Submission Details

MIC-UNK-ea979c74
Molecule(s):
CC(=O)NCC[C@H]1COc2c(NC(=O)Cc3cnccc3C)cc(Cl)cc21

MIC-UNK-ea979c74-1

CC(=O)NCC[C@H]1COc2c(NC(=O)Cc3cnccc3C)cc(Cl)cc21

3-aminopyridine-like Check Availability on Manifold View
CC(=O)NCC[C@H]1COc2c(NC(=O)Nc3cnccc3C)cc(Cl)cc21

MIC-UNK-ea979c74-2

CC(=O)NCC[C@H]1COc2c(NC(=O)Nc3cnccc3C)cc(Cl)cc21

3-aminopyridine-like Check Availability on Manifold View
CC(=O)NCC[C@H]1COc2c(CC(=O)Nc3cnccc3C)cc(Cl)cc21

MIC-UNK-ea979c74-3

CC(=O)NCC[C@H]1COc2c(CC(=O)Nc3cnccc3C)cc(Cl)cc21

3-aminopyridine-like Check Availability on Manifold View
CC(=O)NCC[C@H]1COc2c1cc(Cl)cc2N(CCC1CCCCC1)C(=O)Nc1cnccc1C

MIC-UNK-ea979c74-4

CC(=O)NCC[C@H]1COc2c1cc(Cl)cc2N(CCC1CCCCC1)C(=O)Nc1cnccc1C

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

Merger of N-acetyl-fluorotryptamine (x104) and one of many examples from aminopyridine series (by eye)

Other Notes:

As indole NH faces solvent, I chose to replace indole ring with dihydrobenzofuran system in order to simplify synthesis, place amide-containing chain at proper angle, and increase stability (?) Addition of another lipophilic substituent, like in JOR-UNI-2fc98d0b-12 is possible and probably feasible One of simpler syntheses would use 5-chloro-7-nitrobenzofuran-3(2H)-one as one of starting materials with Wittig reaction, olefin metathesis with allylacetamide and catalytic hydrogenation as key steps

Inspired By:
Discussion:

Contributor: Michal K - Sat, 13 Jun 2020 19:29:35 +0000