- Adamantyl pyran-4-one derivatives and their in vitro antiproliferative activity
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Abstract: Pyran-4-one (maltol, kojic acid and chlorokojic acid 1) esters of adamantan-1-ylacetic acid were prepared through efficient synthetic routes in good yields and evaluated for their in vitro antiproliferative activity on four cancer cell lines: K562 (chronic myelogenous leukemia), HeLa (cervical cancer), Caco-2 (colorectal adenocarcinoma) and NCI-H358 (bronchioalveolar carcinoma). The results indicate that the presence and the position of the adamantyl acyl group or chlorine atom are the necessary requirement for antitumor activity of pyranone systems. Derivatives of kojic acid with either free (compounds 1 and 8) or acylated 5-OH group (compounds 2 and 9) have shown good-to-moderate activity (IC50 values ranging from 13.1 to 43.0?μM) on all cell lines. Adamantyl kojic acid derivative 5 with a free OH group on the position 2 showed activity only on the K562 cell line. It seems that removal of halogen or adamantyl unit from position 2 elicits antileukemic activity, as observed in compound 5. The positive influence of the adamantyl unit was also observed on a 3-OH acylated derivative of maltol I which was also selectively active on the same cell line. 5-O-benzylated adamantyl compounds 6 and 7 and unmodified starting pyranones were found to be inactive. Antibacterial activity of compounds was also evaluated on S. aureus ATCC 13709, M. catarrhalis ATCC 23246, E. faecalis ATCC29212 and E. coli TolC-Tn10, but no activity was observed (MIC values 128–256?μg/mL). Graphical abstract: [Figure not available: see fulltext.]
- Perokovi?, Vesna Petrovi?,Car, ?eljka,Usenik, Andrea,Opa?ak-Bernardi, Teuta,Juri?, Andrea,Tomi?, Sr?anka
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p. 253 - 263
(2019/04/25)
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- Chemo-enzymatic three-step conversion of glucose to kojic acid
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Kojic acid is an important biomolecule, currently produced by fermentation and having a wide range of potential applications. A faster and more direct chemical route could open the door for its large-scale production and wider utilization in biorefineries. Here we describe an efficient method for the preparation of kojic acid from d-glucose via glucosone by a three-step chemo-enzymatic route.
- Lassfolk, Robert,Suonpa?, Anu,Birikh, Klara,Leino, Reko
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p. 14737 - 14740
(2019/12/23)
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- Facile reduction of carboxylic acids to primary alcohols under catalyst-free and solvent-free conditions
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We report the development of a facile protocol for the deoxygenative hydroboration of aliphatic and aryl carboxylic acids to afford corresponding primary alcohols under solvent-free and catalyst-free conditions. The reaction proceeds under ambient temperature exhibits good tolerance towards various functional groups and generates quantitative yields. The plausible mechanism involves the formation of Lewis acid-base adducts as well as the liberation of hydrogen gas.
- Harinath, Adimulam,Bhattacharjee, Jayeeta,Panda, Tarun K.
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p. 1386 - 1389
(2019/02/05)
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- Re-examination of nucleophilic substitution in chlorokojic acid
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Chlorokojic acid was reacted with S2O23 , NO-3 , N-3 , I- , and SCN- . Only the three latter nucleophiles substituted the chlorine atom in the 2-CH2/s
- Uher, Michal,Szymońska, Joanna,Korenova, Anna,Tomasik, Piotr
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p. 301 - 307
(2007/10/03)
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- Drug for ameliorating brain diseases
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The present invention discloses a drug for ameliorating brain diseases which comprises as an active ingredient a compound represented by the following formula (1): STR1 or a salt thereof. Because of inhibiting a decrease in brain neurons and promoting branching of neurites, this drug is efficacious in the prevention and treatment of dementia, etc. in association with degeneration and sloughing of brain neurons.
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