1164-91-6Relevant articles and documents
The Cephalostatins. 22. Synthesis of bis-steroidal pyrazine pyrones
Pettit, George R.,Moser, Bryan R.,Mendonca, Ricardo F.,Knight, John C.,Hogan, Fiona
, p. 1063 - 1069 (2012)
Cephalostatin 1 (1), a remarkably strong cancer cell growth inhibitory trisdecacyclic, bis-steroidal pyrazine isolated from the marine tube worm Cephalodiscus gilchristi, continues to be an important target for practical total syntheses and a model for the discovery of less complex structural modifications with promising antineoplastic activity. In the present study, the cephalostatin E and F rings were greatly simplified by replacement at C-17 with an α-pyrone (in 12), typical of the steroidal bufodienolides, and by a dihydro-γ- pyrone (in 16). The synthesis of pyrazine 12 from 5α- dihydrotestosterone (nine steps, 8% overall yield) provided the first route to a bis-bufadienolide pyrazine. Dihydro-γ-pyrone 16 was synthesized in eight steps from ketone 13. While only insignificant cancer cell growth inhibitory activity was found for pyrones 12 and 16, the results provided further support for the necessity of more closely approximating the natural D-F ring system of cephalostatin 1 in order to obtain potent antineoplastic activity.
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Caglioti,L. et al.
, p. 207 - 208 (1979)
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Schwarz et al.
, p. 128 (1963)
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Nann,B. et al.
, p. 2473 - 2482 (1963)
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Pandit et al.
, p. 627 (1974)
ANTI-CANCER NUCLEAR HORMONE RECEPTOR-TARGETING COMPOUNDS
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Page/Page column 147-148, (2021/05/21)
The disclosure relates to anti-cancer compounds which are anti-cancer PARP inhibitors of formula Al, A2, A3 or A4 conjugated by a linker to a steroid, whereby the steroid targets the conjugate to the nucleus, as well as to methods for their preparation and use. (I)
Controlling the reactive state through cation binding: Photochemistry of enones within zeolites
Uppili, Sundararajan,Takagi, Shinsuke,Sunoj,Lakshminarasimhan,Chandrasekhar,Ramamurthy
, p. 2079 - 2083 (2007/10/03)
The nature of the lowest triplet state of enones is altered by the cations present within Y zeolites. Alkali metal ions, such as Li+, are predicted to interact with the carbonyl unit of enones in a collinear fashion and significantly lower both the p-type n and π-2 orbitals. Excited state energies, estimated at the CIS(D)/6-31+G* level, show that the lowest triplet is n-π* in character for the enones, but switch to π-π* on coordination with Li+. Observed product distribution within zeolite is consistent with this theoretical prediction.