- Direct enantioseparation of axially chiral 1,1′-biaryl-2,2′-diols using amidine-based resolving agents
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Amidine-based optically active resolving agents for enantiomer separation of axially chiral 1,1′-biaryl-2,2′-diols have been developed. A strongly basic amidine bearing no substituents on its nitrogen atoms enables the formation of their diastereomeric salts upon being mixed with weakly acidic phenol derivatives. Enantiopure 1,1′-biaryl-2,2′-diols can be obtained in high yields after only one crystallization of their salts with the chiral amidine derived from dehydroabietic acid. X-ray crystallography revealed that the amidine moiety forms a salt with the phenol group and additional intermolecular NH/π interactions contribute to the efficient chiral recognition process.
- Hirose, Takuji,Kodama, Koichi,Takase, Fusato
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p. 18162 - 18170
(2021/06/07)
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- Antifungal Application of Rosin Derivatives from Renewable Pine Resin in Crop Protection
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In the current work, we synthesized two series of dehydroabietyl amide derivatives from natural product rosin and evaluated their antifungal effects on Valsa mali, Phytophthora capsici, Botrytis cinerea, Sclerotinia sclerotiorum, and Fusarium oxysporum. In vitro and in vivo antifungal activities results indicated that rosin-based amide compounds containing thiophene heterocycles had better inhibitory effects on B. cinerea. In particular, compound 5b (5-fluoro-2-thiophene dehydroabietyl amide) exhibited the excellent antifungal properties against B. cinerea with an EC50 of 0.490 mg/L, which was lower compared to the positive control penthiopyrad (0.562 mg/L). Physiological and biochemical studies showed that the primary action mechanism of compound 5b on B. cinerea changes mycelial morphology, increases cell membrane permeability, and inhibits the TCA pathway in respiratory metabolism. Furthermore, QSAR and SAR studies revealed that charge distribution of rosin-based amides derivatives have a key role in the antifungal activity through the hydrogen bonding, conjugation, and electrostatic interaction between the compounds and the receptors of the target. To sum up, this study contributes to the development of rosin-based antifungal agents with a novel structure and preferable biological activity.
- Gao, Yanqing,Hao, Jin,He, Xiaohua,Li, Jian,Shang, Shibin,Song, Jie,Song, Zhanqian,Tao, Pan,Wu, Chengyu
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p. 4144 - 4154
(2020/04/30)
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- Bridging C?H Activation: Mild and Versatile Cleavage of the 8-Aminoquinoline Directing Group
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8-Aminoquinoline has emerged as one of the most powerful bidentate directing groups in history of C?H activation within the last decade. However, cleavage of its robust amide bond has shown to be challenging in several cases, thus jeopardizing the general synthetic utility of the method. To overcome this limitation, we herein report a simple oxidative deprotection protocol. This transformation rapidly converts the robust amide to a labile imide, allowing subsequent cleavage in a simple one-pot fashion to rapidly access carboxylic acids or amides as final products.
- Berger, Martin,Chauhan, Rajan,Rodrigues, Catarina A. B.,Maulide, Nuno
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supporting information
p. 16805 - 16808
(2016/11/16)
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- New derivatives of dehydroabietic acid target planktonic and biofilm bacteria in S taphylococcus aureus and effectively disrupt bacterial membrane integrity
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The combination of the dehydroabietic acid scaffold with different amino acids resulted in the discovery of a new class of hybrid compounds that targets both planktonic and biofilms bacteria in Staphylococcusaureus strains and are far more potent anti-bio
- Manner, Suvi,Vahermo, Mikko,Skogman, Malena E.,Krogerus, Sara,Vuorela, Pia M.,Yli-Kauhaluoma, Jari,Fallarero, Adyary,Moreira, Vania M.
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- Synthesis, structure analysis and cytotoxicity studies of novel unsymmetrically N,N′-substituted ureas from dehydroabietic acid
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A series of novel unsymmetrically N,N′-substituted ureas were synthesized from dehydroabietic acid and their structures were characterized by IR, 1H-NMR, 13C-NMR spectroscopy and single crystal X-ray diffraction. Three six-membered rings of urea 4c exhibited plane, half-chair and chair configurations, respectively. Their cytotoxicity activities against SMMC7721 liver cancer cells were evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)- 2,5-diphenyltetrazolium bromide) method. The results showed that the title compounds exhibited highly effective cytotoxicity activities against SMMC7721 cells. Their IC50 values are between 8.8 and 14.2 μmol/l. The change of N′ substituted groups resulted little difference to the cytotoxicity activities of ureas, which indicated that the cytotoxicity of this kind of ureas depend strongly on the tricyclic hydrophenanthrene structure.
- Rao, Xiaoping,Song, Zhanqian,He, Ling,Jia, Weihong
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experimental part
p. 1575 - 1578
(2009/10/10)
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