TY  - JOUR
TI  - Synthesis, characterization, crystal structure and bioactivities of 
novel enamine and pyrrole derivatives endowed with 
acetylcholinesterase, α-glycosidase and human carbonic 
anhydrase inhibition effects
AB  - Presented research work is devoted to the synthesis of new heterocyclic compounds containing the ethyl
ester fragment of acetate and glycine and the study of their crystal structure and biological activity. (Z)-Ethyl 2-(3-
oxo-1,3-diphenylprop-1-enylamino)acetate (1) was first obtained on the base of the reaction of dibenzene methane
with glycine ethyl ester hydrochloride in the presence of Y(OTF)3 catalyst in aqueous medium. At the same time,
ethyl-3,5-diphenyl-1H-pyrrole-2-carboxylate (2) was synthesized from the interaction of enamine with tert-BuOK in
the presence of tert-BuOH/DMFA solvent. The structure of new compounds has been studied by 1H, 13C NMR. In
addition, the crystal structure of ethyl-3,5-diphenyl-1H-pyrrole-2-carboxylate (2) is presented. The monoclinic,
yellow crystals, with sizes 0.20 × 0.10 × 0.10 mm3
, one striped: a = 10.5340(6) Е, b = 7.5101(5) Е, c = 20.2352(15)
Å, β = 102.131(2)°, V = 1565.09(18) Е3
, space group P21/c, Z= 4, ds = 1.236 mg/m3
, μ = 0.080 mm-1 were obtained.
The crystalline compound keeps crystallographically independent molecules in the central bicyclic moiety.
Compound 2 holds complex three-organic compound system consisting of pyrrole and benzol rings. In this study, the
IC50 and Ki values of the compounds were calculated to compare their inhibition profiles on acetylcholinesterase
(AChE), α-glycosidase and hCA I, and II isozymes. These compounds demonstrated Ki values in the low micromolar
range for studied enzymes. The best inhibitor for hCA I and II isoenzymes and AChE was the (1) with Ki values of
47.21±5.06, 35.77±3.53 and 103.94±15.36 µM, respectively. On the other hand, compound 2 showed the best
inhibition profile against α-glycosidase with Ki of 63.76±7.12 µM.
AU  - Demir, Yeliz
AU  - Gulcin, ilhami
AU  - Abel, Maharramov
AU  - Safarova, Ayten
AU  - Kurbanova, Malahat
AU  - Taslimi, Parham
AU  - Alwasel, Saleh
AU  - Sujayev, Afsun
AU  - Huseynov, Elnur
DO  - 10.25135/acg.oc101.21.04.2029
PY  - 2021
JO  - Organic Communications
VL  - 14
IS  - 2
SN  - 1307-6175
SP  - 144
EP  - 156
DB  - TRDizin
UR  - http://search/yayin/detay/525724
ER  -