195053-83-9

Upstream product

• 1192560-20-5 2-(4-(1H-imidazol-4-yl)butyl)isoindoline-1,3-dione 
• 76-83-5 trityl chloride 
• 195053-82-8 2-[4-(1-trityl-1H-imidazol-4-yl)butyl]isoindoline-1,3-dione 

Downstream Products

• 405551-79-3 3-(4-chloro-phenyl)-3-pyridin-2-yl-N-[4-(1-trityl-1H-imidazol-4-yl)-butyl]-propionamide 
• 405551-87-3 1-[3-(4-chloro-phenyl)-3-pyridin-2-yl-propyl]-3-[4-(1-trityl-1H-imidazol-4-yl)-butyl]-urea 

Relevant academic research and scientific papers

UR-DEBa242: A Py-5-Labeled Fluorescent Multipurpose Probe for Investigations on the Histamine H3 and H4 Receptors

Comprehensively characterized fluorescent probes for the histamine H3 receptor (H3R) and especially for the H4R orthologs [e.g., human (h) and mouse (m)] are highly needed as versatile complementary tools to radioligands. In view of fluorescent probes for BRET-based binding studies and for localizing the H4R in live cells, we synthesized and biologically characterized Py-5-labeled histamine derivatives. The most notable compound was UR-DEBa242 (26, 1-[4-(1H-Imidazol-4-yl)butyl]-4-{(1E,3E)-4-[4-(dimethylamino)phenyl]buta-1,3-dienyl}-2,6-dimethylpyridinium hydrotrifluoroacetate trifluoroacetate), acting as a partial agonist at the hH3R [pEC50 (reporter gene) 8.77] and as an inverse agonist/antagonist at the h/mH4Rs [pIC50 (reporter gene) 8.76/7.08; pIC50/pKb (β-arrestin2) 7.81/7.30]. In confocal microscopy, 26 proved suitable for hH4R localization and trafficking studies in live cells. BRET-based binding at the NLuc-hH3,4Rs/mH4R [pKd 8.78/7.75/7.18, comparable to binding constants from radioligand binding/flow cytometry; fast association/dissociation (a?2 min)] revealed 26 as a useful molecular tool to determine hH3,4Rs/mH4R binding affinities of ligands binding to these receptors.

Sulfonamides and sulfamides as H3 receptor antagonists

PCT No. PCT/GB97/00358 Sec. 371 Date Oct. 6, 1998 Sec. 102(e) Date Oct. 6, 1998 PCT Filed Feb. 10, 1997 PCT Pub. No. WO97/29092 PCT Pub. Date Aug. 14, 1997Compounds of formula (I) or (II) wherein R1 is C4 to C20 hydrocarbyl (in which one or more hydrogen atoms may be replaced by halogen, and up to three carbon atoms may be replaced by oxygen, nitrogen or sulphur atoms, provided that R1 does not contain an -O-O- group), R2 is H or C1 to C3 alkyl, m is from 1 to 15, n is from 2 to 6, each X group is independently (a), or one X group is -N(R4)-, -O- or -S- and the remaining X groups are independently (a), wherein R3 is H, C1 to C6 alkyl, -CO2R5, -CONR52, -CR52OR6 or -OR5 (in which R5 and R6 are H or C1 to C3 alkyl), and R4 is H or C1 to C6 alkyl, each Y group is independently -C(R3)R4-, or up to two Y groups are -N(R4)-, -O- or -S- and the remaining Y groups are independently -C(R3)R4-, wherein R3 is as defined above, one R4 group in the structure is imidazoyl or imidazoylalkyl and the remaining R4 groups are H or C1 to C6 alkyl, and Z is >C(R7)NR2- or >N-, wherein R7 is any of the groups recited above for R3, and pharmaceutically acceptable salts thereof are ligands at histamine H3 receptors.

Novel H3 receptor antagonists. Sulfonamide homologs of histamine.

Sulfonamides derived from 4(5)-(omega-aminoalkyl)-1H-imidazoles containing chain lengths of three- to five-carbons were synthesized. Good to moderate H3 receptor binding affinities were observed for several butyl and pentyl homologs, whereas binding affinities were considerably weaker in the propyl series. Separation of the imidazole ring and the sulfonamide unit by a four- or five-carbon tether afforded potent H3 receptor antagonists.