Naphthyl Derivatives Research Articles

Structures, dynamics and vibrations of cyclic (H2O)3and its phenyl and naphthyl derivatives

The cyclic water trimer shows a fascinating complexity of its intermolecular potential-energy surface as a function of the three intermolecular torsional coordinates: there are six isometric but permutationally distinct minimum-energy structures of C1 symmetry, which can interconvert by torsional motions via six isometric transition states, also of C1 symmetry. A second type of interconversion can occur through different torsional motions via two C3 symmetric transition structures, and a third interconversion type via a planar C3h symmetric transition structure. The equivalence of the six minima is broken if the ‘free’ H atom of one H2O molecule in the cluster is chemically substituted, yielding three distinct conformers, which occur in enantiomeric pairs. Not all three conformers are necessarily locally stable minima; this depends on the substituent. The phenol–(H2O)2, p-cyanophenol–(H2O)2, 1-naphthol–(H2O)2 and 2-naphthol–(H2O)2 clusters, which are the phenyl, p-cyanophenyl and naphthyl derivatives of (H2O)3, were examined by resonant two-photon ionization spectroscopy in supersonic beams. These clusters exhibit S0→ S1 vibronic spectra with very different characteristics. These reflect the number of cluster structures formed, their low-frequency intermolecular vibrations and indirectly give information about the cluster fluxionality.

Calixcrowns and related molecules

The synthesis of 1,2- and 1,3-calix[4]-bis-crowns, double calix[4]arenes and double calixcrowns have been shown to depend on the reaction conditions (nature of the base, structure of the ditosylates, and the stoichiometry of the reactants). The 1,3-alternate conformation of the 1,3-calix[4]-bis-crowns was shown to be favourable to the selective complexation of cesium cation. The observed Na+/Cs+ selectivity was exploited in separation processes using them as carriers in transport through supported liquid membranes (SLMs). The best Na+/Cs+ selectivity (1/45 000) was observed for the naphthyl derivative 7. Calix(aza) crowns and 1,3-calix[4]-bis-(aza)-crowns were also produced through the preliminary formation of the Schiff base-calixarenes, which were further hydrogenated. The syntheses consisted of the 1,3-selective alkylation of calixarenes followed by cyclization into a 1,3-bridged calixarene or by the direct 1,3-capping of the calixarene with appropriate ditosylates. Soft metal complexation by these ligands is also presented.

DNA triple-helix specific intercalators as antigene enhancers: Unfused aromatic cations

Triple-helical structures involving the interaction of an oligonucleotide third strand with a duplex nucleic acid sequence have recently gained attention as a therapeutic strategy in the "antigene" approach [cf. Helene, C. (1991) Eur. J. Cancer 27, 1466-1471]. This method utilizes the triple helix formed from the cellular duplex and an added third strand to directly regulate the activity of a selected gene. The limited stability of nucleic acid triple-helical interactions, particularly if the third strand has backbone modifications such as methylphosphonate or phosphorothioate substitutions, is a limiting condition for the use of this approach. We have designed and synthesized compounds, on the basis of the following three criteria, that we feel should provide selective interactions and significant stabilization of triplexes: appropriate aromatic surface area for stacking with triplex bases in an intercalation complex, positive charge, and limited torsional freedom in the aromatic system to match the propeller twist of the triple-base interactions in the triplex. A series of quinoline derivatives with an alkylamine side chain at the 4-position and with different aryl substituents at the 2-position has been synthesized as our first compounds. A 2-naphthyl derivative provides significant and selective stabilization of the triplex. In a 0.2 M NaCl buffer, the naphthyl derivative increased the Tm for the triplex (triplex to duplex and third strand transition) by approximately 30 degrees C more than the Tm increase for the duplex (duplex to single strands transition). Spectral changes and energy-transfer results indicate that the naphthyl compound and related derivatives bind to the triplex by intercalation.(ABSTRACT TRUNCATED AT 250 WORDS)

Measurement of quadratic hyperpolarizabilities of unsymmetrical donor-acceptor bi- and polyaryls: effect of size and torsion angle of aryl units

The linear and quadratic nonlinear optical properties of donor-acceptor polyphenyls and naphthyl derivatives are in investigated. The behaviour of the static first-order hyperpolarizability β(O) as a function of the number n of phenyl units separating an acceptor group (cyano) and a donor group (methylthio) is studied for n=1, 2, 3, and compared to that of similar polyphenyls bearing other donor substitutents (N,N-dimethylamino, methoxy). β(O) is also measured for unsymmetrical donor-acceptor biaryls containing at least one napthyl unit. A clear influence of the twist angle between the two units on the quadratic nonlinear response of the molecule is evidenced, allowing for fine control of the transparency/nonlinear efficiency trade-off.

Syntheses of 6N(N?-formyl-D-phenylalanyl)-deoxyamino-?-cyclodextrin and 6N(N?-formyl-L-phenylalanyl)deoxyamino-?-cyclodextrin and their inclusion behavior

6N(N′-formyl-D-phenylalanyl)-deoxyamino-β-cyclodextrin and 6N(N′-formyl-L-phenylal-anyl)-deoxyamino-β-cyclodextrin (I andII) were prepared. These new hosts formed ‘intramolecular host-guest complexes’ and included naphthyl derivatives preferentially with a stoichiometry of 1:1. The inclusion behavior was different between I and II because the cavity shape formed with the CD cavity and the phenylalanine moiety of I was different from that of II.

An evaluation of the structural requirements for the separation of propranolol enantiomers on Pirkle phases following achiral derivatisation

The chromatographic performance of a series of isocyanate and isothiocyanate derivatives of (±)-propranolol has been investigated on three Pirkle-type chiral stationary phases (CSP's), 3,5-dinitrobenzoylphenylglycine (PHE), 3,5-dinitrobenzoylleucine (LEU) and phenethylpropylurea (PEPU). The reaction yield is independent of the substituent group but is affected by choice of solvent. The urea or thiourea derivative group formed is responsible for any separation observed on the amino acid based phases, the retention being related to structure. The structure-retention relationship is not apparent for the π-basic PEPU phase, moreover resolution is not simply related to retention for all three phases. Inversion of elution order of the enantiomers is observed with certain derivatives on the LEU column. The naphthyl and nitrophenyl derivatives generally exhibit enhanced retention, with the naphthylurea derivative generally giving the best resolution on these phases.

Synthesis and biochemistry of fluorescent aromatase inhibitors

Effective aromatase inhibitors have been developed that contain aryl functionalities at the 7α-position of the steroid nucleus. The exact interactions of 7α-substituted androstenediones with the active site of aromatase is unknown. Fluorescent derivatives may provide a useful spectroscopic method for examining the binding of these inhibitors to the microsomal complex and purified aromatase protein. Dinitrophenyl, dansyl, and naphthyl derivatives of 7α-(4'-amino)phenylthio-4-androstene-3,17-dione and androstenedione were synthesized as potential fluorescent agents. An in vitro assay with human placental microsomes was used to evaluate aromatase inhibitory properties. These fluorescent compounds were effective competitive inhibitors and have apparent k i values ranging from 24.1 to 86.7 n m.

4871735 Naphthyl derivatives, pharmaceutical compositions containing these compounds and processes for preparing them

4871735 Naphthyl derivatives, pharmaceutical compositions containing these compounds and processes for preparing them

4871735 Naphthyl derivatives, pharmaceutical compositions containing these compounds and processes for preparing them: Joachi Heider, Manfre Psiorz, Andreas Bomhard, Norbert Hauel, Berthold Narr, Klaus Noll, Christia Lillie, Walter Kobinger, Jurgen Dammgen, Warthausen, Federal Republic of Germany assigned to Dr Karl Thomae GmbH

4871735 Naphthyl derivatives, pharmaceutical compositions containing these compounds and processes for preparing them: Joachi Heider, Manfre Psiorz, Andreas Bomhard, Norbert Hauel, Berthold Narr, Klaus Noll, Christia Lillie, Walter Kobinger, Jurgen Dammgen, Warthausen, Federal Republic of Germany assigned to Dr Karl Thomae GmbH

Mutagenicity of aryl propylene and butylene oxides with Salmonella

10 aryl propylene oxides and 6 aryl butylene oxides were synthesized. Dose-mutagenicity relationships were studied for these compounds and for 1,2-epoxybutane, using both the preincubation and plate incorporation Ames tests with Salmonella typhimurium strains TA100 and TA1535. Structure-mutagenicity relationships were further examined by concurrent testing at single doses with the plate incorporation assay in strain TA100. In both series of compounds, mutagenicity showed very weak correlation to chemical reactivity, molar volume and partition values. However, all compounds were mutagenic in at least one system with the propylene oxides being more mutagenic than the corresponding butylene oxide derivatives. The naphthyl derivatives in each series were the most mutagenic.

Isolation and investigation of the complex Li 3[FeNp 3N 2]· nEt 2O - the product of interaction of molecular nitrogen with a naphthyl derivative of zero-valent iron

The complex Li 3[FeNp 3N 2]· nEt 2O produced by the reaction of N 2, with Li 3FeNp 3· mEt 2O has been isolated and its magnetic properties and IR spectra investigated. The proposed structure of the complex includes the linear fragment FeNNLi.

The synthesis of some derivatives of benzo[f]naphtho[1,8‐bc]thiepin‐12‐one

AbstractThe preparations of benzo[f]naphtho[1,8‐bc]thiepin‐12‐one, its 6‐methyl and 6‐methoxy derivatives and their corresponding sulfoxides and sulfones are described. They involve the coupling of suitable halogen naphthyl derivatives with thiophenoxides with the help of copper and the cyclization of the resulting acids with phosphorus pentoxide in benzene. The oxidations to sulfoxides and sulfones were performed with iodo‐benzene diacetate and hydrogen peroxide, respectively. The ir and pmr spectra are reported.

Charge-transfer spectra of some phenyl and naphthyl derivatives. Relative importance of .sigma.-.pi. and n-.pi. conjugation involving the .pi. silicon-silicon system

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTCharge-transfer spectra of some phenyl and naphthyl derivatives. Relative importance of .sigma.-.pi. and n-.pi. conjugation involving the .pi. silicon-silicon systemHideki Sakurai and Mitsuo KiraCite this: J. Am. Chem. Soc. 1974, 96, 3, 791–794Publication Date (Print):February 1, 1974Publication History Published online1 May 2002Published inissue 1 February 1974https://doi.org/10.1021/ja00810a025RIGHTS & PERMISSIONSArticle Views111Altmetric-Citations24LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (478 KB) Get e-Alerts Get e-Alerts

Chemistry of the Podocarpaceae. XLVIII. Photo-sensitized oxidations of unsaturated ring-c aromatic diterpenoids

Photo-sensitized oxidation of the 6,7-dehydro ring-c aromatic diterpenoids (5), (8) and (38) affords high yields of the corresponding 5-ene-7-ones (62), (63) and (69). Similar oxygenation of 13-methoxy- totara-6,8,11,13-triene (21) gives a hydroperoxide (74) which undergoes a facile rearrangement to a naphthyl derivative (80) in the presence of acid. Photo-sensitized oxidation of the enol acetates derived from the 7-oxo diterpenoids, however, provides a general method for preparation of the corresponding 5-ene-7-one. Reduction of the enone (62) with lithium aluminium hydridealuminium chloride gives a mixture of the 5,8,11,13-tetraene (66) and the 6,8,11,13-tetraene (9) while reduction with sodium borohydride and treatment of the resulting alcohols (61) and (67) with acid gives a mixture of the tetraenes (5) and (68). Photo-oxygenation of the latter mixture provides a convenient method for isolating the tetraene (68). Similar reductions of 13-methoxytotara-5,8,11,13-tetraen-7-one (76) have been examined and products from the action of m-chloroperbenzoic acid on the enol acetates (19), (20) and (7) are reported.

Residual Gas Analysis with a Quadrupole Mass Filter

Two series of residual gas analysis were made by using a quadrupole mass filter for two independent vacuum systems. One of the systems comprises a oil diffusion pump (4″)using silicone DC-705 as a working fluid, and the other two oil diffusion pumps (2.5″) using naphthyl derivative (mono eicosyl). The results of the analysis indicate the existence of an unnegligible amount of the diffusion oil vapor in the vacuum chamber. The two diffusion pump oils gave their own characteristic mass peaks, and tentative assignment was made for the structures of these fragment ions. It was found from the residual. gas analysis that the vacuum system of the naphthyl derivative diffusion pumps is more favorable for carrying out some kind of electron impact experiment.

923. Di-N-substituted 2-halogenoethylamines. Part VII. NN-di-alkyl-2-1′- or -2′-naphthyl derivatives, and some miscellaneous related compounds: synthesis, reactivity, and pharmacology

923. Di-N-substituted 2-halogenoethylamines. Part VII. NN-di-alkyl-2-1′- or -2′-naphthyl derivatives, and some miscellaneous related compounds: synthesis, reactivity, and pharmacology

Chromatography of Thiol Compounds

THE extreme ease of oxidation of the thiol group has hindered the chromatographic separation of mercaptans. Hanes, Hird and Isherwood1 overcame this difficulty by combining the thiol group with N-ethyl maleimide before chromatographic separation. Cysteine and glutathione were separated in this way and detected by spraying the developed papers with ninhydrin. This spray is not specific for mercaptans, however, and Price and Campbell2 expanded the technique by condensing the mercaptans with N-(4-hydroxy-1-naphthyl) isomaleimide and, after chromatographic separation, detecting the naphthyl derivative by spraying with tetra-azotized di-o-anisidine.

Some Naphthyl Derivatives of Barbituric Acid

Some Naphthyl Derivatives of Barbituric Acid