Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity

Reactions of 3-(furan-2-yl)propenoic acids and their esters with arenes in Brønsted superacid TfOH affords products of hydroarylation of the carbon–carbon double bond, 3-aryl-3-(furan-2-yl)propenoic acid derivatives. According to NMR and DFT studies, the corresponding O,C-diprotonated forms of the starting furan acids and esters should be reactive electrophilic species in these transformations. Starting compounds and their hydroarylation products, at a concentration of 64 µg/mL, demonstrate good antimicrobial activity against yeast-like fungi Candida albicans. Apart from that, these compounds suppress Escherichia coli and Staphylococcus aureus.

show abstract

“…3-(Benzofuran-2-yl)propenoic acid (1f) [ 35 ] was obtained as a light orange solid from benzofuran-2-carbaldehyde in a yield of 65%. M.p.…”

Section: Experimental Partmentioning

confidence: 99%

Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity

Kalyaev

Ryabukhin²,

Borisova³

et al. 2022

Molecules

View full text Add to dashboard Cite

show abstract

“…In a previous report 27 , we synthesized stereochemically fixed bridged analogs of ku-76. Among the analogs, several 2′,4-bridged analogs, such as 1a and 1b, were found to be more potent gravitropic bending inhibitors (Fig.…”

mentioning

confidence: 99%

Design and synthesis of strong root gravitropism inhibitors with no concomitant growth inhibition

Nishimura

Makigawa

Sun

et al. 2023

Sci Rep

Self Cite

View full text Add to dashboard Cite

Herein, we describe a highly potent gravitropic bending inhibitor with no concomitant growth inhibition. Previously, we reported that (2Z,4E)-5-phenylpenta-2,4-dienoic acid (ku-76) selectively inhibits root gravitropic bending of lettuce radicles at 5 μM. Based on the structure–activity relationship study of ku-76 as a lead compound, we designed and synthesized various C4-substituted analogs of ku-76. Among the analogs, 4-phenylethynyl analog exhibited the highest potency for gravitropic bending inhibition, which was effective at only 0.01 μM. Remarkably, 4-phenylethynyl analog is much more potent than the known inhibitor, NPA. Substitution in the para position on the aromatic ring of 4-phenylethynyl group was tolerated without diminished activity. In addition, evaluation using Arabidopsis indicated that 4-phenylethynyl analog inhibits gravitropism by affecting auxin distribution in the root tips. Based on the effects on Arabidopsis phenotypes, 4-phenylethynyl analog may be a novel inhibitor that differs in action from the previously reported auxin transport inhibitors.

show abstract

Palladium‐Catalyzed Asymmetric [4+3] Cycloadditions of Indene‐2‐carbaldehydes with 4‐Vinylbenzoxazinanones Toward Polycyclic 5H‐Benzo[b]azepines

2023

View full text Add to dashboard Cite

show abstract

Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity

Cited by 4 publications

References 25 publications

Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity

Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity

Design and synthesis of strong root gravitropism inhibitors with no concomitant growth inhibition

Palladium‐Catalyzed Asymmetric [4+3] Cycloadditions of Indene‐2‐carbaldehydes with 4‐Vinylbenzoxazinanones Toward Polycyclic 5H‐Benzo[b]azepines

Contact Info

Product

Resources

About