- Nitric oxide donating anilinopyrimidines: Synthesis and biological evaluation as EGFR inhibitors
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To search for potent nitric oxide (NO) donating epidermal growth factor receptor (EGFR) inhibitors, a series of phenylsulfonylfuroxan-based anilinopyrimidines 10a-h were synthesized and biologically evaluated. Compounds 10f-h exhibited potent inhibitory activity against EGFR L858R/T790M and were as potent as WZ4002 in inhibition of H1975 cells harboring EGFR L858R/T790M. Additionally, 10h produced high levels of NO in H1975 cells but not in normal human cells, and its antiproliferative activity was diminished by hemoglobin, an NO scavenger. Furthermore, 10h inhibited EGFR activation and downstream signaling in H1975 cells. These results suggest that the strong antiproliferative activity of 10h could be attributed to the synergic effects of high levels of NO production and inhibition of EGFR and downstream signaling in the cancer cells.
- Han, Chun,Huang, Zhangjian,Zheng, Chao,Wan, Ledong,Lai, Yisheng,Peng, Sixun,Ding, Ke,Ji, Hongbin,Zhang, Yihua
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- A convenient method to reduce hydroxyl-substituted aromatic carboxylic acid with NaBH4/Me2SO4/B(OMe)3
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The reduction of hydroxyl-substituted aromatic carboxylic acid with NaBH4/Me2SO4/B(OMe)3 is described. Borane is generated by the reaction of NaBH4 with Me2SO4 in THF, which is as efficient as the commercial one. B(OMe)3 has been successfully applied to increase the reactivity and selectivity of this reaction. The optimum ratio of borane/B(OMe)3/acid is studied, and a variety of hydroxyl-substituted aromatic acids are reduced in good yields.
- Zhou, Yuhan,Gao, Guchao,Li, Hui,Qu, Jingping
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- Copper-catalyzed asymmetric silylative cyclization of cyclohexadienone-containing 1,6-enynes
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The first copper-catalyzed asymmetric silylative cyclization of cyclohexadienone-containing 1,6-enynes has been accomplished through a tandem process: regioselective silylcupration of terminal unactivated alkynes and subsequently enantioselective conjugate addition to cyclohexadienones. This reaction proceeded smoothly to afford the cis-hydrobenzofuran and cis-hydroindole frameworks bearing two consecutive chiral carbon centers in high to excellent yields and moderate enantioselectivities. Additionally, the cyclization products could be readily subjected to several transformations for elaborating synthetic utilities.
- He, Cheng-Yu,Xie, Li-Bo,Ding, Rui,Tian, Ping,Lin, Guo-Qiang
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Read Online
- Synthesis and antiproliferative activity of a new compound containing an α-methylene-γ-lactone group
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The biological activity of compound 9 obtained by introducing an α-methylene-γ-butyrolactone group into 3-(4-hydroxyphenyl)propionic acid, 1, was studied for possible effects on HL-60 cells, murine splenocytes, and human peripheral mononuclear cells (PBMC). 9 induced apoptosis in the HL-60 cell line and has a clear capacity to inhibit proliferation induced in murine splenocytes and PBMC by different mitogenic agents with no apparent toxic side effects. 9 was synthesized from 1, and its structure and stereochemistry were elucidated by spectroscopic methods.
- González, Antonio G.,Silva, Margarita Hernández,Padrón, Juan I.,León, Francisco,Reyes, Eduardo,álvarez-Mon, Melchor,Pivel, Juan P.,Quintana, José,Estévez, Francisco,Bermejo, Jaime
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- New approaches to the synthesis of aromatic polyesters
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A new method of the synthesis of high molecular polybutylene terephthalate (PBT) is developed with the use of Irganox 1010, tris(nonylphenyl) phosphite and hypophosphite as stabilizers and boron nitride or boron oxide as a catalyst is proposed.
- Mikitaev,Bedanokov, A. Yu.,Mikitaev
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- DITERPENES FROM BACCHARIS SPECIES
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The investigation of ten Baccharis species afforded in addition to known compounds eight new diterpenes, four ent-labdanes, three kaurenes and a clerodane derivative.Furthermore, two new p-hydroxyacetophenones, a flavone, 3'-methoxyxanthomicrol and two matricaria ester derivatives were isolated.The structures were elucidated by spectroscopic methods and a few chemical transformations.The chemotaxonomic situation of the large genus is discussed briefly. - Keywords: Baccharis species; Compositae; diterpenes; ent-labdanes; clerodane; ent-kauranes; p-hydroxyacetophenone derivatives; acetylenes; flavone; 3'-methoxyxanthomicrol.
- Bohlmann, Ferdinand,Kramp, Wolfgang,Grenz, Michael,Robinson, Harold,King, Robert M.
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- CINNAMIC ACID BRIDGES BETWEEN CELL WALL POLYMERS IN WHEAT AND PHALARIS INTERNODES
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A method has been devised for the quantitative determination of cinnamic acids participating in ester-ether bridges between cell wall polymers based on the different reactivities of free carboxylic acids and their esters towards borohydride reductants and the different susceptibilities of cinnamic acid ester and benzyl ether linkages to alkaline treatments.Lignin-poylsaccharide containing fractions extracted with dioxane-H2O from cell walls of wheat (Triticum aestivum) and phalaris (phalaris aquatica) internodes are hydrogenated using a Pd/C catalyst at room temperature to convert cinnamic acids to their corresponding dihydrocinnamic acids.The sample is subsequently reduced with LiBH4 in ether-toluene to convert ester-linked dihydrocinnamates to their corresponding alcohols, hydrolysed with 4 M NaOH at 170 deg, and the dihydrocinnamic acid derivatives released from their etherified forms determined by GC.Using model compounds it was shown that these reactions proceeded quantitatively.The results indicate that all of the etherified ferulic acid in the dioxane-H2O-soluble fractions of walls of wheat and phalaris internodes is also ester-linked.It has been calculated that there are nine to 10 ferulic acid ester-ether bridges for every 100 C6-C3 lignin monomers. p-Coumaric acid is not involved in ester-ether bridges. Key Word Index - Triticum aestivum; Phalaris aquatica; Gramineae; lignin; polysaccharide; p-coumaric acid; ferulic acid; esterified cinnamic acid; etherified cinnamic acid.
- Lam, Thi Bach Tuyet,Iiyama, Kenji,Stone, Bruce A.
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- Scope and limitations of biocatalytic carbonyl reduction with white-rot fungi
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The reductive activity of various basidiomycetous fungi towards carbonyl compounds was screened on an analytical level. Some strains displayed high reductive activities toward aromatic carbonyls and aliphatic ketones. Utilizing growing whole-cell cultures of Dichomitus albidofuscus, the reactions were up-scaled to a preparative level in an aqueous system. The reactions showed excellent selectivities and gave the respective alcohols in high yields. Carboxylic acids were also reduced to aldehydes and alcohols under the same conditions. In particular, benzoic, vanillic, ferulic, and p-coumaric acid were reduced to benzyl alcohol, vanillin, dihydroconiferyl alcohol and 1-hydroxy-3-(4-hydroxyphenyl)propan, respectively.
- Zhuk, Tatyana S.,Skorobohatko, Oleksandra S.,Albuquerque, Wendell,Zorn, Holger
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supporting information
(2021/02/02)
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- Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols
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We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.
- Aleku, Godwin A.,Leys, David,Roberts, George W.
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p. 3927 - 3939
(2020/07/09)
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- CLASS OF BIFUNCTIONAL COMPOUNDS WITH QUATERNARY AMMONIUM SALT STRUCTURE
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The invention provides a class of compounds represented by formula (I), having bifunctional active quaternary ammonium salt structure of a β2-adrenoreceptor agonist and an M receptor antagonist, a pharmaceutically acceptable salt, solvate, and optical isomer thereof. A pharmaceutical composition comprising such a compound with quaternary ammonium salt structure, a method for preparing such a compound with quaternary ammonium salt structure and an intermediate thereof, and uses thereof in treating pulmonary disorders are also provided. The compounds of the invention have high selectivity to the M receptor subtype, and have less adverse reaction and lower toxic and side effects in the treatment of pulmonary diseases such as COPD and asthma.
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Paragraph 0241
(2019/11/11)
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- Synthesis and PGE2 inhibitory activity of novel diarylheptanoids
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Prostaglandin E2 (PGE2) is a lipid mediator of inflammation and its inhibition has become a popular drug target due to its harmful physiological roles. Diarylheptanoids are one class of compounds that have shown successful inhibition of PGE2. This paper reports the synthesis and PGE2 inhibitory activity of a series of analogues of a naturally occurring diarylheptanoid. The most efficacious compounds were examined for dose-dependent PGE2 inhibition. Among several promising compounds, the lead candidate exhibited an IC50 value of 0.56 ng/μL or 1.7 μM with no detectable toxicity at the highest dose of 10 ng/μL.
- McLane, Richard D.,Le Cozannet-Laidin, Léon,Boyle, Maxwell S.,Lanzillotta, Lindsey,Taylor, Zachary L.,Anthony, Sarah R.,Tranter, Michael,Onorato, Amber J.
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supporting information
p. 334 - 338
(2018/02/15)
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- MELANIN GENERATION INHIBITOR AND WHITENING AGENT
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PROBLEM TO BE SOLVED: To provide a melanin generation inhibitor and a whitening agent that are excellent in whitening effect and also excellent in safety and temporal stability. SOLUTION: The invention provides a melanin generation inhibitor containing a compound represented by formula [1] as an active ingredient, a whitening agent, as well as a melanin generation inhibiting method and a whitening method by applying such agents to the skin. (R1, R2, R4, and R5 are each independently H, a hydroxyl group, an alkyl group of C1-4, or -O-C(=O)R6; R6 is an alkyl group of C1-4; R3 is H, an alkyl group of C1-4, or -C(=O)R7; and R7 is an alkyl group of C1-8.) SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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- Synthesis of tetrahydropyranyl diarylheptanoids from Dioscorea villosa
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Concise syntheses of four tetrahydropyranyl diarylheptanoids isolated from Dioscorea villosa have been described. The key features include Prins cyclization to construct the tetrahydropyran cores, Keck asymmetric allylation, and Mitsunobu inversion. Optimization of the Prins cyclization conditions in order to minimize racemization has been described. Our syntheses also confirmed the absolute stereochemistry of the natural products.
- Kantee, Kawalee,Rukachaisirikul, Vatcharin,Tadpetch, Kwanruthai
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p. 3505 - 3509
(2016/07/15)
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- CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF
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The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.
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(2014/10/15)
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- NITRIC OXIDE DONOR NEPRILYSIN INHIBITORS
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In one aspect, the invention relates to compounds having the formula: where R1, R2, R3, R7, R8, Z, X, b, and c are as defined in the specification, or a pharmaceutically acceptable salt thereof. These compounds are nitric oxide donors and have neprilysin inhibition activity. In another aspect, the invention relates to pharmaceutical compositions comprising such compounds; methods of using such compounds; and processes and intermediates for preparing such compounds.
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Paragraph 0387; 0388
(2014/01/07)
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- REDUCTION OF C-0 BONDS BY CATALYTIC TRANSFER HYDROGENOLYSIS
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The present invention relates to a method of reducing a C-O bond to the corresponding C-H bond in a substrate which could be a benzylic alcohol, allylic alcohol, ester,or ether or an ether bond beta to a hydroxyl group or alpha to a carbonyl group.
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Page/Page column 15
(2012/09/22)
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- Electron transfer reduction of carboxylic acids using SmI 2-H2O-Et3N
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The first general method for efficient electron transfer reduction of carboxylic acids has been developed. The protocol using SmI2 - H 2O - Et3N allows for reduction of a variety of carboxylic acids in excellent yields and provides an attractive alternative to processes mediated by reactive alkali metals, lithium aluminum hydride, and boron hydrides. Of broader significance, the method allows acyl radical equivalents to be generated from carboxylic acids under mild reaction conditions.
- Szostak, Michal,Spain, Malcolm,Procter, David J.
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supporting information; experimental part
p. 840 - 843
(2012/04/11)
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- Thermolysis of 4-(ω-hydroxyalkyl)-2,6-di-tert-butylphenols
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The process of thermolysis of tert-butylated hydroxyalkyl phenols includes de-tert-butylation, etherification, and fragmentation of the hydroxyalkyl group. On the basis of the proposed schemes of the mechanism of thermal de-tert-butylation the path of the search for catalysts for the synthesis of 4-hydroxyalkylphenols is defined and transformations of the by-products into biologically active substances were considered.
- Krysin,Egorova,Vasil'Ev
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experimental part
p. 275 - 283
(2010/07/15)
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- Oxidative spirocyclization of phenolic sulfonamides: Scope and applications
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A full account of the oxidative dearomatization of para- and ortho-phenolic sulfonamides is provided together with an overview of the chemistry of the products and their elaboration to building blocks for spirocyclic alkaloids. A concise total synthesis of putative lepadiformine complements the discussion. Making building blocks: The oxidative dearomatization of para- and ortho-phenolic sulfonamides provides building blocks for spirocyclic alkaloids (see scheme). The chemistry of the products of this reaction and a concise total synthesis of putative lepadiformine is given.
- Liang, Huan,Ciufolini, Marco A.
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supporting information; experimental part
p. 13262 - 13270
(2011/03/17)
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- Remarkable effect of 2,2′-bipyridyl: Mild and highly chemoselective deprotection of methoxymethyl (MOM) ethers in combination with TMSOTf (TESOTf)-2,2′-bipyridyl
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The remarkable effect of 2,2′-bipyridyl led to the successful development of the mild and highly chemoselective deprotection method of methoxymethyl (MOM) ethers using the combination of TMSOTf (or TESOTf) and 2,2′-bipyridyl; this method can be applied to the direct conversion of the MOM group to other ethereal protective groups (e.g. benzyloxymethyl) with the corresponding alcohols. The Royal Society of Chemistry 2009.
- Fujioka, Hiromichi,Kubo, Ozora,Senami, Kento,Minamitsuji, Yutaka,Maegawa, Tomohiro
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supporting information; experimental part
p. 4429 - 4431
(2009/12/29)
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- Interaction of functionally-substituted 4-alkyl-2,6-di-tert-butylphenols with hydrohalic acids
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Reactions of 4-alkyl-2,6-di-tert-butylphenols containing OH, SH, COOH, and COOMe groups in their para substituents with hydrogen chloride and hydrohalic acids were studied. One-step transformations of 2,6-di-tert-butyl-4-(ω- hydroxyalkyl)phenols to the corresponding 4-(ω-halogenoalkyl)phenols, as well as of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid and its esters to phloretic acid were proposed. 4-(3-Mercaptopropyl)phenol upon heating with conc. HBr undergoes condensation to 3-(4-hydroxyphenyl)propyl 4-(3-mercaptopropyl)phenyl sulfide as the main product.
- Prosenko,Skorobogatov,Dyubchenko,Pinko,Kandalintseva,Shakirov,Pokrovsky
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p. 1119 - 1124
(2008/09/18)
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- BASIC SALTS AND MONOHYDRATES OF CERTAIN ALPHA, BETA-PROPRIONIC ACID DERIVATIVE
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The invention provides novel salts of (S)-2-methoxy-3-[4-{3-(4-methanesulfonyloxyphenyl)propylamino}phenyl] proprionic acid, including Arginine salt of (S)-2-methoxy-3-[4-{3-(4-methanesulfonyloxyphenyl)propilamino}phenyl] proprionic acid monohydrate, Arginine salt of (S)-2-methoxy-3-[4-{3-(4-methanesulfonyloxyphenyl)propylamino}phenyl] proprionic acid, and (S)-2-methoxy-3-[4-{3-(4-methanesulfonyloxyphenyl)propylamino}phenyl] proprionic acid monohydrate. Various aspects and embodiments are included. Compositions containing novel salts of (S)-2-methoxy-3-[4-{3-(4-methanesulfonyloxyphenyl)propylamino}phenyl] proprionic acid are also provided.
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Page/Page column 12
(2008/06/13)
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- Basic salts and monohydrates of certain alpha, beta-propionic acid derivative
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The invention provides novel salts of (S)-2-methoxy-3-[4-{3-(4-methanesulfonyloxyphenyl)propylamino} phenyl] propionic acid, including Arginine salt of (S)-2-methoxy-3-[4-{3-(4-methanesulfonyloxyphenyl)propylamino} phenyl] propionic acid monohydrate, Arginine salt of (S)-2-methoxy-3-[4-{3-(4-methanesulfonyloxyphenyl) propylamino} phenyl] propionic acid, and (S)-2-methoxy-3-[4-{3-(4-methanesulfonyloxyphenyl)propylamino} phenyl] propionic acid monohydrate. Various aspects and embodiments are included. Compositions containing novel salts of (S)-2-methoxy-3-[4-{3-(4-methanesulfonyloxyphenyl) propylamino}phenyl] propionic acid are also provided.
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Page/Page column 5
(2008/06/13)
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- NOVEL COMPOUNDS AND THEIR USE IN MEDICINE, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
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The present invention relates to novel compounds of formula (I) and their pharmaceutically acceptable salts thereof, pharmaceutical compositions containing them. The present invention also relates to a process for the preparation of the above said novel compounds.
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Page/Page column 55-56
(2010/02/11)
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- Synthesis and radioiodination of some 9-aminoacridine derivatives for potential use in radionuclide therapy
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Three derivatives of the DNA intercalating compound 9-aminoacridine, were prepared and radioiodinated for biological experiments. The compounds are the stannyl derivatives 3-{4-[3-(acridin-9-ylamino)-propoxy]-3-trimethylstannyl- phenyl}-propionic acid and acridin-9-yl-{3-[4-(2-amino-ethyl)-2- trimethylstannyl-phenoxy]-propyl}-amine which were synthesized from the corresponding iodo derivatives by palladium catalyzed reactions, and 4-[2-(acridin-9-ylamino)-ethyl]-phenol. The two stannylated compounds and the phenol were used as precursors for radioiodination and were labeled with 125I using chloramine-T as an oxidant achieving high-to-excellent yields. Copyright
- Ghirmai, Senait,Mume, Eskender,Lundqvist, Hans,Tolmachev, Vladimir,Sjoeberg, Stefan
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p. 855 - 871
(2007/10/03)
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- Stereoselectivity control by oxaspiro rings during Diels-Alder cycloadditions to cross-conjugated cyclohexadienones: The syn oxygen phenomenon
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The diastereofacial selectivity operating in Diels-Alder additions involving spirocyclic cross-conjugated cyclohexadienones with dienes of varying reactivity has been investigated. The study has included the ether series 1a-c as well as the lactone/ketone pair 2a/2b. In all cases, the preferred [4+2] cycloaddition pathway consisted of bonding from that π-surface syn to the oxygen atom. 4-Substituted-4-methyl-2,5-cyclohexadienones (monocyclic systems) were also examined and found to undergo bond formation preferentially from the face bearing the more electron-withdrawing of the two groups at the 4 position. Kinetic parameters were determined for the cycloaddition of 1a and 2a to cyclopentadiene. The rate acceleration profile of solvents was in the order CF3CH2OH ? CH3CN~CH2Cl 2 for the production of 9a from 1a and CF3CH2OH ? CH2Cl2 > CH3CN for the production of 21a from 2a, respectively. This spread in polarity had no major impact on product distribution, a phenomenon also reflected in the behavior of 4-substituted-4-methyl-2,5-cyclohexadienones under comparable conditions. Theoretical assessment of these experimental facts was undertaken at the HF/6-31G* level. The facial selectivity is understandable in terms of the secondary interaction between the HOMO of the diene and LUMO of the dienophile as well as the effective hyperconjugation between the newly forming bond and the 4-anti-C-C σ-orbital due to the more electron-donating bond, as defined by the Cieplak model.
- Ohkata, Katsuo,Tamura, Yukiko,Shetuni, Brandon B.,Takagi, Ryukichi,Miyanaga, Wataru,Kojima, Satoshi,Paquette, Leo A.
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p. 16783 - 16792
(2007/10/03)
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- Compounds and their use in medicine, process for their preparation and pharmaceutical compositions containing them
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The present invention relates to novel antidiabetic, hypolipidemic, antiobesity and hypocholesterolemic compounds of formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them.
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- P-hydroxyphenyl propionic acid derivatives as antiproliferative agents
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Derivatives of the compound p-hydroxyphenyl propionic acid characterised by those derivatives having the general formulas (I) and (Ia), where n can take the values 1,2,3; R can be H or CH3 and R1 can be CH3 or H with pharmacological activity and their application in medicine for the treatment of disorders of the immunological system.
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- Cyclohexylamine derivatives as subtype selective nmda receptor antagonists
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Described are cyclohexylamine derivatives of Formula (I), Formula (II) or Formula (III) and their pharmaceutically acceptable salts thereof. The compounds are antagonists of NMDA receptor channel complexes useful for treating cerebral vascular disorders such as, for example, cerebral ischemia, cardiac arrest, stroke, and Parkinson''s disease. The substituents are described in the specification. 1
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- Deprotection of t-butyldimethylsilyl ethers promoted by cerium(IV) triflate
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t-Butyldimetylsilyl ethers are mildly cleft by catalytic amounts of cerium(IV) triflate. Dependence from water amount was observed.
- Bartoli, Giuseppe,Cupone, Giovanna,Dalpozzo, Renato,De Nino, Antonio,Maiuolo, Loredana,Procopio, Antonio,Sambri, Letizia,Tagarelli, Antonio
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p. 5945 - 5947
(2007/10/03)
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- β1- and β2-adrenoceptor antagonist activity of a series of para- substituted N-isopropylphenoxypropanolamines
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To further explore the structure-activity relationships of β- adrenoceptor (β-AR) antagonists, a series of 25 para-substituted N- isopropylphenoxy-propanolamines were synthesised, nine of which are new compounds. All have been examined for their ability to antagonise β1-ARs in rat atria and β2-ARs in rat trachea. Substitution in the para-position of the phenyl ring is thought to confer β3-specificity and the selectivity of these compounds for the β1-AR ranges from 1.5-234. None of the compounds tested were selective for the β2-AR. Of the 25 compounds studied, 22 had reasonable (pA2 > 7) potencies for the rat β1-AR. Only compound 1 displayed reasonable (pA2 > 7) potency for the rat β2-AR. Twenty two compounds were used as the training set for comparative molecular field analysis (CoMFA) of antagonist potency (pA2) at the rat β1- and β2-ARs. The inclusion of a number of additional physical characteristics improved the QSAR analysis over models derived solely using the CoMFA electrostatic and steric fields. The final models predicted the β1- and β2-AR potency of the compounds in the training set with high accuracy (r2 = 0.93 and 0.86 respectively). The final β1-AR model predicted the β1-potencies of two out of the three test compounds, not included in the training set, with residual PA2 values 2-AR model (residual pA2 values -0.38).
- Louis, Simon N.,Nero, Tracy L.,Iakovidis, Dimitri,Colagrande, Felicia M.,Jackman, Graham P.,Louis, William J.
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p. 919 - 937
(2007/10/03)
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- One-pot reduction of carboxylic acids via O-acylisoureas
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A simple one-pot reduction of aliphatic carboxylic acids to primary alcohols, by treatment with dicyclohexylcarbodiimide followed by lithium borohydride, is reported. The same methodology applied to aromatic carboxylic acids is shown to give a mixture of the alcohols with N- cyclohexylcarboxamides.
- Herbert, John M.,Hewson, Alan T.,Peace, James E.
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p. 823 - 832
(2007/10/03)
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- Microwave-assisted Deacetylation on Alumina: a Simple Deprotection Method
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A simple high-yielding method for the deprotection of acetylated phenols and alcohols is described which occurs under mild conditions on an alumina surface using microwave irradiation.
- Varma, Rajender S.,Varma, Manju,Chatterjee, Arnab K.
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p. 999 - 1000
(2007/10/02)
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- Alumina-mediated cleavage of 1-butyldimethylsilyl ethers
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A simple method for the cleavage of 1-butyldimethylsilyl ethers is described which occurs on alumina surface under solvent free conditions within 10-15 minutes. Mild heating, using microwave irradiation facilitates the procedure.
- Varma, Rajender S.,Lamture, Jagannath B.,Varma, Manju
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p. 3029 - 3032
(2007/10/02)
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- Studies on the Chemical Constituents of Rutaceous Plants. Part 45. Novel Phenyl Propanoids: Cuspidiol, Boninenal, and Methyl Boninenalate
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Cuspidiol, boninenal, and methyl boninenalate were established as having the structures 3-phenyl>propanol (1), (E)-3-phenyl>propenal (2), and (E)-3-phenyl>propenal (3) respectively.The three compounds were also independently synthesized.
- Ishii, Hisashi,Ishikawa, Tsutomu,Tohojoh, Toshiaki,Murakami, Keiko,Kawanable, Eri,et al.
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p. 2051 - 2058
(2007/10/02)
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- Methods for the Construction of Linear 1,7-Diarylheptanoids; Synthesis of Di-O-methylcentrolobol and Precursors (Synthetic and Biosynthetic) to the meta,meta-Bridged Biphenyls Myricanol and Myricanone
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1,7-diarylheptanoids are a varied natural product class in which 'linear' types appear to be biosynthetic precursors to macro(carbo)cyclic (3), macro(oxa)cyclic (4), and condensed polycyclic (5) examples.Various methods (suitable for radiolabelling) are described for constructing 'linear' diarylheptanoids, including Grignard couplings (employing activated magnesium) with arylpropanals and oxazonium salts (11a), (11h), (15a), and (15b)> and dithian alkylation (15c)>.Alkyl-lithium treatment of the benzyloxydithian (19b) gave 1,2,3-triphenylcyclopropane.Syntheses via trialkylcyanoborates were frustrated by disproportionation of the intermediate trialkylboranes.The diarylheptanoids synthesised (11a-h) and (15a-e) include synthetic and biosynthetic precursors to meta,meta-bridged biphenyls and related macrocyclic ethers.
- Henley-Smith, Peter,Whiting, Donald A.,Wood, Andrew F.
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p. 614 - 622
(2007/10/02)
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