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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

In the Pipeline

« Polluting the Literature with PAINs | Main | More On Pharma's Ugly Finances »

February 8, 2010

Together At Last

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Posted by Derek

Well, I have no particular need to make azo-linked compounds (see this morning's post for one reason!). And I have to say, although it's mechanistically interesting, I definitely feel no desire to make them by combining a hydroperoxide and a diazonium salt in one pot. This is not a moment destined to take its place alongside the legendary invention of the chocolate/peanut butter cup.

Comments (11) + TrackBacks (0) | Category: Chemical News


COMMENTS

1. Hap on February 8, 2010 2:21 PM writes...

1) Fenton chemistry with diazonium salts - whee! The chemistry version of bungee jumping, perhaps?

2) When I've heard of/seen diazo compounds, they've usually been diaryl rather than monoaryl monoalkyl (as the compound shown in the abstract) or dialkyl (other than the DEAD-type reagents). Is that because there hasn't been a good way to make them, because they aren't stable, both or neither?

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2. vigilante_reviewer on February 8, 2010 2:28 PM writes...

I wonder what you do when you get a paper like this as a reviewer - wave it on because no one is going to try and reproduce it?!

Permalink to Comment

3. Anon on February 8, 2010 2:39 PM writes...

Chemistry is a jungle. There are the lion labs, who make the big kills. They publish in JACS/Angew/Science. Then there are the buzzards who try to feed on the scraps of the lions (Lions lab methodology for furan coupling now works for thiophene!). They publish in tet lett. And we've all met a few jackals, who steal other people's shit (Cordova?). And then there are the monkeys, who jump up and down screeching and throwing crap at each other (chemical blogosphere?). My question is why are we talking about a paper in the Journal of Buzzard Chemistry?

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4. RB Woodweird on February 8, 2010 2:43 PM writes...

"And then there are the monkeys, who jump up and down screeching and throwing crap at each other (chemical blogosphere?)"

Priceless. I lol'd, as they say on the webosphere.

"I wonder what you do when you get a paper like this as a reviewer - wave it on because no one is going to try and reproduce it?!"

I wonder what the legal ramifications would be if this happened. What if a reviewer let an obviously-dangerous procedure be published and someone was hurt trying it?

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5. J-bone on February 8, 2010 3:41 PM writes...

I wonder what you do when you get a paper like this as a reviewer - wave it on because no one is going to try and reproduce it?!

More like you wave it on because you're friends with the PI and want to remain friends so you can ask him to wave one of your spotty manuscripts on without actually reading it.

Permalink to Comment

6. barry on February 8, 2010 4:58 PM writes...

If you need an acetate radical, you can get it from malonate with Mn(OAc)3. There's just no motive for this.

Permalink to Comment

7. Bored on February 8, 2010 6:13 PM writes...

#4 RB Woodweird

Legal ramifications of something published in a journal? Why worry about that when the Internet is awash in websites like this?:

http://www.textfiles.com/uploads/nitro.txt

Permalink to Comment

8. Call me monkey or buzzard on February 9, 2010 8:51 AM writes...

Lions, Monkeys and Buzzards, all masks of your egos and nothing else, the one in search of truth remain researchers, lions too retract their science and jacs papers and there are cases where even nobel laureates´works are also not reproducible! And don´t forget the regionalism and biases existing in the journal world where often you have no choice but to bceome a buzzard or a monkey in your language.

Permalink to Comment

9. Nick on February 9, 2010 9:41 AM writes...

I've noticed a lot of intestinal tract anti-inflammatories are 5-amino salicylic acids (ASA’s) or two diazo-linked salicylic acid molecules. I would think the diazo linkage is easily hydrolyzed and assume that the 5-amino substitution somehow decreases their metabolism/absorption so they can make it to the intestines. I (obviously) have no pharmacokinetic experience; can someone further elaborate? (I know it seems like I’m hijacking this thread, but at least there’s a reference to diazo compounds!)

Permalink to Comment

10. Northern_Chemist on February 9, 2010 10:46 AM writes...

Nick: 5-Aminosalicylic acid (5-ASA, mesalazine) is a bowel-specific anti-inflammatory. Azo compounds are reductively cleaved by intestinal microflora. Therefore azo compounds derived from 5-ASA (such as balsalazide) act as bowel-targetting prodrugs, specifically releasing 5-ASA at the site of action.

Permalink to Comment

11. sepisp on February 10, 2010 4:34 AM writes...

#6: barry, read the paper. There's no need for an acetate radical. Instead, the starting material fragments to acetic acid (AcOH) and a radical. The radical in their case is EtO2CH2CH2*.

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