US EPA

7422192 

Journal Article 

Synthesis and inhibitory properties of some carbamates on carbonic anhydrase and acetylcholine esterase 

Yılmaz, S; Akbaba, Y; Özgeriş, B; Köse, LP; Göksu, S; Gülçin, İ; Alwasel, SH; Supuran, CT; , 

2016 

Yes 

Journal of Enzyme Inhibition and Medicinal Chemistry
ISSN: 1475-6366
EISSN: 1475-6374 

TAYLOR & FRANCIS LTD 

ABINGDON 

31 

6 

1484-1491 

English 

26985691 

10.3109/14756366.2016.1149477 

WOS:000385270300080 

https://www.tandfonline.com/doi/full/10.3109/14756366.2016.1149477
Exit
 

A series of carbamate derivatives were synthesized and their carbonic anhydrase I and II isoenzymes and acetylcholinesterase enzyme (AChE) inhibitory effects were investigated. All carbamates were synthesized from the corresponding carboxylic acids via the Curtius reactions of the acids with diphenyl phosphoryl azide followed by addition of benzyl alcohol. The carbamates were determined to be very good inhibitors against for AChE and hCA I, and II isoenzymes. AChE inhibition was determined in the range 0.209-0.291 nM. On the other hand, tacrine, which is used in the treatment of Alzheimer's disease possessed lower inhibition effect (Ki: 0.398 nM). Also, hCA I and II isoenzymes were effectively inhibited by the carbamates, with inhibition constants (Ki) in the range of 4.49-5.61 nM for hCA I, and 4.94-7.66 nM for hCA II, respectively. Acetazolamide, which was clinically used carbonic anhydrase (CA) inhibitor demonstrated Ki values of 281.33 nM for hCA I and 9.07 nM for hCA II. The results clearly showed that AChE and both CA isoenzymes were effectively inhibited by carbamates at the low nanomolar levels. 

Acetylcholinesterase; carbamates; carbonic anhydrase; enzyme inhibition; synthesis; acetazolamide; acetylcholinesterase; azide; benzyl 6 methoxy 1,2,3,4 tetrahydronaphthalen 2 ylcarbamate; benzyl 7 methoxy 1,2,3,4 tetrahydronaphthalen 2 ylcarbamate; benzyl alcohol; benzyl(4,6 dimethoxy 2,3 dihydro 1h inden 2 yl)carbamate; biphenyl; carbamic acid derivative; carbonate dehydratase I; carbonate dehydratase II; carbonate dehydratase inhibitor; cholinesterase inhibitor; tacrine; unclassified drug; acetylcholinesterase; carbamic acid derivative; carbonate dehydratase; carbonate dehydratase inhibitor; cholinesterase inhibitor; Article; biological activity; carbon nuclear magnetic resonance; drug structure; drug synthesis; enzyme inhibition; human; infrared spectroscopy; inhibition constant; lipophilicity; priority journal; proton nuclear magnetic resonance; structure analysis; metabolism; synthesis; Acetylcholinesterase; Carbamates; Carbon-13 Magnetic Resonance Spectroscopy; Carbonic Anhydrase Inhibitors; Carbonic Anhydrases; Cholinesterase Inhibitors; Humans; Proton Magnetic Resonance Spectroscopy