72050-18-1Relevant academic research and scientific papers
Synthesis of (Z)-N-hydroxy-3-methoxy-3-phenylacrylamide as new selective inhibitor of hepatitis C virus replication
Kozlov,Kleymenova,Konduktorov,Malikova,Kamarova,Novikov,Kochetkov
, p. 191 - 197 (2016/04/19)
According to recently published results, cinnamic hydroxamic acid (CHA) inhibits replication of hepatitis C virus (HCV). We synthesized a structural analogue of CHA, i.e., (Z)-N-hydroxy-3-methoxy3-phenylacrylamide, which inhibited HCV replication five tim
Minimizing Aryloxy Elimination in RhI-Catalyzed Asymmetric Hydrogenation of β-Aryloxyacrylic Acids using a Mixed-Ligand Strategy
Li, Yang,Wang, Zheng,Ding, Kuiling
supporting information, p. 16387 - 16390 (2015/11/09)
The first example of efficient asymmetric hydrogenation of challenging β-aryloxyacrylic acids was realized using a RhI-complex based on the heterocombination of a readily available chiral monodentate secondary phosphine oxide (SPO) and an achiral monodentate phosphine ligand as the catalyst. Excellent enantioselectivities (92->99% ee) were achieved for a wide variety of chiral β-aryloxypropionic acids with minor aryloxy elimination in most cases. The resultant products were readily transformed into biologically active compounds through simple synthetic manipulations.
Discovery of a new class of cinnamyl-triazole as potent and selective inhibitors of aromatase (cytochrome P450 19A1)
McNulty, James,Keskar, Kunal,Crankshaw, Denis J.,Holloway, Alison C.
supporting information, p. 4586 - 4589 (2015/02/06)
Synthesis of a novel class of natural product inspired cinnamyl-containing 1,4,5-triazole and the potent inhibition of human aromatase (CYP 450 19A1) by select members is described. Structure-activity data generated provides insights into the requirements for potency particularly the inclusion of an aryl bromide or chloride residue as a keto-bioisostere.
Structure-activity studies of a series of dipyrazolo[3,4-b:3′,4′-d]pyridin-3-ones binding to the immune regulatory protein B7.1
Green, Neal J.,Xiang, Jason,Chen, Jing,Chen, Lihren,Davies, Audrey M.,Erbe, Dave,Tam, Steve,Tobin, James F.
, p. 2991 - 3013 (2007/10/03)
The interaction of co-stimulatory molecules on T cells with B7 molecules on antigen presenting cells plays an important role in the activation of naive T cells. Consequently, agents that disrupt these interactions should have applications in treatment of transplant rejection as well as autoimmune diseases. To this end, specific small molecule inhibitors of human B7.1 were identified and characterized. Herein, we report the identification of potent small molecule inhibitors of the B7.1-CD28 interaction. In a high-throughput screen we identified several leads that prevented the interaction of B7.1 with CD28 with activities in the nanomolar to low micromolar range. One of these, the dihydrodipyrazolopyridinone 1, was subsequently shown to bind the V-like domain of human B7.1 at equimolar stoichiometry. With this as a starting point, we report here the synthesis and initial in vitro structure-activity relationships of a series of these compounds.
Chromium-copper exchange of Fischer carbene complexes: X-ray crystal structure of a [Cu{=CR1(OR2)}(MeCN)(Et2O)][PF6] complex
Barluenga, Jose,Lopez, Luis A.,Loeber, Oliver,Tomas, Miguel,Garca-Granda, Santiago,Alvarez-Ra, Carmen,Borge, Javier
, p. 3392 - 3394 (2007/10/03)
The chromium-copper interaction is evidenced for chromium-carbene complexes and Cu+ in the CuBr-catalyzed cross-coupling reaction of ethyl diazoacetate (EDA) and Fischer alkoxycarbene - chromium complexes (see scheme). In contrast, with [Cu(MeCN)4][PF6] (0.5 equiv) instead of CuBr a carbene ligand exchange between a chiral alkenylchromium carbene complex (R1 = (E) CH=CH-2-furyl, R2 = (1R, 2S, 5R)-menthyl) and this Cu compound occurs at room temperature. The resulting novel trigonal-planar copper(I) - carbene complex, which contains MeCN and Et2O as the remaining ligands, has been isolated and structurally characterized by X-ray diffraction.
A simple and efficient transformation of fischer carbene complexes into bromomethyl ketones or β-ketoesters
Concellon, Jose M.,Bernad Jr., Pablo L.
, p. 7967 - 7970 (2007/10/03)
Fischer-type carbene complexes react via nucleophilic attack with dibromomethyllithium or haloester lithium enolates to afford bromomethyl ketones or β-ketoesters, respectively.
Synthesis of functionalized phenolic derivatives via the benzannulation of dienylketenes formed by a thermal Wolff rearrangement of α-diazo-β-keto compounds
Collomb, Didier,Deshayes, Christian,Doutheau, Alain
, p. 6665 - 6684 (2007/10/03)
Eleven conjugated dienyl α-diazo-β-keto derivatives were prepared from α,β-unsaturated carbonyl compounds. Their thermolysis induced a Wolff rearrangement generating an intermediate dienyl ketene whose isomer which has the required configuration of the internal double bond underwent a benzannylation thus forming the corresponding phenolic derivatives. When γ-substituted by a methoxy group both stereoisomers of the diazo compounds gave rise to the phenolic derivatives due to the reversible formation of an intermediate cyclobutenone which permitted the isomerization of the nonproductive transient dienylketene into the productive one.
Syntheses of mixed-metal sulfide cubane-type clusters with the novel PdMo3S4 core and reactivities of the unique tetrahedral Pd site surrounded by sulfide ligands toward alkenes, CO, tBuNC, and alkynes
Murata, Takashi,Mizobe, Yasushi,Gao, Hong,Ishii, Youichi,Wakabayashi, Takanori,Nakano, Fumio,Tanase, Tomoaki,Yano, Shigenobu,Hidai, Masanobu,Echizen, Izumi,Nanikawa, Hiroshi,Motomura, Shigeyuki
, p. 3389 - 3398 (2007/10/02)
An incomplete cubane-type cluster [Mo3S4(H2O)9]Cl4 (1) reacted with Pd black in aqueous HC1 to give a mixed-metal cubane-type cluster [PdMo3S4(H2O)9Cl]Cl3 (2). Treatment of 2 with 3.3 equiv of 1,4,7-triazacyclononane (tacn) afforded a well-defined single cubane-type cluster [PdMo3S4(tacn)3Cl]Cl3 (3), while an anion metathesis of 2 by 4-toluenesulfonate (TsO) resulted in the formation of a double cubane-type cluster [Pd2Mo6S8(H2O) 18](OTs)8 (4). Detailed structures of both 3 and 4 have been determined by X-ray crystallography. Crystal data for 3·4H2O: orthorhombic, space group P212121 a = 17.549(3) A?, V = 20.032(4) A?, c = 10.256(2) A?, V = 3605 A?3, Z = 4, and R (Rw) = 0.051 (0.062) for 4014 reflections. For 4·24H2O: triclinic, space group P1, a = 15.799(4) A?, b = 18.079(6) A?, c = 11.873(1) A?, α = 108.75(2)o, β = 108.73(1)o, γ = 70.87(3)o, V = 2944 A?3, Z = 1, R (Rw) = 0.028 (0.036) for 10 089 reflections. Cluster 3 was converted into a series of single cubane-type clusters [PdMo3S4(tacn)3(L)]4+ containing alkenes, CO, and tBuNC coordinated to the tetrahedral Pd site, by the initial anion exchange forming [PdMo3S4(tacn)3C1]X3 (8a, X = ClO4; 8b, X = BF4; 8c, X = PF6) followed by treatment with these molecules. The alkene cluster [PdMo3S4(tacn)3(cis-HOCH 2CH=CHCH2OH)](ClO4)4 (5a′) and the carbonyl cluster [PdMo3S4-(tacn)3(CO)]Cl(ClO4) 3 (6a) have been fully characterized by X-ray analyses. Crystal data for 5a′·2H2O: monoclinic, space group P21/m, a = 12.314(1) A?, b = 12.732(2) A?, c = 15.736(2) A?, β= 94.01(1)o, V = 2461 A?3, Z = 2, R (Rw) = 0.068 (0.081) for 2743 reflections. For 6a·3H2O: orthorhombic, space group Pbca, a = 15.485(13) A?, b = 23.900(6) A?, c = 23.326(7) A?, V = 8633 A?3, Z = 8, and R (Rw) = 0.061 (0.069) for 7761 reflections. Interestingly, cluster 8c catalyzes the reaction of a series of alkynic acid esters R2C≡CCOOR1 with alcohols R3OH to give the trans addition products (Z)-(R3O)R2C=CHCOOR1 (R1 = Me, Et, tBu, Ph, R2 = H, R3 = Me; R1 = R3 = Me, R2 = COOMe, Me; R1 = Ph, R2 = Et, R3 = Me; R1 = Me, R2 = H, R3 = Et, PhCH2) with quite high selectivity under mild conditions with retention of the cluster core.
MESOMERIC ANIONS. X. METHYLATION OF ALKALI-METAL DERIVATIVES OF SOME 1,3-KETONITRILES
Emelina, E. E.,Ershov, B. A.
, p. 692 - 696 (2007/10/02)
The effect of polar factors on the relative nucleophilicity of the oxygen and carbon reaction centers in the alkali-metal derivatives of 2-(X-benzoyl)acetonitriles, 2-(X-benzoyl)propionitriles, and 2-(X-phenyl)acetylacetonitriles was investigated.During methylation with methyl iodide and methyl p-toluenesulfonate in DMFA the ratio of the C- and O-methylation products for all the investigated compounds decreases with increase in the accepting power of the substituent X.It was shown that the sensitivity of the C-reaction center to the effect of the substituent X is greater than that of the O-center.
NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 46.1) TRIMETHYLSILYLDIAZOMETHANE: A CONVENIENT REAGENT FOR THE O-METHYLATION OF PHENOLS AND ENOLS
Aoyama, Toyohiko,Terasawa, Satomi,Sudo, Kimio,Shioiri, Takayuki
, p. 3759 - 3760 (2007/10/02)
Trimethylsilyldiazomethane reacts smoothly with phenols and enols in methanolic acetonitrile solution in the presence of N,N-diisopropylethylamine to give methyl ethers. KEYWORDS --- trimethylsilyldiazomethane; phenol; enol; O-methylation; methyl ether
