Concise syntheses and some biological activities of dl ‐2,5‐di‐ O ‐methyl‐ chiro ‐inositol, dl ‐1,4‐di‐ O ‐methyl‐ scyllo ‐inositol, and dl ‐1,6‐dibromo‐1,6‐dideoxy‐2,5‐di‐ O ‐methyl‐ chiro ‐inositol

Autor: Hulya Akincioglu, Latif Kelebekli, Kadir Aksu, İlhami Gülçin
Rok vydání: 2020
Předmět:
Zdroj: Archiv der Pharmazie. 354:2000254
ISSN: 1521-4184
0365-6233
DOI: 10.1002/ardp.202000254
Popis: The regio- and stereospecific synthesis of O-methyl-chiro-inositols and O-methyl-scyllo-inositol was achieved, starting from p-benzoquinone. After preparing dimethoxy conduritol-B as a key compound, regiospecific bromination of the alkene moiety of dimethoxy conduritol-B and acid-catalyzed ring opening of dimethoxydiacetate conduritol-B epoxide with Ac2 O afforded the desired new chiro-inositol derivatives and scyllo-inositol derivative, respectively. Spectroscopic methods were employed for the characterization of all synthesized compounds. The novel inositols (11-17) had effective inhibition profiles against human carbonic anhydrase isoenzymes I and II (hCA I and II) and acetylcholinesterase (AChE). The novel inositols 11-17 were found to be effective inhibitors against AChE, hCA I, and hCA II enzymes. Ki values were calculated in the range of 87.59 ± 7.011 to 237.95 ± 17.75 μM for hCA I, 65.08 ± 12.39 to 538.98 ± 61.26 μM for hCA II, and 193.28 ± 43.13 to 765.08 ± 209.77 μM for AChE, respectively. Also, due to the inhibitory effects of the novel inositols 11-17 against the tested enzymes, these novel inositols are potential drug candidates to treat some diseases such as glaucoma, epilepsy, leukemia, and Alzheimer's disease.
Databáze: OpenAIRE
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