Talmapimod
2-[6-chloro-5-[(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazine-1-carbonyl]-1-methylindol-3-yl]-N,N-dimethyl-2-oxoacetamide
Molecular Identity
Talmapimod
2-[6-chloro-5-[(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazine-1-carbonyl]-1-methylindol-3-yl]-N,N-dimethyl-2-oxoacetamide
PubChem CID: 9871074
Talmapimod is an indolecarboxamide obtained by formal condensation of the carboxy group of 6-chloro-3-[(dimethylamino)(oxo)acetyl]-1-methylindole-5-carboxylic acid with the secondary amino group of (2S,5R)-1-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazine. It is a potent inhibitor of MAPK and exhibits anti-cancer properties. It has a role as an antineoplastic agent, an apoptosis inducer and an EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor. It is a dicarboxylic acid diamide, a N-acylpiperazine, a N-alkylpiperazine, an indolecarboxamide, a chloroindole, an aromatic amide, an aromatic ketone and a member of monofluorobenzenes.
2D Structure
Properties
C27H30ClFN4O3
Molecular Formula
513.00
Molecular Weight
g/mol
512.1990
Exact Mass
Da
3.7
XLogP
Drug-like (Lipinski: < 5)
65.9
TPSA
Good oral absorption (< 140 A²)
0
H-Bond Donors
5
H-Bond Acceptors
836
Complexity
SMILES
Canonical SMILES
SMILES: CC1CN(C(CN1C(=O)C2=C(C=C3C(=C2)C(=CN3C)C(=O)C(=O)N(C)C)Cl)C)CC4=CC=C(C=C4)FIsomeric SMILES
SMILES: C[C@@H]1CN([C@H](CN1C(=O)C2=C(C=C3C(=C2)C(=CN3C)C(=O)C(=O)N(C)C)Cl)C)CC4=CC=C(C=C4)FSynonyms(20)
Talmapimod309913-83-5SCIO-469SCIO 469Scios 469B1E00KQ6NTCHEBI:906832-[6-chloro-5-[(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazine-1-carbonyl]-1-methylindol-3-yl]-N,N-dimethyl-2-oxoacetamide2-(6-Chloro-5-{[(2r,5s)-4-(4-Fluorobenzyl)-2,5-Dimethylpiperazin-1-Yl]carbonyl}-1-Methyl-1h-Indol-3-Yl)-N,N-Dimethyl-2-Oxoacetamide1H-Indole-3-acetamide, 6-chloro-5-(((2R,5S)-4-((4-fluorophenyl)methyl)-2,5-dimethyl-1-piperazinyl)carbonyl)-N,N,1-trimethyl-alpha-oxo-2-(6-chloro-5-(((2R,5S)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl)carbonyl)-1-methyl-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide2-(6-chloro-5-{(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazine-1-carbonyl}-1-methyl-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamidetalmapimodum1H-Indole-3-acetamide, 6-chloro-5-[[(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethyl-1-piperazinyl]carbonyl]-N,N,1-trimethyl-alpha-oxo-2-(6-chloro-5-((2R,5S)-4-((4-fluorophenyl)methyl)-2,5-dimethylpiperazine-1-carbonyl)-1-methyl-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide
Data from PubChem (NCBI)
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