Asymmetric synthesis and stereochemical structure–activity relationship of (R)- and (S)-8-[1-(2,4-dichlorophenyl)-2-imidazol-1-yl-ethoxy] octanoic acid heptyl ester, a potent inhibitor of allene oxide synthase

Synthesis of 2RS,4RS-1-[2-Phenyl-4-[2-(2-trifluromethoxy-phenoxy)-ethyl]-1,3-dioxolan-2-yl-methyl]-1H-1,2,4-triazole Derivatives as Potent Inhibitors of Brassinosteroid Biosynthesis

“…The key transformation of 2a – h with compound 5 consisted of four steps: (1) formation of ethanones 2a – h ; (2) tosylation of isopropylideneglycerol 3 ; (3) deprotection of isopropylidene ketal 4 ; and (4) ketal formation to generate 6a – h . Compounds 2a – h were prepared by reacting different kinds of commercially available a -bromoketones 1 with triazole in DMF using a method that we described previously [ 23 ]. The alkylation of isopropylidene glycerol 3 was achieved using a method we described previously [ 22 ], and hydrolysis with 1 M HCl in MeOH yielded glyceryl tosylate 5 .…”

Synthesis of novel triazole derivatives as potent inhibitor of allene oxide synthase (CYP74A), a key enzyme in jasmonic acid biosynthesis

“…e inhibitory activity of test compounds was evaluated by a method described previously. 12) e enzyme reaction mixture contained 50 mM sodium phosphate bu er (pH 7.0, 0.1% Tween 20), enzyme (AOS, 5 nM), and designated concentrations of substrate (13(S)-HPOT) at 25°C. Activity was measured by following the decrease in absorption at 235 nm using a Shimadzu UV3100 spectrophotometer (Shimadzu, Kyoto Japan).…”

“…Towards this end, we carried out a systemic search to design speci c inhibitors of JA biosynthesis. [10][11][12] A challenge for design-speci c inhibitors of JAs biosynthesis is to elucidate the target enzyme. Studies on the functions of enzymes of the JA biosynthesis pathway have shown that AOS (allene oxide synthase), a cytochrome P450 enzyme (CYP74A) that catalyzes the rst reaction in the speci c pathway of JA biosynthesis, 13) is an important site for regulating overall JA biosynthesis.…”

“…10) We found that the length of the chain of carboxylic acid moiety markedly a ects the potency of AOS inhibition, and octanoic acid esters analogues exhibit potent inhibitory activity against AOS. 10) Although JM-8686 is a potent inhibitor of AOS and exhibits high binding a nity to recombinant AOS in vitro, 11,12) research focused on controlling JA biosynthesis in plant tissues remain to be accomplished. In the present work, we carried out chemical optimization of a JM series by chemical modi cation of JM-8686 in several points as follows: 1) to improve water solubility of the inhibitors by shortening the ester moiety of JM-8686 using octanoic acid methyl ester as a key structure, 2) to introduce 1,2,4-triazole moiety into the inhibitor instead of imidazole of JM-8686 to evaluate the e ect of 1,2,4-triazole moiety on AOS inhibition, and 3) to introduce di erent aromatic ring structures to inhibitors that mimic the 2,4-dichlorophenyl moiety of JM-series for structureactivity relationship studies (the general structure of target compounds is shown in Fig.…”

Structure-activity relationship study for fungicidal activity of 1-(4-phenoxymethyl-2-phenyl-[1,3]dioxolan-2-ylmethyl)-1H-1,2,4-triazole derivatives against rice blast

“…The structures of lead compounds of brassinosteroid biosynthesis inhibitors: Yucaizol and YCZ-18 used in this study were shown Unauthenticated Download Date | 5/11/18 1:13 AM structures in ring A was carried out by using different α-bromoketone 1a-1i as a starting material. Compound 2a-2i was prepared by reacting compound 1a-1i with triazole in dimetyloformamid (DMF) using the previously described method (Oh et al 2008). The tosylation of isopropylidene glycerol 3 was achieved using standard protocol (tosyl chloride in pyridine at 0°C), and hydrolysis with 1 M HCl in MeOH yielded glyceryl tosylate 5.…”