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Volumn 57, Issue 20, 2001, Pages 4323-4336

Synthesis of stable analogs in blood and conformational analysis of arenastatin A, a potent cytotoxic spongean depsipeptide

Author keywords

Arenastatin A; Depsipeptide; Marine metabolite; Restrained molecular dynamics

Indexed keywords

ARENASTATIN A; ARENASTATIN A DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0035858729     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)00339-8     Document Type: Article
Times cited : (16)

References (19)
  • 12
    • 0342393708 scopus 로고    scopus 로고
    • note
    • The stereochemistry of the epoxy moiety of 3 was established by comparison of the proton chemical shifts due to the 8-H and 6-Me group from the same behavior observed between arenastatin A (1, 8-H: δ 3.68, 6-Me: δ 1.14) and the α-epoxy isomer of 1 (δ 3.59, 1.05). Namely, an obvious difference in chemical shifts of the 8-H and 6-Me groups was observed; the signals of 3 appeared in lower field (δ 3.69, 1.13) than those (δ 3.59, 1.04) of the α-isomer. This physicochemical property enabled us to establish stereochemistry on the 7, 8-epoxy moieties of the other analogs (4-6); 4: δ 3.67, 1.14, the α-epoxy isomer of 4: δ 3.59, 1.03, 5: δ 3.77, 1.11, the α-epoxy isomer of 5: δ 3.57, 1.05, 6: δ 3.68, 1.13, the α-epoxy isomer of 6: δ 3.58, 1.05.
  • 16
    • 0342828443 scopus 로고    scopus 로고
    • note
    • 6-DMSO are listed. δ: 8.27 (1H, d, J=8.6 Hz, 15-NH), 8.21 (1H, d, J=7.9 Hz, 24-NH), 7.38-7.26 (5H, m, 10, 11, 12-H), 7.28 (1H, m, 22-NH), 7.10 (2H, d, J=8.6 Hz, 27-H), 6.80 (2H, d, J=8.6 Hz, 28-H), 6.36 (1H, ddd, J=4.3, 11.6, 15.3 Hz, 3-H), 5.75 (1H, d, J=15.3 Hz, 2-H), 5.10 (1H, brdd, J=5.5, 11.6 Hz, 5-H), 4.35 (1H, ddd, J=5.5, 8.6, 9.7 Hz, 15-H), 4.18 (1H, ddd, J=3.7, 7.9, 11.6 Hz, 24-H), 3.87 (1H, d, J=1.9 Hz, 8-H), 3.69 (3H, s, 29-OMe), 3.50 (1H, m, 22-Ha), 2.96 (3H, m, 7-H, 22-Hb, 25-Ha), 2.62 (2H, m, 4-Ha, 25-Hb), 2.24 (2H, m, 4-Hb, 21-Ha), 2.13 (1H, m, 21-Hb), 1.79 (1H, q-like, J=ca. 7 Hz, 6-H), 1.47 (1H, m, 17-H), 1.28 (1H, m, 16-Ha), 1.11 (1H, m, 16-Hb), 1.03 (3H, d, J=6.8 Hz, 13-H), 0.75, 0.74 (both 3H, d, J=6.7 Hz, 18, 19-H).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.