132884-19-6Relevant academic research and scientific papers
Palladium-catalyzed benzylic C(sp3)–H arylation of o-alkylbenzaldehydes
Lei, Lan,Wu, Ping,Liu, Zhuqing,Lou, Jiang
supporting information, (2021/02/16)
The palladium-catalyzed benzylic C(sp3)–H arylation of o-alkylbenzaldehyde derivatives was achieved utilizing 2-dimethylaminoethylamine as a novel transient directing group. The γ-C(sp3)–H arylation reaction efficiently afforded a variety of arylated o-alkylbenzaldehydes and polycyclic aromatic hydrocarbons (PAHs) in one pot, exhibiting high functional group tolerance with broad substrate scope. The aliphatic diamine auxiliary represents a simple, inexpensive, readily available, and removable directing group for C–H activation. The resultant o-benzylbenzaldehyde products could be diversely transformed into potentially important synthetic intermediates under mild conditions.
SECOND GENERATION GRP94-SELECTIVE INHIBITORS
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Paragraph 0123-0124, (2019/03/12)
The present technology provides compounds selective for the Grp94 isoform, as well as compositions including such compounds, that are useful for treatment of multiple myeloma, melanoma, lung cancer, hepatocellular carcinoma, breast cancer, prostate cancer
Second Generation Grp94-Selective Inhibitors Provide Opportunities for the Inhibition of Metastatic Cancer
Crowley, Vincent M.,Huard, Dustin J. E.,Lieberman, Raquel L.,Blagg, Brian S. J.
supporting information, p. 15775 - 15782 (2017/11/14)
Glucose regulated protein 94 (Grp94) is the endoplasmic reticulum (ER) resident isoform of the 90 kDa heat shock protein (Hsp90) family and its inhibition represents a promising therapeutic target for the treatment of many diseases. Modification of the first generation cis-amide bioisostere imidazole to alter the angle between the resorcinol ring and the benzyl side chain via cis-amide replacements produced compounds with improved Grp94 affinity and selectivity. Structure–activity relationship studies led to the discovery of compound 30, which exhibits 540 nm affinity and 73-fold selectivity towards Grp94. Grp94 is responsible for the maturation and trafficking of proteins associated with cell signaling and motility, including select integrins. The Grp94-selective inhibitor 30 was shown to exhibit potent anti-migratory effects against multiple aggressive and metastatic cancers.
Photochemistry of 1-Phenyl-1,2-dihydronaphthalene in Methanol
Woning, Jan,Lijten, Frank A. T.,Laarhoven, Wim H.
, p. 2427 - 2435 (2007/10/02)
The photochemistry of 1-phenyl-1,2-dihydronaphthalene (1) in methanol and hexane has been investigated.The lack of influence of solvent polarity and of the presence of sulfuric acid on the rate of formation of exo-4-phenylbenzobicyclohex-2-ene (exo-2) from the primary, ring-opened photoproduct cZt-3a of 1 precludes a sudden-polarized, zwitterionic excited state from being involved in the intramolecular photocycloaddition reaction leading to exo-2.The experimental results can be rationalized by assuming that this photoprocess involves a concerted ?4a+ ?2a-type electrocyclic reaction. cis-Dibenzobicycloocta-2,7-diene (8) is proposed to arise by photocyclization of cZc-3b, followed by a thermal rearrangement.On irradiation of 1 with a broad-spectrum lamp, the ratio of the photoproducts exo-2 and 8 is correlated with the ratio of the pe and pa conformers of 1.The novel compound 1-(o-benzylphenyl)allene (6) is also formed under these conditions.Irradiation of 1 at 254 nm yields 8 as the only photoproduct.Photochemical addition of methanol was observed to complete with the photoprocess, leading to exo-2, though at a comparatively low level.A photodecomposition mode of exo-2, presumably involving heterolytic cleavage of the cyclopropane ring, presents the chief source of methoxylated photoproducts at low temperatures in methanol.
