Subscribe to RSS
DOI: 10.1055/s-0040-1720125
A Review of Recent Progress on the Anticancer Activity of Heterocyclic Compounds
B.N. is thankful to Basic Scientific Research, University Grants Commission (BSR UGC) for start up grant No. F.30-358/2017(BSR).
Abstract
Cancer is one of the most daunting illnesses in the world as compared to many other human diseases. This review article aims to summarize the literature that is already published based on heterocyclic anticancer compounds. Under this broad topic we try to shed a light on anticancer potentiality of oxygen-, sulfur-, and nitrogen-containing heterocyclic compounds, such as quinolines, pyrroles, pyrimidines, pyridines, indoles, also sulfonamides linked heterocycles, benzimidazoles and oxadiazoles.
1 Introduction
1.1 Drugs in Use for Cancer Treatment
1.2 Recently Discovered Anticancer Drugs
2 Various Classes of Compounds as Anticancer Agents
2.1 Quinoline Derivatives as Anticancer Agents
2.2 Benzimidazoles as Anticancer Agents
2.3 Indole: A Privileged Scaffold for the Design of Anticancer Agents
2.4 Pyrimidine Derivatives as Anticancer Agents
2.5 Pyridine Derivatives as Anticancer Agents
2.6 Pyrrole Derivatives as Anticancer Agents
2.7 Sulfonamides linked with heterocycles as Anticancer Agents
2.8 Oxadiazole and Its Derivatives as Anticancer Compounds
2.9 Benzothiazole-Triazole Hybrids as Anticancer Compounds
3 Conclusion
Publication History
Received: 13 March 2024
Accepted after revision: 12 June 2024
Article published online:
26 August 2024
© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Arrousse N, Harras MF, El Kadiri S, Haldhar R, Ichou H, Bousta D, Grafov A, Rais Z, Taleb M. Results Chem. 2023; 6: 100996
- 2 Ioele G, Chieffallo M, Occhiuzzi MA, De Luca M, Garofalo A, Ragno G, Grande F. Molecules 2022; 27: 5436
- 3 Bray F, Laversanne M, Weiderpass E, Soerjomataram I. Cancer 2021; 127: 3029
- 4 Negi B, Kumar D, Rawat DS. Curr. Protein Pept. Sci. 2016; 18: 885
- 5 Malusare M, Papule P, Swami GM. Int. Res. J. Modernization Eng. Technol. Sci. 2023; 5: 3963
- 6 Crescioli S, Kaplon H, Chenoweth A, Wang L, Reichert JM, Crescioli S, Kaplon H, Chenoweth A, Wang L, Chenoweth A, Wang L. MAbs 2024; 16: 2297450
- 7 Gogia P, Ashraf H, Bhasin S, Xu Y. Cancers 2023; 15: 3886
- 8 Parashar RK, Negi B. Chemistry of Heterocyclic Compounds . Ane Books Pvt. Ltd./CRC Press; New Delhi/Boca Raton: 2015
- 9 Qadir T, Amin A, Sharma PK, Jeelani I, Abe H. Open Med. Chem. J. 2022; 16: e187410452209010
- 10 Chu X.-M, Wang C, Liu W, Liang L.-L, Gong K.-K, Zhao C.-Y, Sun K.-L. Eur. J. Med. Chem. 2019; 161: 101
- 11 Li S, Huang Q, Liu Y, Zhang X, Liu S, He C, Gong P. Eur. J. Med. Chem. 2013; 64: 62
- 12 Ilovaisky AI, Scherbakov AM, Merkulova VM, Chernoburova EI, Shchetinina MA, Andreeva OE, Salnikova DI, Zavarzin IV, Terent’ev AO. J. Steroid Biochem. Mol. Biol. 2023; 228: 106245
- 13 Amin MM, Abuo-Rahma GE.-D. A, Shaykoon MS. A, Marzouk AA, Abourehab MA. S, Saraya RE, Badr M, Sayed AM, Beshr EA. M. Bioorg. Chem. 2023; 134: 106444
- 14 Kardile RA, Sarkate AP, Lokwani DK, Tiwari SV, Azad R, Thopate SR. Eur. J. Med. Chem. 2023; 245: 114889
- 15 Jeleń M, Morak-Młodawska B, Korlacki R. J. Mol. Struct. 2023; 1287: 135700
- 16a Jain S, Chandra V, Kumar Jain P, Pathak K, Pathak D, Vaidya A. Arabian J. Chem. 2019; 12: 4920 ; and references cited therein
- 16b Ilakiyalakshmi M, Napoleon AA. Arabian J. Chem. 2022; 15: 104168
- 16c Kumar D, Negi B, Rawat DS. Recent Advances in Pharmaceutical Innovation and Research. Springer Nature; Singapore: 2023: 243-292
- 17 Jiang R, Duckett D, Chen W, Habel J, Ling YY, Grasso PL, Kamenecka TM. Bioorg. Med. Chem. Lett. 2007; 17: 6378
- 18 Bispo M. deL. F, de Alcantara CC, de Moraes MO, do Ó Pessoa C, Rodrigues FA. R, Kaiser CR, Wardell SM. S. V, Wardell JL, de Souza MV. N. Monatsh. Chem. 2015; 146: 2041
- 19 Ferrer R, Lobo G, Gamboa N, Rodrigues J, Abramjuk C, Jung K, Lein M, Charris JE. Sci. Pharm. 2009; 77: 725
- 20 Xiang PJ. H, Zhou Y, Yang B, Wang HJ, Hu J, Hu J, Yang SY, Zhao YL. Molecules 2015; 20: 7620
- 21 Jiang N, Zhai X, Li T, Liu D, Zhang T, Wang B, Gong P. Molecules 2012; 17: 5870
- 22 Chen YL, Huang CJ, Huang ZY, Tseng CH, Chang FS, Yang SH, Lin SR, Tzeng CC. Bioorg. Med. Chem. 2006; 14: 3098
- 23 Chen YL, Chung CH, Chen IL, Chen PH, Jeng HY. Bioorg. Med. Chem. 2002; 10: 2705
- 24 Işik A, Acar Çevik U, Çelik I, Bostancı HE, Karayel A, Gündoğdu G, Ince U, Koçak A, Özkay Y, Kaplancıklı ZA. J. Mol. Struct. 2022; 1270: 133946
- 25 Suárez-Moreno GV, Hernández-Romero D, García-Barradas Ó, Vázquez-Vera Ó, Rosete-Luna S, Cruz-Cruz CA, López-Monteon A, Carrillo-Ahumada J, Morales-Morales D, Colorado-Peralta R. Coord. Chem. Rev. 2022; 472: 214790
- 26 Banerjee S, Mukherjee S, Nath P, Mukherjee A, Mukherjee S, Kumar S K A, De S, Banerjee S. Results Chem. 2023; 6: 101013
- 27 Ebenezer O, Oyetunde-Joshua F, Omotoso OD, Shapi M. Results Chem. 2023; 5: 100925
- 28 Garuti L, Roberti M, Malagoli M, Rossi T, Castelli M. Bioorg. Med. Chem. Lett. 2000; 10: 2193
- 29 Chojnacki K, Winska P, Skierka K, Wielechowska M, Bretner M. Bioorg. Chem. 2017; 72: 1
- 30 Abd El-Meguid EA, El-Deen EM. M, Nael MA, Anwar MM. Arab. J. Chem. 2020; 13: 9179
- 31 Tang L, Wu W, Zhang C, Shi Z, Chen D, Zhai X, Jiang Y. Bioorg. Chem. 2021; 114: 105026
- 32 Eldehna WA, El Hassab MA, Abo-Ashour MF, Al-Warhi T, Elaasser MM, Safwat NA, Suliman H, Ahmed MF, Al-Rashood ST, Abdel-Aziz HA, El-Haggar R. Bioorg. Chem. 2021; 110: 104748
- 33 Nazreen S, Almalki AS. A, Elbehairi SE. I, Shati AA, Alfaifi MY, Elhenawy AA, Alsenani NI, Alfarsi A, Alhadhrami A, Alqurashi EA, Alam MM. Molecules 2022; 27: 6899
- 34 Lee YT, Tan YJ, Oon CE. Acta Pharm. Sin. B 2023; 13: 478
- 35 Karthikeyan C, Solomon VR, Lee H, Trivedi P. Arabian J. Chem. 2017; 10: S1788
- 36 Kamal A, Subba Rao AV. S, Lakshma Nayak VL, Subba Reddy NV. S, Swapna K, Ramakrishna G, Alvala M. Org. Biomol. Chem. 2014; 12: 9864
- 37 Trudel S, Li ZH, Wei E, Wiesmann M, Chang H, Chen C, Reece D, Heise C, Stewart AK. Blood 2005; 105: 2941
- 38 Roskoski R. Pharmacol. Res. 2019; 144: 19 ; and references cited therein
- 39 Corona SP, Generali D. Drug Des., Dev. Ther. 2018; 12: 321
- 40 Ramurthy S, Subramanian S, Aikawa M, Amiri P, Costales A, Dove J, Fong S, Jansen JM, Levine B, Ma S, McBride CM, Michaelian J, Pick T, Poon DJ, Girish S, Shafer CM, Stuart D, Sung L, Renhowe PA. J. Med. Chem. 2008; 51: 7049
- 41 Li Y, Tan C, Gao C, Zhang C, Luan X, Chen X, Liu H, Chen Y, Jiang Y. Bioorg. Med. Chem. 2011; 19: 4529
- 42 Galal SA, Khairat SH. M, Ali HI, Shouman SA, Attia YM, Ali MM, Mahmoud AE, Abdel-Halim AH, Fyiad AA, Tabll A, El-Shenawy R, El Abd YS, Ramdan R, El Diwani HI. Eur. J. Med. Chem. 2018; 144: 859
- 43 Bistrović A, Krstulović L, Harej A, Grbčić P, Sedić M, Koštrun S, Pavelić SK, Bajić M, Raić-Malić S. Eur. J. Med. Chem. 2018; 143: 1616
- 44 Zanjirband M, Curtin N, Edmondson RJ, Lunec J. Oncotarget 2017; 8: 69779
- 45 Akunuri R, Vadakattu M, Bujji S, Veerareddy V, Madhavi YV, Nanduri S. Eur. J. Med. Chem. 2021; 220: 113445
- 46 Konus M, Çetin D, Kızılkan ND, Yılmaz C, Fidan C, Algso M, Kavak E, Kivrak A, Kurt-Kızıldoğan A, Otur Ç, Mutlu D, Abdelsalam AH, Arslan S. J. Mol. Struct. 2022; 1263: 133168
- 47 Wan Y, Li Y, Yan C, Yan M, Tang Z. Eur. J. Med. Chem. 2019; 183: 111691
- 48 Nishiguchi GA, Atallah G, Bellamacina C, Burger MT, Ding Y, Feucht PH, Garcia PD, Han W, Klivansky L, Lindvall M. Bioorg. Med. Chem. Lett. 2011; 21: 6366
- 49a More KN, Jang HW, Hong VS, Lee J. Bioorg. Med. Chem. Lett. 2014; 24: 2424
- 49b More KN, Hong VS, Lee A, Park J, Kim S, Lee J. Bioorg. Med. Chem. Lett. 2018; 28: 2513
- 50 Dai Y, Guo Y, Guo J, Pease LJ, Li J, Marcotte PA, Glaser KB, Tapang P, Albert DH, Richardson PL, Davidsen SK, Michaelides MR. Bioorg. Med. Chem. Lett. 2003; 13: 1897
- 51 Giannini G, Marzi M, Di Marzo M, Battistuzzi G, Pezzi R, Brunetti T, Cabri W, Vesci L, Pisano C. Bioorg. Med. Chem. Lett. 2009; 19: 2840
- 52 Hawash M, Ergun SG, Kahraman DC, Olgac A, Hamel E, Cetin-Atalay R, Baytas SN. J. Mol. Struct. 2023; 1285: 135477
- 53 Li J, Si R, Zhang Q, Li Y, Zhang J, Shan Y. Chem.-Biol. Interact. 2022; 368: 110242
- 54 Wang G, He M, Liu W, Fan M, Li Y, Peng Z. Arabian J. Chem. 2022; 15: 103504
- 55 Wang G, He M, Liu W, Fan M, Li Y, Zhiyun Peng Z. Arabian Journal of Chem. 2022; 15: 103504
- 56 Peerzada MN, Khan P, Ahmad K, Hassan MI, Azam A. Eur. J. Med. Chem. 2018; 155: 13
- 57 Wang Q, Arnst KE, Wang Y, Kumar G, Ma D, White SW, Miller DD, Li W, Li W. J. Med. Chem. 2019; 62: 6734
- 58 He Z, Qiao H, Yang F, Zhou W, Gong Y, Zhang X, Wang H, Zhao B, Ma L, Liu H. Eur. J. Med. Chem. 2019; 184: 111764
- 59 El-Sharief AM. S, Ammar YA, Belal A, El-Sharief MA. M. S, Mohamed YA, Mehany AB. M, Ali GA. M. E, Ragab A. Bioorg. Chem. 2019; 85: 399
- 60 Iacopetta D, Catalano A, Ceramella J, Barbarossa A, Carocci A, Fazio A, La Torre C, Caruso A, Ponassi M, Rosano C. Bioorg. Chem. 2020; 105: 104440
- 61 Gurkan-Alp AS, Mumcuoglu M, Andac CA, Dayanc E, Cetin-Atalay R, Buyukbingol E. Eur. J. Med. Chem. 2012; 58: 346
- 62 Fortes MP, da Silva PB. N, da Silva TG, Kaufman TS, Militao GC. G, Silveira CC. Eur. J. Med. Chem. 2016; 118: 21
- 63 Ahmed SA, Naji TS, Mohammad FI. Al-Nahrain J. Sci. 2013; 16: 84
- 64 Mahapatra A, Prasad T, Sharma T. Future J. Pharm. Sci. 2021; 7: 123
- 65 Mahdy H, Elnagar H, Sakr H. Al-Azhar J. Pharm. Sci. 2023; 67: 51
- 66 Li Z, Kou L, Fu X, Xie Z, Xu M, Guo L, Lin T, Gong S, Zhang S, Liu M. J. Enzyme Inhib. Med. Chem. 2022; 37: 1514
- 67 Akhtar W, Nainwal LM, Khan MF, Verma G, Chashoo G, Bakht A, Iqbal M, Akhtar M, Shaquiquzzaman M, Alam MM. J. Fluorine Chem. 2020; 236: 109579
- 68 Haoran W, Akhtar W, Nainwal LM, Kaushik SK, Akhter M, Shaquiquzzaman M, Alam MM. J. Heterocycl. Chem. 2020; 57: 3350
- 69 Xu Y, Hao SY, Zhang XJ, Li WB, Qiao XP, Wang ZX, Chen SW. Bioorg. Med. Chem. Lett. 2020; 30: 126885
- 70 Hu G, Wang C, Xin X, Li S, Li Z, Zhao Y, Gong P. New J. Chem. 2019; 43: 10190
- 71 Qin WW, Sang CY, Zhang LL, Wei W, Tian HZ, Liu HX, Chen SW, Hui L. Eur. J. Med. Chem. 2015; 95: 174
- 72 Kraljević TG, Klika M, Kralj M, Martin-Kleiner I, Jurmanović S, Milić A, Padovan J, Raić-Malić S. Bioorg. Med. Chem. Lett. 2012; 22: 308
- 73 Weinberg LR, Albom MS, Angeles TS, Husten J, Lisko JG, McHugh RJ, Milkiewicz KL, Murthy S, Ott GR, Theroff JP, Tripathy R. Bioorg. Med. Chem. Lett. 2011; 21: 164
- 74 Long L, Luo Y, Hou ZJ, Ma HJ, Long ZJ, Tu ZC, Huang LJ, Liu Q, Lu G. Eur. J. Med. Chem. 2018; 145: 805
- 75 Luo G, Tang Z, Lao K, Li X, You Q, Xiang H. Eur. J. Med. Chem. 2018; 150: 783
- 76 Zhao M, Ren H, Chang J, Zhang D, Yang Y, He Y, Qi C, Zhang H. Eur. J. Med. Chem. 2016; 119: 183
- 77 Jorda R, Havlíček L, Šturc A, Tušková D, Daumová L, Alam M, Škerlová J, Nekardová M, Peřina M, PospíšilT ŠJ. J. Med. Chem. 2019; 62: 4606
- 78 Jorda R, Havlícek L, McNae IW, Walkinshaw MD, Voller J, Šturc A, Navrátilová J, Kuzma M, Mistrík M, Bártek J, Strnad M. J. Med. Chem. 2011; 54: 2980
- 79 Wang R, Chen Y, Zhao X, Yu S, Yang B, Wu T, Guo J, Hao C, Zhao D, Cheng M. Eur. J. Med. Chem. 2019; 183: 111716
- 80 Sivaiah G, Raveesha R, Benaka Prasad SB, Yogesh Kumar K, Raghu MS, Alharti FA, Prashanth MK, Jeon B.-H. J. Mol. Struct. 2023; 1275: 134728
- 81 Alrooqi M, Khan S, Alhumaydhi FA, Asiri SA, Alshamrani M, Mashraqi MM, Alzamami A, Alshahrani AM, Aldahish AA. Anti-Cancer Agents Med. Chem. 2022; 22: 2775
- 82 Marinescu M, Popa CV. Int. J. Mol. Sci. 2022; 23: 5659
- 83 De S, Kumar S K A, Kumar Shah S, Kazi S, Sarkar N, Banerjee S, Deya S. RSC Adv. 2022; 12: 15385
- 84 Albratty M, Alhazmi HA. Arabian J. Chem. 2022; 15: 103846
- 85 Narasimhamurthy KH, Kallesha N, Mohan CD, Rangappa KS. Anticancer Functions of Pyridine Heterocycles . In Cytotoxicity - Understanding Cellular Damage and Response . Sukumaran A, Mansour MA. IntechOpen; London: 2023
- 86 El-Naggar M, Almahli H, Ibrahim HS, Eldehna WM, Abdel-Aziz HA. Molecules 2018; 23: 1459
- 87 Murthy IS, Sreenivasulu R, Alluraiah G, Ramesh Raju G. Russ .J. Gen. Chem. 2019; 89(8): 1718
- 88 Metwally NH, Deeb EA. Bioorg. Chem. 2018; 77: 203
- 89 Li X, Li S, Lu G, Wang D, Liu K, Qian X, Xue W, Meng F. Bioorg. Chem. 2020; 103: 104189
- 90 Wang R, Chen Y, Yang B, Yu S, Zhao X, Zhang C, Hao C, Zhao D, Cheng M. Bioorg. Chem. 2020; 94: 103474
- 91 Ning C, Tao A, Xu J. Eur. J. Med. Chem. 2023; 259: 115687
- 92 Gholap SS. Eur. J. Med. Chem. 2016; 110: 13
- 93 Akhtar J, Khan AA, Ali Z, Haider R, Shahar Yar M. Eur. J. Med. Chem. 2017; 125: 143
- 94 Petri GL, Spanò V, Spatola R, Holl R, Raimondi MV, Barraja P, Montalbano A. Eur. J. Med. Chem. 2020; 208: 112783
- 95 Kilic-Kurt Z, Bakar-Ates F, Aka Y, Kutuk O. Bioorg. Chem. 2019; 83: 511
- 96 Carta D, Bortolozzi R, Sturlese M, Salmaso V, Hamel E, Basso G, Calderan L, Quintieri L, Moro S, Viola G, Ferlin MG. Eur. J. Med. Chem. 2017; 127: 643
- 97 Kurup S, McAllister B, Liskova P, Mistry T, Fanizza A, Stanford D, Slawska J, Keller U, Hoellein A. J. Enzyme Inhibit. Med. Chem. 2018; 33: 74
- 98 El-Gamal MI, Oh CH. J. Enzyme Inhibit. Med. Chem. 2018; 33: 1160
- 99 Mesaros EF, Angeles TS, Albom MS, Wagner JC, Aimone LD, Wan W, Lu L, Huang Z, Olsen M, Kordwitz E, Haltiwanger RC, Landis AJ, Cheng M, Ruggeri BA, Ator MA, Dorsey BD, Ott GR. Bioorg. Med. Chem. Lett. 2015; 25: 1047
- 100 Narva S, Chitti S, Bala BR, Alvala M, Jain N, Kondapalli VG. C. S. Eur. J. Med. Chem. 2016; 114: 220
- 101 Williams IS, Joshi P, Gatchie L, Sharma M, Satti NK, Vishwakarma RA, Chaudhuri B, Bharate SB. Bioorg. Med. Chem. Lett. 2017; 27: 3683
- 102 Alanazi AS, Mirgany TO, Alsaif NA, Alsfouk AA, Alanazi MM. Saudi Pharm. J. 2023; 31: 989
- 103 Niedziałkowski P, Czaczyk E, Jarosz J, Wcisło A, Białobrzeska W, Wietrzyk J, Ossowski T. J. Mol. Struct. 2019; 1175: 488
- 104 Tikhomirov AS, Shtil AA, Shchekotikhin AE. Recent Pat. Anti-Cancer Drug Discovery 2018; 13: 159
- 105 Anifowose A, Agbowuro AA, Tripathi R, Lu W, Tan C, Yang X, Wang B. Med. Chem. Res. 2020; 29: 1199
- 106 Zheng Y, Zhu L, Fan L, Zhao W, Wang J, Hao X, Zhu Y, Hu X, Yuan Y, Shao J, Wang W. Eur. J. Med. Chem. 2017; 125: 902
- 107 Choudhary N, Collignon TE, Tewari D, Bishayee A. Phytomedicine 2022; 105: 154356
- 108 Dobson J, de Queiroz GF, Golding JP. Vet. J. 2018; 233: 8
- 109 Kwiatkowski S, Knap B, Przystupski D, Saczko J, Kędzierska E, Knap-Czop K, Kotlińska J, Michel O, Kotowski K, Kulbacka J. Biomed. Pharmacother. 2018; 106: 1098
- 110 Champeau M, Vignoud S, Mortier L, Mordon S. J. Photochem. Photobiol., B 2019; 197: 111544
- 111 Woźniak M, Nowak M, Lazebna A, Więcek K, Jabłońska I, Szpadel K, Grzeszczak A, Gubernator J, Ziółkowski P. Pharmaceuticals 2021; 14: 374
- 112 Banerjee SM, El-Sheikh S, Malhotra A, Mosse CA, Parker S, Williams NR, Macrobert AJ, Hamoudi R, Bown SG, Keshtgar MR. S. J. Clin. Med. 2020; 9: 483
- 113 Ostańska E, Aebisher D, Bartusik-Aebisher D. Biomed. Pharmacother. 2021; 137: 111302
- 114 Afanasiev MS, Dushkin AD, Grishacheva TG, Afanasiev SS, Karaulov AV. Photodiagn. Photodyn. Ther. 2022; 37: 102620
- 115 Warowicka A, Popenda Ł, Bartkowiak G, Musidlak O, Litowczenko-Cybulska J, Kuźma D, Nawrot R, Jurga S, Goździcka-Józefiak A. Phytomedicine 2019; 64: 152919
- 116 Nowak-Perlak M, Ziółkowski P, Woźniak M. Phytomedicine 2023; 119: 155035
- 117 Stanojković T, Marković V, Matić IZ, Mladenović MP, Petrović N, Krivokuća A, Petković M, Joksović MD. Bioorg. Med. Chem. Lett. 2018; 28: 2593
- 118 Wan Y, Fang G, Chen H, Deng X, Tang Z. Eur. J. Med. Chem. 2021; 226: 113837
- 119 Das R, Tambe G, Shard A. Results Chem. 2023; 5: 100950
- 120 Soliman AM, Alqahtani AS, Ghorab MM. J. Enzyme Inhibit. Med. Chem. 2019; 34: 1030
- 121 Luo Y, Li Y, Qiu K.-M, Lu X, Fu J, Zhu H.-L. Bioorg. Med. Chem. 2011; 19: 6069
- 122 Ghorab MM, Soliman AM, El-Adl K, Hanafy NS. Bioorg. Chem. 2023; 140: 106791
- 123 Cao L, Yao H, Yu L, Ren Y, Liu J, Li X, Jia X. Bioorg. Med. Chem. 2023; 85: 117241
- 124 Saleh NM, El-Gaby MS. A, El-Adl K, Abd El-Sattar NE. A. Bioorg. Chem. 2020; 104: 104350
- 125 Wang K, Song L.-H, Liang Q.-L, Zhang Y, Ma X.-L, Wang Q, Zhang H.-Y, Jiang C.-N, Wei J.-H, Huang R.-Z. Eur. J. Med. Chem. 2023; 254: 115349
- 126 Song J, Gao Q.-L, Wu B.-W, Li D, Shi L, Zhu T, Lou J.-F, Jin C.-Y, Zhang Y.-B, Zhang S.-Y, Liu H.-M. Eur. J. Med. Chem. 2019; 183: 111731
- 127 Reda Aouad M, Almehmadi MA, Faleh Albelwi F, Teleb M, Tageldin GN, Abu-Serie MM, Hagar M, Rezki N. Bioorg. Chem. 2022; 124: 105816
- 128 Swain B, Sahoo SK, Singh P, Angeli A, Yaddanapudi VM, Supuran CT, Arifuddin M. Eur. J. Med. Chem. 2022; 234: 114247
- 129 Liu Y, Wu Y, Sun L, Gu Y, Hu L. Eur. J. Med. Chem. 2020; 191: 112181
- 130 Luo Y, Zhou Y, Song Y, Chen G, Wang Y.-X, Tian Y, Fan W.-W, Yang Y.-S, Cheng T, Zhu H.-L. Bioorg. Med. Chem. Lett. 2018; 28: 3634
- 131 For a review see: Nayak S, Gaonkar SL, Musad EA, Dawsar AM. A. L. J. Saudi Chem. Soc. 2021; 25: 101284
- 132 Boström J, Hogner A, Llinàs A, Wellner E, Plowright AT. J. Med. Chem. 2012; 55: 1817
- 133 Naaz F, Ahmad F, Lone BA, Pokharel YR, Fuloria NK, Fuloria S, Ravichandran M, Pattabhiraman L, Shafi S, Shahar Yar M. Bioorg. Chem. 2020; 95: 103519
- 134 Tantak MP, Malik M, Klingler L, Olson Z, Kumar A, Sadana R, Kumar D. Bioorg. Med. Chem. Lett. 2021; 37: 127842
- 135 Bhatt P, Sen A, Jha A. ChemistrySelect 2020; 5: 3347
- 136 Vinayak A, Sudha M, Lalita KS. Dhaka Univ. J. Pharm. Sci. 2017; 16: 11
- 137 Khalil NA, Kamal AM, Emam SH. Biol. Pharm. Bull. 2015; 38: 763
- 138 Yousef TA, Alhamzani AG, Abou-Krisha MM, Kanthimathi G, Raghu MS, Kumar KY, Prashanth MK, Jeon BH. Heliyon 2023; 9: e20300
- 139 Cho S, Oh S, Um Y, Jung J.-H, Ham J, Shin W.-S, Lee S. Bioorg. Med. Chem. Lett. 2009; 19: 382
- 140 Kumar K, Pradines B, Madamet M, Amalvict R, Kumar V. Eur. J. Med. Chem. 2014; 86: 113
- 141 Karthik Kumar K, Prabu Seenivasan S, Kumar V, Mohan Das T. Carbohydr. Res. 2011; 346: 2084
- 142 de Carvalho da Silva F, de Souza MC. B. V, Frugulhetti II. P, Castro HC, Souza SL. de O, de Souza TM. L, Rodrigues DQ, Souza AM. T, Abreu PA, Passamani F, Rodrigues CR, Ferreira VF. Eur. J. Med. Chem. 2009; 44: 373
- 143 Costa MS, Boechat N, Rangel ÉA, de Carvalho da Silva F, de Souza AM. T, Rodrigues CR, Castro HC, Junior IN, Lourenço MC. S, Wardell SM. S. V, Ferreira VF. Bioorg. Med. Chem. 2006; 14: 8644
- 144 Lal K, Kaushik CP, Kumar A. Med. Chem. Res. 2015; 24: 3258
- 145 Bokor É, Docsa T, Gergely P, Somsák L. Bioorg. Med. Chem. 2010; 18: 1171
- 146 Fallah Z, Tajbakhsh M, Alikhani M, Larijani B, Faramarzi MA, Hamedifar H, Mohammadi-Khanaposhtani M, Mahdavi M. J. Mol. Struct. 2022; 1255: 132469
- 147 Al-Masoudi NA, Al-Soud YA. Tetrahedron Lett. 2002; 43: 4021
- 148 Shawish I, Barakat A, Aldalbahi A, Alshaer W, Daoud F, Alqudah DA, Al Zoubi M, Hatmal MM, Nafie MS, Haukka M, Sharma A, de la Torre BG, Albericio F, El-Faham A. Pharmaceutics 2022; 14: 145
- 149 Oggu S, Akshinthala P, Katari NK, Nagarapu LK, Malempati S, Gundla R, Jonnalagadda SB. Heliyon 2023; 9: e15935
- 150 Matore BW, Banjare P, Guria T, Roy PP, Singh J. Eur. J. Med. Chem. Rep. 2022; 5: 100058
- 151 Valente S, Trisciuoglio D, De Luca T, Nebbioso A, Labella D, Lenoci A, Bigogno C, Dondio G, Miceli M, Brosch G, Del Bufalo D, Altucci L, Mai A. J. Med. Chem. 2014; 57: 6259
- 152 Bondock S, Fadaly W, Metwally MA. Eur. J. Med. Chem. 2010; 45: 3692
- 153 Delmas F, Avellaneda A, Di Giorgio C, Robin M, De Clercq E, Timon-David P, Galy J.-P. Eur. J. Med. Chem. 2004; 39: 685
- 154 Hong S, Kim J, Yun S.-M, Lee H, Park Y, Hong S.-S, Hong S. J. Med. Chem. 2013; 56: 3531
- 155 Ke S, Wei Y, Yang Z, Wang K, Liang Y, Shi L. Bioorg. Med. Chem. Lett. 2013; 23: 5131
- 156 Kaplan-Ozen C, Tekiner-Gulbas B, Foto E, Yildiz I, Diril N, Aki E, Yalcin I. Med. Chem. Res. 2013; 22: 5798
- 157 Khan KM, Rahim F, Wadood A, Taha M, Khan M, Naureen S, Ambreen N, Hussain S, Perveen S, Choudhary MI. Bioorg. Med. Chem. Lett. 2014; 24: 1825
- 158 O’Brien SE, Browne HL, Bradshaw TD, Westwell AD, Stevens MF. G, Laughton CA. Org. Biomol. Chem. 2003; 1: 493
- 159 Oanh DT. K, Van Hai H, Park SH, Kim HJ, Han BW, Kim HS, Hong JT, Han SB, Nam NH. Bioorg. Med. Chem. Lett. 2011; 21: 7509
- 160 Rawat S, Rawat DS, Negi B. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2021; 60: 409
- 161 Rezki N, Almehmadi MA, Ihmaid S, Shehata AM, Omar AM, Ahmed HE. A, Aouad MR. Bioorg. Chem. 2020; 103: 104133
- 162 Subba Rao AV, Swapna K, Shaik SP, Lakshma Nayak V, Srinivasa Reddy T, Sunkari S, Shaik TB, Bagul C, Kamal A. Bioorg. Med. Chem. 2017; 25: 977
- 163 Diao PC, Lin WY, Jian XE, Li YH, You WW, Zhao PL. Eur. J. Med. Chem. 2019; 179: 196
- 164 Lee E, An Y, Kwon J, Kim KI, Jeon R. Bioorg. Med. Chem. 2017; 25: 3614
- 165 Xie X.-X, Li H, Wang J, Mao S, Xin M.-H, Lu S.-M, Mei Q.-B, Zhang S.-Q. Bioorg. Med. Chem. 2015; 23: 6477
- 166 Cao S, Cao R, Liu X, Luo X, Zhong W. Molecules 2016; 21: 6
- 167 Song J, Gao QL, Wu BW, Zhu T, Cui XX, Jin CJ, Wang SY, Wang SH, Fu DJ, Liu HM, Zhang SY, Zhang YB, Li YC. Eur. J. Med. Chem. 2020; 203: 112618
- 168 Osmaniye D, Levent S, Karaduman AB, Ilgın S, Zkay Y, Kaplancikli ZA. Molecules 2018; 23: 2033
- 169 Belal A, Abdelgawad MA. Res. Chem. Intermed. 2017; 43: 3859
- 170 Haider K, Shrivastava N, Pathak A, Prasad Dewangan R, Yahya S, Shahar Yar M. Results Chem. 2022; 4: 100258
- 171 Philoppes JN, Lamie PF. Bioorg. Chem. 2019; 89: 102978