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

Automated summary

In this study, regio- and stereospecific synthesis of O-methyl-chiro-inositols and O-methyl-scyllo-inositol was achieved, leading to compounds with effective inhibition against human enzymes. The novel inositols showed potential as drug candidates for treating diseases such as glaucoma, epilepsy, leukemia, and Alzheimer's disease.