Synthesis of BC-ring model of globostellatic acid X methyl ester, an anti-angiogenic substance from marine sponge

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 12, 2008, Pages 3532-3535

  Kotoku, Naoyuki ^a   Tamada, Nao ^a   Hayashi, Asami ^a   Kobayashi, Motomasa ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Allylic oxidation; Anti angiogenesis; Globostellatic acid X methyl ester; Marine sponge; Ynolate olefination

Indexed keywords

13E,17E GLOBOSTELLATIC ACID X METHYL ESTER; ALLYL COMPOUND; ESTER DERIVATIVE; ETHYLENE GLYCOL; KETONE; METHYL IODIDE; TRITERPENE DERIVATIVE;

ANTIANGIOGENIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; ENDOTHELIUM CELL; HUMAN; HUMAN CELL; LIPID OXIDATION; OLEFINATION; OXIDATION; SPONGE (PORIFERA); STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; UMBILICAL VEIN;

ANGIOGENESIS INHIBITORS; ANIMALS; CELL LINE; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; ENDOTHELIAL CELLS; HUMANS; INDONESIA; KB CELLS; MOLECULAR CONFORMATION; PORIFERA; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRITERPENES;

EID: 44649161793     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.05.018     Document Type: Article

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17. Compound 24 was obtained and evaluated as a E/Z mixture (1:1) at C-3 in the side chain, because compound 24, lacking the carbonyl group conjugated to the side chain, could not be subjected to HPLC separation due to its instability than two other analogues.
18. 3). 5: δ 7.11 (dd, 1H, J = 11.5, 15.0 Hz), 6.69 (d, 1H, J = 15.0 Hz), 6.61 (dd, 1H, J = 11.5, 15.0 Hz), 6.24 (d, 1H, J = 11.0 Hz), 5.95 (d, 1H, J = 11.0 Hz), 2.62-1.94 (m, 9H), 2.40 (s, 3H), 2.04 (s, 3H), 1.84 (br s, 6H), 1.28 (s, 3H). 23: δ 7.01 (dd, 1H, J = 11.5, 15.0 Hz), 6.71 (d, 1H, J = 15.0 Hz), 6.55 (dd, 1H, J = 11.5, 15.0 Hz), 6.20 (d, 1H, J = 11.0 Hz), 6.20 (d, 1H, J = 15.0 Hz), 5.92 (d, 1H, J = 11.0 Hz), 3.96-3.91 (m, 4H), 2.32 (s, 3H), 2.19-1.65 (m, 9H), 1.98 (s, 3H), 1.74 (br s, 6H), 1.12 (s, 3H). 24: δ 6.45 (dd, 1H, J = 11.0, 15.0 Hz), 6.25-6.13 (m, 4H), 5.91 (d, 1H, J = 11.0 Hz), 3.95-3.92 (m, 4H), 2.45-2.05 (m, 2H), 1.94-1.22 (m, 21H), 0.86 (s, 3H).
19. 50 values against HUVECs and KB 3-1 cells.