73346-73-3Relevant articles and documents
Novel protection of 1,2-diol for trans-dihydroxycyclopentene ring construction by the C[sbnd]H insertion of alkylidene carbene: Formal total synthesis of (+)-trehazolin
Ohira, Susumu,Kuboki, Atsuhito,Takimoto, Yoshimi,Matsuda, Kyosuke,Itasaki, Saori,Urushibata, Yuki,Takano, Yoshiyuki,Nakamura, Yuuki
, (2019)
The chiral vicinal diol was protected as 6-methylene-1,4-dioxepane to construct a cyclopentene ring by the C[sbnd]H insertion of alkylidene carbene. The removal of the protecting group was achieved in a few steps, affording the corresponding diol in a reasonable yield. Using these reactions, the known synthetic intermediate for (+)-trehazolin was synthesized from D-diethyl tartrate. In addition, a short route to the intermediate from a D-mannitol derivative was described.
Design, synthesis and biological evaluation of novel diazaspiro[4.5]decan-1-one derivatives as potential chitin synthase inhibitors and antifungal agents
Li, Bing,Wang, Kaiyuan,Zhang, Rui,Li, Baihui,Shen, Yangli,Ji, Qinggang
supporting information, (2019/09/07)
A series of 2,8-diazaspiro[4.5]decan-1-one derivatives were designed, synthesized and screened for their inhibition activities against chitin synthase (CHS) and antimicrobial activities in vitro. The biological assays revealed that compounds 4a, 4e, 4h, 4j, 4o, 4q and 4r exhibited moderated to excellent potency against CHS with IC50 values ranging from 0.12 to 0.29 mM. Compounds 4e, 4j with IC50 value of 0.13 mM, 0.12 mM respectively, showed excellent inhibition potency among these compounds, which were similar to that of polyoxin B whose IC50 value was 0.08 mM. Meanwhile, the screening of the antifungal activity showed that compounds 4j and 4r had the same potency of inhibiting the growth of A. fumigatus with MIC value of 0.08 mmol/L. Compound 4d displayed excellent activity against C. albicans (ATCC 90023) with MIC value of 0.04 mmol/L, which was superior to fluconazole (0.104 mmol/L) and polyoxin B (0.129 mmol/L). The result of antibacterial assay showed that these compounds had little potency against those selected bacteria strains including three Gram-positive bacteria and three Gram-negative bacteria. Furthermore, the combination use of 4c-fluconazole, 4i-fluconazole, 4j-fluconazole, and 4o-fluconazole against C. albicans,A. fumigatus and A. flavus showed additive or synergistic effects. These results indicated that the designed compounds serve as potential chitin synthase inhibitors and have selectively antifungal activities.
Preparation method of chiral catalyst ligand TADDOLs in asymmetric synthesis
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Paragraph 0030; 0031; 0035; 0039; 0047, (2018/04/03)
The invention discloses a preparation method of a chiral catalyst ligand TADDOLs in asymmetric synthesis. The preparation method comprises the following steps of using chiral diethyl tartrate as raw material, and reacting with 2,2-dimethoxypropane and triethyl orthoformate, so as to obtain O,O-isopropylidene diethyl tartrate; enabling brominated aromatic hydrocarbon and isopropyl magnesium bromideto react in a solvent; finally, adding the O,O-isopropylidene diethyl tartrate, so as to obtain a target product, namely the chiral catalyst ligand TADDOLs. The preparation method has the advantagesthat the raw materials are bulk chemicals, the industrial cost is low, the reaction process is moderate and controllable, the post-treatment is concise and efficient, the difficulty in industrial production of the series of compound is decreased, and the cost is reduced; the chiral catalyst ligand TADDOLs has been widely applied into the asymmetric chiral synthesis; especially, when the chiral catalyst ligand TADDOLs and metal form a complex as the catalyst in the chiral oriented synthesis, the effect is obvious; the catalyzing effect is excellent, the process of chiral detachment of despinner compound is reduced, and the synthesis cost of chiral medicine is reduced.
