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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
Author(s) -
Aksu Kadir,
Akincioglu Hulya,
Gulcin Ilhami,
Kelebekli Latif
Publication year - 2021
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.202000254
Subject(s) - chemistry , stereochemistry , cyclitol , inositol , enzyme , chemical synthesis , carbonic anhydrase i , moiety , stereospecificity , carbonic anhydrase , biochemistry , in vitro , catalysis , receptor
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 Ac 2 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. K i 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.