Synthesis and carbonic anhydrase inhibitory properties of amino acid – coumarin/quinolinone conjugates incorporating glycine, alanine and phenylalanine moieties

Figures & data

Scheme 1. Synthesis pathways of the new coumarin and quinolinone conjugates of N-protected amino acids.

Table 1. hCA I, II, IV and XII inhibition with amino acid conjugates reported in the paper, by a stopped-flow, CO₂ hydrase assay, after 6 h ioncubation period between enzyme and inhibitor27.

	KI (μM)*
Compound	hCA I	hCA II	hCA IV	hCA XII
1	>50	>50	0.092	0.49
2	>50	>50	>50	0.79
3	>50	>50	0.14	0.60
4	>50	>50	1.19	0.23
5	>50	>50	0.39	0.58
6	>50	>50	>50	0.11
7	>50	>50	>50	>50
8	>50	>50	>50	>50
9	>50	>50	>50	>50
10	>50	>50	>50	>50
AAZ*	0.25	0.012	0.074	0.006

Acetazolamide (AAZ) was used as a standard inhibitor for all CAs investigated here.

* Mean from three different assays. Errors were in the range of ±10% of the reported values (data not shown).

Khalifah RG. The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem 1971;246:2561–73

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