512-04-9Relevant articles and documents
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Walens et al.
, p. 182,185 (1957)
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Gould et al.
, p. 3685,3687 (1952)
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Krider,Wall
, p. 2938 (1954)
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Bivalent furostene carbamates as antiproliferative and antiinflammatory agents
Pathak, Nandini,Fatima, Kaneez,Singh, Sneha,Mishra, Divya,Gupta, Amit Chand,Kumar, Yogesh,Chanda, Debabrata,Bawankule,Shanker, Karuna,Khan, Feroz,Gupta, Atul,Luqman, Suaib,Negi, Arvind S.
, (2019/09/03)
Breast cancer is the most prevalent cancer in women affecting about 12% of world's female population. It is a multifactorial disease, mostly invasive in nature. Diosgenin and related compounds are potent antiproliferative agents. Carbamate derivatives have been synthesized at C26 of furostene ring after opening spiroketal bond (F-ring) of diosgenin. Compound 10 possessed significant antiproliferative activity against human breast cancer cells by arresting the population at G1 phase of cell division cycle and induced apoptosis. Induction of apoptosis was observed through the caspase signalling cascade by activating caspase-3. Moreover, carbamate 10 exhibited moderate antiinflammatory activity by decreasing the expression of cytokines, TNF-α and IL-6 in LPS-induced inflammation in primary macrophage cells. Furthermore, compound 10 significantly reduced Ehrlich ascites carcinoma significantly in mice. It was well tolerated and safe in acute oral toxicity in Swiss albino mice. The concomitant anticancer and antiinflammatory properties of carbamate 10 are important and thus, can further be optimized for a better anti-breast cancer candidate.
From organocatalysed desilylations to high-yielding benzylidenations of electron-deficient benzaldehydes
Niu, Qun,Xing, Linlin,Li, Chunbao
, p. 358 - 364 (2017/06/19)
A new type of organoprecatalyst (MeSCH2Cl/KI) for desilylation and benzylidenation reactions has been designed. Both reactions are user friendly and high yielding (71->99%) and have fast reaction rates. The desilylation of iodo silyl ethers was achieved with no sequential etherification side reactions like those seen for reactions when using TBAF. In the application of the catalytic system to a 6-TBDMS ether of a glucoside, glucoside benzylidenations using electron-deficient benzaldehydes were achieved in 87% yield compared with the previously reported yields of 69-77%. Altogether, 14 benzylidenation reactions were realised using silyloxy alcohols and electrondeficient benzaldehydes instead of their activated acetal forms. In terms of reaction rates and yields, the order of the benzylidenations is p-fluorobenzaldehyde > benzaldehyde > p-anisaldehyde, and a possible mechanism is discussed. These experiments have preliminarily differentiated this cost-effective catalytic system from the classic Lewis acids.
Unexpected fragmentation of 16β-acetoxy-22-oxocholestanes on the action of methylenetriphenylphosphorane
Valiullina, Zuleykha R.,Khasanova, Lidiya S.,Selezneva, Natalya K.,Gimalova, Fanuza A.,Pivnitsky, Kasimir K.,Miftakhov, Mansur S.
, p. 272 - 273 (2015/02/05)
Treatment of 16β-acetoxy-22-oxocholestanes with methylenetriphenylphosphorane results in the cleavage of C22-C23 bond and formation of bisnorcholanic (22→16)-lactones. The analogous fragmentation also partially proceeds on ButOK action.