Synthesis and screening of substituted 1,4-naphthoquinones (NPQs) as antifilarial agents

Drug Development Research

Volumn 71, Issue 3, 2010, Pages 188-196

  Mathew, Nisha ^a   Karunan, Twinkle ^a   Srinivasan, Lakshmy ^a   Muthuswamy, Kalyanasundaram ^a  

^a VECTOR CONTROL RESEARCH CENTRE   (India)

Author keywords

1, 4 naphthoquinone; Antifilarial; Filariasis; Macrofilaricide; Setaria digitata

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; 2 (4 METHYLPIPERAZIN 1 YL)NAPHTHALENE 1,4 DIONE; 2 [(1,3 DIMETHYLBUTYL)AMINO]NAPHTHALENE 1,4 DIONE; 3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; ANTIFILARIAL AGENT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SETARIA DIGITATA; THIN LAYER CHROMATOGRAPHY;

EID: 77952762066     PISSN: 02724391     EISSN: 10982299     Source Type: Journal    
DOI: 10.1002/ddr.20357     Document Type: Article

References (47)

1. Acheson RM, Sansom BF. 1955. The reaction between quinones and anthranilic acids. J Chem Soc 4440-4443.
2. Awadzi K, Attah SK, Addy ET, Opoku NO, Quartey BT, Lazdins-Helds JK, Ahmed K, Boatin BA, Boakye DA, Edwards G. 2004. Thirty-month follow-up of sub-optimal responders to multiple treatments with ivermectin, in two onchocerciasis-endemic foci in Ghana. Ann Trop Med Parasitol 98:359-370. (Pubitemid 38903480)
3. Bakola-Christianopoulou MN, Ecateriniadou LB, Sarris KJ. 1986. Evaluation of the antimicrobial activity of a new series of hydroxyquinone chelates of some transition metals. Eur J Med Chem 21:385-390.
4. Bayen S, Barooah N, Sarma RJ, Sen T, Karmakar A, Baruah JB. 2007. Synthesis, structure and electrochemical properties of 2, 5-bis(alkyl/arylamino) 1,4-benzoquinones and 2-aryl 1,4-naphthoquinones. Dyes Pigment 75:770-775.
5. Bogdanov PM, Albesa I, Sperandeo NR, De Bertorello MM. 1993. Actividad antibacteriana in vitro de isoxazolilnaftoquinonas. Rev Arg Microbiol 25:119-128.
6. Brinworth RI, Fairlie DP. 1995. Hydroxyquinones are competitive non-peptide inhibitors of HIV-1 proteinase. Biochim Biophys Acta 1253:5-8.
7. Bullock FJ, Tweedie JF, McRitchie DD, Tucker MA. 1970. Antiprotozoal quinones: 2-amino-1,4-naphthoquinoneimines potential antimalarials. Eur J Med Chem 13:550-552.
8. Chatterjee RK, Fatma N, Murthy PK, Sinha P, Kulshrestha DK, Dhawan BN. 1992. Macrofilaricidal activity of the stembark of Streblus asper and its major active constituents. Drug Dev Res 26:67-78.
9. Comley JCW, Rees MJ, Turner CH, Jenkins DC. 1989. Colorimetric quantitation of filarial viability. Int J Parasitol 19:77-83.
10. Elslager EF, Werbel ML, Worth DF. 1970. Synthetic schistosomicides. XIV. 1,4-naphthoquinone mono(O-acyloximes), 4-amino-1, 2-naphthoquinones, 2-amino-3-chloro-1,4-naphthoquinones, and other naphthoquinones. J Med Chem 13:104-109.
11. Esscolastico C, Santa Maria MD, Claramunt RM, Jimeno ML, Alkorta I, Foces-Foces C, Cano FH, Elguero J. 1994. Imidazole and benzimidazole addition to quinines. Formation of meso and d,l Isomers and crystal structure of the d,l isomer of 2, 3-bis(benzimidazol-1′-yl)-1,4-dihydroxybenzene. Tetrahedron 50:12489-12510.
12. Gafner S, Wolfender JL, Nianga M, Stoceckli-Evans H, Hostettmann K. 1996. Antifungal and antibacterial naphthoquinones from Newbouldia leavis roots. Phytochemistry 42:1315-1320.
13. Gershon H, Shanks L. 1975. Fungitoxicity of 1,4-naphthoquinones to Candida albicans and Trichophyton menthagrophytes. Can J Microbiol 21:1317-1320.
14. Gupta HP, Singh R, Srivastava OP, Khana JM, Mathur IS, Gupta SK. 1981. Anti-fungal property of some substituted naphthoquinones, anthraquinone and imidazolquinones. Indian J Microbiol 21:57-59.
15. Hakobu S, Yojiro H, Masazumi S, Yoshio K, Seiji T, Toru H. 1979. Naphthoquinone herbicides. Tokyo, Koho: Jpn Kokai. p 6.
16. Kallmayer HJ, Tappe C. 1987. Quinone-amine reactions. Part 23: 4-Amino-1,2-naphthoquinone derivatives of the desipramine-type psychodrugs. Pharm Acta Helv 62:2-6.
17. Kinnamon KE, Engle RR, Poon BT, Ellis WY, McCall JW, Dzimianski MT. 1999. Polyamines: agents with macrofilaricidal activity. Ann Trop Med Parasitol 93:851-858.
18. Kita Y, Tohma H, Inagaki M, Hatanaka K, Yakura T. 1992. Total synthesis of discorhabdin C: a general aza spiro dienone formation from O-silylated phenol derivatives using a hypervalent iodine reagent. J Am Chem Soc 114:2175-2180.
19. Konoshima T, Kozuka N, Koyama J, Okatani T, Tagahara K, Tokuda H. 1989. Studies on inhibitors of skin tumor promotion. VI. Inhibitory effects of quinones on Epstein-Barr virus activation. J Nat Prod 52:987-995. (Pubitemid 19270609)
20. Kumamoto T, Kitani Y, Tsuchiya H, Yamaguchi K, Seki H, Ishikawa T. 2007. Total synthesis of (7)-methyl-kinamycin C. Tetrahedron 63:5189-5199.
21. Lakshmy S, Nisha M, Kalyanasundaram M. 2009. In vitro antifilarial activity of Glutathione S transferase inhibitors. Parasitol Res 105:1179-1182.
22. Lancini G, Zanichelli W. 1977. Antibiotics. Perlman D, editor. New York: Academic Press. p 531-600.
23. Lanz T, Tropf S, Marner F-J, Schroder J, Schroder G. 1991. The role of cysteines in polyketide synthases. Site-directed mutagenesis of resveratrol and chalcone synthases, two key enzymes in different plant-specific pathways. J Biol Chem 266:9971-9976.
24. Lin T-S, Xu S-P, Zhu L-Y, Cosby L, Sartonelli A. 1989. Synthesis of 2,3-diaziridinyl-1,4-naphthoquinone sulfonate derivatives as potential antineoplastic agents. J Med Chem 32:1467-1471.
25. Lin T-S, Xu S-P, Zhu L-Y, Divo A, Sartonelli A. 1991. Synthesis and antimalarial activity of 2-aziridinyl- and 2,3-bis(aziridinyl)-1,4- naphthoquinonyl sulfonate and acylate derivatives. J Med Chem 34:1634-1639.
26. Mazumder A, Shaomeng W, Neamati N, Nicklaus M, Sunder S, Chen J, Milne G, Rice W, Pommier Y. 1996. Antiretroviral agents as inhibitors of both human immunodeficiency virus type 1 integrase and protease. J Med Chem 39:2472-2481.
27. Nagaoka H, Kishi Y. 1981. Further synthetic studies on rifamycins. Tetrahedron 37:3873-3888.
28. Naoe A, Ishibashi M, Yamamoto Y. 2003. Cribrarione A, a new antimicrobial naphthoquinone pigment from a myxomycete Cribraria purpurea. Tetrahedron 59:3433-3435. (Pubitemid 36513717)
29. Nasal A, Siluk D, Kaliszan R. 2003. Chromatographic retention parameters in medicinal chemistry and molecular pharmacology. Curr Med Chem 10:381-426.
30. Nisha M, Kalyanasundaram M. 2007. Antifilarial agents. Expert Opin Ther Patents 17:767-789.
31. Nisha M, Paily KP, Vanamail P, Abidha, Kalyanasundaram M, Balaraman K. 2002. Macrofilaricidal activity of the plant plumbago indica/rosea in vitro. Drug Dev Res 56:33-39.
32. Nisha M, Kalyanasundaram M, Paily KP, Abidha, Vanamail P, Balaraman K. 2007. In vitro screening of medicinal plant extracts for macrofilaricidal activity. Parasitol Res 100:575-579.
33. Nisha M, Misra-Bhattacharya S, Vanamail P, Kalyanasundaram M. 2008. Antifilarial lead molecules isolated from Trachyspermum ammi. Molecules 13:2156-2168.
34. Omura S, Nakagawa A, Yamada H, Hata T, Furusaki A, Watanabe T. 1973. Structures and biological properties of Kinamycin A, B, C, and D. Chem Pharm Bull 21:931-940.
35. Rastogi RP, Dhawan BN. 1990. Anticancer and antiviral activities in Indian medicinal plants: a review. Drug Dev Res 19:1-12.
36. Roushdi IM,Mikhail AA, Ahmed IC. 1976. Synthesis of some quinones of potential therapeutic interest. Acta Pharm Jugosl 26:287-294.
37. Salmon-Chemin L, Buisine E, Yardley V, Kohler S, Marie-Ange D, Landry V, Sergheraert C, Croft SL, Krauth-Siegel L, Davioud-Charvet E. 2001. 2- and 3-substituted 1,4-naphthoquinone derivatives as subversive substrates of trypanothione reductase and lipoamide dehydrogenase from Trypanosoma cruzi: synthesis and correlation between redox cycling activities and in vitro cytotoxicity. J Med Chem 44:548-565.
38. Singh SN, Chatterjee RK, Srivastava AK. 1994. Effect of glycosides of Streblus asper on motility, glucose uptake, and certain enzymes of carbohydrate metabolism of Setaria cervi. Drug Dev Res 32:191-195.
39. Srivastava SK, Chauhan PMS, Bhaduri AP, Murthy PK, Chatterjee RK. 2000. Secondary amines as new pharmacophores as for macrofilaricidal drug. Bioorg Med Chem Lett 10:313-314.
40. Takagi K, Matsuoka M, Hamano K, Kitao T. 1984. Amination of 5,8-dihydroxy-1,4-naphthoquinone. Dyes Pigments 5:241-251.
41. Thomas G. 2000. Medicinal chemistry. An introduction. New York: John Wiley & Sons.
42. Townson S, Ramirez R, Fakorede F, Mouries MW, Nwaka S. 2007. Challenges in drug discovery for novel antifilarials. Expert Opin Drug Discov 2(Suppl 1):S63-S73.
43. Touraire C, Caupole R, Payard M, Commenges G, Bessieres MH, Bories C, Loiseal PM, Gayral P. 1996. Synthesis and protozoocidal activities of quinines. Eur J Med Chem 31:507-511.
44. Tucker JHR, Collinson SR. 2002. Recent developments in the redox-switched binding of organic compounds. Chem So Rev 31:147-156.
45. Uchiyama N, Kiuchi F, Ito M, Honda G, Takeda Y, Khodzhimatov OK, Ashurmetov OA. 2006. Trypanocidal constituents of Dracocephalum komarovi. Tetrahedron 62:4355-4359.
46. Williams DR, Clark MP. 1998. Synthesis of Atovaquone. Tetrahedron Lett 39:7629-7632.
47. William RA, Anja KL. 2001. Herbicide-induced oxidative stress in photosystem II. Trends Biochem Sci 26:648-653.