24070-51-7Relevant academic research and scientific papers
Phosphorothioic acids and related compounds as surrogates for H 2S-synthesis of chiral tetrahydrothiophenes
Robertson, Forest J.,Wu, Jimmy
supporting information; experimental part, p. 2775 - 2780 (2012/03/22)
The convenient preparation of chiral tetrahydrothiophenes (THTs) in high enantiopurity via phosphorothioic acids and related compounds is reported. We consider these to be safer alternatives to the use of H2S which is a highly toxic gas. Each o
Microwave-assisted synthesis and evaluation of substituted aryl propyl acridone-4-carboxamides as potential chemosensitizing agents for cancer
Velingkar, Vinaykumar S.,Dandekar, Vikrant D.
, p. 268 - 275 (2013/01/10)
A novel class of compounds with structure Aryl propyl acridone-4- carboxamides were synthesized by conventional and microwave (MW) irradiation methods and evaluated for their inhibitory effects on the transport activity of P- glycoprotein (P-gp) by standard Hoechst 33342 assay method. The title compounds with phenoxy substitution exhibited better activity.
Design, synthesis and evaluation of substituted N-(3-arylpropyl)-9,10- dihydro-9-oxoacridine-4-carboxamides as potent MDR reversal agents in cancer
Velingkar,Dandekar
experimental part, p. 504 - 510 (2012/01/06)
A novel class of molecules with structure N-(3-arylpropyl)-9,10-dihydro-9- oxoacridine-4-carboxamides (20-29) were designed by generating a pharmacophore for potent MDR reversal activity using phase drug design software. The designed molecules were synthesized by a novel synthesis route and evaluated for their inhibitory effects on the transport activity of P-glycoprotein (P-gp) by standard Hoechst 33342 assay method. Based on the pIC50 values of ten title compounds screened, three compounds exhibited better activity as compared to Verapamil used as standard.
Simplified heterocyclic analogues of fluoxetine inhibit inducible nitric oxide production in lipopolysaccharide-induced BV2 cells
Park, Ju-Young,Kim, Seung-Woo,Lee, Ja-Kyeong,Im, Weon Bin,Jin, Byung Kwan,Yoon, Sung-Hwa
experimental part, p. 538 - 544 (2012/02/15)
A series of fluoxetine, where the N-methylamino group was replaced and then simplified, were synthesized and their inhibitory effect was tested for nitric oxide (NO) production and inducible NO synthase (iNOS) expression in lipopolysaccharide (LPS)-induced BV2 cells. Although the synthesized compounds generally revealed weaker activity or greater cytotoxicity than fluoxetine, compound 10a, in which the N-methylamino group in fluoxetine was replaced by morpholine, and the trifluoromethylphenyl ring was substituted with simple oxo group, suppressed NO production dose-dependently at 10, 20 and 40 μM concentrations with less cytotoxicity than fluoxetine, and inhibited iNOS mRNA and protein expression at the same concentrations in LPS-induced BV2 cells. The results suggested that the trifluoromethylphenyl ring moiety in fluoxetine is not necessary for the suppression of NO production and that 10a has the potential as a potent inhibitor of NO production.
An efficient and general approach to β-functionalized ketones
Jingliang, Jiao,Nguyen, Larry X.,Patterson, Dennis R.,Flowers II, Robert A.
, p. 1323 - 1326 (2008/01/01)
Figure presented The oxidation of selected anlons (N3 -, SCN-, I-, and Br-) by eeric ammonium nitrate (CAN) in the presence of substituted cyclopropyl alcohols provides a novel approach to β-functionalized ketones. The protocol has a number of advantages including short reaction times, ease of reagent handling, and mild, neutral reaction conditions. Overall, this method provides an alternative pathway to important starting materials and intermediates in organic synthesis.
Synthesis, X-ray structure, thermal stability and reactions of triaryl(3-oxoalkyl)bismuthonium salts
Matano, Yoshihiro,Azuma, Nagao,Suzuki, Hitomi
, p. 2543 - 2550 (2007/10/02)
Treatment of triarylbismuth difluorides 2 with siloxycyclopropanes 3 in the presence of trimethylsilyl trifluoromethanesulfonate (triflate) or boron trifluoride-diethyl ether gave the corresponding triaryl(3-oxoalkyl)bismuthonium salts 4 as crystals.X-ray crystallographic analysis of the triflate 4a showed that the central bismuth atom has a distorted tetrahedral geometry with weak intramolecular coordination by the oxygen atoms of the carbonyl group and triflate anion.Whilst all onium salts 4 are thermally stable in a solid state, the triflate 4a slowly decomposed in chloroform to give triphenylbismuthane 6 and an ester 7 quantitatively.In nucleophilic solvents such as MeOH, DMSO and DMF, both triflate 4a and tetrafluoroborate 4d underwent decomposition in a complicated way to afford the bismuthane 6, 3-methoxypropanoyl compounds 8a,b, α,β-unsaturated carbonyl compounds 9a,b, diphenylbismuth triflate 10a or tetrafluoroborate 10b and alkoxysulfonium salts 11a,b.The formate 12 was an additional product from 4d in DMF.The bismuthonium salt 4d reacted with dimethyl sulfide 13 and sodium benzenesulfinate 15 to afford the sulfonium salt 14 and the sulfonyl ketone 16, respectively.Reaction of the salt 4d with potassium halides 17 in DMF gave the enone 9b, formate 12 and halogeno ketone 18 in varying yields depending on the nucleophilic nature of the halogen anions employed.When treated with KOBut, the salt 4d underwent facile β-elimination to yield the enone 9b.In all of these reactions, the triphenylbismuthane moiety behaved as a good leaving group.
An efficient synthesis of optically active eprozinol
Sakuraba,Nakajima,Achiwa
, p. 1457 - 1460 (2007/10/02)
A synthetic route to optically active eprozinol has been developed by efficient asymmetric hydrogenations of α- and β-amino ketone hydrochloride derivatives with MCCPM-rhodium catalyst.
Preparation of Aromatic Iodoacetyl Derivatives by Direct Iodination with a Potassium Iodide-Potassium Iodate-Sulfuric Acid System
Okamoto, Tsuyoshi,Kakinami, Takaaki,Nishimura, Tetsuo,Irwan-Hermawan,Kajigaeshi, Shoji
, p. 1731 - 1733 (2007/10/02)
The reaction of aromatic acetyl derivatives with potassium iodide and potassium iodate in acetic acid in the presence of sulfuric acid at room temperature gave iodoacetyl derivatives in good yields.
Preparation and Reactivities of (η3-1- and 2-Trimethylsiloxyallyl)Fe(CO2)NO Complexes. Intermediates Functioning as Equivalents of β- and α-Acyl Carbocations and Acyl Carbanions
Itoh, Keiji,Nakanishi, Saburo,Otsuji, Yoshio
, p. 2965 - 2977 (2007/10/02)
(η3-1- and 2-Trimethylsiloxyallyl)Fe(CO)2NO complexes were prepared by the reaction of the corresponding siloxyallylic halides with Bu4N.These complexes reacted with both of carbon nucleophiles and carbon electrophiles preferentially at the less hindered sites of the allylic ligands.In these reactions, (η3-1-trimethylsiloxyallyl)Fe(CO)2NO complexes served as synthetically equivalent synthons for both of β-acyl carbocations and β-acyl carbanions and (η3-2-trimethylsiloxyallyl)Fe(CO)2NO complexes as both of α-acyl carbocations and α-acyl carbanions.The stereochemical courses of the reactions are described.
