17736-45-7Relevant academic research and scientific papers
Synthesis of acyclic and cyclic phosphonates based on substituted 2-hydroxybenzylic alcohols
Brel, V. K.,Mikulenkova, E. A.,Mironov, V. F.,Tatarinov, D. A.,Terekhova, N. V.
, p. 2147 - 2152 (2020)
A convenient synthesis of benzylic phosphonates and 2,3-dihydrobenzo[d][1,2]oxaphosphole 2-oxides substituted at the aromatic ring, as well as their precursors, 2-hydroxybenzylic alcohols, from the derivatives of salicylic aldehyde, salicylic acid, and 2-hydroxyacetophenone bearing an additional hydroxy or methoxy group at the para position of the aromatic ring was developed. For the first time, the possibility of selective demethylation of the methoxy group positioned ortho to the methylene phosphonate fragment with retention of the methoxy group at the para position was shown.
Iridium-Catalyzed C(sp3)?H Addition of Methyl Ethers across Intramolecular Carbon–Carbon Double Bonds Giving 2,3-Dihydrobenzofurans
Ohmura, Toshimichi,Kusaka, Satoshi,Torigoe, Takeru,Suginome, Michinori
supporting information, p. 4448 - 4453 (2019/09/16)
Intramolecular addition of an O-methyl C(sp3)?H bond across a carbon-carbon double bond occurs in the iridium-catalyzed reaction of methyl 2-(propen-2-yl)phenyl ethers. The Ir/(S)-DTBM-SEGPHOS catalyst promotes the reaction efficiently in toluene at 110–135 °C to afford 3,3-dimethyl-2,3-dihydrobenzofurans. Enantioselective C(sp3)?H addition is achieved in the reaction of methyl 2-(1-siloxyethenyl)phenyl ethers, affording enantioenriched 3-hydroxy-2,3-dihydrobenzofuran derivatives with up to 96% ee. (Figure presented.).
Discovery of 2-((4-resorcinolyl)-5-aryl-1,2,3-triazol-1-yl)acetates as potent Hsp90 inhibitors with selectivity over TRAP1
Hong, Ki Bum,Jung, Sejin,Kang, Byoung Heon,Kang, Soosung,Kim, Darong,Lee, Changwook,Lee, Ji Hoon,Lee, Won Seok,Yang, Sujae,Yoon, Nam Gu
supporting information, (2019/12/25)
As the most abundant heat shock protein (HSP), Hsp90 is actively involved in tumor cell growth and various responses to anti-carcinogenic stress. Hsp90 has thus emerged as a potential drug target. A structure-based drug design approach was applied to develop novel resorcinolyltriazole derivatives as Hsp90 inhibitors. Structure-activity relationships (SARs) and molecular docking were investigated to provide a rationale for binding affinity and paralog selectivity. Click chemistry between iodoethynylresorcinol and an azido derivative was used to synthesize a new family of 2-((4-resorcinolyl)-5-aryl-1,2,3-triazol-1-yl) acetates that exhibited Hsp90 binding affinities of 40–100 nM (IC50). Among the synthesized molecules, the triazole alkyl acetates displayed the highest Hsp90 binding affinities. Their potency against Hsp90 was over 100-fold stronger than against TRAP1 and 1–3-fold stronger than against Grp94. In particular, compounds 18, 19, and 30 had Hsp90 inhibitory activities of ~45 nM (IC50) and they displayed over 350-fold selectivity for Hsp90 over TRAP1.
Branched-Selective Decarboxylative Heck Reaction with Electronically Unbiased Olefins
Shen, Jianchen,Xu, Biping,Zhang, Min,Su, Weiping
supporting information, p. 2768 - 2773 (2018/05/30)
We describe the PdII-catalyzed decarboxylative Heck reaction of aromatic carboxylic acids with an array of electronically unbiased olefins, which allows regioselective formation of less common branched products in good yield. This protocol enab
Iron-catalyzed olefin hydrogenation at 1 bar H2 with a FeCl3-LiAlH4 catalyst
Gieshoff, Tim N.,Villa, Matteo,Welther, Alice,Plois, Markus,Chakraborty, Uttam,Wolf, Robert,Jacobi Von Wangelin, Axel
supporting information, p. 1408 - 1413 (2015/03/18)
The scope and mechanism of a practical protocol for the iron-catalyzed hydrogenation of alkenes and alkynes at 1 bar H2 pressure were studied. The catalyst is formed from cheap chemicals (5 mol% FeCl3-LiAlH4, THF). A homogeneous mechanism operates at early stages of the reaction while active nanoparticles form upon ageing of the catalyst solution. This journal is
Catalytic oxidative 1,2-shift in 1,1′-disubstituted olefins using arene(iodo)sulfonic acid as the precatalyst and oxone as the oxidant
Purohit, Vikram C.,Allwein, Shawn P.,Bakale, Roger P.
supporting information, p. 1650 - 1653 (2013/06/27)
An efficient, catalytic hypervalent iodine-mediated oxidative 1,2-shift of 1,1′-disubstituted olefins is described. This methodology provides concise access to homobenzylic ketones with electron-donating substituents. In the case of cyclic systems, this transformation results in ring-expanded β-benzocycloalkanones, which are useful for further elaboration.
4-SUBSTITUTED-6-ISOPROPYL-BENZENE-1,3-DIOL COMPOUNDS AND THEIR USE
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Page/Page column 100-101, (2009/06/27)
The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain 4-substituted-6-isopropyl-benzene 1,3-diol compounds (referred to herein as IBD compounds), which, inter alia, inhibit heat shock protein 90 (HSP90) function. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HSP90 function, and in the treatment of diseases and conditions that are mediated by HSP90, that are ameliorated by the inhibition of HSP90 function, etc., including proliferative conditions such as cancer, etc.
