The rearrangement of isomeric linear decyn-1-ols by reaction with the sodium salt of 1,3-diaminopropane

Macaulay, Suzanne R.

doi:10.1139/v80-409

Cited by 10 publications

(3 citation statements)

References 6 publications

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“…Alcohol 3b (0.5 g, 3.1 mmol) was obtained as a colorless oil in a 73% yield. The spectroscopic data gathered for 3b are in complete agreement with the spectroscopic data reported in the literature for this compound. − …”

Section: Methodssupporting

confidence: 86%

Synthesis of the Novel N-(2-Hexadecynoyl)-l-Homoserine Lactone and Evaluation of Its Antiquorum Sensing Activity in Chromobacterium violaceum

Sanabria-Ríos,

García-Del-Valle,

Bosh-Fonseca

et al. 2024

ACS Omega

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Chromobacterium violaceum is commonly found in soil and freshwater within tropical and subtropical regions.Although not a common occurrence, this bacterium has the potential to cause severe diseases in humans and animals, such as liver and lung abscesses and septicemia. Herein we report the synthesis of novel N-acyl homoserine lactones (HSLs) to evaluate their effectiveness as antiquorum sensing (anti-QS) agents in C. violaceum. The HSLs were prepared through three synthetic approaches, where hexanoic acid, decanoic acid, 6-decynoic acid, or 2-hexadecynoic acid (2-HDA) was treated with commercially available L-homoserine lactone (HSL) hydrobromide in either dichloromethane or tetrahydrofuran in the presence of EDC and DMAP. The effectiveness of HSLs as anti-QS agents was assessed through susceptibility tests and violacein quantification. The most effective anti-QS inhibitor among all N-acyl-HSLs tested was the N-(2-hexadecynoyl)-L-homoserine lactone (HSL 4). Further experimental approaches, such as quantification of acyl-homoserine lactones and biofilm inhibitory tests, were carried out to determine the effect of HSL 4 on these QS-dependent mechanisms. These experiments showed that HSL 4 was highly effective at inhibiting the production of HSLs and biofilm in C. violaceum at 0.25, 0.50, and 1 mg/mL. In addition, the cytotoxicity activity was evaluated against Vero cells to determine the selectivity of HSL 4 as a nontraditional antibacterial agent. HSL 4 was not toxic against Vero cells at concentrations ranging from 0.0039 to 1 mg/mL. Molecular docking experiments were conducted to study the interactions between novel HSLs and CviR (PDB ID 3QP5), a receptor that plays a significant role in C. violaceum QS. In silico studies indicate that HSL 4 exhibits better interactions with Leu 72 and Gln 95 of the CviR binding pocket when compared to the other analogs. These results validate previous in vitro studies, such as susceptibility tests and violacein production assays. The findings above indicate that novel acetylenic HSLs may potentially be agents that combat bacterial communication and biofilm formation. However, further investigation is necessary to expand the spectrum of bacterial strains capable of resisting antibiotics through QS and evaluate the compounds' cytotoxicity in other cell lines.

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Section: Methodssupporting

confidence: 86%

Synthesis of the Novel N-(2-Hexadecynoyl)-l-Homoserine Lactone and Evaluation of Its Antiquorum Sensing Activity in Chromobacterium violaceum

Sanabria-Ríos,

García-Del-Valle,

Bosh-Fonseca

et al. 2024

ACS Omega

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“…Most of these alkanes were removed by column chromatography and subsequent recrystallization. When NaH/diaminopropane20, 21 was used as the isomerization agent, about 50 % of non‐functionalized alkanes were formed besides the intended product 3 . Other conditions such as KH/diaminopropane22 and NaNH 2 /diaminopropane23 were tested only once and gave incomplete conversions.…”

Section: Resultsmentioning

confidence: 99%

An Efficient Synthesis of Liquid Crystalline Gigantocycles Combining Banana-Shaped and Rod-Like Mesogenic Units

et al. 2002

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Pick your Pd partners: A number of catalytic systems have been developed for palladium‐catalyzed CH activation/CC bond formation. Recent studies concerning the palladium(II)‐catalyzed coupling of CH bonds with organometallic reagents through a PdII/Pd0 catalytic cycle are discussed (see scheme), and the versatility and practicality of this new mode of catalysis are presented. Unaddressed questions and the potential for development in the field are also addressed. In the past decade, palladium‐catalyzed CH activation/CC bond‐forming reactions have emerged as promising new catalytic transformations; however, development in this field is still at an early stage compared to the state of the art in cross‐coupling reactions using aryl and alkyl halides. This Review begins with a brief introduction of four extensively investigated modes of catalysis for forming CC bonds from CH bonds: PdII/Pd0, PdII/PdIV, Pd0/PdII/PdIV, and Pd0/PdII catalysis. A more detailed discussion is then directed towards the recent development of palladium(II)‐catalyzed coupling of CH bonds with organometallic reagents through a PdII/Pd0 catalytic cycle. Despite the progress made to date, improving the versatility and practicality of this new reaction remains a tremendous challenge.

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“…The isomeric linear decyn-1-01 system, which has been used in a previous study (3), was employed to compare potential isomerization reagents. The isomer with the triple bond furthest removed from the free terminus, 2-decyn-1-01, was the starting material in this work.…”

Section: Resultsmentioning

confidence: 99%

Some alkali metal alkyl amides as alkyne isomerization reagents: selective isomerization of one triple bond of a diynol

Abrams¹,

Nucciarone²,

Steck³

1983

Can. J. Chem.

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61, 1073 (1983).The lithium and sodium salts of 1.2-diaminocthanc. l,3-diarninopropane. n-butylamine, and the lithium salt of isobutylaminc were studied as potential rcapcnts for isomcrization of triple bonds in alkyn-I-01s. The sodium salts of the diamincs afforded high yields of the o-alkyn-1-01. Somewhat surprisingly. the sodium salt of n-butylamine also effects isomerization to the terminal position. The lithium salt of 1,3-diaminopropanc gave the highest conversion of 2-to 3-alkyn-1-01, A novel, selective rearrangement of one triple bond of a diynol. a 2.0-to 3.w-diyn-1-01 isomcrization, was incorporated into a synthesis of the insect sex pheromone 3.13-octadccadienol acetate. On a 6valuC I'utilisd des sels de sodium et dc lithium du diarnino-1.2 Cthane. du diamino-1.3 propane, de la n-butylaminc et du sel de lithium dc I'isobutylamine en tant qu'apents potentiels d'isomdrisation des triples liaisons des alcynols-I. Les scls dc sodium des dialnines donnent des rendemcnts dlevds en o-alcynols-I. Par opposition le sel de sodium de la n-butylamine affcctc aussi I'isornCrisarion vers la position terminale. LC sel dc lithium du diamino-1.3 propane donne le plus fort pourcentage dc transformation des alcync-l 01s-I en alcyne-3 01s-I. Dans le cadre dc la synthkse de la phCromone scxuclle des insectes, I 'acetate d'octadecadienc-3.13 ol, on a introduit une nouvelle transposition sdlcctive d'une triple liaison d'un diynol ii savoir I'isomdrisation d'un 2.0-diync 01-1 en un 3,o-diyne ol-I.[Traduit par le journal]

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The rearrangement of isomeric linear decyn-1-ols by reaction with the sodium salt of 1,3-diaminopropane

Cited by 10 publications

References 6 publications

Synthesis of the Novel N-(2-Hexadecynoyl)-l-Homoserine Lactone and Evaluation of Its Antiquorum Sensing Activity in Chromobacterium violaceum

Synthesis of the Novel N-(2-Hexadecynoyl)-l-Homoserine Lactone and Evaluation of Its Antiquorum Sensing Activity in Chromobacterium violaceum

An Efficient Synthesis of Liquid Crystalline Gigantocycles Combining Banana-Shaped and Rod-Like Mesogenic Units

Some alkali metal alkyl amides as alkyne isomerization reagents: selective isomerization of one triple bond of a diynol

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