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Naphthalene Derivatives (naphthalene + derivative)

Distribution by Scientific Domains

Chemistry	87%

Distribution within Chemistry

General & Introductory Chemistry	42%

Selected Abstracts

Amino Acid Derivatives, Part 4: Synthesis and Anti-HIV Activity of New Naphthalene Derivatives

ARCHIV DER PHARMAZIE, Issue 7 2010
Nawar S. Hamad
Abstract A new series of 2-(naphthalen-2-yloxy)- N -[(aryl-5-thioxo-4,5-dihydro-1H -1,2,4-triazol-3-yl)methyl] acetamides 5a,f was synthesized from naphthalene-derived glycine derivative 2 via the hydrazinoacetamide analogs 4a,f. Alternatively, treatment of 4a with H2SO4 afforded 2-(naphthalen-2-yloxy)- N -((5-(phenylamino)-1,3,4-thiadiazol-2-yl)methyl) acetamide 6a. Alkylation or sulphonylation of 5a afforded the S-alkylated derivatives 7 and 8, respectively. Interestingly, treatment of 3 with methoxide ion gave the triazine derivative 9. The synthesized compounds have been screened for their inhibitory activity against HIV-1 and HIV-2 in MT-4 cells. However, 7 was found to be the potent inhibitor in vitro for the replication of HIV-1 (EC50 = 0.20 ,g/mL), suggesting a new lead in the development of an antiviral agent. [source]

Synthetic Route to 1,3-Disubstituted Naphthalene Derivatives.

CHEMINFORM, Issue 14 2003
Ibrahim Demirtas
Abstract For Abstract see ChemInform Abstract in Full Text. [source]

Rhodium/Phosphine/Amine,HBr Catalyst System for Highly Selective Cross-Cyclodimerization of Aryl- and Alkylalkynes: Efficient Access to Multisubstituted Naphthalene Derivatives

CHEMISTRY - A EUROPEAN JOURNAL, Issue 2 2010
Koichi Sakabe
Trinity: The combination of rhodium/phosphine/amine,HBr enables the highly selective catalytic cross-cyclodimerization of diarylacetylenes with aliphatic alkynes to afford the corresponding multiply substituted naphthalenes in good-to-high yields. The catalyst system also allows the use of some alkenes as the coupling partners, which provides a facile route to highly functionalized dihydronaphthalenes (see scheme). [source]

Novel DNA-Damaging Tropolone Derivatives from Goupia glabra

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 21 2003
Dulce Mesa-Siverio
Abstract Two novel tropolone derivatives 1 and 2 have been isolated from Goupia glabra. Their structures were determined by extensive 1D and 2D NMR spectroscopic studies. Compound 2 constitutes the first example isolated from a natural source of a Diels,Alder adduct between a tropolone and a naphthalene derivative. Compounds 1 and 2 exhibit significant toxicity towards a panel of DNA damage checkpoint defective yeast mutants, and behave as genotoxins, which highlights their potential to be used as anticancer drugs. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003) [source]

Antimalarial compounds from Kniphofia foliosa roots

PHYTOTHERAPY RESEARCH, Issue 6 2005
Abraham Abebe Wube
Abstract During the course of screening Ethiopian medicinal plants for their antimalarial properties, it was found that the dichloromethane extract of the roots of Kniphofia foliosa Hochst. (Asphodelaceae), which have long been used in the traditional medicine of Ethiopia for the treatment of abdominal cramps and wound healing, displayed strong in vitro antiplasmodial activity against the chloroquine-sensitive 3D7 strain of Plasmodium falciparum with an ED50 value of 3.8 µg/mL and weak cytotoxic activity against KB cells with an ED50 value of 35.2 µg/mL. Five compounds were isolated from the roots and evaluated for their invitro antimalarial activity. Among the compounds tested, 10-(chrysophanol-7,-yl)-10-(,)-hydroxychrysopanol-9-anthrone and chryslandicin, showed a high inhibition of the growth of the malaria parasite, P. falciparum with ED50 values of 0.260 and 0.537 µg/mL, respectively, while the naphthalene derivative, 2-acetyl-1-hydroxy-8-methoxy-3-methylnaphthalene, exhibited a less significant antimalarial activity with an ED50 value of 15.4 µg/mL. To compare the effect on the parasite with toxicity to mammalian cells, the cytotoxic activities of the isolated compounds against the KB cell line were evaluated and 10-(chrysophanol-7,-yl)-10-(,)-hydroxychrysopanol-9-anthrone and chryslandicin displayed very low toxicity with ED50 values of 104 and 90 µg/mL, respectively. This is the first report of the inhibition of the growth of P. falciparum by anthraquinone-anthrone dimers and establishes them as a new class of potential antimalarial compounds with very little host cell toxicity. Copyright © 2005 John Wiley & Sons, Ltd. [source]

Exclusive ,-Substitution in the Reaction of Octafluoronaphthalene with Secondary Amines

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 4 2004
Vladimir I. Sorokin
Abstract The reaction between octafluoronaphthalene and dimethylamine, pyrrolidine or piperidine in DMF, dimethyl(ethylene)urea (DMEU) or without solvent leads to the exclusive substitution of ,-fluorine atoms giving naphthalene derivatives with four NR2 groups. This was proved by 19F NMR of the products and a crystal structure determination for 1,4,5,8-tetrafluoro-2,3,6,7-tetrakis(piperidin-1-yl)naphthalene. The main feature of the reaction in DMF was a transamidation process. The remaining four fluorine atoms in the synthesised tetraamines could be smoothly replaced by reduction with LiAlH4. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004) [source]

Tunable haptotropic metal migration in fused arenes: towards organometallic switches,

THE CHEMICAL RECORD, Issue 2 2004
Karl Heinz Dötz
Abstract Tricarbonyl chromium complexes of naphthalene derivatives are synthesized by chromium-templated [3,+,2,+,1]-benzannulation and subjected to thermally induced haptotropic rearrangement experiments. Thermodynamic and kinetic parameters for the metal shift demonstrate the influence of the arene substitution pattern. In turn, the chromium template may be tuned as well by phosphorus coligands which allow to accelerate or slow down the isomerization process; this effect quantitatively reflects the steric and electronic properties of the coligand sphere. Proper adjustment of the template allows for a photo-induced reverse migration of the chromium moiety which results in a switchable organometallic device. Experiments with enantiopure arene chromium complexes indicate a stereospecific metal migration. The rearrangement proceeds by an intramolecular mechanism in both directions. Haptotropic isomerization reactions are not limited to bicyclic arenes and can be extended from naphthalenes to phenanthrene or tetra- and pentacyclic heteroarene systems. © 2004 The Japan Chemical Journal Forum and Wiley Periodicals, Inc. Chem Rec 4: 61,71; 2004: Published online in Wiley InterScience (www.interscience.wiley.com) DOI 10.1002/tcr.20007 [source]

A New, Efficient and Stereoselective Synthesis of Tricyclic and Tetracyclic Compounds by Samarium Diiodide Induced Cyclisations of Naphthyl-Substituted Arylketones,An Easy Access to Steroid-Like Skeletons

CHEMISTRY - A EUROPEAN JOURNAL, Issue 21 2007
Francesca Aulenta Dr.
Abstract In this report, we present the application of samarium diiodide induced cyclisations of naphthyl-substituted ketones towards an easy and stereoselective access to tri- and tetracyclic-functionalised compounds. Typical naphthalene derivatives were studied to investigate the scope and limitations of this novel cyclisation process. The model substrates studied demonstrate that the samarium ketyl cyclisations are essentially restricted to the formation of six-membered rings. The diastereoselectivity of these reactions is strongly influenced by the connection of the alkyl side chain to the naphthalene core. ,-Naphth-1-yl-substituted ketones furnished cyclisation products, such as 17 or 22,26, as single diastereomers, whereas ,-naphth-2-yl-substituted precursors gave mixtures of diastereomers,as demonstrated by the conversion of model compound 10 into tricyclic products 18,a/18,b, or that of cyclohexanone derivative 33 into tetracyclic diastereomers 34,a/34,b. Cyclic ketones as ketyl precursors furnished steroid-like tetracyclic skeletons; however, due to the cis/cis fusion of rings B/C and C/D these products have an "unnatural" bowl-like shape. Several of the cyclisation products have been identified by X-ray analyses, which not only proved the constitutions, but also the relative configurations and the preferred conformations. Steroid analogue 23 was subjected to subsequent transformations, which demonstrate that the styrene-like double bond of such compounds can be used for further structural diversification. First attempts to synthesise related azasteroids by incorporating nitrogen atoms into the ketone moiety are also reported. Thus, pyrrolidine derivatives 44 and 47 as well as piperidine derivatives 50 and 52 were subjected to samarium diiodide induced cyclisations. The expected tetracyclic products 48, 49,a/49,b, 51 and 53,a/53,b were obtained in moderate to good yields. The stereoselectivities observed follow the rules already established for the all-carbon precursors. The resulting products, bearing a nitrogen atom in ring D, are interesting azasteroid analogues with "unnatural" configuration. [source]