e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Identification of 2-arylbenzimidazoles as potent human histamine H 4 receptor ligands

A Lee-Dutra, KL Arienti, DJ Buzard, MD Hack…

Index: Lee-Dutra, Alice; Arienti, Kristen L.; Buzard, Daniel J.; Hack, Michael D.; Khatuya, Haripada; Desai, Pragnya J.; Nguyen, Steven; Thurmond, Robin L.; Karlsson, Lars; Edwards, James P.; Breitenbucher, J. Guy Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 23 p. 6043 - 6048

Full Text: HTML

Citation Number: 53

Abstract

A series of 2-arylbenzimidazoles was synthesized and found to bind with high affinity to the human histamine H4 receptor. Structure–activity relationships were investigated through library preparation and evaluation as well as traditional medicinal chemistry approaches, leading to the discovery of compounds with single-digit nanomolar affinity for the H4 receptor.

CHEMBRDG-BB 4003414 Structure

CHEMBRDG-BB 4003414

~%

4-[4-(4-methylpiperazin-1-yl)but-1-enyl]benzaldehyde Structure

4-[4-(4-methylp...

4-Bromobenzaldehyde Structure

4-Bromobenzaldehyde

~%

4-[4-(4-methylpiperazin-1-yl)but-1-enyl]benzaldehyde Structure

4-[4-(4-methylp...

methylpiperazine Structure

methylpiperazine

~%

4-[4-(4-methylpiperazin-1-yl)but-1-enyl]benzaldehyde Structure

4-[4-(4-methylp...

4-(4-formylphenyl)but-3-ynyl methanesulfonate Structure

4-(4-formylphen...

~%

4-[4-(4-methylpiperazin-1-yl)but-1-enyl]benzaldehyde Structure

4-[4-(4-methylp...

4-[4-(4-methylpiperazin-1-yl)but-1-ynyl]benzaldehyde Structure

4-[4-(4-methylp...

~%

4-[4-(4-methylpiperazin-1-yl)but-1-enyl]benzaldehyde Structure

4-[4-(4-methylp...

N/A Structure

3-IODO-4-HYDROXYBENZONITRILE Structure

3-IODO-4-HYDROX...

3-Butyn-1-ol Structure

~99%

2-(2-hydroxyethyl)-1-benzofuran-5-carbonitrile Structure

2-(2-hydroxyeth...

4-Hydroxybenzonitrile Structure

4-Hydroxybenzon...

~%

2-(2-hydroxyethyl)-1-benzofuran-5-carbonitrile Structure

2-(2-hydroxyeth...

methylpiperazine Structure

methylpiperazine

1-(3-formylphenoxy)-3-chloropropane Structure

1-(3-formylphen...

~%

3-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehyde Structure

3-[3-(4-methylp...

3-Hydroxybenzaldehyde Structure

3-Hydroxybenzal...

~%

3-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehyde Structure

3-[3-(4-methylp...

2-(2-hydroxyethyl)-1-benzofuran-5-carbonitrile Structure

2-(2-hydroxyeth...

Methanesulfonyl chloride Structure

Methanesulfonyl...

~99%

2-(5-cyano-1-benzofuran-2-yl)ethyl methanesulfonate Structure

2-(5-cyano-1-be...

3-IODO-4-HYDROXYBENZONITRILE Structure

3-IODO-4-HYDROX...

~%

2-(5-cyano-1-benzofuran-2-yl)ethyl methanesulfonate Structure

2-(5-cyano-1-be...

4-Hydroxybenzonitrile Structure

4-Hydroxybenzon...

~%

2-(5-cyano-1-benzofuran-2-yl)ethyl methanesulfonate Structure

2-(5-cyano-1-be...

methylpiperazine Structure

methylpiperazine

2-(5-cyano-1-benzofuran-2-yl)ethyl methanesulfonate Structure

2-(5-cyano-1-be...

~46%

2-[2-(4-methylpiperazin-1-yl)ethyl]-1-benzofuran-5-carbonitrile Structure

2-[2-(4-methylp...

2-(2-hydroxyethyl)-1-benzofuran-5-carbonitrile Structure

2-(2-hydroxyeth...

~%

2-[2-(4-methylpiperazin-1-yl)ethyl]-1-benzofuran-5-carbonitrile Structure

2-[2-(4-methylp...

3-IODO-4-HYDROXYBENZONITRILE Structure

3-IODO-4-HYDROX...

~%

2-[2-(4-methylpiperazin-1-yl)ethyl]-1-benzofuran-5-carbonitrile Structure

2-[2-(4-methylp...

4-Hydroxybenzonitrile Structure

4-Hydroxybenzon...

~%

2-[2-(4-methylpiperazin-1-yl)ethyl]-1-benzofuran-5-carbonitrile Structure

2-[2-(4-methylp...

2-[2-(4-methylpiperazin-1-yl)ethyl]-1-benzofuran-5-carbonitrile Structure

2-[2-(4-methylp...

~57%

2-[2-(4-methylpiperazin-1-yl)ethyl]-1-benzofuran-5-carbaldehyde Structure

2-[2-(4-methylp...

methylpiperazine Structure

methylpiperazine

2-(5-cyano-1-benzofuran-2-yl)ethyl methanesulfonate Structure

2-(5-cyano-1-be...

~46%

2-[2-(4-methylpiperazin-1-yl)ethyl]-1-benzofuran-5-carbaldehyde Structure

2-[2-(4-methylp...

2-(2-hydroxyethyl)-1-benzofuran-5-carbonitrile Structure

2-(2-hydroxyeth...

~%

2-[2-(4-methylpiperazin-1-yl)ethyl]-1-benzofuran-5-carbaldehyde Structure

2-[2-(4-methylp...

3-IODO-4-HYDROXYBENZONITRILE Structure

3-IODO-4-HYDROX...

~%

2-[2-(4-methylpiperazin-1-yl)ethyl]-1-benzofuran-5-carbaldehyde Structure

2-[2-(4-methylp...

4-Hydroxybenzonitrile Structure

4-Hydroxybenzon...

~%

2-[2-(4-methylpiperazin-1-yl)ethyl]-1-benzofuran-5-carbaldehyde Structure

2-[2-(4-methylp...

2-(5-cyano-1-benzofuran-2-yl)ethyl methanesulfonate Structure

2-(5-cyano-1-be...

~%

2-[2-(4-methylpiperazin-1-yl)ethyl]-1-benzofuran-5-carbaldehyde Structure

2-[2-(4-methylp...

methylpiperazine Structure

methylpiperazine

4-(4-Chlorobutoxy)benzaldehyde Structure

4-(4-Chlorobuto...

~%

4-[4-(4-methylpiperazin-1-yl)butoxy]benzaldehyde Structure

4-[4-(4-methylp...

4-hydroxybenzaldehyde Structure

4-hydroxybenzal...

~%

4-[4-(4-methylpiperazin-1-yl)butoxy]benzaldehyde Structure

4-[4-(4-methylp...

4-Bromobenzaldehyde Structure

4-Bromobenzaldehyde

3-Butyn-1-ol Structure

~99%

CHEMBRDG-BB 4003414 Structure

CHEMBRDG-BB 4003414

tert-butyl 4-(3-hydroxyphenyl)piperazine-1-carboxylate Structure

tert-butyl 4-(3...

~%

4-[3-(4-methylpiperazin-1-yl)phenoxy]benzaldehyde Structure

4-[3-(4-methylp...

3-(1-Piperazinyl)phenol Structure

3-(1-Piperaziny...

~%

4-[3-(4-methylpiperazin-1-yl)phenoxy]benzaldehyde Structure

4-[3-(4-methylp...

CHEMBRDG-BB 4003414 Structure

CHEMBRDG-BB 4003414

Methanesulfonyl chloride Structure

Methanesulfonyl...

~99%

4-(4-formylphenyl)but-3-ynyl methanesulfonate Structure

4-(4-formylphen...

4-Bromobenzaldehyde Structure

4-Bromobenzaldehyde

~%

4-(4-formylphenyl)but-3-ynyl methanesulfonate Structure

4-(4-formylphen...

3-Chloro-4-hydroxybenzaldehyde Structure

3-Chloro-4-hydr...

~%

3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehyde Structure

3-chloro-4-[3-(...

methylpiperazine Structure

methylpiperazine

N/A Structure

~%

2-methoxy-4-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehyde Structure

2-methoxy-4-[3-...

4-hydroxy-o-anisaldehyde Structure

4-hydroxy-o-ani...

~%

2-methoxy-4-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehyde Structure

2-methoxy-4-[3-...

methylpiperazine Structure

methylpiperazine

4-(4-formylphenyl)but-3-ynyl methanesulfonate Structure

4-(4-formylphen...

~41%

4-[4-(4-methylpiperazin-1-yl)but-1-ynyl]benzaldehyde Structure

4-[4-(4-methylp...

CHEMBRDG-BB 4003414 Structure

CHEMBRDG-BB 4003414

~%

4-[4-(4-methylpiperazin-1-yl)but-1-ynyl]benzaldehyde Structure

4-[4-(4-methylp...

4-Bromobenzaldehyde Structure

4-Bromobenzaldehyde

~%

4-[4-(4-methylpiperazin-1-yl)but-1-ynyl]benzaldehyde Structure

4-[4-(4-methylp...

2-Chloro-4-hydroxybenzaldehyde Structure

2-Chloro-4-hydr...

~%

2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehyde Structure

2-chloro-4-[3-(...

3-Hydroxy-4-methylbenzaldehyde Structure

3-Hydroxy-4-met...

~%

4-methyl-3-[4-(4-methylpiperazin-1-yl)butoxy]benzaldehyde Structure

4-methyl-3-[4-(...

methylpiperazine Structure

methylpiperazine

3-methoxy-4-(3-chloropropoxy) benzaldehyde Structure

3-methoxy-4-(3-...

~%

3-methoxy-4-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehyde Structure

3-methoxy-4-[3-...

Vanillin Structure

~%

3-methoxy-4-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehyde Structure

3-methoxy-4-[3-...

methylpiperazine Structure

methylpiperazine

N/A Structure

~%

3,5-dimethyl-4-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehyde Structure

3,5-dimethyl-4-...

3,5-Dimethyl-4-hydroxybenzaldehyde Structure

3,5-Dimethyl-4-...

~%

3,5-dimethyl-4-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehyde Structure

3,5-dimethyl-4-...

4-[4-(4-methylpiperazin-1-yl)but-1-ynyl]benzaldehyde Structure

4-[4-(4-methylp...

~80%

4-[4-(4-methylpiperazin-1-yl)butyl]benzaldehyde Structure

4-[4-(4-methylp...

methylpiperazine Structure

methylpiperazine

~%

4-[4-(4-methylpiperazin-1-yl)butyl]benzaldehyde Structure

4-[4-(4-methylp...

CHEMBRDG-BB 4003414 Structure

CHEMBRDG-BB 4003414

~%

4-[4-(4-methylpiperazin-1-yl)butyl]benzaldehyde Structure

4-[4-(4-methylp...

4-(4-formylphenyl)but-3-ynyl methanesulfonate Structure

4-(4-formylphen...

~%

4-[4-(4-methylpiperazin-1-yl)butyl]benzaldehyde Structure

4-[4-(4-methylp...

4-Bromobenzaldehyde Structure

4-Bromobenzaldehyde

~%

4-[4-(4-methylpiperazin-1-yl)butyl]benzaldehyde Structure

4-[4-(4-methylp...