Synthesis of diaryl ethers with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions

Figures & data

Figure 1. Some selected natural diaryl ethers 1–5.

Scheme 1. The synthesis of diaryl ethers 11–14.

Table 1. Reagents, products and yields.

Table 2. Human carbonic anhydrase I and II isoenzymes (hCA I and II), acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes inhibition effects of some novel diaryl ethers 11–14.

	IC50 (nM)								Ki (nM)
Compounds	hCA I	r^2	hCA II	r^2	AChE	r^2	BChE	r^2	hCA I	hCA II	AChE	BChE
11	161.16	0.9661	111.77	0.9780	18.93	0.9671	45.89	0.9850	104.01 ± 5.05	103.84 ± 3.11	17.64 ± 0.34	14.39 ± 0.24
12	111.77	0.9768	103.43	0.9436	11.91	0.9823	37.87	0.9868	102.01 ± 2.81	113.40 ± 2.55	15.35 ± 0.22	22.90 ± 0.42
13	144.37	0.9530	97.605	0.9731	16.78	0.9867	40.06	0.9765	127.13 ± 4.92	93.85 ± 2.85	16.86 ± 0.23	12.58 ± 0.13
14	133.27	0.9577	88.846	0.9907	15.29	0.9837	19.63	0.9906	108.35 ± 5.02	73.71 ± 1.50	18.34 ± 0.43	9.07 ± 0.22
AZA*	130.74	0.9923	64.166	0.9949	–	–	–	–	190.56 ± 1.31	40.81 ± 1.35	–	–
TAC**	–	–	–	–	39.15	0.9951	15.07	0.9895	–	–	23.49 ± 0.74	46.80 ± 0.22

*Acetazolamide (AZA) was used as a standard inhibitor for both hCA I and II isoenzymes.

** Tacrine (TAC) was used as a standard inhibitor for AChE and BChE enzymes.