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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: Twitter: Dereklowe

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May 24, 2010

Great Moments in Heterocyclic Chemistry

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Posted by Derek

Something definitely went wrong with this paper: check out the thiophenes, which look through the whole paper just like they do in that abstract. It's another who-let-that-through moment for Bioorganic and Medicinal Chemistry Letters. Perhaps it's all a plot, to get you to read every paper in the hopes that something bizarre will turn up. . .

Comments (25) + TrackBacks (0) | Category: The Scientific Literature


1. Anonymous on May 24, 2010 11:21 PM writes...

also look at the alpha-bromo acetamide and all the other grease. Maybe this is what happens when the goverment/army starts doing drug discovery. Maybe they ought to just fund research in someone else's lab.

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2. Rock on May 25, 2010 12:32 AM writes...

I have reviewed about ten papers for BOMCl in the past few years and recommended "do no publish" for half of them. How many were actually rejected? "0". The current peer review system for most journals is a big joke and that includes the ACS journals.

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3. mmol on May 25, 2010 4:18 AM writes...

......and the nitro groups. ChemDraw will actually "check" structures, even for referees!

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4. CRH on May 25, 2010 7:49 AM writes...

Agree with Rock. I reviewed a manuscript last year and gave it a full rejection - really a bad paper. Just a week or so later I received notification that the manuscript was accepted with minor revisions. I looked at the reviewers comments and mine was outright reject, and the second reviewer was accept with major revision. I emailed the editor to see what was up and he said after talking with the author, *cough, cough friend* he was going to allow publication with only the typos being corrected.

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5. Anonymous on May 25, 2010 7:54 AM writes...

This paper came from the infamous Walter Reed!

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6. Anonymous on May 25, 2010 8:27 AM writes...

The current peer review system for most journals is a big joke and that includes the ACS journals.


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7. Boycott BMCL? on May 25, 2010 9:24 AM writes...

In my experience the ACS journals (at least JMC and JACS) take reviewers seriously. However, the editor(s) of BMCL seem to completely ignore reviewers' comments - I've recommended rejecting several very low quality manuscripts and have seen them published with no substantial changes. It is sufficiently frustrating that I no longer review for them.

This blog has sufficient readership that perhaps if we started a public boycott movement it could force BMCL to be more receptive (and respectful) to their reviewers.

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8. bbooooooya on May 25, 2010 9:35 AM writes...

"BMCL to be more receptive (and respectful) to their reviewers'

A worthy goal, but good luck with that. Elsevier cares about making $. As long as people keep subscribing, no reason to introduce any quality control.

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9. rtw on May 25, 2010 9:45 AM writes...

ChemDraw 12 insists on putting a Hydrogen on that double bonded sulur making the exact mass 462.83, drawn as I suspect that it should be as a normal Thiophene the exact mass should ne 460.81. Did they run a high res MS on the structure by any change to get its exact mass? Unfortunately I don't subscribe or have access to the full paper, but I imagine their synthesis is is pretty wacked out to end up with what they have drawn. Were any of the authors heterocyclic chemists?

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10. zDNA on May 25, 2010 9:49 AM writes...

Great...I just submitted my first manuscript to BMCL just yesterday. Makes me feel a whole lot better. Ick. On the upside, it'll probably be accepted.

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11. Vader on May 25, 2010 9:57 AM writes...

I'm no organic chemist, but the sulfurs jumped out at me. Six bonds I can believe if four of them are double bonds to oxygen, but three bonds? I'm assuming from comments that that's the problem?

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12. Hap on May 25, 2010 10:14 AM writes...

The thiophene double bonds are shifted one position from where they should have been - putting three bonds to S means that it should have a (+) charge, and the neighboring carbon a (-) charge, which is just a relatively unstable resonance form for the thiophene.

The problem is that both the authors and reviewers should have caught the error, since they both ought to know organic chemistry and (perhaps) have error checking in their structure software to say, "Are you sure you have this right?" The error kind of slaps a reader in the face, which should have been the case with the reviewers at least (the authors probably tuned it out, because they had seen it too much). It's a mistake someone ought to have caught.

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13. David P on May 25, 2010 10:26 AM writes...

No, these are Experimental Therapeutics. Really really experimental.

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14. CRH on May 25, 2010 10:58 AM writes...

Another point that burns me when reviewing or reading BMCL is there is no mention of purity of compounds, or methods used for purification. There should always be, at least, a footnote stating that all compounds were characterized by LCMS and/or 1H NMR and found to be in agreement. LCMS probably would not have helped here; but common sense would make the reviewer ask for experimental details. This is simply shameful.

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15. john on May 25, 2010 11:43 AM writes...

Boy, I don't know which is worse, the misplaced bonds on the thiophene or an N-aryl, N-sulfonyl bromoacetamide. I bet that baby is a pretty good Br+ donor.

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16. Wavefunction on May 25, 2010 11:43 AM writes...

Walter Reed Army Hospital...maybe this is supposed to be the next nerve agent. Otherwise the terrorists win.

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17. cynical1 on May 25, 2010 12:08 PM writes...

As a US tax payer, I'd like to propose some budget cuts...........

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18. weirdo on May 25, 2010 12:29 PM writes...

I'm not sure what's worse, being an author on this POS or being thanked "for critical review of the manuscript".

And, what, no comments on the N-S-CCl3 molecules? The authors make a big point about avoiding toxicity, but they have a strange way of addressing it.

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19. RM on May 25, 2010 1:41 PM writes...

Wavefunction @16: "maybe this is supposed to be the next nerve agent"

One specific to organic chemists, perhaps?

"That's ... you can't ... who ... how did this ... anyone with half ... ERK!" (keels over from sheer incredulity)

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20. Sili on May 25, 2010 4:10 PM writes...

If I'm allowed to choose, I think I prefer the Eastereggs in Angewandte.

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21. pdf on May 25, 2010 7:01 PM writes...

Here is another example from the same journal. Check structure 1:

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22. Rock on May 25, 2010 7:55 PM writes...

I should clarify that I have had better luck keeping bad papers out of the ACS journals as a reviewer. However, they are just as bad in not following through on suggested revisions. I blame the editors for this.
As for BOMCl, I have been using the abstracts in my RSS reader as a teaching tool for my team to recognize crap.

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23. medchem23 on May 26, 2010 4:46 AM writes...

Best thing is that not only do reviewers comments get ignored but you then have to pay the publisher for the privelige of reading the work that you and your colleagues (in the wider sense) have submitted and/or reviewed. I think that in the age of the internet these journals really aren't the best vehicle for scientific publication anymore. We should all be submitting papers to open access web-based journals and contributing to the online peer review of the material published.

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24. medchem23 on May 26, 2010 4:50 AM writes...

Oh, and Derek, I think you really are in a serious conflict of interest situation here and given the popularity of your blog you shouldn't really be dissing a competitor journal like this.

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25. jonathan on May 27, 2010 3:48 AM writes...

While this structural mistake is inexcusable (and the structure as a proposed probe - highly reactive), and referees need to be respected more, I find many very useful and good papers in BOMCL, particularly those from Pharma.

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