2976-80-9Relevant academic research and scientific papers
P-Methylbenzyl Group: Oxidative Removal and Orthogonal Alcohol Deprotection
Ikeuchi, Kazutada,Murasawa, Kentaro,Ohara, Kenya,Yamada, Hidetoshi
supporting information, p. 6638 - 6642 (2019/09/30)
We describe the practical removal of p-methylbenzyl (MBn) protections of alcohols by treatment with 2,3-dichloro-5,6-dicyano-p-benzoquinone. When a molecule bears benzyl and MBn groups, the oxidant selectively removes the latter groups. Further, the MBn groups tolerate ceric ammonium nitrate, resulting in chemoselective removal of the p-methoxybenzyl group in the presence of the MBn groups. These orthogonal alcohol deprotections would provide novel synthetic strategies of organic compounds.
Development of Phenyl Cyclohexylcarboxamides as a Novel Class of Hsp90 C-terminal Inhibitors
Garg, Gaurav,Forsberg, Leah K.,Zhao, Huiping,Blagg, Brian S. J.
supporting information, p. 16574 - 16585 (2017/11/13)
Inhibition of the heat shock protein 90 (Hsp90) C-terminus represents a promising therapeutic strategy for the treatment of cancer. Novobiocin, a coumarin antibiotic, was the first Hsp90 C-terminal inhibitor identified, however, it manifested poor anti-proliferative activity (SKBr3, IC50≈700 μm). Subsequent structure–activity relationship (SAR) studies on novobiocin led to development of several analogues that exhibited improved anti-proliferative activity against several cancer cell lines. Recent studies demonstrate that the biphenyl core could be used in lieu of the coumarin ring system, which resulted in more efficacious analogues. In continuation of previous efforts, the work described herein has identified the phenyl cyclohexyl core as a novel scaffold for Hsp90 C-terminal inhibition. Structure–activity relationship (SAR) studies on this scaffold led to the development of compounds that manifest mid-nanomolar activity against SKBr3 and MCF-7 breast cancer cell lines through Hsp90 inhibition.
Hydrogen Borrowing Catalysis with Secondary Alcohols: A New Route for the Generation of β-Branched Carbonyl Compounds
Akhtar, Wasim M.,Cheong, Choon Boon,Frost, James R.,Christensen, Kirsten E.,Stevenson, Neil G.,Donohoe, Timothy J.
, p. 2577 - 2580 (2017/03/01)
A hydrogen borrowing reaction employing secondary alcohols and Ph? (Me5C6) ketones to give β-branched carbonyl products is described (21 examples). This new C-C bond forming process requires low loadings of [Cp?IrCl2]2, relatively low temperatures, and up to 2.0 equiv of the secondary alcohol. Substrate-induced diastereoselectivity was observed, and this represents the first example of a diastereoselective enolate hydrogen borrowing alkylation. By utilizing the Ph? group, the β-branched products could be straightforwardly cleaved to the corresponding esters or amides using a retro-Friedel-Crafts reaction. Finally, this protocol was applied to the synthesis of fragrance compound (±)-3-methyl-5-phenylpentanol.
NEW BICYCLIC THIOPHENYLAMIDE COMPOUNDS
-
Page/Page column 224; 225, (2014/01/09)
The invention provides novel compounds having the general formula (I) wherein R1, R2, R3, R4, R5, R6, R7, A, E and n are as described herein, compositions including the compounds and use thereof as fatty-acid binding protein (FABP) 4/5 inhibitors in the treatment of e.g. type 2 diabetes, atherosclerosis or cancer.
CYCLOHEXANE ANALOGUES AS GPR119 AGONISTS
-
Page/Page column 41, (2012/03/12)
This invention relates to a series of substituted cyclohexane containing analogues which are agonists of GPR119 intended to treat metabolic diseases mediated by GPR119 including Type I & II diabetes mellitus. Diabetes mellitus is an ever-increasing threat to human health causing various complications (blindness, kidney failure, neuropathy, heart attack, stroke, etc.). Recently it was found that activation of GPR119 which is highly expressed in pancreatic beta cells causes glucose dependent insulin secretion and GLP-1 release. Many pharmaceuticals are currently developing GPR119 agonists and herein we disclose alternative GPR119 agonists. Our invention describes GPR119 agonists having structural Formula (I), pharmaceutically acceptable salt or solvate of Formula (I), isomer or prodrug of Formula (I), and combination therapy of Formula (I) with other anti-diabetic drugs like DPP-IV inhibitors and/or insulin sensitizers.
2-iodoxybenzenesulfonic acid as an extremely active catalyst for the selective oxidation of alcohols to aldehydes, ketones, carboxylic acids, and enones with oxone
Uyanik, Muhammet,Akakura, Matsujiro,Ishihara, Kazuaki
supporting information; experimental part, p. 251 - 262 (2009/06/28)
Electron-donating group-substituted 2-iodoxybenzoic acids (IBXs) such as5-Me-IBX (1g), 5-MeO-IBX (1h), and 4,5-Me2-IBX were superior to IBX 1a as catalysts for the oxidation of alcohols with Oxone (a trad emark of DuPont) under nonaqueous conditions, although Oxone was almost insoluble in most organic solvents. The catalytic oxidation proceeded more rapidly and cleanly in nitromethane. Furthermore, 2-iodoxybenzenesulfonic acid (IBS, 6a) was much more active than modified IBXs. Thus, we established a highly efficient and selective method for the oxidation of primary and secondary alcohols to carbonyl compounds such as aldehydes, carboxylic acids, and ketones with Oxone in nonaqueous nitromethane, acetonitrile, or ethyl acetate in the presence of 0.05-5molpercentof 6a, which was generated in situ from 2-iodobenzenesulfonic acid (7a) or its sodium salt. Cycloalkanones could be further oxidized to α,β- cycloalkenones or lactones by controlling the amounts of Oxone under the same conditions as above. When Oxone was used under nonaqueous conditions, Oxone wastes could be removed by simple filtration. Based on theoretical calculations, we considered that the relatively ionic character of the intramolecular hypervalent iodine-OSO2 bond of IBS might lower the twisting barrier of the alkoxyperiodinane intermediate 16.
Electrostatic effects on the reactions of cyclohexanone oxocarbenium ions
Baghdasarian, Glen,Woerpel
, p. 6851 - 6858 (2007/10/03)
Nucleophilic substitution reactions of 4-substituted cyclohexanone acetals display different selectivities depending upon the electronic nature of the substituent. Alkyl groups favor equatorial positions in the oxocarbenium ions, but alkoxy groups prefer
Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 14: Regioselectivity of the opening reactions with MeOH of remote O-substituted 1,2-epoxycyclohexanes under gas-phase operating conditions
Crotti, Paolo,Di Bussolo, Valeria,Favero, Lucilla,Pineschi, Mauro,Marianucci, Francesco,Renzi, Gabriele,Amici, Giuseppina,Roselli, Graziella
, p. 7513 - 7524 (2007/10/03)
The regiochemical behavior of cyclohexene oxides bearing a remote O-functionality was determined in the gas-phase in opening reactions with MeOH, using a gaseous acid (D3/+, C(n)H5/+, Me2F+
Intramolecular allylstannane-aldehyde cyclizations: Stereochemical results with flexible tethers for reactions forming vinylcyclohexanols
Keck, Gary E.,Dougherty, Shawn M.,Savin, Kenneth A.
, p. 6210 - 6217 (2007/10/02)
Intramolecular Lewis acid-promoted cyclization reactions of both (Z)- and (E)-3-phenyl-8-(tri-n-butylstannyl)oct-6-enal and (Z)- and (E)-3-(benzyloxy)-8-(tri-n-butylstannyl)oct-6-enal have been examined using a variety of Lewis acids, specifically BF
