Molecular Modeling and 3D-QSAR Studies in 2-Aziridinyl-and 2,3-Bis(Aziridinyl)-1,4-Naphthoquinonyl Sulfonate and Acylate Derivatives as Potential Antimalarial Agents

References

• 1998 . WHO Report , www.who.int/inf-fs/en/fact094.html.
   Google Scholar
• Glosh , A. , Edwards , M. J. and Jacobs-Lorena , M. 2000 . The Journey of the Malaria Parasite in the Mosquito: Hopes for the New Century . Parasitol. Today , 16 : 196 – 201 .
   Google Scholar
• Macreadie , I. , Ginsburg , H. , Sirawaraporn , W. and Tillry , L. 2000 . Antimalarial drug development and new targets . Parasitol. Today , 16 : 438 – 443 .
   PubMedGoogle Scholar
• Geary , T. G. , Edgar , S. A. and Jensen , J. B. 1986 . Chemotherapy of Parasitic Diseases , Edited by: Campbell , W. C. and Rew , R. S. 209 – 236 . New York : Plenum Press .
   Google Scholar
• Peters , W. 1985 . The problem of drug resistance in malaria . Parasitology , 90 : 705 – 715 .
   PubMed Web of Science ®Google Scholar
• Moran , J. S. and Bernard , K. W. 1989 . The spread of chloroquin-resistant malaria in Africa . J. Am. Med. Assoc. , 262 : 245 – 248 .
   PubMed Web of Science ®Google Scholar
• Wyler , D. J. 1983 . Malaria-resurgence, resistance and research . N. Engl. J. Med. , 308 : 875 – 878 .
   PubMed Web of Science ®Google Scholar
• Anders , R. F. and Saul , A. 2000 . Malaria vaccines . Parasitol. Today , 16 : 444 – 450 .
   PubMedGoogle Scholar
• Winstanley , P. A. 2000 . Chemotherapy for falciparum malaria: the armoury, the problems and the prospects . Parasitol. Today , 16 : 146 – 153 .
   PubMedGoogle Scholar
• Haji , H. , Smith , T. , Charlwood , J. D. and Meuwissen , J. H. 1996 . Absence of relationships between selected human factors and natural infectivity of Plasmodium falciparum to mosquitoes in an area of high transmission . Parasitology , 113 : 425 – 431 .
   Google Scholar
• Abouabdellah , A. , Begue , J.-P. , Bonnet-Delpon , D. , Gantier , J. C. , Nga , T. T. T. and Thac , T. D. 1996 . Synthesis and in vivo antimalarial activity of 12α-trifluoromethyl-hydroartemisinin . Bioor. Med. Chem. Lett. , 6 : 2717 – 2720 .
   Google Scholar
• Posner , G. H. , Ploypradith , P. , Parker , M. H. , O'Dowd , H. , Woo , S.-H. , Northrop , J. , Krasavin , M. , Dolan , P. , Kensler , T. W. , Xie , S. and Shapiro , T. A. 1999 . Antimalarial, antiproliferative, and antitumor activities of artemisinin-derived, chemically robust, trioxane dimers . J. Med. Chem. , 42 : 4275 – 4280 .
   PubMedGoogle Scholar
• Li , Y. , Zhu , Y.-M. , Jiang , H.-J. , Pan , J.-P. , Wu , G.-S. , Wu , J.-M. , Shi , Y.-L. , Yang , J.-D. and Wu , B.-A. 2000 . Synthesis and antimalarial activity of artemisinin derivatives containing an amino group . J. Med. Chem. , 43 : 1635 – 1640 .
   PubMed Web of Science ®Google Scholar
• Mekonnen , B. , Weiss , E. , Katz , E. , Ma , J. , Ziffer , H. and Kyle , D. E. 2000 . Synthesis and antimalarial activities of base-catalyzed adducts of 11-azaartemisinin . Bioorg. Med. Chem. , 8 : 1111 – 1116 .
   Google Scholar
• Posner , G. H. , Maxwell , J. P. , O'Dowd , H. , Krasavin , M. , Xie , S. and Shapiro , T. A. 2000 . Antimalarial sulfide, sulfone, and sulfonamide trioxanes . Bioorg. Med. Chem. , 8 : 1361 – 1370 .
   PubMed Web of Science ®Google Scholar
• O'Neill , P. M. , Miller , A. , Bishop , L. P. D. , Hindley , S. , Maggs , J. L. , Ward , S. A. , Roberts , S. M. , Scheinmann , F. , Stachulski , A. V. , Posner , G. H. and Park , B. K. 2001 . Synthesis, antimalarial activity, biomimetic Iron (II) chemistry, and in vivo metabolism of novel, potent C-10-phenoxy derivatives of dihydroartemisinin . J. Med. Chem. , 44 : 58 – 68 .
   PubMed Web of Science ®Google Scholar
• Jefferies , D. 1998 . Selection of novel ligands from phage display libraries: an alternative approach to drug and vaccine discovery? . Parasitol. Today , 14 : 202 – 206 .
   Google Scholar
• Shahabuddin , M. , Cociancich , S. and Zieler , H. 1998 . The search for novel malaria transmission-blocking targets in the mosquito midgut . Parasitol. Today , 14 : 493 – 497 .
   Google Scholar
• Calas , M. , Ancelin , M. L. , Cordina , G. , Portefaix , P. , Piquet , G. , Vidal-Sailhan , V. and Vial , H. 2000 . Antimalarial activity of compounds interfering with Plasmodium falciparum phospholipid metabolism: comparison between mono-and bisquaternary ammonium salts . J. Med. Chem. , 43 : 505 – 516 .
   PubMed Web of Science ®Google Scholar
• McCullough , K. J. , Wood , J. K. , Bhattacharjee , A. K. , Dong , Y. , Kyle , D. E. , Milhous , W. K. and Vennerstrom , J. L. 2000 . Methyl-substituted dispiro-1,2,4,5-tetraoxanes: correlations of structural studies with antimalarial activity . J. Med. Chem. , 43 : 1246 – 1249 .
   PubMed Web of Science ®Google Scholar
• Rastelli , G. , Sinawaraporn , W. , Sompornpisut , P. , Vilaivan , T. , Kamchonwongpaisan , S. , Quarrell , R. , Lowe , G. , Thebtaranonth , Y. and Yuthavong , Y. 2000 . Interaction of pyrimethamine, cycloguanil, WR 99210 and their analogues with Plasmodium falciparum dihydrofolate reductase: structural basis of antifolate resistance . Bioorg. Med. Chem. , 8 : 1117 – 1128 .
   PubMed Web of Science ®Google Scholar
• Karle , J. M. and Bhattacharjee , A. K. 1999 . Stereoelectronic features of the cinchona alkaloids determine their differential antimalarial activity . Bioorg. Med. Chem. , 7 : 1769 – 1774 .
   Google Scholar
• Biot , C. , Delhaes , L. , N'Diaye , C. M. , Maciejewski , L. A. , Camus , D. , Dive , D. and Brocard , J. S. 1999 . Synthesis and antimalarial activity in vitro of potential metabolites of ferrochloroquine and related compounds . Bioorg. Med. Chem. , 7 : 2843 – 2847 .
   PubMed Web of Science ®Google Scholar
• Vennerstrom , J. L. and Eaton , J. W. 1988 . Oxidants, oxidant drugs, and malaria . J. Med. Chem. , 31 : 1269 – 1277 .
   PubMed Web of Science ®Google Scholar
• Wan , Y.-P. , Portor , T. H. and Folkers , K. 1974 . Antimalarial quinones for prophylaxis based on a rationale of inhibition of electron transfer in plasmodium . Proc. Natl Acad. Sci. USA , 71 : 952 – 956 .
   PubMed Web of Science ®Google Scholar
• Hudson , A. T. , Randall , A. W. , Fry , M. , Ginger , C. D. , Hill. , B. , Latter , V. S. , McHardy , N. and Williams , R. B. 1985 . Novel anti-malarial hydroxynaphthoquinones with potent broad spectrum anti-protozoal activity . Parasitology , 90 : 45 – 55 .
   PubMed Web of Science ®Google Scholar
• Hammond , D. J. , Burchell , J. R. and Pudney , M. 1985 . Inhibition of pyrimidine biosynthesis de novo in Plasmodium falciparum by 2-(4-t-Butylcyclohexyl)-3-hydroxy-1,4-naphthoquinone in vitro . Mol. Biochem. Parasitol. , 14 : 97 – 109 .
   PubMed Web of Science ®Google Scholar
• Percy , M. and Howells , R. E. 1986 . The interaction of the naphthoquinone derivative menoctone and dihydrofolate reductase inhibitors on Plasmodium falciparum in vitro . Ann. Trop. Med. Parasitol. , 80 : 359 – 360 .
   Web of Science ®Google Scholar
• Heiga , L. A. E. , Katzhendler , J. , Gean , K. F. and Bachrach. , U. 1990 . Antimalarial activity of substituted anthraquinones . Biochem. Pharmacol. , 39 : 1620 – 1623 .
   Google Scholar
• Lin , T.-S. , Zhu , L.-Y. , Xu , S.-P. , Divo , A. A. and Sartorelli , A. C. 1991 . Synthesis and antimalarial activity of 2-aziridinyl-and 2,3-bis(aziridinyl)-1,4-naphtoquinonyl sulfonate and acylate derivatives . J. Med. Chem. , 34 : 1634 – 1639 .
   PubMed Web of Science ®Google Scholar
• Golender , V. E. and Vorpagel , E. R. 1993 . “ Theory, Methods and Applications. ” . In 3D-QSAR in Drug Design. , Edited by: Kubinyi , H. 137 – 149 . Leiden : ESCOM Science Publishers .
   Google Scholar
• Vishanadhan , V. N. , Weinstein , J. N. and Ghose , A. K. 1990 . Mapping the binding site of the nucleoside transporter protein: a 3D-QSAR study . Biochem. Biophy. Acta , 1039 : 356 – 366 .
   Google Scholar
• 1993 . “ Insight II ” . San Diego : Biosym Technologies . version 2.3.0
   Google Scholar
• Stewart , J. J. P. 1990 . MOPAC: a semiempirical molecular orbital program . J. Comput. Aided Mol. Des. , 4 : 1 – 105 .
   PubMed Web of Science ®Google Scholar
• “ Apex-3D User Guidebook ” . San Diego, , CA, USA : MSI (Biosym) .
   Google Scholar