Concise syntheses and some biological activities ofdl-2,5-di-<i>O</i>-methyl-<i>chiro</i>-inositol,dl-1,4-di-<i>O</i>-methyl-<i>scyllo</i>-inositol, anddl-1,6-dibromo-1,6-dideoxy-2,5-di-<i>O</i>-methyl-<i>chiro</i>-inositol

The regio- and stereospecific synthesis ofO-methyl-chiro-inositols andO-methyl-scyllo-inositol was achieved, starting fromp-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 Ac2O afforded the desired newchiro-inositol derivatives andscyllo-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 inositols11-17were 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 mu M for hCA I, 65.08 +/- 12.39 to 538.98 +/- 61.26 mu M for hCA II, and 193.28 +/- 43.13 to 765.08 +/- 209.77 mu M for AChE, respectively. Also, due to the inhibitory effects of the novel inositols11-17against the tested enzymes, these novel inositols are potential drug candidates to treat some diseases such as glaucoma, epilepsy, leukemia, and Alzheimer's disease.

Journal

ARCHIV DER PHARMAZIE

Year

2021

Volume

354

Issue

2

ISSN

0365-6233

eISSN

1521-4184

DOI

10.1002/ardp.202000254

WoS UID

WOS:000573666200001