Genius CUBANE Synthesis by Nobel Laureate & Overpriced Drugs | Organic Chemistry (MacMillan)
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- Опубліковано 10 чер 2024
- 🤔 Cubane is a frequently discussed - and highly coveted - top chemistry meme molecule. This interdisciplinary video showcases the synthesis and application of cubanes in medicinal chemistry by presenting research work from MacMillan and co-workers. Given their proof-of-concept on the cystic fibrosis drug Lumacaftor, we also walk through a high-level primer on cystic fibrosis disease landscape and current treatments.
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00:00 Cube time
01:23 Refresh on BCP, cubane and COT isosteres
02:51 MacMillan's work: 1,3 di-substituted cubanes
04:55 1,2 di-substituted cubanes
05:57 Photoredox/cross-coupling with Copper
07:33 Cuba-Lumacaftor synthesis and properties
09:48 Cystic fibrosis (CF) primer incl. treatments (most notably, Orkambi and Trikafta)
12:58 Financials
15:05 Unexpected appearance by deuterium
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Key references:
- Cubanes in Medicinal Chemistry: J. Med. Chem. 2019, 62, 1078
- General Access to Cubanes as Benzene Bioisosteres: Nature 2023; doi.org/10.1038/s41586-023-06... / ChemRxiv: chemrxiv.org/engage/api-gatew...
- Cyclooctatetraene: A Bioactive Cubane Paradigm Complement: Chemistry. 2019, 25, 2729
- 1,2-Difunctionalized bicyclo[1.1.1]pentanes:Long-sought-after mimetics forortho/meta-substituted arenes: PNAS 2021, 118, e2108881118
- An example for BCP: Application of the Bicyclo[1.1.1]pentane Motif as a Nonclassical Phenyl Ring Bioisostere in the Design of a Potent and Orally Active γ-Secretase Inhibitor: J. Med. Chem. 2012, 55, 3414
Some recommended books on organic synthesis:
- Clayden, Greeves, Warren; Organic Chemistry (basic organic chemistry knowledge)
- Wyatt, Warren; Organic Synthesis: The Disconnection Approach (excellent introduction to retrosynthesis)
- Kurti, Czako; Strategic Applications of Named Reactions in Organic Synthesis (extensive toolkit of functional group reactions and applications thereof with common conditions)
- Nicolaou; Classics in Total Synthesis 1-3 (the ultimate total synthesis trilogy)
- Nicolaou; Molecules That Changed the World (the world's most important molecules and their impact on everyday life)
- Carreira, Kvaerno; Classics in Stereoselective Synthesis (compilation of the groundbreaking methods of stereoselective synthesis and application to synthesis of stereochemically complex structures) - Наука та технологія
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Massive thank you to all channel supporters!
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Do you have a discord?
@@hellothere3163 Will set one up soon to connect with folks!
Tom I know you'll be watching this.... You should be writing your thesis.
Don’t listen to him, Tom! You have a plenty of time
That's right Tom, plus, the sooner you fall behind the more time you have to catch up!
I finished a chapter this week ok i'm on a breakkkkkkkkkkkkkkk
@@ExtractionsAndIre 😂 Have you got an alert set up for any video with cubane references?! Lol
@@keithcarpenter5254 No I just like cubane videos! And this is a good one!
Finally... enough classes in biochemistry, organic chemistry, and medicinal chemistry and I can FULLY comprehend this video. Solid video as always.
Nice 🔥 and thank you!
Hypercubane looks like straight out of the Journal for Immaterial Science.
Thats just what I thought, lol. Need to read into those predictive calculations and see if its interesting enough for a future video
Ohhh this is gonna trigger @ExtractionsAndIre
🤣🤣🤣🤣🤣
Awesome job on the video! Really beautiful chemistry here!
Thank you!!
You know, with how difficult Cubane is to synthesize, we should call it Cu-Pain instead lol
Noice
Wild. I had no idea about these structures. No doubt this is gonna cost me 4 hours of reading time this weekend! Great vid. Oh, plus Argentina.
You cant talk about Cubane without mention the australian guy!
Glad to see the channel growing and that you have more time to make videos
Thanks man! Unfortunately Ive been quite busy recently but hope I can get back to the same pace in summer
👀
i am finishing my first year in biomedical sciences, do i understand everything in this video? no. Does it make me want to continue studying so that i can understand everything? absolutly.
Great video
Amazing, thats the spirit!
i'm finishing my first year in farmaceutical chemistry. i didn't understand much either. but it still fascinates me
I’m just waiting for Cubane drugs🔥
Cuba-cocaine probably goes hard
Or 6 step LSD synth you uploaded x cubane
So there really is no plausible, chemical pathology for any physical/psychological illness? If a molecule look's neat, like a house, see what it does in a mouse?
Lol
get a little cubestasy ?
@@pucky8231 the world just isn’t ready for cuba-methamphetamine
@@rileymerson8781 *tweaks geometrically*
waiting for nilered to synthesize cubane :)
Very exciting to see new ways to this! I'm hoping that it's obvious use in quantum machines is soon
😂
Excellent vids m8
Thanks!!
Still waiting for someone to come up with nice synthetic routes to make polysubstituted cubanes. I have a specific motif I dream of trying to make, but the benzene variant is 1,2,4,5-tetrasubstituted. While I have a few half-arsed ideas based on digging in some old literature, I doubt they would work tbh.
I saw a question about cubane in a chemistry Olympiad.
Do you have a source for the quasi favorskii hypothesis?
Source is Bredt's rule, haha
Quick search gave this for example: www.studocu.com/in/document/pondicherry-university/advanced-organic-chemistry/quasi-favorskii-rearrangement/46811769
"friend deuterium" = NileRed
cody's lab, you lost your chance when you had it
Cubane sounds like a rappers name.
I thought it was the guy from Shark Tank , Mark Cubane 😜
I was thinking grunge
Kurt Cubane 😂
Nein, nicht wirklich...
Ein Österreicher.
Uni oder Rosensteingasse auch?
Close! But DACH region is correct
@@totalsynthesis Warum meine Antwort darauf gelöscht werden mußte, erschließt sich mir überhaupt nicht...
@@irgendwieanders2121 Wait what? I didn't delete anything. I only delete comments on my psychedelic videos which attract bunch of spamming fake accounts selling shrooms
ua-cam.com/video/uQ3YLRpaMlU/v-deo.html
bycyclopentanes u mean?
just say "propellanes"