Submission Details

JOH-UNI-50ce7ec3
Molecule(s):
C=CS(=O)(=O)N(C(=O)Cc1cccc(Cl)c1)c1cncc2ccccc12

JOH-UNI-50ce7ec3-1

C=CS(=O)(=O)N(C(=O)Cc1cccc(Cl)c1)c1cncc2ccccc12

3-aminopyridine-like Check Availability on Manifold View
O=C(Cc1cccc(Cl)c1)N(c1cncc2ccccc12)S(=O)(=O)F

JOH-UNI-50ce7ec3-2

O=C(Cc1cccc(Cl)c1)N(c1cncc2ccccc12)S(=O)(=O)F

3-aminopyridine-like Check Availability on Manifold View
C=CS(=O)(=O)N(C(=O)Cc1cccc(Cl)c1)c1cnc(C(F)F)c2ccccc12

JOH-UNI-50ce7ec3-3

C=CS(=O)(=O)N(C(=O)Cc1cccc(Cl)c1)c1cnc(C(F)F)c2ccccc12

3-aminopyridine-like Check Availability on Manifold View
O=C(Cc1cccc(Cl)c1)N(c1cnc(C(F)F)c2ccccc12)S(=O)(=O)F

JOH-UNI-50ce7ec3-4

O=C(Cc1cccc(Cl)c1)N(c1cnc(C(F)F)c2ccccc12)S(=O)(=O)F

3-aminopyridine-like Check Availability on Manifold View
C=CS(=O)(=O)N(C(=O)Cc1cccc(Cl)c1)c1cnc(C(F)F)cc1C

JOH-UNI-50ce7ec3-5

C=CS(=O)(=O)N(C(=O)Cc1cccc(Cl)c1)c1cnc(C(F)F)cc1C

3-aminopyridine-like Check Availability on Manifold View
Cc1cc(C(F)F)ncc1N(C(=O)Cc1cccc(Cl)c1)S(=O)(=O)F

JOH-UNI-50ce7ec3-6

Cc1cc(C(F)F)ncc1N(C(=O)Cc1cccc(Cl)c1)S(=O)(=O)F

3-aminopyridine-like Check Availability on Manifold View
Design Rationale:

Amide with acrylamide etc warheads may be unstable, at least in our hands. Amide-vinylsulphonamides might be a more viable option to combine a lead scaffold with a Michael acceptor.

Other Notes:

ArN(Ac)SO2(CH=CH2) is easily synthesised via ArNHSO2(CH=CH2) and Ac2O. Possibly synthesis, in our case, would involve forming the ArNH(vinylsulphonamide) then coupling with e.g. acid anyhride or chloride. See: Eur. J. Org. Chem. 2018, 829–836; DOI: 10.1002/ejoc.201701715.

Discussion:

Contributor: John Spencer, Uni of Sussex - Sat, 12 Dec 2020 17:20:30 +0000