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Volumn 70, Issue 13, 2005, Pages 5103-5110

Dispiro-1,2,4-trioxane analogues of a prototype dispiro-1,2,4-trioxolane: Mechanistic comparators for artemisinin in the context of reaction pathways with iron(II)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; CARBON; FREE RADICAL POLYMERIZATION; MALARIA CONTROL; STEREOCHEMISTRY;

EID: 20844440050     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050385+     Document Type: Article
Times cited : (115)

References (57)
  • 1
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    • Klayman, D. L. Science 1985, 228, 1049-1055.
    • (1985) Science , vol.228 , pp. 1049-1055
    • Klayman, D.L.1
  • 10
    • 0037021405 scopus 로고    scopus 로고
    • Artemisinin: Mechanisms of action, resistance and toxicity
    • Meshnick, S. R. Artemisinin: Mechanisms of Action, Resistance and Toxicity. Int. J. Parasitol. 2002, 32, 1655-1660.
    • (2002) Int. J. Parasitol. , vol.32 , pp. 1655-1660
    • Meshnick, S.R.1
  • 29
    • 6444243043 scopus 로고    scopus 로고
    • (b) Ahmed, A.; Dussault, P. H. Org. Lett. 2004, 6, 3609-3611. In this paper, the same Co(thd)2 catalyst is employed as the method of choice for hydroperoxysilylation.
    • (2004) Org. Lett. , vol.6 , pp. 3609-3611
    • Ahmed, A.1    Dussault, P.H.2
  • 30
    • 20844439798 scopus 로고    scopus 로고
    • note
    • 50 of 130 ng/mL for 7 was 4-fold higher.
  • 34
    • 20844444082 scopus 로고    scopus 로고
    • note
    • 1H NMR signals appropriate for quantitation: δ 3.57 (s), 2.20 (t), and 7.08 (d), respectively.
  • 37
    • 20844448313 scopus 로고    scopus 로고
    • note
    • For 5-7, we also observed small quantities of benzaldehyde O-benzyl oxime (δ 8.14) (ref 25) that may have arisen from Fe(III) oxidation of O-benzylhydroxylamine to form benzaldehyde that subsequently reacted with O-benzylhydroxylamine.
  • 48
    • 20744460991 scopus 로고    scopus 로고
    • note
    • Conformational analysis of 4-6 using MMFF94 with the Monte Carlo method revealed that the chair conformations of the cyclohexane rings in 4-6 are the most stable conformations. Also, in both the trioxolane and trioxane rings there exist two stable conformations of the same energy. The four stable conformations of each compound were subjected to ab initio geometry optimizations via HF/6-31G*. Again, the trioxolane and trioxane rings were found to have two equal energy conformations. Consequently, only two conformations of the cyclohexane ring where the peroxide linkage was in either the axial or equatorial positions were considered.
  • 52
    • 20844458174 scopus 로고    scopus 로고
    • note
    • Alternate pathways (refs 10 and 39) to account for the formation of 28 from 27 have been proposed.
  • 54
    • 0023195486 scopus 로고
    • 2) of epiartemisinin to give mainly the secondary carbon-centered radical. (a) Acton, N.; Klayman, D. L. Planta Med. 1987, 266-268.
    • (1987) Planta Med. , pp. 266-268
    • Acton, N.1    Klayman, D.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.