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November 4, 2007
Nerve, Lots and Lots of Nerve
Sometimes I think that my chemical intuition is all haywire. Medicinal chemists, after they've seen several projects succeed and fail, accumulate a set of prejudices and opinions about what sorts of molecules are more likely to lead to good things (and what sorts are more likely to waste your time).
Many of these are uncontroversial: no one, for example, is going to tell you to load up your molecule with plenty of guanidines or acid chlorides. But there's a big middle ground where the arguing starts. Sulfonamides - like 'em or hate 'em? How about ureas? Tetrazoles as carboxylic acid isosteres? All of these groups are found in marketed drugs, but you can find experienced medicinal chemists whose noses wrinkle at them, because they feel that too many such compounds fail to make them worthwhile. Me, I don't like napthalenes, and I never put one on a drug candidate molecule. The next multibillion-dollar drug will probably have one, just wait.
But the reason I think my intuition is off is the molecule shown to the right (and thanks to KinasePro for bringing it to my attention. Where do I start? That screwy thiopyran ring? With its screwy thioketal? The multiple methyl esters, when I wouldn't even want to have one? Man, is that one ugly structure. But, as KP points out, the company that developed this shimmering vision is trying to sell it. That's right, they actually have the nerve to ask for money for this beast. So what's wrong with them? Or is there something wrong with me, because I'd never have that kind of gall, not even if I practiced for years. . .
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