49580-59-8Relevant academic research and scientific papers
Synthesis and biological testing of ester pheromone analogues for two fruitworm moths (Carposinidae)
Barker, David,Chhagan, Asha,Park, Kye Chung,Pilkington, Lisa I.,Suckling, David M.,Twidle, Andrew M.
, p. 9557 - 9567 (2020/10/13)
A range of ester pheromone analogues for carposinid moths were synthesized and evaluated for biological activity. The analogues aimed to take advantage of the structural commonality of (7Z)-alken-11-ones found in this family. Analogues were tested on two pest species: Heterocrossa rubophaga and Coscinoptycha improbana. Two of the analogues, (2Z)-nonenyl nonanoate and (4Z)-heptyl undecenoate, elicited significant electroantennogram responses. Only (4Z)-heptyl undecenoate gave consistent responses with both moth species in single sensillum recording. Field trapping trials were conducted with these two analogues both individually and in combination with the pheromone of each of the two moth species. No attraction was observed to either of the analogues alone, by either moth species. However, when (4Z)-heptyl undecenoate was coupled with the pheromone, it produced a strong inhibitory effect in H. rubophaga, reducing male moth trap catch by over 95%. No inhibitory effect on male moth trap catch was observed in C. improbana.
Fe-catalyzed synthesis of (13z)-eicos-13-en-10-one, the main sex pheromone component of carposina niponensis
Shakhmaev,Sunagatullina, A. Sh,Zorin
, p. 128 - 131 (2017/09/30)
(13Z)-Eicos-13-en-10-one, the main sex pheromone component of Carposina niponensis, was synthesized stereoselectively via Fe-catalyzed cross-coupling of ethyl (4Z)-5-chloropent-4-enoate with hexylmagnesiumbromide to give ethyl (4Z)-undec-4-enoate and repeated Fe-catalyzed cross-coupling of its acid chloride with nonylmagnesiumbromide.
Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl- 4(1H)-quinolones
Wube, Abraham A.,Hüfner, Antje,Thomaschitz, Christina,Blunder, Martina,Kollroser, Manfred,Bauer, Rudolf,Bucar, Franz
experimental part, p. 567 - 579 (2011/03/17)
A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships.
Chemistry and photochemistry attending the inactivation of Escherichia coli β-hydroxydecanoyl thiol ester dehydrase by an acetylenic diazoketone
Henderson,Larsen,Schwab
, p. 5025 - 5034 (2007/10/02)
β-Hydroxydecanoyl thiol ester dehydrase from Escherichia coli, an enzyme that catalyzes both dehydration and allylic rearrangement reactions, has been shown previously to undergo mechanism-based inactivation by the acetylenic substrate analog 1-diazo-4-undecyn-2-one (DUO). Details of the chemistry and photochemistry of DUO are now presented. Analysis of DUO-inactivated dehydrase by 15N NMR spectrosocpy indicates that DUO quantitatively alkylates histidine-70. Long-wavelength photoirradiation leads to spectrophotometrically observable changes in the DUO-dehydrase adduct. The structural changes were characterized by a combination of methods. Samples of protein that had been inactivated with [1-13C]-, [2-13C]-, and [3-13C] DUO were analyzed by 13C NMR spectroscopy, both prior and subsequent to photoirradiation. By comparisons of the chemical shifts of the enriched atoms of the inactivator moiety with those of model compounds, it was confirmed that the α-diazoketone moiety is retained in DUO-inactivated dehydrase and that photoirradiation leads to Wolff rearrangement of the α-diazoketone moiety followed by attack of a nucleophile on the resulting ketone. Proteolytic degradation of photoirradiated, DUO-inactivated dehydrase gave peptides that were analyzed by Edman sequencing and by mass spectrometry. The results are consistent with a single protein modification (at H70), and attack on the ketone by water, leading to a carboxylic acid. Samples of intact native, DUO-inactivated, and photoirradiated, DUO-inactivated dehydrase were analyzed by electrospray ionization mass spectrometry, the results of which clearly support the hypothesis that the ketone suffers attack by water. In light of recent results from X-ray crystallography, it is proposed that the water that attacks the ketone is one of two bound water molecules with specific roles in the binding and/or catalytic turnover of substrate. A Michael addition-elimination mechanism is presented to explain the unexpected hydrolytic lability of the DUO-dehydrase adduct.
NEW SYNTHETIC METHOD OF (Z)-4-ALKENOIC ACIDS USING RING-OPENING REACTION OF (Z)-4-HEXENOLIDE WITH ORGANOCOPPER REAGENT
Fujisawa, Tamotsu,Umezu, Kazuto,Kawashima, Masatoshi
, p. 1795 - 1798 (2007/10/02)
(Z)-4-Hexenolide reacted regioselectively with diorganocuprates to give (Z)-4-alkenoic acids in high yields.Synthetic utility was demonstrated by the convenient synthesis of cis-jasmone.
ONE-POT SYNTHESIS OF (Z)-4-ALKENOIC ACIDS
Fujisawa, Tamotsu,Sato, Toshio,Kawara, Tatsuo,Naruse, Kouichi
, p. 1123 - 1124 (2007/10/02)
The reaction of β-propiolactone with di-(Z)-1-alkenylcuprates, prepared from Grignard reagents, copper(I) iodide and acetylene, gave (Z)-4-alkenoic acids in high yields in one-pot operation.
