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July 16, 2014
What Structures Have Turned on You?
When you ask a bunch of medicinal chemists to look over a list of structures - screening hits, potential additions to the compound collection, that sort of thing - you'll find that everyone will cross some of them off. But the agreement between the chemists on which ones need to go, that's the tough part. It's been shown that we don't overlap very much in our preferences, at least when it comes to the structures we'd prefer not to try to advance. That's because we don't overlap as well as we think we do when it comes to the rules we're using.
So here's a question, which might illustrate the point: what compound classes or scaffolds have you been burned by? I think that's one big factor that we all use when we're evaluating one of those compound lists - which ones are in that "Fooled me once" category? For me, a recent experience with NH pyrroles has me reluctant to go there again. And I'm not interested in things with napthalenes hanging off of them, naproxen notwithstanding. I'd also rather not see Mannich products, since I've personally seen a number of those misbehave.
So what's on your list? I think that everyone can agree on things like rhodanines, although even those have their partisans. But what semi-decent looking compounds will you go ahead and blackball, based on your own nasty experiences with them?
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