(6-Chloro-1H-benzoimidazol-2-yl)-(4-methyl-piperazin-1-yl)-methanone

Product Name(6-Chloro-1H-benzoimidazol-2-yl)-(4-methyl-piperazin-1-yl)-methanone
CAS73903-17-0
MFC13H15ClN4O
MW278.74
EINECS
MOL File73903-17-0.mol

Chemical Properties

form	Solid
color	White to off-white

Usage And Synthesis

Uses

JNJ10191584 (VUF6002) is an orally active and selective histamine H4 receptor antagonist with a Ki value of 26 nM. JNJ10191584 shows 540-fold selectivity to H4 receptor over H3 receptor with a Ki value of 14.1 μM. JNJ10191584 inhibits chemotaxis of eosinophils and mast cells with IC50 values of 530 nM and 138 nM, respectively[1][2].

Definition

ChEBI: (6-chloro-1H-benzimidazol-2-yl)-(4-methyl-1-piperazinyl)methanone is a member of benzimidazoles.

in vivo

JNJ10191584 (10 μg/μL; intra locus coeruleus (LC) administration; once) abolishs VUF-induced anti-allodynic effect in spared nerve injury (SNI) mice^[1]. JNJ10191584 (10 μg/μL; intra LC administration; once) prevents the anti-allodynic effect of VUF 8430 in SNI mice^[1]. JNJ10191584 (6 μg/mouse; intrathecal administration; pretreat once) prevents VUF 8430-induced anti-allodynic effect in SNI mice^[1].

IC 50

Human H₄ Receptor: 26 nM (Ki); human H₃ receptor: 14.1 μM (Ki)

References

[1] Venable JD, et al. Preparation and biological evaluation of indole, benzimidazole, and thienopyrrole piperazine carboxamides: potent human histamine h(4) antagonists. J Med Chem. 2005 Dec 29;48(26):8289-98. DOI:10.1021/jm0502081
[2] Sanna MD, et al. Histamine H4 receptor stimulation in the locus coeruleus attenuates neuropathic pain by promoting the coeruleospinal noradrenergic inhibitory pathway. Eur J Pharmacol. 2020 Feb 5;868:172859. DOI:10.1016/j.ejphar.2019.172859