1448-96-0Relevant articles and documents
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Martin,J. et al.
, p. 1676 - 1681 (1974)
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Design, synthesis and biological evaluation of potential antibacterial butyrolactones
Sweidan, Alaa,Chollet-Krugler, Marylene,van de Weghe, Pierre,Chokr, Ali,Tomasi, Sophie,Bonnaure-Mallet, Martine,Bousarghin, Latifa
, p. 5823 - 5833 (2016)
Novel butyrolactone analogues were designed and synthesized based on the known lichen antibacterial compounds, lichesterinic acids (B-10 and B-11), by substituting different functional groups on the butyrolactone ring trying to enhance its activity. All synthesized butyrolactone analogues were evaluated for their in vitro antibacterial activity against Streptococcus gordonii. Among the derivatives, B-12 and B-13 had the lowest MIC of 9.38 μg/mL where they have shown to be stronger bactericidals, by 2–3 times, than the reference antibiotic, doxycycline. These two compounds were then checked for their cytotoxicity against human gingival epithelial cell lines, Ca9–22, and macrophages, THP-1, by MTT and LDH assays which confirmed their safety against the tested cell lines. A preliminary study of the structure–activity relationships unveiled that the functional groups at the C4position had an important influence on the antibacterial activity. An optimum length of the alkyl chain at the C5position registered the best antibacterial inhibitory activity however as its length increased the bactericidal effect increased as well. This efficiency was attained by a carboxyl group substitution at the C4position indicating the important dual role contributed by these two substituents which might be involved in their mechanism of action.
Separation of a mixture of paraconic acids from Cetraria islandica (L.) Ach. employing a fluorous tag-catch and release strategy
Horhant, David,Lamer, Anne-Cécile Le,Boustie, Jo?l,Uriac, Philippe,Gouault, Nicolas
, p. 6031 - 6033 (2007)
A light-fluorous catch and release approach application has been designed to the separation of a mixture of three paraconic acids extracted from the Island moss (Cetraria islandica (L.) Ach.). The (+)-protolichesterinic acid was caught and released via a Micha?l/retro-Micha?l addition sequence with a fluorous thiol, while the resulting two other compounds were classically separated, allowing the isolation of (+)-roccellaric acid for the first time in this lichen.
Stereodivergent Synthesis of Chiral Paraconic Acids via Dynamic Kinetic Resolution of 3-Acylsuccinimides
Sarkale, Abhijeet M.,Maurya, Vidyasagar,Giri, Sachin,Appayee, Chandrakumar
supporting information, p. 4266 - 4270 (2019/06/18)
A direct N-heterocyclic carbene (NHC) catalysis of maleimides with alkyl aldehydes is established for the synthesis of 3-acylsuccinimides. The first dynamic kinetic resolution of 3-acylsuccinimides is accomplished through asymmetric transfer hydrogenation. These two catalytic methodologies are utilized for the synthesis of each enantiomer of trans-paraconic acids in three steps and cis-paraconic acids in four steps with good yields and high stereoselectivities. This stereodivergent synthetic methodology is applied for the synthesis of seven bioactive paraconic acid natural products.
Diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid
Fernandes, Rodney A.,Halle, Mahesh B.,Chowdhury, Asim K.,Ingle, Arun B.
experimental part, p. 60 - 66 (2012/05/07)
A diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid, common members of the paraconic acids is described. The synthesis is based on a diastereoselective orthoester Johnson-Claisen rearrangement of a (Z)-allyl alcohol with a vicinal dioxolane moiety as key steps. The synthesis is completed in 10 steps and with overall yields of 15.9% for (+)-nephrosterinic acid and 16.4% for (+)-protolichesterinic acid.
