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Drug-like Molecules

Examples of retrosynthesis on more complex, drug-like molecules.

4-Phenylpyridine (Suzuki coupling product)

SMILES: c1ccc(-c2ccncc2)cc1

This biaryl compound is typically synthesized via Suzuki-Miyaura cross-coupling.

RENKIN's graph-based suzuki_retro rule disconnects the biaryl bond into an aryl bromide + an aryl-H fragment (suzuki_retro tracks only these two organic fragments, not a boronic ester/acid as a separate species — the missing boronate activation on the aryl-H side is implicit, not modeled):

c1ccc(-c2ccncc2)cc1
    → Brc1ccccc1 + c1ccccn1
    [suzuki_retro]

or

c1ccc(-c2ccncc2)cc1
    → Brc1ccncc1 + c1ccccc1
    [suzuki_retro]

Both bromobenzene (Brc1ccccc1) and pyridine (c1ccccn1) are in the default building block stock.

4-Fluorobiphenyl

SMILES: Fc1ccc(-c2ccccc2)cc1

RENKIN finds two Suzuki disconnection modes (again, aryl bromide + aryl-H — see the note above about the implicit boronate side):

  1. Fluorine-substituted arene as the bromide partner: 

    Fc1ccc(-c2ccccc2)cc1
    → Fc1ccc(Br)cc1 + c1ccccc1

  2. Or the reverse: 

    Fc1ccc(-c2ccccc2)cc1
    → Brc1ccccc1 + Fc1ccccc1

Paracetamol (Acetaminophen)

SMILES: CC(=O)Nc1ccc(O)cc1

Amide bond disconnection:

CC(=O)Nc1ccc(O)cc1
    → CC(=O)O + Nc1ccc(O)cc1
    [amide_cleavage]
  • Acetic acid (CC(=O)O) — in stock
  • 4-Aminophenol (Nc1ccc(O)cc1) — in stock

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