.; Yuan, X.; Qin, M.; Chen, B. Asian J. Org. Chem., 2019, 8(8), 1332-1335.
[http://dx.doi.org/10.1002/ajoc.201900323]
[76]
Arabshahi, H.J.; Van Rensburg, M.; Pilkington, L.I.; Jeon, C.Y.; Song, M.; Gridel, L.M.; Leung, E.; Barker, D.; Vuica-Ross, M.; Volcho, K.P.; Zakharenko, A.L.; Lavrikef, O.I.; Reynisson, J. MedChemComm, 2015, 6(11), 2.
[77]
Luo, Q.; Huang, R.; Xiao, Q.; Yao, Y.; Lin, J.; Yan, S.J. J. Org. Chem., 2019, 84(4), 1999-2011.
[http://dx.doi.org/10.1021/acs.joc.8b03008] [PMID: 30652868]
[78]
Motati, D.R.; Amaradhi, R.; Ganesh, T. Org. Chem. Front., 2021, 8(3), 466-513.
[http://dx.doi.org/10.1039/D0QO01079K]
[79]
Zebbiche, Z.; Tekin, S.; Küçükbay, H.; Yüksel, F.; Boumoud, B. Arch. Pharm., 2021, 354(5)2000377
[http://dx.doi.org/10.1002/ardp.202000377] [PMID: 33368627]
[80]
Kumar, A.; Pericherla, K.; Kaswan, P.; Pandey, K. Synthesis, 2015, 47(7), 887-912.
[http://dx.doi.org/10.1055/s-0034-1380182]
[81]
El-Naggar, M.; Almahli, H.; Ibrahim, H.; Eldehna, W.; Abdel-Aziz, H. Molecules, 2018, 23(6), 1459.
[http://dx.doi.org/10.3390/molecules23061459] [PMID: 29914120]
[82]
Gomha, S.M.; Muhammad, Z.A.; Abdel-aziz, M.R.; Abdel-aziz, H.M.; Gaber, H.M.; Elaasser, M.M. J. Heterocycl. Chem., 2018, 55(2), 530-536.
[http://dx.doi.org/10.1002/jhet.3088]
[83]
Saeedi, M.; Safavi, M.; Allahabadi, E.; Rastegari, A.; Hariri, R.; Jafari, S.; Bukhari, S.N.A.; Mirfazli, S.S.; Firuzi, O.; Edraki, N.; Mahdavi, M.; Akbarzadeh, T. Arch. Pharm., 2020, 353(10)2000101
[http://dx.doi.org/10.1002/ardp.202000101] [PMID: 32657467]
[84]
Chang, L.; Lai, J.; Yuan, G. Chin. J. Chem., 2016, 34(9), 887-894.
[http://dx.doi.org/10.1002/cjoc.201600255]
[85]
Bartko, S.G.; Hamzik, P.J.; Espindola, L.; Gomez, C.; Danheiser, R.L. J. Org. Chem., 2020, 85(2), 548-563.
[http://dx.doi.org/10.1021/acs.joc.9b02628] [PMID: 31797669]
[86]
Wu, J.; Xu, W.; Yu, Z.X.; Wang, J. J. Am. Chem. Soc., 2015, 137(29), 9489-9496.
[http://dx.doi.org/10.1021/jacs.5b06400] [PMID: 26158786]
[87]
Gao, Y.; Chen, R.; Ma, Y. Synthesis, 2019, 51(20), 3875-3882.
[http://dx.doi.org/10.1055/s-0037-1610725]
[88]
Shen, J.; Cai, D.; Kuai, C.; Liu, Y.; Wei, M.; Cheng, G.; Cui, X. J. Org. Chem., 2015, 80(13), 6584-6589.
[http://dx.doi.org/10.1021/acs.joc.5b00635] [PMID: 26029797]
[89]
Song, Z.; Huang, X.; Yi, W.; Zhang, W. Org. Lett., 2016, 18(21), 5640-5643.
[http://dx.doi.org/10.1021/acs.orglett.6b02883] [PMID: 27775367]
[90]
Upadhyay, A.; Sharma, L.K.; Singh, V.K.; Singh, R.K.P. Tetrahedron Lett., 2016, 57(50), 5599-5604.
[http://dx.doi.org/10.1016/j.tetlet.2016.10.111]
[91]
Wei, H.; Li, Y.; Xiao, K.; Cheng, B.; Wang, H.; Hu, L.; Zhai, H. Org. Lett., 2015, 17(24), 5974-5977.
[http://dx.doi.org/10.1021/acs.orglett.5b02903] [PMID: 26651162]
[92]
Huang, H.; Cai, J.; Xie, H.; Tan, J.; Li, F.; Deng, G.J. Org. Lett., 2017, 19(14), 3743-3746.
[http://dx.doi.org/10.1021/acs.orglett.7b01564] [PMID: 28661155]
[93]
Duan, J.; Zhang, L.; Xu, G.; Chen, H.; Ding, X.; Mao, Y.; Rong, B.; Zhu, N.; Guo, K. J. Org. Chem., 2020, 85(12), 8157-8165.
[http://dx.doi.org/10.1021/acs.joc.0c01081] [PMID: 32478514]
[94]
Salem, M.S.; Sakr, S.I.; El-Senousy, W.M.; Madkour, H.M.F. Arch. Pharm., 2013, 346(10), 766-773.
[http://dx.doi.org/10.1002/ardp.201300183] [PMID: 24105721]
[95]
Siddiqui, N.; Ahsan, W.; Alam, M.S.; Ali, R.; Srivastava, K.; Ahmed, S. Bull. Korean Chem. Soc., 2011, 32(2), 576-582.
[http://dx.doi.org/10.5012/bkcs.2011.32.2.576]
[96]
El-Dean, A.M.K.; Abd-Ella, A.A.; Hassanien, R.; El-Sayed, M.E.A.; Abdel-Raheem, S.A. ACS Omega, 2019, 4(5), 8406-8412.
[http://dx.doi.org/10.1021/acsomega.9b00932] [PMID: 31459929]
[97]
Hamza, E.K.; Hamdy, N.A.; Zarie, E.S.; Fakhr, I.M.I.; Elwahy, A.H.M.; Awad, H.M. J. Heterocycl. Chem., 2020, 57(1), 182-196.
[http://dx.doi.org/10.1002/jhet.3764]
[98]
Song, Y.L.; Tian, C.P.; Wu, Y.; Jiang, L.; Shen, L.Q. Steroids, 2019, 143, 53-61.
[http://dx.doi.org/10.1016/j.steroids.2018.12.007] [PMID: 30590064]
[99]
Ibrahim, B.A.; Mohareb, R.M. J. Heterocycl. Chem., 2020, 57(11), 4023-4035.
[http://dx.doi.org/10.1002/jhet.4112]
[100]
Lachowicz, J.I.; Nurchi, V.M.; Crisponi, G.; Jaraquemada-Pelaez, M.G.; Arca, M.; Pintus, A. Dalton Trans., 2016, 45, 6517-6528.
[101]
Sun, B.; Dong, Y.; Lei, K.; Wang, J.; Zhao, L.; Liu, M. Bioorg. Med. Chem., 2019, 27(12), 2427-2437.
[http://dx.doi.org/10.1016/j.bmc.2019.02.009] [PMID: 30765301]
[102]
Gomha, S.M.; Abdelrazek, F.M.; Abdelrahman, A.H.; Metz, P. J. Heterocycl. Chem., 2018, 55(7), 1729-1737.
[http://dx.doi.org/10.1002/jhet.3210]
[103]
El-Gohary, N.S.; Shaaban, M.I. Eur. J. Med. Chem., 2018, 157, 729-742.
[http://dx.doi.org/10.1016/j.ejmech.2018.08.008] [PMID: 30138804]
[104]
Salem, M.S.; Ali, M.A.M. Biol. Pharm. Bull., 2016, 39(4), 473-483.
[http://dx.doi.org/10.1248/bpb.b15-00586] [PMID: 27040621]
[105]
Ravula, S.; Bobbala, R.R.; Kolli, B. J. Heterocycl. Chem., 2020, 57(6), 2535-2538.
[http://dx.doi.org/10.1002/jhet.3968]
[106]
Mohamed, E.A.; Ismail, N.S.M.; Hagras, M.; Refaat, H. Future. J. Pharm. Sci., 2021, 7(1), 24.
[http://dx.doi.org/10.1186/s43094-020-00165-4]
[107]
Naik, N.S.; Shastri, L.A.; Shastri, S.L.; Chougala, B.M.; Shaikh, F.; Madar, J.M.; Kulkarni, R.C.; Dodamani, S.; Jalalpure, S.; Joshi, S.D.; Sunagar, V. ChemistrySelect, 2019, 4(1), 285-297.
[http://dx.doi.org/10.1002/slct.201802927]
[108]
Ravi, C.; Qayum, A.; Chandra Mohan, D.; Singh, S.K.; Adimurthy, S. Eur. J. Med. Chem., 2017, 126, 277-285.
[http://dx.doi.org/10.1016/j.ejmech.2016.11.037] [PMID: 27889631]
[109]
Cocco, M.T.; Congiu, C.; Lilliu, V.; Onnis, V. Bioorg. Med. Chem., 2007, 15(4), 1859-1867.
[http://dx.doi.org/10.1016/j.bmc.2006.11.031] [PMID: 17142048]
[110]
Abdel-aziz, H.M.; Gomha, S.M.; El-Sayed, A.A.; Mabkhot, Y.N.; Alsayari, A.; Muhsinah, A.B. BMC Chem., 2019, 13(1), 137.
[http://dx.doi.org/10.1186/s13065-019-0652-1] [PMID: 31891163]
[111]
Sahu, R.; Mishra, R.; Kumar, R.; Majee, C. Salahuddin.; Mazumder, A.; Kumar, A. Indian J. Pharm. Sci., 2021, 83(2), 162-185.
[http://dx.doi.org/10.36468/pharmaceutical-sciences.763]
[112]
Shi, Y.K.; Wang, B.; Shi, X.L.; Zhao, Y.D.; Yu, B.; Liu, H.M. Eur. J. Med. Chem., 2018, 145, 11-22.
[http://dx.doi.org/10.1016/j.ejmech.2017.12.094] [PMID: 29310026]
[113]
Nayak, S.; Gaonkar, S.L.; Musad, E.A.; Dawsar, A.M.A. J. Saudi Chem. Soc., 2021, 25(8)101284
[http://dx.doi.org/10.1016/j.jscs.2021.101284]
[114]
Michalska, P.; Mayo, P.; Fernández-Mendívil, C.; Tenti, G.; Duarte, P.; Buendia, I.; Ramos, M.T.; López, M.G.; Menéndez, J.C.; León, R. Antioxidants, 2020, 9(8), 650.
[http://dx.doi.org/10.3390/antiox9080650] [PMID: 32708053]
[115]
Chaban, T.; Matiychuk, V.; Ogurtsov, V.; Chaban, I.; Harkov, S.; Nektegaev, I. Pharmacia, 2018, 65(4), 51-62.
[116]
El-Dash, Y.; Khalil, N.A.; Ahmed, E.M.; Hassan, M.S.A. Bioorg. Chem., 2021, 107104610
[http://dx.doi.org/10.1016/j.bioorg.2020.104610] [PMID: 33454504]
[117]
Hamdy, N.A.; Gamal-Eldeen, A.M. Eur. J. Med. Chem., 2009, 44(11), 4547-4556.
[http://dx.doi.org/10.1016/j.ejmech.2009.06.023] [PMID: 19616348]
[118]
Wójcicka, A.; Redzicka, A. Pharmaceuticals, 2021, 14(4), 354.
[http://dx.doi.org/10.3390/ph14040354] [PMID: 33920479]
[119]
Dowarah, J.; Singh, V.P. Bioorg. Med. Chem., 2020, 28(5)115263
[http://dx.doi.org/10.1016/j.bmc.2019.115263] [PMID: 32008883]
[120]
Paronikyan, E.G.; Petrou, A.; Fesatidou, M.; Geronikaki, A.; Dashyan, S. Chem. Commun., 2015, 51, 17273-17276.
[121]
Paronikyan, E.G.; Harutyunyan, A.S.; Paronikyan, R.G. Russ. J. Org. Chem., 2020, 56(3), 422-428.
[http://dx.doi.org/10.1134/S1070428020030094]
[122]
Ulloora, S.; Shabaraya, R.; Aamir, S.; Adhikari, A.V. Bioorg. Med. Chem. Lett., 2013, 23(5), 1502-1506.
[http://dx.doi.org/10.1016/j.bmcl.2012.12.035] [PMID: 23352511]
[123]
Singh, K.; Pal, R.; Khan, S.A.; Kumar, B.; Akhtar, M.J. J. Mol. Struct., 2021, 1237130369
[http://dx.doi.org/10.1016/j.molstruc.2021.130369]
[124]
Dashyan, S.S.; Paronikyan, R.G.; Mamyan, S.S.; Paronikyan, E.G. ARKIVOC, 2022, 2022(2), 43-53.
[http://dx.doi.org/10.24820/ark.5550190.p011.659]
[125]
Naik, M.M.; Deshpande, M.N.; Borges, R.; Biradar, B.S.; Shingade, S.G. J. Drug Deliv. Ther., 2017, 7(7), 202-205.
[126]
Zhmurenko, L.A.; Molodavkin, G.M.; Voronina, T.A.; Lezina, V.P. Pharm. Chem. J., 2012, 46(1), 15-19.
[http://dx.doi.org/10.1007/s11094-012-0726-z]
[127]
De, S.; Aamna, B.; Sahu, R.; Parida, S.; Behera, S.K.; Dan, A.K. Eur. J. Med. Chem., 2022, 240114576
[http://dx.doi.org/10.1016/j.ejmech.2022.114576] [PMID: 35816877]
[128]
Kumar, S.; Sharma, P.K.; Dudhe, R.; Kumar, N.J. Chronotherapy. Drug Deliv., 2011, 2(2), 71-78.
[129]
Huang, Y.M.; Alharbi, N.S.; Sun, B.; Shantharam, C.S.; Rakesh, K.P.; Qin, H.L. Eur. J. Med. Chem., 2019, 181111566
[http://dx.doi.org/10.1016/j.ejmech.2019.111566] [PMID: 31401538]
[130]
Stalinskaya, A.L.; Martynenko, N.V.; Shulgau, Z.T.; Shustov, A.V.; Keyer, V.V.; Kulakov, I.V. Molecules, 2022, 27(12), 3701.
[http://dx.doi.org/10.3390/molecules27123701] [PMID: 35744830]
[131]
De, A.; Sarkar, S.; Majee, A. Chem. Heterocycl. Compd., 2021, 57(4), 410-416.
[http://dx.doi.org/10.1007/s10593-021-02917-3] [PMID: 33994556]
[132]
Zemali, D.; Ouahrani, M.R.; Nacer, S.N. Eur. J. Biol. Res., 2022, 12(3), 207-215.
[133]
Patel, N.B.; Chauhan, N.B.; Pathan, S.S.; Patel, V.M.; Mistry, B.M. Indian J. Chem. Sect. B, 2020.
[134]
Desai, N.C.; Vaja, D.V. Int. Lett. Chem. Phys. Astronomy, 2018, 77, 35-52.
[http://dx.doi.org/10.56431/p-2746bu]
[135]
Mohammad Abu-Taweel, G.; Ibrahim, M.M.; Khan, S.; Al-Saidi, H.M.; Alshamrani, M.; Alhumaydhi, F.A.; Alharthi, S.S. Crit. Rev. Anal. Chem., 2022, 1-18.
[http://dx.doi.org/10.1080/10408347.2022.2089839] [PMID: 35724248]
[136]
Tahir, T.; Ashfaq, M.; Saleem, M.; Rafiq, M.; Shahzad, M.I.; Kotwica-Mojzych, K.; Mojzych, M. Molecules, 2021, 26(16), 4872.
[http://dx.doi.org/10.3390/molecules26164872] [PMID: 34443460]
[137]
Khidre, R.E.; Radini, I.A.M. Sci. Rep., 2021, 11(1), 7846.
[http://dx.doi.org/10.1038/s41598-021-86424-7] [PMID: 33846389]
[138]
El-Sharkawy, K.A.; AlBratty, M.M.; Alhazmi, H.A. Braz. J. Pharm. Sci., 2018, 54(4)e00153
[http://dx.doi.org/10.1590/s2175-97902018000400153]
[139]
Hosni, H.; Abdulla, M. Acta Pharm., 2008, 58(2), 175-186.
[http://dx.doi.org/10.2478/v10007-008-0005-4] [PMID: 18515227]
[140]
Al-Omar, M.A.; Amr, A.E.G.E.; Al-Salahi, R.A. Arch. Pharm., 2010, 343(11-12), 648-656.
[http://dx.doi.org/10.1002/ardp.201000088] [PMID: 21110344]
[141]
Salam, O.I.A.; Al-Omar, M.A.; Khalifa, N.M.; Amr, A.E.G.E.; Abdallah, M.M.Z. Naturforsch. C J. Biosci., 2013, 68(7-8), 264-268.
[http://dx.doi.org/10.1515/znc-2013-7-802] [PMID: 24066510]
[142]
Ambhore, A.N.; Kamble, S.S.; Kadam, S.N.; Kamble, R.D.; Hebade, M.J.; Hese, S.V.; Gaikwad, M.V.; Meshram, R.J.; Gacche, R.N.; Dawane, B.S. Comput. Biol. Chem., 2019, 80, 54-65.
[http://dx.doi.org/10.1016/j.compbiolchem.2019.03.002] [PMID: 30901601]
[143]
Verma, S.K.; Verma, R.; Verma, S.; Vaishnav, Y.; Tiwari, S.P.; Rakesh, K.P. Eur. J. Med. Chem., 2021, 209112886
[http://dx.doi.org/10.1016/j.ejmech.2020.112886] [PMID: 33032083]
[144]
Devi, N.; Singh, D.; Rawal, R.K.; Bariwal, J.; Singh, V. Curr. Top. Med. Chem., 2016, 16(26), 2963-2994.
[http://dx.doi.org/10.2174/1568026616666160506145539] [PMID: 27150367]
[145]
Navarrete-Vázquez, G.; Molina-Salinas, G.M.; Duarte-Fajardo, Z.V.; Vargas-Villarreal, J.; Estrada-Soto, S.; González-Salazar, F.; Hernández-Núñez, E.; Said-Fernández, S. Bioorg. Med. Chem., 2007, 15(16), 5502-5508.
[http://dx.doi.org/10.1016/j.bmc.2007.05.053] [PMID: 17562368]
[146]
Ahmad, M. Braz. J. Pharm. Sci., 2020, 56.
[147]
Attaby, A.F.; Abdel Fattah, M.A.; Shaif, M.L.; Elsayed, M.M. Curr. Org. Chem., 2010, 14(20), 2522-2530.
[http://dx.doi.org/10.2174/138527210793358303]
[148]
Attaby, F.A.; Abdel-Fattah, A.M.; Shaif, L.M.; Elsayed, M.M. Phosphorus Sulfur Silicon Relat. Elem., 2009, 185(1), 129-139.
[http://dx.doi.org/10.1080/10426500902717333]

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