1- -lH-imidazole

In 2004, Alterman et al. used a microwave-assisted Ullmann-type protocol for the synthesis of N-(f-butyl)-3-[4-(lH-imidazol-l-yl)benzyl]-5-isobutylthiophene-2-sulfonamide (Scheme 106) [61]. Deprotection of the sulfonamide followed by carbamate formation via reaction with butyl chloro-formate finally gave the target compound for biological evaluation as selective angiotensin II AT2 receptor agonist. The IH-imidazole derivative, however, showed only a low affinity for the AT2 receptor (Ki value > 10 p,M). 

Kitbunnadaj R, Zuiderveld OP, Christophe B,etal. Identification of 4-(lH-imidazol-4(5)-ylmethyl) pyridine (immethridine) as a novel, potent, and highly selective histamine H(3) receptor agonist. fMed Chem 2004 47 2414-17. 

The classical histamine H3 antagonist thioperamide has been labelled and evaluated as radioligand for the H3 receptor by Alves-Rodrigues et al [27], [3H]thioperamide was synthesised from [3H]4-(lH-imidazol-4-yl)piperidine, labelled with tritium in the 2 or 5 position of the imidazole and at the 4 position of the piperidine, and cyclohexylisothiocyanate (scheme 10) [28], It was purified with a semipreparative HPLC method and isolated with a specific activity of 6 Ci/mmol. 

J. A. Bristol, I. Sircar, W. H. Moos, D. B. Evans, and R. E. Weishaar, /. Med. Chem., 27, 1099 (1984). Cardiotonic Agents. 1. 4,5-Dihydro-6-[4-(lH-imidazol-l-yl)phenyl]-3(2H)-pyri-dazines Novel Positive Inotropic Agents for the Treatment of Congestive Heart Failure. 

A nanorod morphology of ZnO has been obtained by calcination of [Zn(3-bpdh) (NO ) [114], [Zn(p-3-bpdh)(N02)J [115],and [Zn(4,4 -bipy)ClJ [116] compounds 3-bpdh = 2,5-bis(3-pyridyl)-3,4-diaza-2,4-hexadiene 4,4 -bipy = 4,4-bipyridine). Moreover, the calcination of 2D MOCP, [Zn(ox)(4,4 -bipy)] ox=Cfi ) produces ZnO radial nanoneedles [1171. Thermal decomposition of 3D MOCP [Zn(L2)] H2L2 = 4-[(lH-imidazol-4-yl)methylaminolbenzoic acid) at different temperatures shows that an increase in the thermolysis temperature influences the morphology of the derived oxides and changes it from spheres into nanorods [1181. 

Scheme Schematic representation of 4-(lH-imidazole-l-yl)benzoic acid (HIBA). (Reproduced with permission from Ref 24. Copyright 2009 American Chemical Society.)...

Chemical Name 1-(2-[(4-chlorophenyl)methoxy] -2-(2,4-dichlorophenyl)ethyl)-lH-imidazole nitrate... 

PREPARATION OF 2,4-DISUBSTITUTED IMIDAZOLES 4-(4-METHOXYPHENYL)-2-PHENYL-lH-IMID AZOLE... 

Methoxyphenyl)-2-phenyl-lH-imidazole. A 2-L, three-necked, round-bottomed flask equipped with an addition funnel, reflux condenser, and mechanical stirrer is charged with 500 mL of tetrahydrofuran (THF) and 125 mL of water. Benzamidine hydrochloride monohydrate (50 g, 0.29 mol) (Note 1) is added, followed by the slow, portionwise addition of potassium bicarbonate (54.4 g, 0.57 mol) (Note 2). The reaction mixture is vigorously heated to reflux. A solution of 4-methoxyphenacyl bromide (65.3 g, 0.29 mol) in 325 mL of THF is then added dropwise via the addition funnel over a period of 30 min while the reaction is maintained at reflux. After completion of the addition, the mixture is heated at reflux for 18-20 hr (Note 3), then cooled in an ice bath (Note 4), and THF is removed under reduced pressure using a rotary evaporator. An additional 100 mL of water is added, and the resulting suspension is stirred at 50-60°C for 30 min. The mixture is cooled in an ice bath and the solids are collected by filtration. The filter cake is rinsed with two 100-mL portions of water and air-dried in the filter funnel for 2 hr. The crude product is transferred to a 500-mL flask and 150 mL of diisopropyl ether and 150 mL of hexanes are added. The mixture is stirred for 2 hr at room temperature, and the solids are again collected by filtration. The filter cake is dried in a vacuum oven for 48 hr (68°C/ca. 100 mm) to give 68.6 g (96%) of the desired imidazole as an off-white solid (Notes 5, 6). 

Methoxyphenyl)-2-phenyl-1 H-imidazole lH-Imidazole, 4-(methoxyphenyl)- 2- phenyl- (53458-08-5)... 

C5H5N3 98873-55-3) see Lanoconazole A -cyano-Ai -[2-([(5-methyl-lH-imidazol-4-yl)mcthylJ-thio]ethyl]carbamimidothioic acid methyl ester (C, H 5N5S2 52378-40-2) see Cimetidine... 

The structure of a second polymorph of 4,5-diphenyl- lH-imidazole has been discussed, with the new form exhibiting significantly different phenyl/imidazole dihedral angles and mode of crystal packing relative to the known form [53], A new triclinic polymorph of 1,4-dibenzoyl-butane was found, differing from the monoclinic form in the torsional angles of the central chain [54], Two polymorphs of diphenyl-(4-pyridyl)methyl methacrylate have been found, where the molecules in the two forms contain weak C—H— n and C—H O/N contacts that lead to the existence of different conformations [55]. 

The construction of a custom-built parallel reactor with expandable reaction vessels that accommodate the pressure build-up during a microwave irradiation experiment has also been reported [88]. The system was used for the parallel synthesis of a 24-member library of substituted 4-sulfanyl-lH-imidazoles [88]. 

A different multicomponent route to imidazoles has been described by the group of O Shea, involving the diversity-tolerant three-component condensation of an aldehyde, a 2-oxo-thioacetamide, and an alkyl bromide (5 equivalents) in the presence of ammonium acetate (Scheme 6.201) [364]. This allowed the preparation of a 24-membered 4(5)-alkylthio-lH-imidazole demonstration library from 21 different aldehydes, 12 alkyl bromides, and two 2-oxo-thioacetamides. The library was synthesized in a parallel format using a custom-built reaction vessel. Alkylthioimidazoles... 

Fig. 20. Chelating ligands lH-imidazole-4,5-dicarboxylate (L2 ) and the N-protonated form lH-imidazol-3-ium-4,5-dicarboxylate (LH ) (177).

Since Plieger et al. (171) were able to obtain a crystal structure for [Be(H20)2( 1-methyl-lH-imidazol-3-ium-4,5-dicarboxylate)]+, we compared the calculated and measured bond lengths and found satisfactory agreement between experimental and calculated structures. However, there is a clear influence of the strong hydrogen-bonding network in the X-ray structure. 

Figure 6 Representative (A) phenol-type and (B) phenylboronic acid-type enhancers for luminol/hydrogen peroxide/peroxidase system. KIH-201, 2-(4 -hydroxy-3 -methoxy-benzylidene)-4-cyclopentene-1,3-dione HDI, 2-(4-hydroxyphenyl)-4,5-diphenylimida-zole HPI, 2-(4-hydroxyphenyl)-4,5-di(2-pyridyl)imidazole DPPA, 4-[4,5-di(2-pyridyl)-lH-imidazol-2-yl]phenylboronic acid).

Urocanic acid (2-propanoic acid 3-[lH-imidazol-4-yl] is located superficially in the stratum comeum. Metabolism of epidermal UCA does not occur in situ due to the absence of urocanase, resulting in the accumulation of UCA in the epidermis. Upon UV exposure, naturally occurring trans-UCA converts to the d.s-isomer, in a dose dependent manner, until the photostationary state is reached, when equal quantities of trans- and m-UCA are found in the skin.15 Based on an analysis of the action spectrum for UV-induced immune suppression, and the fact that no immune suppression was observed in mice whose stratum comeum was previously removed by tape stripping, De Fabo and Noonan suggested that urocanic acid was the photoreceptor for UV-induced immune suppression.16 Since the initial experiments many others have documented, the ability of ris-UCA to initiate immune suppression, documented its presence in the serum of UV-irradiated mice, and demonstrated that m-UCA plays a role in UV-induced skin cancer induction. (For a more complete review of the role of m-UCA in immune suppression see two excellent reviews by Norval and colleagues.1718)... 

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