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Life in the Drug Labs

Our Friend the Nitrogen Atom

My lab is starting work on another new project, which this time means another five-membered ring system that I haven’t worked on before. I’ve done a lot of them, but this class I’ve missed out on somehow.
If you’re going to do organic chemistry in a drug company, you’d better be on good terms with nitrogen atoms. I’d say that drugs with them outnumber drugs without by 10:1. The reasons aren’t mysterious – amines can take up protons or donate them at just around the pHs that you find in living systems. And even the not-so-basic ones are still essential players. Nitrogen is a fine partner for hydrogen bonds, both donating and receiving, and those are the common currency of biomolecules, in my opinion.
So you’ll be making plenty of amines and amides, and you’ll be making plenty of the small-ring nitrogen compounds – imidazoles, oxazoles, pyrazoles and so on. My advice to grad students and post-docs is to learn some heterocyclic chemistry if you plan to interview in the drug industry, assuming we ever get around to hiring people again. (OK, don’t panic – it’s not that bad, not yet – but I fear that there’s going to be a sadly reasonable supply of experienced candidates available this year.) Tell ’em that you know how to crank out the thiazoles and the oxadiazoles – it sure won’t hurt, and it might just help.
As those of you outside chemistry may have suspected from all that gibberish, these systems have a systematic nomenclature. It gets a little tongue-twisty after a while, though, particularly if you’re not being paid to say them (and make them.) I turned out a whole series of isoxazolidinones once, for example, a name that doesn’t come trippingly off the tongue without a little preparation. Active compounds, you ask? You bet! So active that every one of them did something in mice, and what’s more, every one did something different. But that, unfortunately, is not a feature that we value. So much for our “commitment to diversity”, eh?