1084949-58-5

Basic information

• Product Name: 3-(triphenylmethyl)-5-butylimidazole
• Synonyms: 3-(triphenylmethyl)-5-butylimidazole
• CAS NO: 1084949-58-5
• Molecular Weight: 366.506
• Mol File: 1084949-58-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3-(triphenylmethyl)-5-butylimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(triphenylmethyl)-5-butylimidazole(1084949-58-5)
• EPA Substance Registry System: 3-(triphenylmethyl)-5-butylimidazole(1084949-58-5)

Safety Data

• Hazardous Substances Data: 1084949-58-5(Hazardous Substances Data)

Upstream product

• 592-41-6 1-hexene 
• 26818-07-5 1-bromo-2-hexanone 
• 76-83-5 trityl chloride 
• 146953-86-8 4-n-Butyl-imidazole 
• 33016-47-6 (1-tritylimidazol-4-yl)carboxaldehyde 
• 1431151-50-6 (Z)-1-trityl-4-(but-1-enyl)imidazole 

Downstream Products

• 1084949-70-1 5-butyl-2-hydroxymethyl-1-[[2'-[[N-(2-chlorotrityl)]tetrazol-5-yl]biphenyl-4-yl]methyl]imidazole 
• 1084949-39-2 5-butyl-2-hydroxymethyl-1-[[2'-(2H-tetrazol-5-yl)biphenyl-4-yl]methyl]imidazole trifluoroacetic acid 
• 1084949-34-7 5-butyl-1-[[2'-(2H-tetrazol-5-yl)biphenyl-4-yl]methyl]imidazole trifluoroacetic acid 
• 1084949-66-5 5-butyl-1-[[2'-[[N-(2-chlorotrityl)]tetrazol-5-yl]biphenyl-4-yl]methyl]imidazole 
• 1295434-59-1 Br^(1-)*C₅₉H₅₁N₆⁽¹⁺⁾ 
• 1431152-53-2 4-bromo-5-butyl-N,N'-bis{[2'-(tert-butoxycarbonyl)biphenyl-4-yl]methyl}imidazolium bromide 
• 1431152-54-3 5-butyl-4-iodo-N,N'-bis{[2'-(tert-butoxycarbonyl)biphenyl-4-yl]methyl}imidazolium bromide 
• 1431152-56-5 C₃₅H₃₂BrN₁₀⁽¹⁺⁾*Br^(1-) 
• 1431152-57-6 5-butyl-4-iodo-N,N'-bis{[2'-[2H-tetrazol-5-yl]biphenyl-4-yl]methyl}imidazolium bromide 
• 1431152-59-8 5-butyl-4-chloro-N,N'-bis{[2'-carboxybiphenyl-4-yl]methyl}imidazolium bromide 
• 1431152-60-1 4-bromo-5-butyl-N,N'-bis{[2'-carboxybiphenyl-4-yl]methyl}imidazolium bromide 
• 1431152-61-2 5-butyl-4-iodo-N,N'-bis{[2'-carboxybiphenyl-4-yl]methyl}imidazolium bromide 
• 1431152-65-6 5-butyl-4-chloro-2-hydroxymethyl-N,N'-bis{[2'-(tert-butoxycarbonyl)biphenyl-4-yl]methyl}imidazolium bromide 
• 1431152-66-7 4-bromo-5-butyl-2-hydroxymethyl-N,N'-bis{[2'-(tert-butoxycarbonyl)biphenyl-4-yl]methyl}imidazolium bromide 

Relevant articles and documents

Synthesis of new 1,4- and 1,5-disubstituted N-ethyl acetate and N-α-butyro-γ-lactone alkylimidazole derivatives as N-acylhomoserine lactone analogs

New alkylimidazoles functionalized with a homoserine lactone or an alkyloxycarbonyl moiety have been synthesized as N-acylhomoserine lactones (AHLs) analogs. The 1,4-disubstituted imidazole derivatives were prepared by alkylation of 4(5)-alkylimidazoles with α-bromo-γ-butyrolactone or ethyl α-bromoacetate. An alternative route was preferred for the synthesis of their 1,5-disubstituted counterparts based on the use of a N1-protected alkylimidazole, its alkylation to an N3-imidazolyl-α-acetate and deprotection to the desired 1,5-disubstituted esters and subsequent alkylation of the acetate moiety with cyclic ethylene sulfate followed by acid-catalyzed cyclization. The ability to modulate bacterial quorum sensing of all new compounds was compared to that of previously reported AHL analogs in which the amide bond is replaced by a heterocyclic group.

Rational design, efficient syntheses and biological evaluation of N,N'-symmetrically bis-substituted butylimidazole analogs as a new class of potent Angiotensin II receptor blockers

A series of symmetrically bis-substituted imidazole analogs bearing at the N-1 and N-3 two biphenyl moieties ortho substituted either with tetrazole or carboxylate functional groups was designed based on docking studies and utilizing for the first time an extra hydrophobic binding cleft of AT1 receptor. The synthesized analogs were evaluated for their in vitro antagonistic activities (pA2 values) and binding affinities (-logIC50 values) to the Angiotensin II AT1 receptor. Among them, the potassium (-logIC50 = 9.04) and the sodium (-logIC50 = 8.54) salts of 4-butyl-N,N'-bis{[2′-(2H-tetrazol-5-yl)biphenyl-4-yl]methyl}imidazolium bromide (12a and 12b, respectively) as well as its free acid 11 (-logIC 50 = 9.46) and the 4-butyl-2-hydroxymethyl-N,N'-bis{[2′-(2H- tetrazol-5-yl)biphenyl-4-yl]methyl}imidazolium bromide (14) (-logIC50 = 8.37, pA2 = 8.58) showed high binding affinity to the AT1 receptor and high antagonistic activity (potency). The potency was similar or even superior to that of Losartan (-logIC50 = 8.25, pA2 = 8.25). On the contrary, 2-butyl-N,N'-bis{[2′-[2H-tetrazol-5-yl)]biphenyl- 4-yl]methyl}imidazolium bromide (27) (-logIC50 = 5.77) and 2-butyl-4-chloro-5-hydroxymethyl-N,N'-bis{[2′-[2H-tetrazol-5-yl)] biphenyl-4-yl]methyl}imidazolium bromide (30) (-logIC50 = 6.38) displayed very low binding affinity indicating that the orientation of the n-butyl group is of primary importance. Docking studies of the representative highly active 12b clearly showed that this molecule has an extra hydrophobic binding feature compared to prototype drug Losartan and it fits to the extra hydrophobic cavity. These results may contribute to the discovery and development of a new class of biologically active molecules through bis-alkylation of the imidazole ring by a convenient and cost effective synthetic strategy.

1,(3,)5-SUBSTITUTED IMIDAZOLES, THEIR USE IN THE TREATMENT OF HYPERTENSION AND METHODS FOR THEIR PREPARATION

The present invention provides novel 1,5 and 1,3,5-substituted imidazole compounds in hydrophilic or lipophilic form, which are useful as angiotensin II ATI receptor antagonists suitable for transdermal delivery. The invention also provides pharmaceutical compositions containing such compounds, processes and intermediates for preparing compounds and their use in methods of treating hypertension and cardiovascular diseases.