19493-09-5Relevant articles and documents
Efficient Synthesis of (+/-)-Solavetivone and (+/-)-2H2>Solavetivone
Murai, Akio,Sato, Shingo,Masamune, Tadashi
, p. 2282 - 2285 (1984)
An alternative and efficient synthesis of the title compounds is described.The synthesis involves cycloaddition of 2-methylene-4-methoxy-6-methyl-4-cyclohexenylacetonitrile with methyl vinyl ketone as a key step.
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de Groot,A. et al.
, p. 2214 - 2217 (1968)
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Synthesis of A-Ring Precursors of 1α,25-Dihydroxyvitamin D3 Analogues Functionalized at C-2
Sigüeiro, Rita
, p. 6797 - 6803 (2017)
A flexible approach to an A-ring building block for new 1α,25-dihydroxyvitamin D analogues functionalized at C-2 as potential clinical candidates is described. The synthesis of alcohol 5 starts from (R)-carvone, and uses a Criegee rearrangement to selecti
Synthesis and photodynamic properties of pyrazole-indole hybrids in the human skin melanoma cell line G361
?a?kus, Algirdas,?ukauskait?, Asta,Bieliauskas, Aurimas,Ho?íková, Barbora,Kleizien?, Neringa,Kolá?ová, Hana,Kry?tof, Vladimír,Malina, Luká?,Simerská, Helena,Varvuolyt?, Gabriel?
, (2020)
Three conjugated pyrazole-indole hybrids, 5, 7 and 10, were synthesized from easily accessible 3-(hexyloxy)-1-phenyl-1H-pyrazole-4-carbaldehyde 1 and 5-iodo-3,3-dimethyl-2-phenyl-3H-indole 4 employing olefination reactions (Wittig, Ramirez), Vilsmeier-Haa
Total synthesis of amphilectane-type diterpenoid (±)-7- isocyanoamphilecta-11(20),15-diene
Miyaoka, Hiroaki,Okubo, Yusuke
, p. 547 - 550 (2011)
The total synthesis of amphilectane-type diterpenoid (±)-7- isocyanoamphilecta-11(20),15-diene, isolated from the tropical marine sponge Cymbastela hooperi, was achieved. The synthesis involves construction of a cis-decalin ring by an intramolecular Diels-Alder reaction and construction of an all-trans-perhydrophenalene ring by an intramolecular Michael reaction as the key steps. Georg Thieme Verlag Stuttgart.
Asymmetric synthesis and absolute stereochemistry of a labdane-type diterpenoid isolated from the rhizomes of: Isodan yuennanensis
Deng, Heping,Cao, Wei,Zhang, Zhijiang,Liu, Bo
, p. 6225 - 6230 (2016)
The first synthesis of a labdane-type diterpenoid isolated from Isodon yuennanensis was achieved in fourteen steps from commercially available starting material, (+)-sclareolide. The synthesis features the Barton nitrite ester reaction to introduce an oxi
SYNTHETIC AND STEREOCHEMICAL STUDIES RELATED TO TRANS-CLERODANE DITERPENOIDS AND CONGENERS
Sarma, Aluru S.,Gayen, Ashok K.
, p. 3385 - 3386 (1983)
Synthesis of a key trans-clerodane diterpenoid intermediate 6, which is also a degradation product of ilimaquinone, is described.In view of a discrepancy in our earlier work on correlation of the stereochemistry of ketoester (5), with that of avarol, the
Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters
Frydrych, Ivo,Urban, Milan,?arek, Jan,Benická, Sandra,D?ubák, Petr,Gurská, Soňa,Hajdúch, Marián,Kotulová, Jana,Li?ková, Barbora,Olejníková, Denisa,Pokorny, Jan
, (2021/07/28)
A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Compounds 4.22, 4.30, 4.33, 4.39 had IC50 below 5 μmol/L; 4.22 and 4.39 were selected for studies of the mechanism of action. Cell cycle analysis revealed an increase in the number of apoptotic cells at 5 × IC50 concentration, where activation of irreversible changes leading to cell death can be expected. Both 4.22 and 4.39 led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 × IC50 and almost complete inhibition at 5 × IC50. Interestingly, compound 4.39 at 5 × IC50 caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations. Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds 4.22 and 4.39 trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacological parameters of derivative 4.22 were superior to 4.39, therefore 4.22 was the finally selected candidate for the development of anticancer drug.
Synthesis of C-linked α-Gal and α-GalNAc-1′-hydroxyalkanes by way of C2 functionality transfer
Nolen, Ernest G.,Hornik, Ezra S.,Jeans, Kendra B.,Zhong, Weiyu,LaPaglia, Danielle M.
supporting information, (2021/05/06)
Inspired by reports of water sculpted Tn antigen (α-GalNAc-O-Ser/Thr) epitopes and our interest in producing metabolically more stable C-linked analogs of Tn, we explored the utility of C2 functionality on α-Gal-C-alkenes to deliver hydroxyl to the pendant alkenyl chain. Toward this end, a cyclic carbonate approach gave rise to a single C-linked α-Gal-1′(S)-hydroxyethane in 3 steps, and use of a 2-(hydroxyimino)galactoside cyclization transferred an oxygen to a pendant cis-substituted C-linked alkene affording the R-configuration at the newly formed stereocenter (7:1 dr). Reduction and acetylation of the resultant isoxazoline demonstrated this approach as a viable route to C-linked α-GalNAc-1′-hydroxyalkanes.
Stable Singlet Carbenes as Organic Superbases
Bertrand, Guy,Grotjahn, Douglas B.,Jazzar, Rodolphe,Junor, Glen P.,Vermersch, Fran?ois,Yazdani, Sima
supporting information, p. 27253 - 27257 (2021/11/22)
A simple experimental procedure for scaling carbene Br?nsted basicity is described. The results highlight the strong basicity of pyrazol-4-ylidenes, a type of mesoionic carbene, also named cyclic-bentallenes (CBA). They are more basic (pKaH >42.7 in acetonitrile) than the popular proazaphosphatrane Verkade bases, and even the Schwesinger phosphazene superbase P4(tBu). The basicity of these compounds can readily be tuned, and they are accessible in multigram quantities. These results open new avenues for carbon centered superbases.
