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March 9, 2012
The carbonyl group is one of the most fundamental structure in organic chemistry: C-double-bond-O. But you can substitute that oxygen with a sulfur and get to a whole new series of compounds - so how come we don't see so many of those in drugs?
Well, not all of them are stable. Plain old thioketones are pretty reactive, not to mention their appalling stink. And even though they're not as bad as thioketones, the corresponding thioamides and thioureas are known to be more lively than their oxygen counterparts. Many medicinal chemists avoid them because of a reputation for trouble, which I think is probably earned and not just an irrational prejudice. But there are drugs and pharmacological tools with these structures, still.
The thiocarbonyl shows up in a number of heterocycles, too, and there the situation gets a bit murkier. The highest-profile member of this group, unfortunately, may well be the rhodanines, which have come up several times on this blog, most recently here. I'm not a fan of those guys, but here's a question: are there thiocarbonyl structures that are better behaved? Do people like me look down on the whole functional group because of a few (well, more than a few) bad actors?
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