90554-82-8Relevant academic research and scientific papers
Synthesis of sorbicillinoid analogues with anti-inflammation activities
Zhang, Meng,Wang, Fangfang,Ding, Wenjuan,Xu, Zhipeng,Li, Xiaosan,Tian, Danmei,Zhang, Youwei,Tang, Jinshan
, (2022/01/06)
Recently, we demonstrated potential anti-inflammatory effects of sorbicillinoids isolated from marine fungi. Here, we report the synthesis of a series of new sorbicillinoid analogues and assessed their anti-inflammatory activities. Our results reveal that side chain substitution with (E)-2-butenoyl, (E)-3-(4-fluorophenyl)-2-propenoyl, and (E)-3-(3,4,5-trimethoxyphenyl)-2-propenoyl significantly enhanced the inhibitory effects of the derivatives on nitric oxide (NO) production and inducible NO synthesis (iNOS) expression stimulated by lipopolysaccharides (LPS) in mouse macrophage. Further chemical derivatization shows that the monomethylresorcinol skeleton worked better than the dimethylresorcinol skeleton in inhibiting LPS-induced inflammatory response in cultured cells. Among the 29 synthesized sorbicillinoid analogues, compounds 4b and 12b exhibited the strongest anti-inflammatory activities, holding the promise of being developed into lead compounds that can be explored as potent anti-inflammation agents.
Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides
Evindar, Ghotas,Batey, Robert A.
, p. 1802 - 1808 (2007/10/03)
A general method for the formation of benzoxazoles via a copper-catalyzed cyclization of ortho-haloanilides is reported. This approach complements the more commonly used strategies for benzoxazole formation which require 2-aminophenols as substrates. The reaction involves an intramolecular C-O cross-coupling of the ortho-haloanilides and is believed to proceed via an oxidative insertion/reductive elimination pathway through a Cu(I)/Cu(III) manifold. The reaction is also applicable to the formation of benzothiazoles. A variety of ligands including 1,10-phenanthroline and N,N′- dimethylethylenediamine were shown to provide ligand acceleration/stabilization in the reaction. Optimal conditions for cyclization used a catalyst combination of CuI and 1,10-phenanthroline (10 mol %). The method was amenable to a parallel-synthesis approach, as demonstrated by the synthesis of a library of benzoxazoles and benzothiazoles substituted at various positions in the ring. Most examples utilized the cyclization of ortho-bromoanilides, but orthoiodoanilides and ortho-chloroanilides also undergo a reaction under these conditions. The rate of reaction of the ortho-haloanilides follows the order I > Br > Cl, consistent with oxidative addition being the rate-determining step.
Asymmetric total synthesis of sperabillins B and D via lithium amide conjugate addition
Davies, Stephen G.,Haggitt, Jane R.,Ichihara, Osamu,Kelly, Richard J.,Leech, Michael A.,Mortimer, Anne J. Price,Roberts, Paul M.,Smith, Andrew D.
, p. 2630 - 2649 (2007/10/03)
Diastereoselective conjugate addition of homochiral lithium (R)-N-allyl-N-α-methylbenzylamide to methyl (2E,5E)-hepatadienoate, followed by protecting group manipulation and subsequent iodocyclocarbamation allows a concise route to the core fragment, methyl (3R,5R,6R)-3,6-diamino-5- hydroxyheptanoate, of sperabillins B and D. Differentiation between the C-3 and C-6 primary amino groups of this core amino acid was readily achieved by treatment with acetone, giving the 5,6-isopropylidene and C-3-imine protected diamine, with subsequent regioselective acylation of the C-6-nitrogen facilitating the total synthesis of sperabillin D in 10.8% overall yield, and the first asymmetric synthesis of sperabillin B in 5.8% overall yield.
Photo-Fries and Fries reaction of 5,8-dihydro-1-naphthyl esters
Sriraghavan, Kamaraj,Ramakrishnan, Vayalakkavoor T.
, p. 1791 - 1796 (2007/10/03)
Systematic studies were performed on the photo-Fries and the Fries reaction of aliphatic, aliphatic unsaturated, aromatic and aromatic unsaturated esters of 5,8-dihydro-1-naphthol. The Fries reaction of 5,8-dihydro-1-naphthyl acetate in various solvents is also reported.
Conjugate addition reactions of α-aminoalkylcuprates with α,β-alkenyl-, α,β-alkynyl-, α,β-allenyl-, and α,β-γ,δ-dienyl carboxylic acid derivatives, nitriles, and sulfoxides
Dieter,Lu,Velu
, p. 8715 - 8724 (2007/10/03)
α-Aminoalkylcuprates prepared from α-lithio carbamates and CuCN·2LiCl participate in 1,4-addition reactions with α,β-unsaturated esters, thiol esters, imides, and nitriles in poor to excellent yields depending upon the electron-withdrawing substituent and the substitution pattern of the unsaturated substrate. These reagents also undergo conjugate addition reactions with α,β-alkynyl esters, sulfoxides, and nitriles and with α,β-β,γ-unsaturated allenyl esters. Excellent stereocontrol is achieved in the conjugate additions of α-aminoalkylcuprates to the allenyl esters, while poor stereoselectivity results in the conjugate additions to the alkynyl derivatives. Deprotection and cyclization of the alkynyl adducts affords pyrrolin-2-ones, while similar treatment of the allenyl adducts affords 4-alkylidine- pyrrolidin-2-ones and pyrrolizidinones.
Stereoselectivity and Generality of the Palladium-Catalysed Cyclopropanation of α,β-Unsaturated Carboxylic Acids Derivatized with Oppolzer's Sultam
Vallaerda, Jerk,Appelberg, Ulf,Csoeregh, Ingeborg,Hacksell, Uli
, p. 461 - 470 (2007/10/02)
A series of α,β-unsaturated carboxylic acids derivatized with camphorsultam 1 a s a chiral auxiliary has been stereoselectively cyclopropanated. the selectivity of the reaction produces cyclopropanated products with the 1R,2R absolute configuration as indicated by the optical rotations as well as by an X-ray structure determineation.The temperature dependence of the reaction was studied with three substrates. the highest stereoselectivity was obtained at temperatures above 25 deg C.Branching at the α- or β-carbons disfavours complete conversion, and electron-withdrawing substituents at these positions seem to prevent the reaction.The auxiliary was removed by using titanium(IV) isopropoxide in benzyl alcohol followed by alkaline hydrolysis of the intermediate ester. the potent 5-HT1A receptor agonist (1R,2S)-2-(2-hydroxyphenyl)-N,N-dipropylcyclopropylamine 13 was synthesized by this method
Compound and use
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, (2008/06/13)
A compound contains a ligand group and at least one group of the general formula --XRn where X is a linking group which contains at least one hetero-atom, R is a saturated hydrocarbyl group containing at least six carbon atoms or is an unsaturated hydrocarbyl group containing at least three carbon atoms. The ligand group can be a polyhydroxyhydrocarbyl, a triazole, an imidazole, an indazole, a thiazole, an oxazole, a carbamate, an xanthate or a phthalazine. The compounds can be used to improve bonding between a metal and a coating material in contact with the metal surface. The metal may be a tire cord and the coating material rubber or a rubber composition.
