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March 8, 2010
Not Gonna Make That One
A discussion at work the other day got me to thinking: what structures do you medicinal chemists out there just refuse to work on? Any? We all have our own prejudices - in fact, if you get enough chemists into one conference room, one or another of them will probably rule out just about any structure you propose. Try that sometime, and be sure to sneak a few marketed drugs in there to tick people off. Don't like organoazides? Michael acceptors? Nitroaromatics? Epoxides? Chloromethyl ketones? They're out there working in the real world and making real money.
Now, I'm not saying that you should concentrate on these things. The success rate for (say) chloromethyl ketones is surely lower than for a lot of other compound classes, and there's only so much time and money available. That's why I have personal rules like "No Naphthyls". If someone shows me a structure with a raw naphthalene hanging off it that works, well, good for them, and I guess I'd work on it on that basis. But I won't contribute any myself, because I think the odds are too low.
But I have even more deep-seated prejudices. There are some structures that I just don't think have a chance, even if it looks like they work at first. I'd rather kill them immediately than take the (grave) chance of wasting everyone's time. The first thing I can think of on such a list would be quinones and their ilk. There are just too many other bad things that they're capable of. Now that I've said this, I feel sure that someone is come up in the comments with an example of a quinone that's making five hundred million dollars a year or something. But I sure can't think of one myself, and I just don't see the point of trying to make a drug out of such a structure (unless their lively reactivity is part of some nasty mechanism all its own, in which case, good luck to you).
So call me close-minded. But no quinones.
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