Submission Details
Molecule(s):
PET-UNK-6c2be958-1
Duplicate of:
VLA-UCB-05e51b3f-15
O=C(CCl)N(C(=O)Cc1cccc(Cl)c1)c1cncc2ccccc12
Design Rationale:
Warhead is attached to amide N of ADA-UCB-6c2cb422-1 using a one-carbon linker (as opposed to being directed bonded to nitrogen/carbon as is case for PET-UNK-5ecb6237-1/NIR-WEI-75ed5c39-1). Using a carbonyl carbon (sp2) to link the warhead gets round the problems associated with an sp3 carbon linker (PET-UNK-a692de38-1 addresses these problems by using a nitrogen atom as a linker). I have used DAN-LON-a5fc619e-3 as a 'generic' inspiration for the chloroacetyl warhead.
Other Notes:
I am assuming that the design can be synthesized directly from ADA-UCB-6c2cb422-1 and perceived ease of synthesis is a significant factor in this proposal. My understanding is that rotation around C(=O)-N bonds in imides is easier than for amides. I would anticipate that the reactivity of a chloroacetimide will be more like a chloroacetone than a chloroacetamide (I'm not sufficiently familiar with the generic warhead class to know whether reactivity differs significantly between the two warheads).