Synthesis and SAR Studies of Praziquantel Derivatives with Activity Against Schistosoma Japonicum

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2013 Aug 6

PMID 23912271

Citations 7

Authors

Wen-Long Wang

Li-Jun Song

Xia Chen

Xu-Ren Yin

Wen-Hua Fan

Gu-Ping Wang

Chuan-Xin Yu

Bainian Feng

Affiliations

Soon will be listed here.

Abstract

The synthesis and structure-activity relationship (SAR) studies of praziquantel derivatives with activity against adult Schistosoma japonicum are described. Several of them showed better worm killing activity than praziquantel and could serve as leads for further optimization.

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References

Wang W, Wang L, Liang Y . Susceptibility or resistance of praziquantel in human schistosomiasis: a review. Parasitol Res. 2012; 111(5):1871-7. DOI: 10.1007/s00436-012-3151-z. View

A Sayed A, Simeonov A, Thomas C, Inglese J, Austin C, Williams D . Identification of oxadiazoles as new drug leads for the control of schistosomiasis. Nat Med. 2008; 14(4):407-12. PMC: 2700043. DOI: 10.1038/nm1737. View

Bissinger E, Heinke R, Spannhoff A, Eberlin A, Metzger E, Cura V . Acyl derivatives of p-aminosulfonamides and dapsone as new inhibitors of the arginine methyltransferase hPRMT1. Bioorg Med Chem. 2011; 19(12):3717-31. DOI: 10.1016/j.bmc.2011.02.032. View

Caixeta S, Magalhaes L, de Melo N, Wakabayashi K, Aguiar G, Aguiar D . Chemical composition and in vitro schistosomicidal activity of the essential oil of Plectranthus neochilus grown in Southeast Brazil. Chem Biodivers. 2011; 8(11):2149-57. DOI: 10.1002/cbdv.201100167. View

Cao H, Liu H, Domling A . Efficient multicomponent reaction synthesis of the schistosomiasis drug praziquantel. Chemistry. 2010; 16(41):12296-8. DOI: 10.1002/chem.201002046. View

Liu H, William S, Herdtweck E, Botros S, Domling A . MCR synthesis of praziquantel derivatives. Chem Biol Drug Des. 2011; 79(4):470-7. PMC: 3712825. DOI: 10.1111/j.1747-0285.2011.01288.x. View

Jao S, Chen J, Yang K, Li W . Design of potent inhibitors for Schistosoma japonica glutathione S-transferase. Bioorg Med Chem. 2005; 14(2):304-18. DOI: 10.1016/j.bmc.2005.07.077. View

Ronketti F, Venkata Ramana A, Chao-Ming X, Pica-Mattoccia L, Cioli D, Todd M . Praziquantel derivatives I: Modification of the aromatic ring. Bioorg Med Chem Lett. 2007; 17(15):4154-7. DOI: 10.1016/j.bmcl.2007.05.063. View

de Moraes J, Almeida A, Brito M, Marques T, Lima T, de Sousa D . Anthelmintic activity of the natural compound (+)-limonene epoxide against Schistosoma mansoni. Planta Med. 2013; 79(3-4):253-8. DOI: 10.1055/s-0032-1328173. View

10.

Dezube B, Von Roenn J, Holden-Wiltse J, Cheung T, Remick S, Cooley T . Fumagillin analog in the treatment of Kaposi's sarcoma: a phase I AIDS Clinical Trial Group study. AIDS Clinical Trial Group No. 215 Team. J Clin Oncol. 1998; 16(4):1444-9. DOI: 10.1200/JCO.1998.16.4.1444. View

11.

Stelma F, Talla I, Sow S, Kongs A, Niang M, Polman K . Efficacy and side effects of praziquantel in an epidemic focus of Schistosoma mansoni. Am J Trop Med Hyg. 1995; 53(2):167-70. DOI: 10.4269/ajtmh.1995.53.167. View

12.

Meyer T, Sekljic H, Fuchs S, Bothe H, Schollmeyer D, Miculka C . Taste, a new incentive to switch to (R)-praziquantel in schistosomiasis treatment. PLoS Negl Trop Dis. 2009; 3(1):e357. PMC: 2614124. DOI: 10.1371/journal.pntd.0000357. View

13.

Rai G, A Sayed A, Lea W, Luecke H, Chakrapani H, Prast-Nielsen S . Structure mechanism insights and the role of nitric oxide donation guide the development of oxadiazole-2-oxides as therapeutic agents against schistosomiasis. J Med Chem. 2009; 52(20):6474-83. PMC: 2772170. DOI: 10.1021/jm901021k. View

14.

Kim D, Reddy K, Kim M, Li Y, Nadas J, Cho Y . (3-Chloroacetyl)-indole, a novel allosteric AKT inhibitor, suppresses colon cancer growth in vitro and in vivo. Cancer Prev Res (Phila). 2011; 4(11):1842-51. PMC: 3244047. DOI: 10.1158/1940-6207.CAPR-11-0158. View

15.

Andrews P, Thomas H, Pohlke R, Seubert J . Praziquantel. Med Res Rev. 1983; 3(2):147-200. DOI: 10.1002/med.2610030204. View

16.

Woelfle M, Seerden J, de Gooijer J, Pouwer K, Olliaro P, Todd M . Resolution of praziquantel. PLoS Negl Trop Dis. 2011; 5(9):e1260. PMC: 3176743. DOI: 10.1371/journal.pntd.0001260. View

17.

Song L, Li J, Xie S, Qian C, Wang J, Zhang W . Thioredoxin glutathione reductase as a novel drug target: evidence from Schistosoma japonicum. PLoS One. 2012; 7(2):e31456. PMC: 3285170. DOI: 10.1371/journal.pone.0031456. View

18.

Caffrey C, Evan Secor W . Schistosomiasis: from drug deployment to drug development. Curr Opin Infect Dis. 2011; 24(5):410-7. DOI: 10.1097/QCO.0b013e328349156f. View

19.

Patra M, Ingram K, Pierroz V, Ferrari S, Spingler B, Gasser R . [(η(6)-Praziquantel)Cr(CO)3] derivatives with remarkable in vitro anti-schistosomal activity. Chemistry. 2013; 19(7):2232-5. DOI: 10.1002/chem.201204291. View

20.

Domling A, Khoury K . Praziquantel and schistosomiasis. ChemMedChem. 2010; 5(9):1420-34. DOI: 10.1002/cmdc.201000202. View