Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2022; 54(19): 4235-4245
DOI: 10.1055/s-0040-1719901
DOI: 10.1055/s-0040-1719901
special topic
SYNTHESIS Conference Special Topic ISySyCat21
Tryptanthrin and Its Derivatives in Drug Discovery: Synthetic Insights
P. Brandão acknowledges ‘Fundação para a Ciência e a Tecnologia’ (FCT) for the PhD grant PD/BD/128490/2017 - CATSUS FCT-PhD Program (PD/00248/2012). This work was also supported by FCT through projects UIDB/00313/2020 and UIDP/00313/2020, co-funded by COMPETE2020-UE (Coimbra Chemistry Centre (CQC)). This work also received financial support from FCT/MCTES through the project UIDB/50006/2020.
Abstract
Tryptanthrin is a golden-yellow, naturally occurring alkaloid that can be obtained from multiple sources and through different synthetic methodologies. This tetracyclic compound displays several relevant biological activities. The potential of this tetracyclic alkaloid has been widely explored, and several researchers have focused their attention on expanding the variety of tryptanthrin derivatives by using a range of synthetic strategies. In this short review, we aim to address recent developments in the synthesis of the tryptanthrin core, as well as the development of new strategies employed by synthetic organic chemists to obtain novel tryptanthrin derivatives with potential biological activity, using different tools from the chemists’ toolbox, such as photocatalysis, solvent-free approaches, and multicomponent reactions.
Publication History
Received: 29 November 2021
Accepted after revision: 17 January 2022
Article published online:
07 March 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Friedländer P, Roschdestwensky N. Ber. Dtsch. Chem. Ges. 1915; 48: 1841
- 2 Schindler F, Zähner H. Arch. Mikrobiol. 1971; 79: 187
- 3 Fedeli W, Mazza F. J. Chem. Soc., Perkin Trans. 2 1974; 1621
- 4a Yoshikawa M, Murakami T, Kishi A, Sakurama T, Matsuda H, Nomura M, Matsuda H, Kubo M. Chem. Pharm. Bull. 1998; 46: 886
- 4b Bergman J, Lindström J.-O, Tilstam U. Tetrahedron 1985; 41: 2879
- 4c Yu H, Li T.-N, Ran Q, Huang Q.-W, Wang J. J. Ethnopharmacol. 2021; 265: 113325
- 4d Honda G, Tosirisuk V, Tabata M. Planta Med. 1980; 38: 275
- 4e Garcellano RC, Moinuddin SG. A, Young RP, Zhou M, Bowden ME, Renslow RS, Yesiltepe Y, Thomas DG, Colby SM, Chouinard CD, Nagy G, Attah IK, Ibrahim YM, Ma R, Franzblau SG, Lewis NG, Aguinaldo AM, Cort JR. J. Nat. Prod. 2019; 82: 440
- 4f Oberthür C, Hamburger M. Planta Med. 2004; 70: 642
- 5 Pedras MS. C, Abdoli A, To QH, Thapa C. Chem. Biodivers. 2019; 16: e1800579
- 6 Ramkissoon A, Seepersaud M, Maxwell A, Jayaraman J, Ramsubhag A. Molecules 2020; 25: 3744
- 7a Wagner-Döbler I, Rheims H, Felske A, El-Ghezal A, Flade-Schröder D, Laatsch H, Lang S, Pukall R, Tindall BJ. Int. J. Syst. Evol. Microbiol. 2004; 54: 1177
- 7b Shaaban M, Maskey RP, Wagner-Döbler I, Laatsch H. J. Nat. Prod. 2002; 65: 1660
- 7c Hosoe T, Nozawa K, Kawahara N, Fukushima K, Nishimura K, Miyaji M, Kawai K.-I. Mycopathologia 1999; 146: 9
- 7d Jarrah MY, Thaller V. J. Chem. Res., Synop. 1980; 186: 2601
- 8 Rasmussen LE. L, Lee TD, Daves GD, Schmidt MJ. J. Chem. Ecol. 1993; 19: 2115
- 9 Caspers B, Franke S, Voigt CC. In Chemical Signals in Vertebrates 11 . Springer; New York: 2008: 151
- 10a Honda G, Tabata M, Tsuda M. Planta Med. 1979; 37: 172
- 10b Hesse-Macabata J, Morgner B, Elsner P, Hipler U.-C, Wiegand C. Sci. Rep. 2020; 10: 1863
- 11a Costa DC. M, de Azevedo MM. B, Silva DO. E, Romanos MT. V, Souto-Padrón TC. B. S, Alviano CS, Alviano DS. Nat. Prod. Res. 2017; 31: 2077
- 11b Tripathi A, Wadia N, Bindal D, Jana T. Indian J. Biochem. Biophys. 2012; 49: 435
- 12a Xu LJ, Jiang W, Jia H, Zheng LS, Xing JG, Liu AL, Du GH. Front. Cell. Infect. Microbiol. 2020; 10
- 12b Tsai Y.-C, Lee C.-L, Yen H.-R, Chang Y.-S, Lin Y.-P, Huang S.-H, Lin C.-W. Biomolecules 2020; 10: 366
- 12c Mani JS, Johnson JB, Steel JC, Broszczak DA, Neilsen PM, Walsh KB, Naiker M. Virus Res. 2020; 284
- 13a Miao S, Shi X, Zhang H, Wang S, Sun J, Hua W, Miao Q, Zhao Y, Zhang C. Int. J. Mol. Sci. 2011; 12: 3831
- 13b Feng X, Liao DD, Liu DY, Ping A, Li ZY, Bian JL. J. Med. Chem. 2020; 63: 15115
- 14 Chang HN, Yeh YC, Chueh HY, Pang JH. S. Phytomedicine 2019; 58
- 15a Danz H, Stoyanova S, Wippich P, Brattström A, Hamburger M. Planta Med. 2001; 67: 411
- 15b Danz H, Stoyanova S, Thomet OA. R, Simon H.-U, Dannhardt G, Ulbrich H, Hamburger M. Planta Med. 2002; 68: 875
- 15c Wang Z, Wu X, Wang C.-L, Wang L, Sun C, Zhang D.-B, Liu J.-L, Liang Y.-N, Tang D.-X, Tang Z.-S. Molecules 2018; 23: 1062
- 15d Agafonova IG, Moskovkina TV. Appl. Magn. Reson. 2015; 46: 781
- 15e Pergola C, Jazzar B, Rossi A, Northoff H, Hamburger M, Sautebin L, Werz O. Br. J. Pharmacol. 2012; 165: 765
- 15f Lee S, Kim D.-C, Baek HY, Lee K.-D, Kim Y.-C, Oh H. Arch. Pharm. Res. 2018; 41: 419
- 15g Kawaguchi S, Sakuraba H, Kikuchi H, Numao N, Asari T, Hiraga H, Ding JL, Matsumiya T, Seya K, Fukuda S, Imaizumi T. Mol. Immunol. 2021; 129: 32
- 16a Kwon YW, Cheon SY, Park SY, Song J, Lee JH. Front. Cell. Neurosci. 2017; 11
- 16b Jung EH, Jung JY, Ko HL, Kim JK, Park SM, Jung DH, Park CA, Kim YW, Ku SK, Cho IJ, Kim SC. Arch. Pharm. Res. 2017; 40: 1071
- 17 Iwaki K, Ohashi E, Arai N, Kohno K, Ushio S, Taniguchi M, Fukuda S. J. Ethnopharmacol. 2011; 134: 450
- 18a Jahne EA, Eigenmann DE, Sampath C, Butterweck V, Culot M, Cecchelli R, Gosselet F, Walter FR, Deli MA, Smiesko M, Hamburger M, Oufir M. Planta Med. 2016; 82: 1021
- 18b Zhang X, Xia J, Zhang W, Luo Y, Sun W, Zhou W. Integr. Med. Res. 2017; 6: 269
- 20 Kaur R, Manjal SK, Rawal RK, Kumar K. Bioorg. Med. Chem. 2017; 25: 4533
- 21a Veisi H. Curr. Org. Chem. 2011; 15: 2438
- 21b Finkbeiner P, Nachtsheim BJ. Synthesis 2013; 45: 979
- 21c Dandia A, Gupta SL, Maheshwari S. In Green Chemistry: Synthesis of Bioactive Heterocycles . Springer; New Delhi: 2014: 277
- 21d Yusubov MS, Zhdankin VV. Res. Effic. Tech. 2015; 1: 49
- 22 Pattarawarapan M, Wiriya N, Hongsibsong S, Phakhodee W. J. Org. Chem. 2020; 85: 15743
- 23 Amara R, Awad H, Chaker D, Bentabed-Ababsa G, Lassagne F, Erb W, Chevallier F, Roisnel T, Dorcet V, Fajloun Z, Vidal J, Mongin F. Eur. J. Org. Chem. 2019; 5302
- 24 Brandão P, Pinheiro D, Sérgio Seixas De Melo J, Pineiro M. Dyes Pigm. 2020; 173: 107935
- 25 Sultan S, Gupta V, Shah BA. ChemPhotoChem 2017; 1: 120
- 26 Obafemi CA, Adegbite OB, Fadare OA, Iwalewa EO, Omisore NO, Sanusi K, Yilmaz Y, Ceylan Ü. Heliyon 2021; 7: e05756
- 27 Xie L, Lu C, Jing D, Ou X, Zheng K. Eur. J. Org. Chem. 2019; 3649
- 28 Kaishap PP, Duarah G, Pal M. Synth. Commun. 2021; 1: 3740
- 29 Pena-Solorzano D, Guilombo CE. G, Ochoa-Puentes C. Sustain. Chem. Pharm. 2019; 14
- 30 Rai B, Shukla RD, Kumar A. Green Chem. 2018; 20: 822
- 31 Mane AH, Patil AD, Kamat SR, Salunkhe RS. ChemistrySelect 2018; 3: 6454
- 32 Hou H, Li H, Han Y, Yan C. Org. Chem. Front. 2018; 5: 51
- 33 Abe T, Terasaki M. Helv. Chim. Acta 2018; 101: e1700284
- 34 Guo S, Zhai J, Fan X. Org. Biomol. Chem. 2017; 15: 1521
- 35a Jao C.-W, Lin W.-C, Wu Y.-T, Wu P.-L. J. Nat. Prod. 2008; 71: 1275
- 35b Chang C.-F, Hsu Y.-L, Lee C.-Y, Wu C.-H, Wu Y.-C, Chuang T.-H. Int. J. Mol. Sci. 2015; 16: 3980
- 36 Ishikura M, Itoh T, Abe T, Choshi T, Nishiyama T. Heterocycles 2017; 95: 507
- 37a Kang G, Luo Z, Liu C, Gao H, Wu Q, Wu H, Jiang J. Org. Lett. 2013; 15: 4738
- 37b Deryabin PI, Moskovkina TV, Shevchenko LS, Kalinovskii AI. Russ. J. Org. Chem. 2017; 53: 418
- 38 Feng F.-F, Wang X.-Q, Sun L, Cheung CW, Nie J, Ma J.-A. Org. Lett. 2021; 23: 4379
- 39 Wang N, Liu H, Gao H, Zhou J, Zheng L, Li J, Xiao H.-P, Li X, Jiang J. Org. Lett. 2019; 21: 6684
- 40 Deryabin PI, Moskovkina TV, Bukreev AV, Andina AV, Gerasimenko AV. Russ. J. Org. Chem. 2018; 54: 622
- 41 Filatov AS, Knyazev NA, Shmakov SV, Bogdanov AA, Ryazantsev MN, Shtyrov AA, Starova GL, Molchanov AP, Larina AG, Boitsov VM, Stepakov AV. Synthesis 2019; 51: 713
- 42 Yavari I, Askarian-Amiri M. Synth. Commun. 2021; 51: 1602
- 43 Beyrati M, Hasaninejad A. Tetrahedron Lett. 2017; 58: 1947
- 44 Beyrati M, Forutan M, Hasaninejad A, Rakovský E, Babaei S, Maryamabadi A, Mohebbi G. Tetrahedron 2017; 73: 5144
- 45 Schepetkin IA, Khlebnikov AI, Potapov AS, Kovrizhina AR, Matveevskaya VV, Belyanin ML, Atochin DN, Zanoza SO, Gaidarzhy NM, Lyakhov SA, Kirpotina LN, Quinn MT. Eur. J. Med. Chem. 2019; 161: 179
- 46 Popov A, Klimovich A, Styshova O, Moskovkina T, Shchekotikhin A, Grammatikova N, Dezhenkova L, Kaluzhny D, Deriabin P, Gerasimenko A, Udovenko A, Stonik V. Int. J. Mol. Med. 2020; 46: 1335
- 47 Guda R, Korra R, Balaji S, Palabindela R, Eerla R, Lingabathula H, Yellu NR, Kumar G, Kasula M. Bioorg. Med. Chem. Lett. 2017; 27: 4741
- 48 Catanzaro E, Betari N, Arencibia JM, Montanari S, Sissi C, De Simone A, Vassura I, Santini A, Andrisano V, Tumiatti V, De Vivo M, Krysko DV, Rocchi MB. L, Fimognari C, Milelli A. Eur. J. Med. Chem. 2020; 202: 112504
- 49 Zheng XD, Hou BL, Wang R, Wang YY, Wang CL, Chen H, Liu L, Wang JL, Ma XM, Liu JL. Tetrahedron 2019; 75: 130351
- 50 Yang D, Zhang SN, Fang X, Guo LL, Hu N, Guo ZL, Li XS, Yang SS, He JC, Kuang CX, Yang Q. J. Med. Chem. 2019; 62: 9161
- 51 Brandão P, Marques C, Pinto E, Pineiro M, Burke AJ. New J. Chem. 2021; 45: 14633
- 52 Li YY, Zhang SN, Wang R, Cui MH, Liu W, Yang Q, Kuang CX. Bioorg. Med. Chem. Lett. 2020; 30: 127159