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DBL%20Hendrix%20small.png College chemistry, 1983

Derek Lowe The 2002 Model

Dbl%20new%20portrait%20B%26W.png After 10 years of blogging. . .

Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: derekb.lowe@gmail.com Twitter: Dereklowe

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In the Pipeline: Don't miss Derek Lowe's excellent commentary on drug discovery and the pharma industry in general at In the Pipeline

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March 24, 2014

Nitrogen Heterocycles Ahoy

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Posted by Derek

Here's the sort of review that every working medicinal chemist will want to take a look at: Jeffrey Bode and graduate student Cam-Van T. Vo are looking at recent methods to prepare saturated nitrogen heterocycles. If you do drug discovery, odds are that you've worked with more piperidines, pyrrolidines, piperazines, morpholines, etc. than sticks can be shaken at. New ways to make substituted variations on these are always welcome, and it's good to see the latest work brought together into one place.

There's still an awful lot to do in this area, though. As the review mentions, a great many methods rely on nitrogen protecting groups. From personal experience, I can tell you that my heart sinks a bit when I see some nice ring-forming reaction in the literature and only then notice that the piperidine (or what have you) has a little "Ts" or "Ns" stuck to it. I know that these things can be taken off, but it's still a pain to do, and especially if you want to make a series of compounds. Protecting-group-free routes in saturated heterocyclic chemistry are welcome indeed.

Comments (9) + TrackBacks (0) | Category: Chemical News


COMMENTS

1. BG on March 24, 2014 10:20 AM writes...

Is there a nitrogen protecting group that medicinal chemists prefer over others?

Permalink to Comment

2. M on March 24, 2014 10:42 AM writes...

@1. BG, The BOC protecting group is most common in medicinal chemistry. It is easy to introduce, easy to remove, and stable to reaction conditions that tend to be used in med chem.

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3. ed on March 24, 2014 11:03 AM writes...

publishing in an open access journal would have been a big +1.

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4. DCRogers on March 24, 2014 11:10 AM writes...

@3, know of anyone who has put together a list of the most reputable 'open-access' journals that scientists trying to ween themselves off of proprietary journals (I'm looking at you, ACS!) should consider?

I see lots of fancy names out there, hard to find the wheat in all the chaff.

Permalink to Comment

5. chipsahoy on March 24, 2014 5:01 PM writes...

O SnAP (someone's gotta say it)

Permalink to Comment

6. A. nonymaus on March 24, 2014 9:50 PM writes...

Re: 4
PLoS journals are what I'd call the top tier of open-access. They tend to be heavily slanted towards biology though. Other suggestions?
Re: 1
The simplest protecting group for nitrogen is the proton. N-oxides are also easily installed and removed.

Permalink to Comment

7. M on March 25, 2014 4:56 AM writes...

Concerning the SnAP chemistry. How about tin containing reactions in medicinal chemistry? The prepared N-heterocycles are most likely not the final compounds. Therefore, any leftover tin traces should be removed before the final testing?

Permalink to Comment

8. PK rep on March 25, 2014 5:55 AM writes...

Who wants a saturated nitrogen heterocycle beside Sprague-Dawley rats?

Permalink to Comment

9. Anon on March 25, 2014 9:14 PM writes...

Re:4 and 6:

Beilstein Journal of Organic Chemistry is a good open-access journal. Free to access, free to submit.

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