Displacement Reactions on 1-Azulylmethyltrimethylammonium Iodide<sup>1,2</sup>

Anderson, Arthur G.; Anderson, Robert Griffin; Fujita, T.S.

doi:10.1021/jo01059a100

Cited by 26 publications

(12 citation statements)

References 2 publications

(2 reference statements)

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“…To introduce a leaving group for the nucleophilic displacement reaction, azulene was aminomethylated with N,N,N%,N%-tetramethyldiaminomethane, paraformaldehyde and acetic acid and subsequently converted to the corresponding quarternary ammonium salt 2 with methyl iodide [9]. Reaction of 2 with diethyl acetaminomalonate sodium salt gave the azulenylmethyl derivative 3, which upon saponification of the ethyl ester moieties and decarboxylation of the corresponding h-dicarboxylic acid 4, yielded the racemic acetyl amino acid 5.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of ?-(1-azulenyl)-L-alanine as a potential blue-colored fluorescent tryptophan analog and its use in peptide synthesis

et al. 2000

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Acetyl-beta-(1-azulenyl)-D,L-alanine has been synthesized in high overall yield by the malonic ester condensation procedure, and the racemate has been enzymatically resolved with acylase I from Aspergillus melleus. The enantiomerically pure L-amino acid is of interest as a blue-colored fluorescent tryptophan analog. The bioactivity data of a heptagastrin analog containing it suggests that the planar aromatic azulene moiety may indeed mimic the tryptophan side chain to some extent, and the spectral properties of the azulene moiety makes beta-(1-azulenyl)-L-alanine of potential value as a UV and fluorescence probe in synthetic peptides, and possibly even in proteins if bioincorporation succeeds with chemically misacylated tRNAs.

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Section: Resultsmentioning

confidence: 99%

Synthesis of ?-(1-azulenyl)-L-alanine as a potential blue-colored fluorescent tryptophan analog and its use in peptide synthesis

et al. 2000

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“…39 Starting material for the preparation of ͑thio͒ethers IV-VI was 1-azulylmethyltrimethylammonium iodide which was treated with the sodium salts of the respective anthracene-9-yl-͑thio͒alcohols. 40 After column chromatography the final purity of compounds I-VI was Ͼ95% as controlled by 1 H and 13 C NMR spectroscopy. The solvents 1,1,2-trichloro-trifluoro-ethane ͑Aldrich, Ͼ99.9%͒ and xenon ͑Messer-Griesheim, Ͼ99.99%͒ could be used without purification.…”

Section: B Experimental Techniquementioning

confidence: 99%

Intramolecular vibrational energy redistribution in bridged azulene-anthracene compounds: Ballistic energy transport through molecular chains

Schwarzer

Kutne

Schröder

et al. 2004

The Journal of Chemical Physics

108

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Intramolecular vibrational energy flow in excited bridged azulene-anthracene compounds is investigated by time-resolved pump-probe laser spectroscopy. The bridges consist of molecular chains and are of the type (CH(2))(m) with m up to 6 as well as (CH(2)OCH(2))(n) (n=1,2) and CH(2)SCH(2). After light absorption into the azulene S(1) band and subsequent fast internal conversion, excited molecules are formed where the vibrational energy is localized at the azulene side. The vibrational energy transfer through the molecular bridge to the anthracene side and, finally, to the surrounding medium is followed by probing the red edge of the azulene S(3) absorption band at 300 nm and/or the anthracene S(1) absorption band at 400 nm. In order to separate the time scales for intramolecular and intermolecular energy transfer, most of the experiments were performed in supercritical xenon where vibrational energy transfer to the bath is comparably slow. The intramolecular equilibration proceeds in two steps. About 15%-20% of the excitation energy leaves the azulene side within a short period of 300 fs. This component accompanies the intramolecular vibrational energy redistribution (IVR) within the azulene chromophore and it is caused by dephasing of normal modes contributing to the initial local excitation of the azulene side and extending over large parts of the molecule. Later, IVR in the whole molecule takes place transferring vibrational energy from the azulene through the bridge to the anthracene side and thereby leading to microcanonical equilibrium. The corresponding time constants tau(IVR) for short bridges increase with the chain length. For longer bridges consisting of more than three elements, however, tau(IVR) is constant at around 4-5 ps. Comparison with molecular dynamics simulations suggests that the coupling of these chains to the two chromophores limits the rate of intramolecular vibrational energy transfer. Inside the bridges the energy transport is essentially ballistic and, therefore, tau(IVR) is independent on the length.

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“…As secondary antibodies, αrabbit IgG (DAKO, Tokyo, Japan) antibodies, which were conjugated with horseradish peroxidase, were used. [1], N-butylguaiazulenecarboxamide [2], N-pentylguaiazulenecarboxamide [3], N-(2-hydroxyethyl)guaiazulenecarboxamide [4], N-(3-hydroxypropyl)guaiazulenecarboxamide [5], N-(2-methoxyethyl)guaiazulenecarboxamide [6], N-(3-methoxypropyl)guaiazulenecarboxamide [7], N- (2-aminopropyl)guaiazulenecarboxamide [8], N- (3-aminobutyl)guaiazulenecarboxamide [9], N- (2-(2-aminoethoxy)ethoxyethyl)guaiazulenecarboxamide [10] were synthesized, according to previous reports (11)(12)(13)(14). All compounds were dissolved in DMSO at 40 mM and stored at -20˚C before use.…”

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confidence: 99%

In Vitro Anti-tumor Activity of Azulene Amide Derivatives

Wada

Maruyama

Irie

et al. 2018

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Displacement Reactions on 1-Azulylmethyltrimethylammonium Iodide^1,2

Cited by 26 publications

References 2 publications

Synthesis of ?-(1-azulenyl)-L-alanine as a potential blue-colored fluorescent tryptophan analog and its use in peptide synthesis

Synthesis of ?-(1-azulenyl)-L-alanine as a potential blue-colored fluorescent tryptophan analog and its use in peptide synthesis

Intramolecular vibrational energy redistribution in bridged azulene-anthracene compounds: Ballistic energy transport through molecular chains

In Vitro Anti-tumor Activity of Azulene Amide Derivatives

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Displacement Reactions on 1-Azulylmethyltrimethylammonium Iodide1,2

Cited by 26 publications

References 2 publications

Synthesis of ?-(1-azulenyl)-L-alanine as a potential blue-colored fluorescent tryptophan analog and its use in peptide synthesis

Synthesis of ?-(1-azulenyl)-L-alanine as a potential blue-colored fluorescent tryptophan analog and its use in peptide synthesis

Intramolecular vibrational energy redistribution in bridged azulene-anthracene compounds: Ballistic energy transport through molecular chains

In Vitro Anti-tumor Activity of Azulene Amide Derivatives

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Displacement Reactions on 1-Azulylmethyltrimethylammonium Iodide^1,2