Further potential compounds to make with 2-phenylpropan-1-ol fragments

[david1597]

There are, to date, three compounds containing the 2-phenylpropan-1-ol fragment:

We've discussed the first and third in that row a lot...current synthetic efforts are already heavily focused on exploring H-bond donor analogues of OSM-S-412 (#3), itself initially arising from a biosynthesis using MMV693155 (OpenSourceMalaria/OSM_To_Do_List/issues/513) and we have a poll to investigate this further: OpenSourceMalaria/OSM_To_Do_List/issues/555.

Looking back through the inherited compounds I realised that MMV670947 also has a similar structure, and has good potency. So, should we not just be focused on H-bond donors on that ring but investigating substitution more widely? We had begun to discuss that already a little across at #3.

All of the following, some probably better ideas than others, could be made in our labs with chemicals we already have available to us through the following methodology.

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[MFernflower]

@david1597 Random Q - How will the cyanide group survive reduction?

My vote is for the P-cyano and P-CF3oxy variants respectively!

[mattodd]

@MFernflower it'll depend how hard you hit it, and what with. A search on e.g. SciFinder for pertinent examples will be the step you take before you enter the lab.

[MFernflower]

Re-posted from slack:
This will squash any fears of quinone formation and can easy be oxidized to an acetyl compound

Too pricey for such a simple idea? (replacing aryl hydroxy with aryl acetyl) @david1597

[MFernflower]

@david1597 A compound made from this precursor might be an interesting idea (phenolic OH to ring nitrogen same position) Sorry about graphic size I got the image from Wikipedia

[david1597]

Some of the suggestions above were incorporated into the poll in OpenSourceMalaria/OSM_To_Do_List#555 which was used to plan which compounds to make in this series.

Those that were successfully made will be listed in #3.