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. 2019 Jul 23;8(7):995–1011. doi: 10.1002/open.201900227

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©201x The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

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Overlapped images of Series 3 ethyl (10 c) and isobutyl (10 f) derivatives. The ethyl imidazole (10 c, cyan) interacts through the imidazole with the heme indirectly via an interstitial water molecule bonded to Ser237, and through the phenyl ring via an interstitial water molecule bonded to Thr77. The isobutyl imidazole (10 f, magenta) interacts with the heme in a similar manner as observed for 10 c, but forms an additional interaction through the pyrazole ring and occupies the binding site more fully.