Literature summary for 3.4.21.6 extracted from

Imaeda, Y.; Kawamoto, T.; Tobisu, M.; Konishi, N.; Hiroe, K.; Kawamura, M.; Tanaka, T.; Kubo, K.
Discovery of piperazinylimidazo[1,2-a]pyridines as novel S4 binding elements for orally active factor Xa inhibitors (2008), Bioorg. Med. Chem., 16, 3125-3140.

Crystallization (Commentary)

Crystallization (Comment)	Organism
molecular modeling of complex with inhibitor [5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methanol. The imidazo[1,2-a]pyridine ring is deeply buried inside the hydrophobic S4 site and makes hydrophobic contacts with the aromatic rings of Tyr99, Phe174, and Trp215 without the salt bridge with any amino acid residue in this site. The imidazo[1,2-a]pyridine ring extends across the face of the Phe174 phenyl ring with a favorable pi-pi stacking interaction	Homo sapiens

Crystallization (Comment)

Organism

molecular modeling of complex with inhibitor [5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methanol. The imidazo[1,2-a]pyridine ring is deeply buried inside the hydrophobic S4 site and makes hydrophobic contacts with the aromatic rings of Tyr99, Phe174, and Trp215 without the salt bridge with any amino acid residue in this site. The imidazo[1,2-a]pyridine ring extends across the face of the Phe174 phenyl ring with a favorable pi-pi stacking interaction

Homo sapiens

Inhibitors

Inhibitors	Comment	Organism
1-[5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]-2-ethylpropan-2-ol	-	Homo sapiens
1-[5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]ethanol	-	Homo sapiens
1-[5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]propan-2-ol	-	Homo sapiens
2-[5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]propan-2-ol	-	Homo sapiens
5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)-2-methylimidazo[1,2-a]pyridine	-	Homo sapiens
5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)imidazo[1,2-a]pyridine	-	Homo sapiens
[5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methanol	selective and orally bioavailable inhibitor	Homo sapiens
[5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methanol	good oral bioavailability after oral administration at a dose of 3 mg/kg in fasted monkeys. Pharmakokinetics study	Macaca fascicularis

Organism

Organism	UniProt	Comment	Textmining
Homo sapiens	-	-	-
Macaca fascicularis	-	-	-

Source Tissue

Source Tissue	Comment	Organism	Textmining
commercial preparation	-	Homo sapiens	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
Arg-Gly-Arg-4-nitroanilide + H2O	-	Homo sapiens	Arg-Gly-Arg + 4-nitroaniline	-	?
Arg-Gly-Arg-4-nitroanilide + H2O	-	Macaca fascicularis	Arg-Gly-Arg + 4-nitroaniline	-	?

IC50 Value

IC50 Value	IC50 Value Maximum	Comment	Organism	Inhibitor
0.000009	-	pH 8.3, 37°C	Homo sapiens	[5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methanol
0.000012	-	pH 8.3, 37°C	Homo sapiens	5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)-2-methylimidazo[1,2-a]pyridine
0.000018	-	pH 8.3, 37°C	Homo sapiens	1-[5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]propan-2-ol
0.000018	-	pH 8.3, 37°C	Homo sapiens	2-[5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]propan-2-ol
0.00002	-	pH 8.3, 37°C	Homo sapiens	1-[5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]ethanol
0.000021	-	pH 8.3, 37°C	Homo sapiens	5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)imidazo[1,2-a]pyridine
0.000022	-	pH 8.3, 37°C	Homo sapiens	1-[5-(4-[3-[(6-chloronaphthalen-2-yl)sulfonyl]propanoyl]piperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]-2-ethylpropan-2-ol