Corrigendum

Pettit, George R.; Inoue, Masuo; Kamano, Yoshiaki; Dufresne, Claude; Christie, Nigel D.; Niven, Margaret L.; Herald, Delbert L.

doi:10.1039/c39880001440

Cited by 22 publications

(31 citation statements)

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“…To increase the supply of cephalostatin 1 and expand knowledge of structure-activity relationships in the important cephalostatin series (18)(19)(20)(21)(22) we have been utilizing a large-scale (450 kg wet wt., includes coenecium) recollection-of the relatively small (-5 m m long) Southwest Indian Ocean marine worm Cephalodiscus gilchristi (Pterobranchia, Hemichordata Phylum). Previously we described the isolation and structural elucidation of cephalostatins 1-13 (1, [18][19][20][21][22], disteroidal alkaloids that are powerful human cancer cell line and murine P388 lymphocytic leukemia (PS system) cell growth inhibitors (ED,, 10-'-10-~ kg/mL). Further investigation of the antineoplastic and (or) cytotoxic constituents of this marine worm have now resulted in discovery of two new disteroidal alkaloids, cephalostatins 14 (5a) and 15 (Sb), with potent activity against a diverse group of human solid tumor types (in vitro) in the U.S. National Cancer Institute's (NCI) disease-oriented '~d v a n c e 284 refers to ref.…”

Section: Introductionmentioning

confidence: 99%

Antineoplastic agents 285. Isolation and structures of cephalostatins 14 and 15

Pettit

Ichihara

et al. 1994

Can. J. Chem.

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,2260 (1994).The tube-inhabiting marine worm, Cephalodiscus gilchristi has been found to produce a series of cytotoxic and antineoplastic disteroidal alkaloids. A substantial study concerned with discovery of new cell growth inhibitory constituents of this marine animal has led to isolation of cephalostatins 14 (50) and 15 (5b). The structures were determined by interpretation of spectral data, principally high-field (400 and 500 MHz) NMR and HRFABMS combined with NMR spectral relationships to cephalostatin 1 (4) where the structure was previously assigned by X-ray crystal structure analysis. The stereochemical assignments were established employing the ROESY NMR technique. Both new cephalostatins significantly inhibited growth of the P388 lymphocytic leukemia and a selection of human cancer cell lines. The two new cephalostatins further enhance knowledge of structure-activity parameters for these potentially important steroidal alkaloids. On a trouvC que le ver marin habitant un tube, Cephalodiscus gilchristi, produit une sCrie d'alcaloi'des distCroi'daux cytotoxiques et antinCoplastiques. Une Ctude importante relative B la dCcouverte de nouveaux constituants de cet animal marin inhibants la croissance de nouvelles cellules a conduit B I'isolement des cephalostatines 14 (50) et 15 (5b). On a dCtermini le structures par I'interprCtation des donnCes spectrales obtenues principalement par RMN A champ ClevC (400 et 500 MHz) et par HRFABMS combink avec des relations spectrales avec la ctphalostatine 1 (4) dont la structure a Cte attribuCe anterieurernent par diffraction des rayons X. Les attributions stCrkochimiques ont Ct C faites par la technique REOSY de la RMN. Les deux nouvelles cCphalostatines inhibent fortement la croissance de la leuctmie lymphocytaire P388 ainsi qu'une selection de cellules humaines can&reuses. Les deux nouvelles ~Cphalostatines augmentent nos connaissances sur les paramktres structure-activitC de ces alcaloi'des stCroi'daux potentiellement importants.[Traduit par la ridaction]

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Section: Introductionmentioning

confidence: 99%

Antineoplastic agents 285. Isolation and structures of cephalostatins 14 and 15

Pettit

Ichihara

et al. 1994

Can. J. Chem.

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“…THF at 0 ºC, 0.55 ml (5 eq) of BH 3 .THF (1.0 M solution) was dropwise added and stirred for 15 min. The reaction mixture was kept overnight in a refrigerator at 5 ºC.…”

Section: Preparation Of 8x and 8ymentioning

confidence: 99%

Novel Reactions in the Cephalostatin Series

Nawasreh

2009

COC

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This work aimed at selective synthesis of analogues of cephalostatin 1, a highly anti-cancer marine natural product according to NCI measurements. We summarized here the work done in our laboratories of five years studying the selectivity of certain reactions of cephalostatin-like bis-steroidal pyrazines and hence, the biological activity variation. This study includes chemo-, regio-and stereoselective reactions of analogues starting from the symmetrical bis-steroidal diketone (3), which can be synthesized in a gram scale from the commercially available hecogenine acetate (1a). The following routes have been tested: the regioselective hydroboration of the exocyclic double bond at C-12, the regioselective F-ring opening of the spiroketals moieties, the chemo-and regioselective hydroboration of 14,15 double bond and finally, the chemo-and regioselective reduction of the carbonyl group at C-12.

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“…Two families of dimeric steroid-pyrazine marine alkaloids, the cephalostatins [1] and ritterazines [2], have been recently discovered. These compounds exhibit an extraordinarily strong cytotoxic activity, superior to that of all standard chemotherapeutics, including taxol, adriamycin, cisplatin, 5-¯uorouracil, and others [3].…”

Section: Introductionmentioning

confidence: 99%