메뉴 건너뛰기




Volumn 46, Issue 20, 2003, Pages 4244-4258

Structure-activity relationships of the antimalarial agent artemisinin. 8. Design, synthesis, and CoMFA studies toward the development of artemisinin-based drugs against leishmaniasis and malaria

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYARTEMISININ; ARTEMISININ; ARTEMISININ DERIVATIVE; ARTEMISITENE; LACTONE; OCTAHYDRO 3,6ALPHA DIMETHYL 3,12 EPOXY 9ALPHA (3' PHENYLPROPYL) 12H PYRANO[4,3 J] 1,2 BENZODIOXEPIN 10(3H) ONE; OCTAHYDRO 3,6ALPHA DIMETHYL 3,12 EPOXY 9ALPHA [3' (4 N,N DIMETHYLAMINOPHENYL)PROPYL] 12H PYRANO[4,3 J] 1,2 BENZODIOXEPIN 10(3H) ONE; OCTAHYDRO 3,6ALPHA DIMETHYL 3,12 EPOXY 9ALPHA [3' [3,5 BIS(TRIFLUOROMETHYL)PHENYL]PROPYL] 12H PYRANO[4,3 J] 1,2 BENZODIOXEPIN 10(3H) ONE; OCTAHYDRO 3,6ALPHA DIMETHYL 3,12 EPOXY 9BETA (2' CYANOETHYL) 12H PYRANO[4,3 J] 1,2 BENZODIOXEPIN 10(3H) ONE; OCTAHYDRO 3,6ALPHA DIMETHYL 3,12 EPOXY 9BETA [3' (4 METHANESULFONYLPHENYL)PROPYL] 12H PYRANO[4,3 J] 1,2 BENZODIOXEPIN 10(3H) ONE; OCTAHYDRO 3,6ALPHA DIMETHYL 3,12 EPOXY 9BETA [3' (4 METHYLTHIOPHENYL)PROPYL] 12H PYRANO[4,3 J] 1,2 BENZODIOXEPIN 10(3H) ONE; OCTAHYDRO 3,6ALPHA DIMETHYL 3,12 EPOXY 9BETA [3' (4 N,N DIMETHYLAMINOPHENYL)PROPYL] 12H PYRANO[4,3 J] 1,2 BENZODIOXEPIN 10(3H) ONE; UNCLASSIFIED DRUG;

EID: 0141680852     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030181q     Document Type: Article
Times cited : (104)

References (75)
  • 1
    • 0001123285 scopus 로고    scopus 로고
    • Antimalarial activity of artemisinin (qinghaosu) and related trioxanes: Mechanism(s) of Action
    • Cumming, J. N.; Ploypradith, P.; Posner, G. H. Antimalarial activity of artemisinin (qinghaosu) and related trioxanes: Mechanism(s) of Action. Adv. Pharmacol. (San Diego) 1997, 37, 253-297.
    • (1997) Adv. Pharmacol. (San Diego) , vol.37 , pp. 253-297
    • Cumming, J.N.1    Ploypradith, P.2    Posner, G.H.3
  • 2
    • 0000531811 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships of peroxidic antimalarials based on artemisinin
    • Avery, M. A.; Alvim-Gaston, M.; Woolfrey, J. R. Synthesis and structure-activity relationships of peroxidic antimalarials based on artemisinin. Adv. Med. Chem. 1999, 4, 125-217.
    • (1999) Adv. Med. Chem. , vol.4 , pp. 125-217
    • Avery, M.A.1    Alvim-Gaston, M.2    Woolfrey, J.R.3
  • 3
    • 0021948029 scopus 로고
    • Qinghaosu (artemisinin): An antimalarial drug from China
    • Klayman, D. L. Qinghaosu (artemisinin): An antimalarial drug from China. Science 1985, 228, 1049-1055.
    • (1985) Science , vol.228 , pp. 1049-1055
    • Klayman, D.L.1
  • 4
    • 0036009409 scopus 로고    scopus 로고
    • From mechanistic studies on artemisinin derivatives to new modular antimalarial drugs
    • Robert, A.; Dechy-Cabaret, O.; Cazelles, J.; Meunier, B. From mechanistic studies on artemisinin derivatives to new modular antimalarial drugs. Acc. Chem. Res. 2002, 35, 167-174.
    • (2002) Acc. Chem. Res. , vol.35 , pp. 167-174
    • Robert, A.1    Dechy-Cabaret, O.2    Cazelles, J.3    Meunier, B.4
  • 5
    • 0036001107 scopus 로고    scopus 로고
    • How might qinghaosu (artemisinin) and related compounds kill the intraerythrocytic malaria parasite? A chemist's view
    • Wu, Y. How might qinghaosu (artemisinin) and related compounds kill the intraerythrocytic malaria parasite? A chemist's view. Acc. Chem. Res. 2002, 35, 255-259.
    • (2002) Acc. Chem. Res. , vol.35 , pp. 255-259
    • Wu, Y.1
  • 6
    • 0037039929 scopus 로고    scopus 로고
    • Alkylating capacity and reaction products of antimalarial trioxanes after activation by a heme model
    • Cazelles, J.; Robert, A.; Meunier, B. Alkylating capacity and reaction products of antimalarial trioxanes after activation by a heme model. J. Org. Chem. 2002, 67, 609-619.
    • (2002) J. Org. Chem. , vol.67 , pp. 609-619
    • Cazelles, J.1    Robert, A.2    Meunier, B.3
  • 7
    • 0034700205 scopus 로고    scopus 로고
    • A possible antimalarial action mode of qinghaosu (artemisinin) series compounds. Alkylation of reduced glutathione by C-centered primary radicals produced from antimalarial compound qinghaosu and 12-(2,4-dimethoxyphenyl)-12-deoxoqinghaosu
    • Wang, D.-Y.; Wu, Y.-L. A possible antimalarial action mode of qinghaosu (artemisinin) series compounds. Alkylation of reduced glutathione by C-centered primary radicals produced from antimalarial compound qinghaosu and 12-(2,4-dimethoxyphenyl)-12-deoxoqinghaosu. J. Chem. Soc. Chem. Commun. 2000, 22, 2193-2194.
    • (2000) J. Chem. Soc. Chem. Commun. , vol.22 , pp. 2193-2194
    • Wang, D.-Y.1    Wu, Y.-L.2
  • 8
    • 0033516474 scopus 로고    scopus 로고
    • Artemisinin, an endoperoxide antimalarial, disrupts the hemoglobin catabolism and heme detoxification systems in malarial parasite
    • Pandey A. V.; Tekwani, B. L.; Sing, R. L.; Chauhan, V. S. Artemisinin, an endoperoxide antimalarial, disrupts the hemoglobin catabolism and heme detoxification systems in malarial parasite. J. Biol. Chem. 1999, 274, 19383-19388.
    • (1999) J. Biol. Chem. , vol.274 , pp. 19383-19388
    • Pandey, A.V.1    Tekwani, B.L.2    Sing, R.L.3    Chauhan, V.S.4
  • 9
    • 0032522115 scopus 로고    scopus 로고
    • Unified mechanistic framework for the Fe(II)-induced cleavage of qinghaosu and derivatives/analogues. The first spin-trapping evidence for the previously postulated secondary C-4 radical
    • Wu, W.-M.; Wu, Y.; Wu, Y.-L.; Yao Z.-J.; Zhou, C.-M.; Li, Y.; Shan, F. Unified mechanistic framework for the Fe(II)-induced cleavage of qinghaosu and derivatives/analogues. The first spin-trapping evidence for the previously postulated secondary C-4 radical. J. Am. Chem. Soc. 1998, 120, 3316-3325.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 3316-3325
    • Wu, W.-M.1    Wu, Y.2    Wu, Y.-L.3    Yao, Z.-J.4    Zhou, C.-M.5    Li, Y.6    Shan, F.7
  • 10
    • 0031041266 scopus 로고    scopus 로고
    • Correlation of antimalarial activity of artemisinin derivatives with binding affinity with ferroprotoporphyrin IX
    • Paitayatat, S.; Tarmchompoo, B.; Thebtatranonth, Y.; Yuthavong, Y. Correlation of antimalarial activity of artemisinin derivatives with binding affinity with ferroprotoporphyrin IX. J. Med. Chem. 1997, 40, 633-638.
    • (1997) J. Med. Chem. , vol.40 , pp. 633-638
    • Paitayatat, S.1    Tarmchompoo, B.2    Thebtatranonth, Y.3    Yuthavong, Y.4
  • 11
    • 0001815264 scopus 로고    scopus 로고
    • From qinghao, marvelous herb of antiquity, to the antimalarial trioxane qinghaosu-Some remarkable new chemistry
    • Haynes, R. K.; Vonwiller, S. C. From qinghao, marvelous herb of antiquity, to the antimalarial trioxane qinghaosu-Some remarkable new chemistry. Acc. Chem. Res. 1997, 30, 73-79.
    • (1997) Acc. Chem. Res. , vol.30 , pp. 73-79
    • Haynes, R.K.1    Vonwiller, S.C.2
  • 13
    • 0033580871 scopus 로고    scopus 로고
    • Ring opening of artemisinin (qinghaosu) and dihydroartemisinin and interception of the open hydroperoxides with formation of N-oxides-A chemical model for antimalarial action
    • (b) Haynes, R. K.; Hung-On, P. H.; Voerste, A. Ring opening of artemisinin (qinghaosu) and dihydroartemisinin and interception of the open hydroperoxides with formation of N-oxides-A chemical model for antimalarial action. Tetrahedron Lett. 1999, 40, 4715-4718.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 4715-4718
    • Haynes, R.K.1    Hung-On, P.H.2    Voerste, A.3
  • 14
    • 0032568952 scopus 로고    scopus 로고
    • The Plasmodium falciparum translationally controlled tumor protein homologue and its reaction with the antimalarial drug artemisinin
    • Bhisutthibhan, J.; Pan, X. Q.; Hossler, P. A.; Walker, D. J. The Plasmodium falciparum translationally controlled tumor protein homologue and its reaction with the antimalarial drug artemisinin. J. Biol. Chem. 1998, 273, 16192-16198.
    • (1998) J. Biol. Chem. , vol.273 , pp. 16192-16198
    • Bhisutthibhan, J.1    Pan, X.Q.2    Hossler, P.A.3    Walker, D.J.4
  • 16
    • 0037154773 scopus 로고    scopus 로고
    • Anhydrodihydroartemisinin and its 10-trifluoromethyl analogue: Access to novel D-ring-contracted artemisinin trifluoromethyl ketones
    • Grellepois, F.; Chorki, F.; Crousse, B.; Ourevitch, M.; Bonnet-Delpon, D.; Jean-Pierre, B. Anhydrodihydroartemisinin and its 10-trifluoromethyl analogue: Access to novel D-ring-contracted artemisinin trifluoromethyl ketones. J. Org. Chem. 2002, 67, 1253-1260.
    • (2002) J. Org. Chem. , vol.67 , pp. 1253-1260
    • Grellepois, F.1    Chorki, F.2    Crousse, B.3    Ourevitch, M.4    Bonnet-Delpon, D.5    Jean-Pierre, B.6
  • 17
    • 0037168048 scopus 로고    scopus 로고
    • Synthesis, stability, and antimalarial activity of new hydrolytically stable and water-soluble (+)-Deoxoartelinic acid
    • Jung, M.; Lee, K.; Kendrick, H.; Robinson, B. L.; Croft, S. L. Synthesis, stability, and antimalarial activity of new hydrolytically stable and water-soluble (+)-Deoxoartelinic acid. J. Med. Chem. 2002, 45, 4940-4944.
    • (2002) J. Med. Chem. , vol.45 , pp. 4940-4944
    • Jung, M.1    Lee, K.2    Kendrick, H.3    Robinson, B.L.4    Croft, S.L.5
  • 18
    • 0037194666 scopus 로고    scopus 로고
    • Orally active, water-soluble antimalarial 3-Aryltrioxanes: Short synthesis and preclinical efficacy testing in rodents
    • Posner, G. H.; Jeon, H. B.; Ploypradith, P.; Paik, I. H.; Borstnik, K.; Xie, S.; Shapiro, T. A. Orally active, water-soluble antimalarial 3-Aryltrioxanes: Short synthesis and preclinical efficacy testing in rodents. J. Med. Chem. 2002, 45, 3824-3828.
    • (2002) J. Med. Chem. , vol.45 , pp. 3824-3828
    • Posner, G.H.1    Jeon, H.B.2    Ploypradith, P.3    Paik, I.H.4    Borstnik, K.5    Xie, S.6    Shapiro, T.A.7
  • 19
    • 0037186497 scopus 로고    scopus 로고
    • Mechanism-based design of parasite-targeted artemisinin derivatives: Synthesis and antimalarial activity of new diamine containing analogues
    • Hindley, S.; Ward, S. A.; Storr, R. C.; Searle, N. L.; Bray, P. G.; Park, B. K.; Davies, J.; O'Neill, P. M. Mechanism-based design of parasite-targeted artemisinin derivatives: Synthesis and antimalarial activity of new diamine containing analogues. J. Med. Chem. 2002, 45, 1052-1063.
    • (2002) J. Med. Chem. , vol.45 , pp. 1052-1063
    • Hindley, S.1    Ward, S.A.2    Storr, R.C.3    Searle, N.L.4    Bray, P.G.5    Park, B.K.6    Davies, J.7    O'Neill, P.M.8
  • 21
    • 0035832054 scopus 로고    scopus 로고
    • Michael addition of artemisitene
    • Liao, X.-B.; Han, J.-Y.; Li, Y. Michael addition of artemisitene. Tetrahedron Lett. 2001, 42, 2843-2845.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2843-2845
    • Liao, X.-B.1    Han, J.-Y.2    Li, Y.3
  • 23
    • 0034786625 scopus 로고    scopus 로고
    • Synthesis of new artemisinin analogues from artemisinic acid modified at C-3 and C-13 and their antimalarial activity
    • (a) Han, J.; Lee, J. G.; Min, S. S.; Park, S. H.; Angerhofer, C. K.; Cordell, G. A.; Kim, S. U. Synthesis of new artemisinin analogues from artemisinic acid modified at C-3 and C-13 and their antimalarial activity. J. Nat. Prod. 2001, 64, 1201-1205.
    • (2001) J. Nat. Prod. , vol.64 , pp. 1201-1205
    • Han, J.1    Lee, J.G.2    Min, S.S.3    Park, S.H.4    Angerhofer, C.K.5    Cordell, G.A.6    Kim, S.U.7
  • 24
    • 0035924213 scopus 로고    scopus 로고
    • C-16 artemisinin derivatives and their antimalarial and cytotoxic activities: Syntheses of artemisinin monomers, dimers, trimers, and tetramers by nucleophilic additions to artemisitene
    • (b) Ekthawatchai, S.; Kamchonwongpaisan, S.; Kongsaeree, P.; Tarnchompoo, B.; Thebtaranonth, Y.; Yuthavong, Y. C-16 artemisinin derivatives and their antimalarial and cytotoxic activities: Syntheses of artemisinin monomers, dimers, trimers, and tetramers by nucleophilic additions to artemisitene. J. Med. Chem. 2001, 44, 4688-4695.
    • (2001) J. Med. Chem. , vol.44 , pp. 4688-4695
    • Ekthawatchai, S.1    Kamchonwongpaisan, S.2    Kongsaeree, P.3    Tarnchompoo, B.4    Thebtaranonth, Y.5    Yuthavong, Y.6
  • 25
    • 0037115230 scopus 로고    scopus 로고
    • Efficacy and safety of Dihydroartemisinin-Piperaquine (Artekin) in Cambodian children and Adults with uncomplicated Falciparum malaria
    • and references therein
    • Denis, M. B.; Davis, T. M. E.; Hewitt, S.; Incardona, S.; Nimol, K.; Fandeur, T.; Poravuth, Y.; Lim, C.; Socheat, D. Efficacy and safety of Dihydroartemisinin-Piperaquine (Artekin) in Cambodian children and Adults with uncomplicated Falciparum malaria. Clin. Infect. Dis. 2002, 35, 1469-1476, and references therein.
    • (2002) Clin. Infect. Dis. , vol.35 , pp. 1469-1476
    • Denis, M.B.1    Davis, T.M.E.2    Hewitt, S.3    Incardona, S.4    Nimol, K.5    Fandeur, T.6    Poravuth, Y.7    Lim, C.8    Socheat, D.9
  • 29
    • 0025646009 scopus 로고
    • Metabolism of antimalarial sesquiterpene lactones
    • (d) Lee, I. S.; Hufford, C. D. Metabolism of antimalarial sesquiterpene lactones. Pharm., Ther. 1990, 48, 345-355.
    • (1990) Pharm., Ther. , vol.48 , pp. 345-355
    • Lee, I.S.1    Hufford, C.D.2
  • 30
    • 0035194318 scopus 로고    scopus 로고
    • Selective toxicity of dihydroartemisinin and holotransferrin toward human breast cancer cells
    • Singh, N. P.; Lai, H. Selective toxicity of dihydroartemisinin and holotransferrin toward human breast cancer cells. Life Sci. 2001, 70, 49-56.
    • (2001) Life Sci. , vol.70 , pp. 49-56
    • Singh, N.P.1    Lai, H.2
  • 35
    • 0030938872 scopus 로고    scopus 로고
    • Synthesis and cytotoxicity of novel artemisinin analogues
    • Jung, M. Synthesis and cytotoxicity of novel artemisinin analogues. Bioorg. Med. Chem. Lett. 1997, 7, 1091-1094.
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 1091-1094
    • Jung, M.1
  • 36
    • 0035850259 scopus 로고    scopus 로고
    • Antifungal activity of Artemisia annua endophyte cultures against phytopathogenic fungi
    • Liu, C. H.; Zou, W. X.; Lu, H.; Tan, R. X. Antifungal activity of Artemisia annua endophyte cultures against phytopathogenic fungi. J. Biotechnol. 2001, 88, 277-282.
    • (2001) J. Biotechnol. , vol.88 , pp. 277-282
    • Liu, C.H.1    Zou, W.X.2    Lu, H.3    Tan, R.X.4
  • 37
    • 0001109199 scopus 로고    scopus 로고
    • Antimicrobial activity of artemisinin and its precursors
    • Vikas, D.; Rao, P. S.; Lakshmi, N. M. Antimicrobial activity of artemisinin and its precursors. Curr. Sci. 2000, 78, 709-713.
    • (2000) Curr. Sci. , vol.78 , pp. 709-713
    • Vikas, D.1    Rao, P.S.2    Lakshmi, N.M.3
  • 38
    • 0027523748 scopus 로고
    • Effects of qinghaosu (artemisinin) and its derivatives on experimental cutaneous leishmaniasis
    • Yang, D. M.; Liew, F. Y. Effects of qinghaosu (artemisinin) and its derivatives on experimental cutaneous leishmaniasis. Parasitology 1993, 106, 7-11.
    • (1993) Parasitology. , vol.106 , pp. 7-11
    • Yang, D.M.1    Liew, F.Y.2
  • 39
    • 0019349091 scopus 로고
    • Leishmaniasis
    • Kern, P. Leishmaniasis. Antibiot. Chemother. 1981, 30, 203-223.
    • (1981) Antibiot. Chemother. , vol.30 , pp. 203-223
    • Kern, P.1
  • 41
    • 0033369324 scopus 로고    scopus 로고
    • Recent strategies for the chemotherapy of visceral leishmaniasis
    • Loiseau, P. M.; Bories, C. Recent strategies for the chemotherapy of visceral leishmaniasis. Curr. Opin. Infect. Dis. 1999, 12, 559-564.
    • (1999) Curr. Opin. Infect. Dis. , vol.12 , pp. 559-564
    • Loiseau, P.M.1    Bories, C.2
  • 43
    • 0034098340 scopus 로고    scopus 로고
    • HIV-Leishmania infantum co-infection: Humoral and cellular immune responses to the parasite after chemotherapy
    • Moreno, J.; Canavate, C.; Chamizo, C.; Laguna, F.; Alvar, J. HIV-Leishmania infantum co-infection: Humoral and cellular immune responses to the parasite after chemotherapy. Trans R. Soc. Trop. Med. Hyg. 2000, 94, 328-332.
    • (2000) Trans R. Soc. Trop. Med. Hyg. , vol.94 , pp. 328-332
    • Moreno, J.1    Canavate, C.2    Chamizo, C.3    Laguna, F.4    Alvar, J.5
  • 45
    • 0023759929 scopus 로고
    • Leishmania mexicana: Chemistry and biochemistry of sodium stibogluconate (Pentostam)
    • Berman, J. D.; Grog, I. M. Leishmania mexicana: Chemistry and biochemistry of sodium stibogluconate (Pentostam). Exp. Parasitol. 1988, 67, 96-103.
    • (1988) Exp. Parasitol. , vol.67 , pp. 96-103
    • Berman, J.D.1    Grog, I.M.2
  • 46
    • 0028822932 scopus 로고
    • New mechanisms of drug resistance in parasitic protozoa
    • Brost, P.; Ouellette, M. New mechanisms of drug resistance in parasitic protozoa. Annu. Rev. Microbiol. 1995, 49, 427-460.
    • (1995) Annu. Rev. Microbiol. , vol.49 , pp. 427-460
    • Brost, P.1    Ouellette, M.2
  • 47
    • 0027249951 scopus 로고
    • Practical progress and new drugs for changing patterns of leishmaniasis
    • Olliaro, P. L.; Bryceson, A. D. M. Practical progress and new drugs for changing patterns of leishmaniasis. Parasitol. Today 1993, 9, 323-328.
    • (1993) Parasitol. Today , vol.9 , pp. 323-328
    • Olliaro, P.L.1    Bryceson, A.D.M.2
  • 48
    • 0028641193 scopus 로고
    • Comparison of glucose versus fat emulsion in the preparation of amphotericin B for use in kala-azar
    • Thakur, C. P. Comparison of glucose versus fat emulsion in the preparation of amphotericin B for use in kala-azar. Trans R. Soc. Trop. Med. Hyg. 1994, 88, 689-699.
    • (1994) Trans R. Soc. Trop. Med. Hyg. , vol.88 , pp. 689-699
    • Thakur, C.P.1
  • 50
    • 0032969901 scopus 로고    scopus 로고
    • Current progress in the chemistry, medicinal chemistry and drug design of artemisinin based antimalarials
    • (a) Vroman, J. A.; Alvim-Gaston, M.; Avery, M. A. Current progress in the chemistry, medicinal chemistry and drug design of artemisinin based antimalarials. Curr. Pharm. Design 1999, 5, 101-138.
    • (1999) Curr. Pharm. Design , vol.5 , pp. 101-138
    • Vroman, J.A.1    Alvim-Gaston, M.2    Avery, M.A.3
  • 51
    • 0031978237 scopus 로고    scopus 로고
    • Conjugate addition of a cyano-Gilman cuprate to an acrylic acid: Homologation of artemisinic acid and subsequent conversion to 16-butylartemisinin
    • (b) Vroman, J. A.; Elsohly, H. N.; Avery, M. A. Conjugate addition of a cyano-Gilman cuprate to an acrylic acid: Homologation of artemisinic acid and subsequent conversion to 16-butylartemisinin. Synth. Commun. 1998, 28, 1555-1562.
    • (1998) Synth. Commun. , vol.28 , pp. 1555-1562
    • Vroman, J.A.1    Elsohly, H.N.2    Avery, M.A.3
  • 52
    • 0030003137 scopus 로고    scopus 로고
    • Structure-activity relationships of the antimalarial agent artemisinin. 4. Effect of substitution at C-3
    • (c) Avery, M. A.; Mehrotra, S.; Bonk, J. D.; Vroman, J. A.; Goins, D. K. ; Miller, R. Structure-activity relationships of the antimalarial agent artemisinin. 4. Effect of substitution at C-3. J. Med. Chem. 1996, 39, 2900-2906.
    • (1996) J. Med. Chem. , vol.39 , pp. 2900-2906
    • Avery, M.A.1    Mehrotra, S.2    Bonk, J.D.3    Vroman, J.A.4    Goins, D.K.5    Miller, R.6
  • 53
    • 0037122747 scopus 로고    scopus 로고
    • Structure-activity relationships of the antimalarial agent artemisinin. 6. The development of predictive in vitro potency models using CoMFA and HQSAR methodologies
    • (d) Avery, M. A.; Alvim-Gaston, M.; Rodrigues, C. R.; Barreiro, E. J.; Cohen, F. E.; Sabnis, Y. A.; Woolfrey, J. R. Structure-activity relationships of the antimalarial agent artemisinin. 6. The development of predictive in vitro potency models using CoMFA and HQSAR methodologies. J. Med. Chem. 2002, 45, 292-303.
    • (2002) J. Med. Chem. , vol.45 , pp. 292-303
    • Avery, M.A.1    Alvim-Gaston, M.2    Rodrigues, C.R.3    Barreiro, E.J.4    Cohen, F.E.5    Sabnis, Y.A.6    Woolfrey, J.R.7
  • 54
    • 0037068498 scopus 로고    scopus 로고
    • Structure-activity relationships of the antimalarial agent artemisinin. 7. Direct modification of (+)-artemisinin and in vivo antimalarial screening of new, potential preclinical antimalarial candidates
    • (a) Avery, M. A.; Alvim-Gaston, M.; Vroman, J. A.; Wu, B.; Ager, A.; Peters, W.; Robinson, B. L.; Charman, W. Structure-activity relationships of the antimalarial agent artemisinin. 7. Direct modification of (+)-artemisinin and in vivo antimalarial screening of new, potential preclinical antimalarial candidates. J. Med. Chem. 2002, 45, 4321-4335.
    • (2002) J. Med. Chem. , vol.45 , pp. 4321-4335
    • Avery, M.A.1    Alvim-Gaston, M.2    Vroman, J.A.3    Wu, B.4    Ager, A.5    Peters, W.6    Robinson, B.L.7    Charman, W.8
  • 55
    • 0027725172 scopus 로고
    • Structure-activity relationships of the antimalarial agent artemisinin. 1. Synthesis and comparative molecular field analysis of C-9 analogues of artemisinin and 10-deoxoartemisinin
    • (b) Avery, M. A.; Gao, F.; Chong, W. K. M.; Mehrotra, Sanjiv; Milhous, W. K., Structure-activity relationships of the antimalarial agent artemisinin. 1. Synthesis and comparative molecular field analysis of C-9 analogues of artemisinin and 10-deoxoartemisinin. J. Med. Chem. 1993, 36, 26, 4264-75.
    • (1993) J. Med. Chem. , vol.36 , pp. 4264-4275
    • Avery, M.A.1    Gao, F.2    Chong, W.K.M.3    Mehrotra, S.4    Milhous, W.K.5
  • 56
    • 0029845745 scopus 로고    scopus 로고
    • Structure-activity relationships of the antimalarial agent artemisinin. 5. Analogues of 10-deoxoartemisinin substituted at C-3 and C-9
    • (c) Avery, M. A.; Mehrotra, S.; Theresa, L. J.; Bonk, J. D.; Vroman, J. A.; Miller R. Structure-activity relationships of the antimalarial agent artemisinin. 5. Analogues of 10-deoxoartemisinin substituted at C-3 and C-9. J. Med. Chem. 1996, 39, 4149-4155.
    • (1996) J. Med. Chem. , vol.39 , pp. 4149-4155
    • Avery, M.A.1    Mehrotra, S.2    Theresa, L.J.3    Bonk, J.D.4    Vroman, J.A.5    Miller, R.6
  • 57
    • 0029619657 scopus 로고
    • Structure-activity relationships of the antimalarial agent artemisinin. 2. Effect of heteroatom substitution at O-11: Synthesis and bioassay of N-alkyl-11-aza-9-desmethylartemisinins
    • (d) Avery, M. A.; Bonk, J. D.; Chong, W. K. M.; Mehrotra, S.; Miller, R. ; Milhous, W.; Goins, D. K.; Venkatesan, S.; Wyandt, C.; Khan, I.; Avery, B. A. Structure-activity relationships of the antimalarial agent artemisinin. 2. Effect of heteroatom substitution at O-11: Synthesis and bioassay of N-alkyl-11-aza-9-desmethylartemisinins. J. Med. Chem. 1995, 38, 26, 5038-44.
    • (1995) J. Med. Chem. , vol.38 , pp. 5038-5044
    • Avery, M.A.1    Bonk, J.D.2    Chong, W.K.M.3    Mehrotra, S.4    Miller, R.5    Milhous, W.6    Goins, D.K.7    Venkatesan, S.8    Wyandt, C.9    Khan, I.10    Avery, B.A.11
  • 58
    • 0025240909 scopus 로고
    • Synthesis of (+)-8a,9-secoartemisinin and related analogues
    • (e) Avery, M. A.; Chong, W. K. M.; Detre, G. Synthesis of (+)-8a,9-secoartemisinin and related analogues. Tetrahedron Lett. 1990, 31, 13, 1799-802.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 1799-1802
    • Avery, M.A.1    Chong, W.K.M.2    Detre, G.3
  • 59
    • 0029042289 scopus 로고
    • Replacement of the nonperoxidic trioxane oxygen atom of artemisinin by carbon: Total synthesis of (+)-13-carbaartemisinin and related structures
    • (f) Avery, M. A.; Fan, P.; Karle, Jean, M.; Miller, R.; Goins, K. Replacement of the nonperoxidic trioxane oxygen atom of artemisinin by carbon: Total synthesis of (+)-13-carbaartemisinin and related structures. Tetrahedron Lett, 1995, 36, 23, 3965-8.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3965-3968
    • Avery, M.A.1    Fan, P.2    Karle, J.M.3    Miller, R.4    Goins, K.5
  • 60
    • 0025011828 scopus 로고
    • Tricyclic analogue of artemisinin: Synthesis and antimalarial activity of (+)-4,5-secoartemisinin and (-)-5-nor-4,5-secoartemisinin
    • (g) Avery, M. A.; Chong, W. K. M.; Bupp, J. E. Tricyclic analogue of artemisinin: Synthesis and antimalarial activity of (+)-4,5-secoartemisinin and (-)-5-nor-4,5-secoartemisinin. J. Chem. Soc. Chem. Commun. 1990, 21, 1487-9.
    • (1990) J. Chem. Soc. Chem. Commun. , vol.21 , pp. 1487-1489
    • Avery, M.A.1    Chong, W.K.M.2    Bupp, J.E.3
  • 61
    • 0141558051 scopus 로고    scopus 로고
    • Preparation of antimalarial analogues of artemisinin
    • WO 9114689 A1 19911003, 1991
    • (h) Avery, M. A.; Chong, W. K. M.; Bupp, J. Preparation of antimalarial analogues of artemisinin. WO 9114689 A1 19911003, 1991. Chem. Abstr. 117, 48951.
    • Chem. Abstr. , vol.117 , pp. 48951
    • Avery, M.A.1    Chong, W.K.M.2    Bupp, J.3
  • 63
    • 0035077738 scopus 로고    scopus 로고
    • DNA transformation of Leishmania infantum axenic amastigotes and their use in drug screening
    • (a) Sereno, D.; Roy, G.; Lemesre, J. L.; Papadopoulou, B.; Ouellette, M. DNA transformation of Leishmania infantum axenic amastigotes and their use in drug screening. Antimicrob. Agents Chemother. 2001, 45, 1168-1173.
    • (2001) Antimicrob. Agents Chemother. , vol.45 , pp. 1168-1173
    • Sereno, D.1    Roy, G.2    Lemesre, J.L.3    Papadopoulou, B.4    Ouellette, M.5
  • 64
    • 0025784808 scopus 로고
    • Cytotoxicity of T2 toxin and its metabolites with the neutral red cell viability assay
    • (b) Babich, H.; Borenfreund, E. Cytotoxicity of T2 toxin and its metabolites with the neutral red cell viability assay. App. Envt Microbiol. 1991, 57, 2101-2103.
    • (1991) App. Envt Microbiol. , vol.57 , pp. 2101-2103
    • Babich, H.1    Borenfreund, E.2
  • 65
    • 0032262632 scopus 로고    scopus 로고
    • Structure, absolute configuration, and conformation of the antimalarial compound, artemisinin
    • Lisgarten, J. N.; Potter, B. S.; Bantuzeko, C.; Palmer, R. A. Structure, absolute configuration, and conformation of the antimalarial compound, artemisinin. J. Chem. Crystallogr. 1998, 28, 539-543.
    • (1998) J. Chem. Crystallogr. , vol.28 , pp. 539-543
    • Lisgarten, J.N.1    Potter, B.S.2    Bantuzeko, C.3    Palmer, R.A.4
  • 67
    • 49149147973 scopus 로고
    • Iterative partial equalization of orbital electronegativity: A rapid access to atomic charges
    • Gasteiger, J.; Marsili, M. Iterative partial equalization of orbital electronegativity: A rapid access to atomic charges. Tetrahedron 1980, 36, 3219-3222.
    • (1980) Tetrahedron , vol.36 , pp. 3219-3222
    • Gasteiger, J.1    Marsili, M.2
  • 69
    • 0027672324 scopus 로고
    • Sample-distance partial least squares: PLS optimized for many variables, with application to CoMFA
    • Bush, B. L.; Nachbar, R. B., Jr. Sample-distance partial least squares: PLS optimized for many variables, with application to CoMFA. J. Comput-Aided Mol. Des. 1993, 7, 587-619.
    • (1993) J. Comput-Aided Mol. Des. , vol.7 , pp. 587-619
    • Bush, B.L.1    Nachbar R.B., Jr.2
  • 70
    • 0029655006 scopus 로고
    • 2-guided region selection for comparative molecular field analysis: A simple method to achieve consistent results
    • 2-guided region selection for comparative molecular field analysis: A simple method to achieve consistent results. J. Med. Chem, 1995, 38, 1060-1066.
    • (1995) J. Med. Chem. , vol.38 , pp. 1060-1066
    • Cho, S.J.1    Tropsha, A.2
  • 71
    • 0542427980 scopus 로고    scopus 로고
    • 2 guided region selection for CoMFA studies
    • Kubinyi, H., Folkers, G., Martin, Y. C., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands
    • 2 guided region selection for CoMFA studies. In 3D QSAR methodology: CoMFA and related approaches; Kubinyi, H., Folkers, G., Martin, Y. C., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1998; Vol. III, pp 57-69.
    • (1998) 3D QSAR Methodology: CoMFA and Related Approaches , vol.3 , pp. 57-69
    • Tropsha, A.1    Cho, S.J.2
  • 72
    • 84987100711 scopus 로고
    • Crossvalidation, bootstrapping, and partial least squares Compared with multiple regression in conventional QSAR studies
    • Cramer, R. D., III; Bunce, J. D.; Patterson, D. E. Crossvalidation, bootstrapping, and partial least squares Compared with multiple regression in conventional QSAR studies. Quant. Struct.-Act. Relat. 1988, 7, 18-25.
    • (1988) Quant. Struct.-Act. Relat. , vol.7 , pp. 18-25
    • Cramer R.D. III1    Bunce, J.D.2    Patterson, D.E.3
  • 73
    • 0032011824 scopus 로고    scopus 로고
    • Comparison of 3D quantitative structure-activity relationship models: Analysis of the in vitro antimalarial activity of 154 artemisinin analogues by hypothetical active-site lattice and comparative molecular field analysis
    • Woolfrey, J. R.; Avery, M. A.; Doweyko, A. M. Comparison of 3D quantitative structure-activity relationship models: Analysis of the in vitro antimalarial activity of 154 artemisinin analogues by hypothetical active-site lattice and comparative molecular field analysis. J. Comput-Aided. Mol. Des. 1998, 12, 165-181.
    • (1998) J. Comput-Aided. Mol. Des. , vol.12 , pp. 165-181
    • Woolfrey, J.R.1    Avery, M.A.2    Doweyko, A.M.3
  • 74
    • 0036315633 scopus 로고    scopus 로고
    • Molecular docking and 3-D QSAR studies on the possible antimalarial mechanism of artemisinin analogues
    • Cheng, F.; Shen, J.; Luo, X.; Zhu, W.; Gu, J.; Ji, R.; Jiang, H.; Chen, K. Molecular docking and 3-D QSAR studies on the possible antimalarial mechanism of artemisinin analogues. Bioorg. Med. Chem. 2002, 10, 2883-2891.
    • (2002) Bioorg. Med. Chem. , vol.10 , pp. 2883-2891
    • Cheng, F.1    Shen, J.2    Luo, X.3    Zhu, W.4    Gu, J.5    Ji, R.6    Jiang, H.7    Chen, K.8
  • 75
    • 0034952056 scopus 로고    scopus 로고
    • Dose-dependent differential effect of hemin on protein synthesis and cell proliferation in Leishmania donovani promastigots cultures in vitro
    • Pal, J. K.; Purandare, M. J. Dose-dependent differential effect of hemin on protein synthesis and cell proliferation in Leishmania donovani promastigots cultures in vitro. J. Biosci. (Indian Acad. Sci.) 2001, 26, 225-231.
    • (2001) J. Biosci. (Indian Acad. Sci.) , vol.26 , pp. 225-231
    • Pal, J.K.1    Purandare, M.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.