Recent Advances in the Synthesis of 2-Hydroxy-1,4-naphthoquinone (Lawsone) Derivatives

This work is dedicated to Prof. Srinivasan Chandrasekaran on his 78^th birthday

Abstract

Lawsone, also known as 2-hydroxy-1,4-naphthoquinone, has been extensively studied and found to be a crucial precursor in the production of a diverse range of natural products such as molecular scaffolds, which are highly sought-after for biological research purposes. Due to its unique chemical composition, lawsone has been utilized for over a century as a starting material for the synthesis of numerous biologically active molecules and materials, and its intriguing properties have been showcased across a wide range of scientific and technological applications. Additionally, the various characteristics of lawsone have been widely used in organic synthesis processes. Recent advances in the synthesis of different scaffolds starting from lawsone, and their applications, are discussed in detail in the current review covering the period 2017 to 2023.

1 Introduction

2 Synthetic Developments on 2-hydroxy-1,4-naphthoquinone

3 Conclusions

Key words

multicomponent reactions - chemoenzymatic reactions - heterocyclic compounds - 2-hydroxy-1,4-naphthaquinone - magnetic nanoparticles - tandem reactions - green chemistry

Publication History

Received: 03 August 2023

Accepted after revision: 05 October 2023

Accepted Manuscript online:
06 October 2023

Article published online:
16 November 2023

• References

• 1 Sarang H, Rajani P, Vasanthakumari MM, Kumara PM, Siva R, Ravikanth G, Shaanker RU. Antonie van Leeuwenhoek 2017; 110: 853
• 2 Jordão AK, Vargas MD, Pinto AC, da Silva F. dC, Ferreira VF. RSC Adv. 2015; 5: 67909
• 3 Barreto E. dS, Baêta BE, Pereira M. rC, Pasquini D, Guimarães V. rM, Gurgel LV. Energy Fuels 2020; 34: 16228
• 4 Thakur GA, Kadu RK, Patil VR, Thakur PB. ChemistrySelect 2020; 5: 13628
• 5 Pradhan R, Dandawate P, Vyas A, Padhye S, Biersack B, Schobert R, Ahmad A, Sarkar FH. Curr. Drug Targets 2012; 13: 1777
• 6 Heo J.-Y, Cho C.-H, Jeon H.-S, Cheong B.-S, Cho H.-G. Spectrochim. Acta, Part A 2011; 83: 425
• 7 Xavier MR, Santos MM. S, Queiroz MG, de Lima Silva MS, Goes AJ. S, De Morais MA. Jr. Mol. Biol. Rep. 2020; 47: 1173
• 8 Sharma S, Dutta NB, Bhuyan M, Das B, Baishya G. Org. Biomol. Chem. 2020; 18: 6537
• 9 Chakraborty S, Das G, Ghosh S, Mal D. Org. Biomol. Chem. 2016; 14: 10636
• 10 Kot M, Karcz W, Zaborska W. Bioorg. Chem. 2010; 38: 132
• 11 Thi TA. D, Le-Nhat-Thuy G, Thi QG. N, Thi PH, Tuan AN, Mai HH, Ha TN, Le TA, Nguyen TV. Chem. Heterocycl. Compd. 2021; 57: 137
• 12 Sharma D, Chetia D, Rudrapal M. Asian J. Chem. 2016; 28: 782
• 13 Fu Z, Qian K, Li S, Shen T, Song Q. Tetrahedron Lett. 2016; 57: 1104
• 14 Sánchez-Calvo JM, Barbero GR, Guerrero-Vásquez G, Durán AG, Macías M, Rodríguez-Iglesias MA, Molinillo JM, Macías FA. Med. Chem. Res. 2016; 25: 1274
• 15 Narayanan SV, Kumar M, Gnanaraj VR, Rajan SC, Selvaraj V, Ananthakumar S. MedComm Biomater. Appl. 2023; 2: e29
• 16 Satoh T, Kudoh M, Tsuji T, Kita S, Mori T, Sudoh S. Bull. Chem. Soc. Jpn. 2007; 80: 1103
• 17 Kathawate L, Shinde Y, Yadav R, Salunke-Gawali S. J. Therm. Anal. Calorim. 2013; 111: 1003
• 18 Feng J, Weitner M, Shi W, Zhang S, Zhang Y. Front. Microbiol. 2016; 7: 62
• 19 Gholampour M, Seradj H, Pirhadi S, Khoshneviszadeh M. Bioorg. Med. Chem. 2020; 28: 115718
• 20 Mone N, Harihar S, Salunke-Gawali S, Satpute S, Patil A, Mokashi V, Jadhav M, Butcher RJ. Inorg. Chim. Acta 2023; 546: 121290
• 21 de Sena Pereira VS, de Oliveira CB. S, Fumagalli F, da Silva Emery FF, da Silva NB, de Andrade-Neto VF. Toxicol. Rep. 2016; 3: 756
• 22 de Luna Martins D, do Amaral e Silva NA, Ferreira VF, da Silva Rangel L, dos Santos JA. A, Faria RX. Acta Tropica 2022; 231: 106414
• 23 Kim EE, Onyango EO, Pace JR, Abbot TM, Fu L, Gribble GW. Tetrahedron Lett. 2016; 57: 864
• 24 Shaabani S, Naimi-Jamal MR, Maleki A. Dyes Pigm. 2015; 122: 46
• 25 Mollazehi F, Shaterian HR. Appl. Organomet. Chem. 2018; 32: e4183
• 26 Ekennia AC, Osowole AA, Onwudiwe DC, Babahan I, Ibeji CU, Okafor SN, Ujam OT. Appl. Organomet. Chem. 2018; 32: e4310
• 27 Cardoso SH, de Oliveira CR, Guimarães AS, Nascimento J, dos Santos Carmo J. dO, de Souza Ferro JN, de Carvalho Correia AC, Barreto E. Chem.-Biol. Interact. 2018; 291: 55
• 28 Yoshioka E, Kohtani S, Miyabe H. Molbank 2015; 2015: M841
• 29 Yang F, Wang H, Jiang L, Yue H, Zhang H, Wang Z, Wang L. RSC Adv. 2015; 5: 5213
• 30 Maheswari CS, Tamilselvi V, Ramesh R, Lalitha A. Org. Prep. Proced. Int. 2020; 52: 22
• 31 Afsharnezhad M, Bayat M, Hosseini FS. Mol. Diversity 2020; 24: 379
• 32 Daloee TS, Behbahani FK. Polycyclic Aromat. Compd. 2020; 42: 681
• 33 Gracious SN, Kerru N, Maddila S, van Zyl WE, Jonnalagadda SB. Synth. Commun. 2020; 50: 1960
• 34 Safaei-Ghomi J, Bateni FS, Babaei P. Appl. Organomet. Chem. 2020; 34: e5657
• 35 Mollabagher H, Taheri S, Mojtahedi MM, Seyedmousavi S. RSC Adv. 2020; 10: 1995
• 36 Olyaei A, Sadeghpour M. RSC Adv. 2022; 12: 13837
• 37 Yazdani-Elah-Abadi A, Razeghi M, Shams N, Kangani M, Mohebat R. Org. Prep. Proced. Int. 2020; 52: 48
• 38 Mohammadrezaei M, Mohebat R, Tabatabaee M. Org. Prep. Proced. Int. 2019; 51: 477
• 39 Bakthadoss M, Srinivasan J, Hussain MA, Sharada DS. RSC Adv. 2019; 9: 24314
• 40 Yazdani-Elah-Abadi A, Mohebat R, Maghsoodlou M.-T. RSC Adv. 2016; 6: 84326
• 41 Mohebat R, Yazdani-Elah-Abadi A. Chin. Chem. Lett. 2017; 28: 1340
• 42 Yazdani-Elah-Abadi A, Mohebat R, Lashkari M. Polycyclic Aromat. Compd. 2017; 40: 268
• 43 Abadi MZ. H, Mohebat R, Mosslemin MH. Polycyclic Aromat. Compd. 2017; 40: 159
• 44 Mohebat R, Simin N, Yazdani-Elah-Abadi A. Polycyclic Aromat. Compd. 2017; 39: 148
• 45 Dehghan P, Mohebat R. Polycyclic Aromat. Compd. 2018; 40: 1164
• 46 Ghorbani-Choghamarani A, Mohammadi M, Shiri L, Taherinia Z. Res. Chem. Intermed. 2019; 45: 5705
• 47 Safaei-Ghomi J, Tavazo M, Shahbazi-Alavi H. Z. Naturforsch., B 2019; 74: 733
• 48 Safaei-Ghomi J, Bakhtiari A. Appl. Organomet. Chem. 2019; 33: e5201
• 49 Olyaei A, Aghajanzadeh A, Feizy E, Sadeghpour M. J. Chin. Chem. Soc. 2020; 68: 704
• 50 Daraie M, Tamoradi T, Heravi MM, Karmakar B. J. Mol. Struct. 2021; 1245
• 51 Le-Nhat-Thuy G, Thi TA. D, Thi QG. N, Thi PH, Nguyen TA, Nguyen HT, Thi TH. N, Nguyen HS, Nguyen TV. Bioorg. Med. Chem. Lett. 2021; 43: 128054
• 52 Theresa LV, Sreekumar K. J. Mol. Struct. 2023; 1275
• 53 Rani PR. K, Fernandez A, George A, Remadevi VK, Sudarsanakumar MR, Laila SP, Arif M. Spectrochim. Acta, Part A 2015; 135: 1156
• 54 Brahmachari G, Begam S, Nurjamal K. ChemistrySelect 2018; 3: 3400
• 55 Fu Z, Qian K, Li S, Shen T, Song Q. Tetrahedron Lett. 2016; 57: 1104
• 56 Brahmachari G, Nayek N. ACS Omega 2017; 2: 5025
• 57 Khodabakhshi S, Mori BA. P, Baghernejad M, Kiani S. Polycyclic Aromat. Compd. 2017; 39: 434
• 58 Maleki A, Aghaei M, Kari T. Polycyclic Aromat. Compd. 2017; 39: 266
• 59 Brahmachari G, Nayek N. ChemistrySelect 2018; 3: 3621
• 60 Kumari P, Bharti R, Parvin T. Mol. Diversity 2019; 23: 205
• 61 Wang Q, Wang B, Deng H, Shangguan Y, Lin Y, Zhang Y, Zhang Z, Xiao Y, Guo H, Zhang C. J. Org. Chem. 2019; 84: 1006
• 62 Balouchzehi D, Hassanabadi A. Polycyclic Aromat. Compd. 2019; 41: 851
• 63 Kumari P, Yadav R, Bharti R, Parvin T. Mol. Diversity 2020; 24: 107
• 64 Lakshmanan S, Ramalakshmi N. Synth. Commun. 2016; 46: 2045
• 65 Krytska K, Ryles HT, Sano R, Raman P, Infarinato NR, Hansel TD, Makena MR, Song MM, Reynolds CP, Mossé YP. Clin. Cancer Res. 2016; 22: 948
• 66 Patil A, Gajare S, Rashinkar G, Salunkhe R. Catal. Lett. 2019; 150: 127
• 67 Vairaperumal V, Perumal M, Sengodu P, Shanumuganthan S, Paramasivam M. ChemistrySelect 2019; 4: 3006
• 68 Gajare S, Patil A, Kale D, Bansode P, Patil P, Rashinkar G. Catal. Lett. 2019; 150: 243
• 69 Farahani HV, Bayat M, Nasri S. Silicon 2019; 12: 41
• 70 Zheng Z, Lin J, Sun Y, Zhang S. Tetrahedron Lett. 2020; 61: 151382
• 71 Kandhasamy S, Arthi N, Arun RP, Verma RS. Mater. Sci. Eng., C 2019; 102: 773
• 72 Mousavi SR, Nodeh HR, Afshari EZ, Foroumadi A. Catal. Lett. 2019; 149: 1075
• 73 Bayat M, Safari F, Nasri S, Hosseini FS. Monatsh. Chem. 2019; 150: 703
• 74 Borthakur S, Baruah S, Sarma B, Gogoi S. Org. Lett. 2019; 21: 2768
• 75 Dubovtsev AY, Dmitriev MV, Maslivet AN. Russ. J. Org. Chem. 2019; 55: 406
• 76 Borra S, Chandrasekhar D, Newar UD, Maurya RA. J. Org. Chem. 2019; 84: 1042
• 77 Tsanakopoulou M, Tsovaltzi E, Tzani MA, Selevos P, Malamidou-Xenikaki E, Bakalbassis EG, Domingo LR. Org. Biomol. Chem. 2019; 17: 692
• 78 Nouri A, Marjani AP, Khalafy J. J. Heterocycl. Chem. 2019; 56: 2912
• 79 Behbahani FS, Tabeshpour J, Mirzaei S, Golmakaniyoon S, Tayarani-Najaran Z, Ghasemi A, Ghodsi R. Arch. Pharm. (Weinheim) 2019; 352: e1800307
• 80 Li SY, Sun ZK, Zeng XY, Zhang Y, Wang ML, Hu SC, Song JR, Luo J, Chen C, Luo H, Pan WD. Molecules 2019; 24: 4138
• 81 Monroy-Cardenas M, Mendez D, Trostchansky A, Martinez-Cifuentes M, Araya-Maturana R, Fuentes E. Front. Chem. 2020; 533
• 82 Olyaei A, Taheri N, Sadeghpour M. Res. Chem. Intermed. 2020; 47: 1211
• 83 Khalafy J, Arlan FM, Marjani AP, Sarchami V. J. Heterocycl. Chem. 2020; 57: 3961
• 84 Wu L, Ma X, Yang X, Zhang C. Eur. J. Med. Chem. 2020; 203: 112594
• 85 Turhan K, Pektas B, Turkan F, Tugcu FT, Turgut Z, Taslimi P, Karaman HS, Gulcin I. Arch. Pharm. (Weinheim) 2020; 353: e2000030
• 86 Chipoline IC, da Fonseca AC. C, da Costa GR. M, de Souza MP, Rabelo VW.-H, de Queiroz LN, de Souza TL. F, de Almeida EC. P, Abreu PA, Pontes B, Ferreira VF, da Silva FC, Robbs BK. Bioorg. Chem. 2020; 101: 103984
• 87 Duan W, Li Z, Chen F, Zhang M, Deng H, Song L. J. Fluorine Chem. 2020; 235
• 88 Li X, Sun P, Xie K, Zhou D, Peng J, Fan A, Zhang J, Chen C. J. Org. Chem. 2020; 85: 9313
• 89 Lambat TL, Mahmood SH, Ledade PV, Banerjee S. ChemistrySelect 2020; 5: 8864
• 90 Safari J, Tavakoli M, Ghasemzadeh MA. Polyhedron 2020; 182
• 91 Rahnamafar R, Moradi L, Khoobi M. J. Heterocycl. Chem. 2020; 57: 1825
• 92 Kamalzare M, Bayat M, Maleki A. R. Soc. Open Sci. 2020; 7: 200385
• 93 Taheri M, Mohebat R. Green Chem. Lett. Rev. 2020; 13: 165
• 94 Nariya P, Shukla F, Vyas H, Devkar R, Thakore S. Synth. Commun. 2020; 50: 1724
• 95 Song R, Yu B, Friedrich D, Li J, Shen H, Krautscheid H, Huang SD, Kim MH. Commun. Biol. 2020; 3: 529
• 96 Keykha Z, Fadaeian M, Hassanabadi A, Ghasemzadeh MA. Polycyclic Aromat. Compd. 2020; 42: 3434
• 97 Thi TA. D, Le-Nhat-Thuy G, Thi QG. N, Thi PH, Tuan AN, Mai HH, Ha TN, Le TA, Nguyen TV. Chem. Heterocycl. Compd. 2021; 57: 137
• 98 Madani Qamsari F, Moradi S, Foroumadi A, Mahdavi M, Moghimi A. Iran. J. Chem. Chem. Eng. 2021; 40: 437
• 99 Yadav R, Parvin T. New J. Chem. 2021; 45: 10388
• 100 Olyaei A, Mohamadi A, Rahmani N. RSC Adv. 2021; 11: 12990
• 101 Thi QG. N, Le-Nhat-Thuy G, Thi TA. D, Thi PH, Tuan AN, Thi TH. N, Nguyen TT, Ha TN, Mai HH, Nguyen TV. Bioorg. Med. Chem. Lett. 2021; 37: 127841
• 102 Yadav R, Parvin T, Panday AK, Choudhury LH. Mol. Diversity 2021; 25: 2161
• 103 Nguyen H.-T, Thi TA. D, Thi PH, Le-Nhat-Thuy G, Thi QG. N, Tuan AN, Thi TA. L, Nguyen TV. Tetrahedron Lett. 2021; 81
• 104 Shen Z, Zhang F, Li C. Synlett 2021; 32: 1117
• 105 Olyaei A, Adl A, Vessally E. Res. Chem. Intermed. 2021; 47: 2207
• 106 Krishna AV, Ramachary DB. Org. Biomol. Chem. 2022; 20: 3948
• 107 Koumpoura CL, Nguyen M, Bijani C, Vendier L, Salina EG, Buroni S, Degiacomi G, Cojean S, Loiseau PM, Benoit-Vical F, Garcia-Sosa AT, Anne R, Baltas M. ACS Omega 2022; 7: 35635
• 108 Olyaei A, Abediha S, Sadeghpour M, Adl A. ChemistrySelect 2022; 7: e202201650
• 109 Nariya P, Kumar S, Seshadri S, Patel M, Thakore S. J. Mol. Struct. 2022; 1267
• 110 Abdollahi-Basir MH, Shirini F, Tajik H, Ghasemzadeh MA. J. Mol. Struct. 2022; 1263
• 111 Wang L, Zhang J, Lang M, Wang J. Org. Chem. Front. 2016; 3: 603
• 112 Filho EV, Antoniazi MK, Ferreira RQ, dos Santos GF. S, Pessoa C, Guimarães CJ, Neto JB. V, Silva AM. S, Greco SJ. Eur. J. Org. Chem. 2022; e202200442
• 113 Shirzaei F, Shaterian HR. J. Mol. Struct. 2022; 1256
• 114 Costa D, Francisco A, Matuck B, Furtado P, de Oliveira A, Rabelo V, Sathler P, Abreu P, Ferreira V, da Silva LC, da Silva F. J. Braz. Chem. Soc. 2022; 33: 48
• 115 Choura E, Elghali F, Bernard PJ, Msalbi D, Marco-Contelles J, Aifa S, Ismaili L, Chabchoub F. Molecules 2022; 27: 7878
• 116 Chaudhary A, Khanna G, Chopra H, Gaba R. Res. Chem. Intermed. 2022; 48: 2267
• 117 Pasha MA, Anebouselvy K, Ramachary DB. Tetrahedron 2022; 117–118: 132793
• 118 Peraka S, Hussain A, Ramachary DB. J. Org. Chem. 2018; 83: 9795
• 119 Ramachary DB, Pashsa MA, Thirupathi G. Angew. Chem. Int. Ed. 2017; 129: 13110