Dragon

In 1972 Bruce Lee defeated Chuck Norris (here) and team Far East has been winning ever since. China is on a monumental roll. If we fast-forward to present day and for example summarize the table of contents for one recent issue of Synlett, we get (seriously, check it out):

  • 35 Chinese articles
  • 2 Japanese articles
  • 1 Canadian article (by Chinese authors)

Denial is futile. This is what we have, move along.

The compound of the day is the natural product beauty-queen psychotripine (1), spotted in a fresh paper from – you guessed it – China:
Org. Lett., Article ASAP (DOI: 10.1021/ol202536b)

psychotripine

The story goes something like this. A compound was for the first time isolated and characterized. Due to its structural complexity, this took quite a while. Computers were needed. Since other compounds in the same class are known to be cytotoxic (i.e. potential anti-cancer drugs), the authors tested the activity of this compound in such an assay. It turned out to be inactive.

This may sound a little harsh, but science is almost always this unrewarding. This little story is pretty illustrative. We start with a well-founded idea, it takes us ages to prove or disprove it, and only in extreme cases are the results useful. This is why science is so damn expensive. There are no short-cuts to the absolute truth.

I would like wrap this one up with a glimmer of hope! Dear authors, I think your compound is active, although perhaps not exactly in the way you first thought. Screw cancer – enter CNS! Evidence:

  • Name: psychotripine – HELLO?!
  • Structure: I see phenethylamines.
  • Figure 1: you could not have come up with Figure 1 unless you were tripping balls.

    •  
      Figure 1

 

8 Responses to The way of the dragon

  1. Maks Fomich says:

    I like the substance! :-)

  2. David Kroll says:

    Frankly, I think the legend to Figure 1 should simply be, “Bring it.”

    Fantastic story – how have I missed you? You’re in my blogroll now!

  3. drfreddy says:

    Thank you. Frankly, I had not read yours either, but anyone who writes about himself in third person (About David) has my blessing. That’s how I roll too :)

    Seriously – like your page a lot!

  4. Snap! I just saw your blog entry about this about 2 h after posting the ridiculous NMR pic myself.

    http://www.lukesci.com/2011/10/25/terrible-science-diagrams-2-nmr-of-psychotropine/

    I hope to post more regularly about science diagram fails.

  5. James says:

    Don’t have access to the paper (only the SI) but not sure I buy this structure. The biosynthetic pathway of this class of molecules is generally from oxidative dimerization/oligimerization of N-methyl tryptamine, and if you open up all the aminals generally you can see it. Not here – in this molecule there’s an isoquinoline unit, which is unprecedented. There are also two other features generally never observed in these families of molecules – the ortho-aminal (? not sure what you call that) – generally appears as an amidine when the C is at that oxidation state, c.f. perophoramidine, and also that methylene bridged aminal. That, and the fact that they had to do some computational work, doesn’t suggest to me that it’s *wrong* per se, but that it might be another “nomofungin”.

  6. James says:

    Scratch previous inane comment. Looks like calycanthine that has gone oxidative dimerization at the 7-position and then 2 point oxidations. Weird, but not crazy.

  7. CatalysisAlex says:

    Fantastic situation analysis.
    Although, I always wondered if bruce were still alive, if Chuck would beat him in a modern day show down….

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