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Author: Subject: naturally derived aryl cyclohexylamines
Globey
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[*] posted on 26-7-2009 at 11:47
naturally derived aryl cyclohexylamines


Anyone thought of using toluene as the aromatic (benzyl chloride/bromide), menthone as the cyclohexyl, and ethylamine or ammonia as the amine? Thinking there might be unfavorable steric issues with the isopropyl and the amine.

Would this be the correct nomenclature?

N-ethyl-1-benzyl-2-isopropyl-5-methylcyclohexylamine or
1-benzyl-2-isopropyl-5-methylcyclohexylamine

Wondering about pharmacology. Seems the lowest amines (below ethyl) are anti-convulsants, and not general anesthetics.
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setback
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[*] posted on 26-7-2009 at 13:34


Is there some kind of reference to be had?
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Globey
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[*] posted on 26-7-2009 at 15:56


none that i know, was just hoping to spur some interest. if it's not otc, it's not interesting;)
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Paddywhacker
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[*] posted on 26-7-2009 at 21:12


Is that the Alekhine reaction you are talking about?

Please explain.
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Polverone
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Globey
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[*] posted on 27-7-2009 at 10:37


You see I checked, M8, &having marched over to Jerry's book (& Merck Index as well), that reaction was referenced no where. Now, what's the rxn. where, on one's way to jail in an ice cream truck, one oxidizes allylic olefins directly to the ket=1 using Pd and slightly higher than atmospheric? y'all too smart for me :(
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Paddywhacker
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[*] posted on 27-7-2009 at 20:42


Sure sounds like Alekhine's Defense to me, but maybe you haven't described it enough. What you have said is very little to go on for anyone who doesn't know what you are talking about.

If you cannot describe your reaction clearly, then draw a picture. A good diagram is better than ten pages of mumbling.
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Globey
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[*] posted on 28-7-2009 at 06:33


What I initially said in my 1st post, should be plenty good for both the chemist, and the lay person alike. I try to write like a Scientific American article, so pretty much anyone can understand me. My posts aren't aimed at chemists with pencils up their asses...have faith that my 1st post i s exactly what I intended it to be, and if you can't work with that, don't post reply just to show how clever you are. This isn't a beauty contest or a challenge. As far as I'm concerned, everything after the 1st post is garbage so far (including my post right here). Don't get me started again. If you can't/won't reply to my thread constructively, just don't. My opening up this thread wasn't intended as a lure for smart Ace's.
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Paddywhacker
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[*] posted on 28-7-2009 at 11:06


Globey, I know organic chemistry well, but "Anyone thought of using toluene as the aromatic (benzyl chloride/bromide), menthone as the cyclohexyl, and ethylamine or ammonia as the amine? Thinking there might be unfavorable steric issues with the isopropyl and the amine" is not an understandable question.

Obviously you are referring to some reaction, or to some sequence of reactions that use an aromatic hydrocarbon (or chlorinated hydrocarbon), a cyclohexyl compound (maybe a ketone), and ammonia or an amine. That isn't even enough information to Google. What on earth are you talking about?

Possibly you are forming an imine from the menthone and amine and then alkylating it with the aromatic, but you'll have to spell that out.

[Edited on 28-7-2009 by Paddywhacker]
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querjek
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[*] posted on 28-7-2009 at 11:36


Sounds like an attempt at something PCP-like... not that I have any problems with that, but the reagents sound as if they'd work out to something like it.

[Edited on 28-7-2009 by querjek]

[Edited on 28-7-2009 by querjek]




it's all about chemistry.
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Globey
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[*] posted on 28-7-2009 at 13:46


Paddywhacker...use your imagination. YES, you are CORRECT, an imine intermediate. There are reasons to be vague. querjek, you got it! I refuse to believe us SM'ers have no imagination.

So anyway, so much for trying to be even somewhat discreet, DOH! But then, again, once more, getting back to the spirit of the topic, wonder how this rxn would run if menthone was substituted for cyclohexanone, and benzyl bromide was sub for phenylmgbr. Not asking for a purist to poke holes into everything just because I'm a bit vague. Am more interested in intuition/imagination. Under favorable proper conditions, what might be the outcome. My inital guess is that the isopropyl group would pose some steric hindrance. Thanks;)
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Paddywhacker
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[*] posted on 28-7-2009 at 15:22


Camphor is the most readily available substuted cyclohexanone, AFAIK.
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Globey
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[*] posted on 28-7-2009 at 19:05


^^^strictly a borane, right, but I see what you mean. used to be able to buy cubes of synthetic camphor at drug store, and even tried it once (adam gottleib's legal highs said it had a nice subtle effect). I felt nothing...but took care of my bad breath!
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querjek
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[*] posted on 29-7-2009 at 06:47


Sorry Globey--your post was sooo vague before that I felt people should at least have an idea of what the reactants would become.

Have you considered DEET + 1,4-dichlorobutane/pentane? I've thought about that in the past... the end molecule would be pretty close to something...




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[*] posted on 29-7-2009 at 08:51


Globey, instead of wasting our time by trying to guess what the hell you are asking about, you could have at least checked the literature before posting and provided a starting point in the first post (or at least a scheme or something comprehensive!).
There are several papers on the structure-activity relationship of NMDA antagonists. None of them claims the benzyl group is isosteric to phenyl in PCP-like ligands like you suggest. On the contrary, the benzyl is not a viable bioisostere to the aryl. Therefore your 1-benzyl-2-isopropyl-5-methylcyclohexylamine isomers do not fit the requirements for receptor binding. A bit of topic, but the benzyl group is however isosteric with the cyclohexyl moiety in NMDA antagonists and therefore 1,2-diarylethylamines have substantial activity (for example, 1-(1,2-diphenylethyl)piperidine is just about equipotent to PCP in blocking NMDA receptors).
In the 1-arylcyclohexylamine series, the position 2 and 4 of the cyclohexyl ring can tolerate the methyls in either cis or trans configuration, retaining some activity and in some cases even increasing it, but the isopropyl is most likely too large. See some papers on the SAR of these compounds for more info:

Quantitative Structure-Activity Relationship Analysis of Phencyclidine Derivatives. I
Molecular Pharmacology, 34 (1988) 863-879.
European Journal of Medicinal Chemistry, 14 (1979) 301-308.
Quantitative Structure-Activity Relationships, 13 (1994) 159-164.

For the methyl substitution on the cyclohexyl moiety, see:
J. Med. Chem., 34 (1991) 2615-2623.
J. Med. Chem., 33 (1990) 1452-1458. (contains also the 1-benzylcyclohexylamine as homologue which was inactive in their tests)




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