Antifungal 3,5-disubstituted furanones: From 5-acyloxymethyl to 5-alkylidene derivatives

Methodology for Synthesis of Enantiopure 3,5‐Disubstituted Pyrrol‐2‐ones

“…Because esterification at the final stage was unsuccessful, we derivatized the alcohol as an aryloxy group. In line with our previous results, we hoped that the lower leaving group ability of the aryloxy group would suppress the elimination process 3a. According to a modified synthetic plan, the amino group of methyl L ‐serinate 25 was protected as a carbamate to furnish compound 26 (88 % yield), which was then subjected to a Mitsunobu reaction by using phenol, triphenylphosphine, and diethyl azodicarboxylate (DEAD, Scheme ).…”

Structure and Antibacterial Activity of 3-(3,4-Dimethoxyphenyl)furan-2(5H)-ones

“…Substitution of arylamino group (6-9) for 4-hydroxyl group (1) maintained the potency or showed a mild increase in activity, while the 2-bromoethoxy group is present at this place, leading to an inactive compound (2). However, the bromine atom in the side chain of 2 was replaced by an aliphatic amino group (3)(4)(5), resulting in a 3-to 10-fold increase in activity, with compound 5 being the most active (MIC 50 = 7.3 lg/mL).…”

“…Compounds with c-butyrolactone-core show diverse biological activities such as anti-oxidative, anti-inflammatory and antibacterial activity [1][2][3], and have been receiving increasing attention in recent years [4,5]. In 2006, Lattmann et al [6] reported 5-alkoxy-4-aminofuran-2(5H)-ones (Scheme 1) showing good antibacterial activity against multiresistant Staphylococcus aureus.…”

“…As a part of our ongoing studies on furan-2(5H)-ones, we designed and synthesized a series of 3-(3,4-dimethoxyphenyl)-furan-2(5H)-ones for screening antibacterial activity. For confirmation of the structure the obtained compounds (1)(2)(3)(4)(5)(6)(7)(8)(9), the single crystal structure of 3-(3,4-dimethoxyphenyl)-4-(2-(4-methylpiperazin-1-yl)ethoxy) furan-2(5H)-one (5) was selected to determine.…”

Monomers for Adhesive Polymers, 14 Synthesis and Radical Polymerization of 4-[11-(Acryloyl-methyl-amino)-undecyloxy]-phthalic Acid and {10-[1,3-Bis(methacrylamido)-propoxy]-decyloxy}-phthalic Acid

“…The reaction of the easily accessible 4‐hydroxy‐phtalic acid dimethyl ester with 6 and K 2 CO 3 in DMF proceeded with a good yield (73%) within 6 d at room temperature, the final removal of the methyl ester protecting group, however, failed due to degradation of the acrylate‐double bond under the required strongly basic conditions. Whereas the synthesis of an acid‐labile tert ‐butyl ester of 6 could not successfully be accomplished, the methoxymethyl (MOM) ester ( 7 ) was accessible in up to a 64% yield via reaction of 6 with MOM‐chloride or ‐bromide and Hünig's base in dichloromethane at 0 °C, following a procedure for the synthesis of hydroxy‐benzoic acid MOM ester . As byproduct from this reaction, 4‐methoxymethoxy‐phthalic acid dimethoxymethyl ester was isolated in a 16% yield, the formation of which could not be suppressed even at a lower temperature (–78 °C).…”