Studies on Imidazole Compounds. I. 4-Methylimidazole and Related Compounds

Turner, Robert A.; Huebner, Charles F.; Scholz, Caesar R.

doi:10.1021/ja01176a059

Cited by 65 publications

(16 citation statements)

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“…used the route outlined in Scheme 3 to synthesize α-substituted histidines. 4-Chloromethylimidazole hydrochloride 8 [ 18 ], was added to a solution of an appropriate 2-alkyl acetoacetate 9a – d , f or 2-acetylbutyrolactone 9e in ethanol solution containing sodium ethoxide to afford the 2-alkyl 2-(4-imidazolylmethyl)acetoacetate 10 . When the keto ester 10 was allowed to react with a slight excess of hydrazoic acid in sulfuric acid solution, the N -acetylhistidine esters 11a – e were obtained in 50–70% yields.…”

Section: Chemistrymentioning

confidence: 99%

Conformationally Constrained Histidines in the Design of Peptidomimetics: Strategies for the χ-Space Control

Stefanucci

Pinnen

Feliciani

et al. 2011

IJMS

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A successful design of peptidomimetics must come to terms with χ-space control. The incorporation of χ-space constrained amino acids into bioactive peptides renders the χ1 and χ2 torsional angles of pharmacophore amino acids critical for activity and selectivity as with other relevant structural features of the template. This review describes histidine analogues characterized by replacement of native α and/or β-hydrogen atoms with alkyl substituents as well as analogues with α, β-didehydro unsaturation or Cα-Cβ cyclopropane insertion (ACC derivatives). Attention is also dedicated to the relevant field of β-aminoacid chemistry by describing the synthesis of β2- and β3-models (β-hHis). Structural modifications leading to cyclic imino derivatives such as spinacine, aza-histidine and analogues with shortening or elongation of the native side chain (nor-histidine and homo-histidine, respectively) are also described. Examples of the use of the described analogues to replace native histidine in bioactive peptides are also given.

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Section: Chemistrymentioning

confidence: 99%

Conformationally Constrained Histidines in the Design of Peptidomimetics: Strategies for the χ-Space Control

Stefanucci

Pinnen

Feliciani

et al. 2011

IJMS

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“…4-Aminomethylimidazole dihydrochloride (7) was prepared according to the literature. [33] Flash chromatography was performed on silica gel (230-400 mesh) from Silicycle. Thinlayer chromatography (TLC) and preparatory TLC were performed on precoated glass-backed plates of silica gel 60 F 254 from EMD Chemicals.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Enzymatic Incorporation of Modified Deoxyadenosine Triphosphates

2008

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Several deoxyadenosine triphosphates containing modifications at the 8-position have been synthesized. Suitably protected 8-bromodeoxyadenosines were coupled with five imidazole-containing moieties by nucleophilic aromatic substitution or Sonagashira coupling to give modified nucleosides that were then triphosphorylated. Incorporation assays were performed for these modified residues with many com-

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“…where m is about 1400-Laurylated poly(ethy1enimine) with imidazole groups was prepared by the following method. To a solution of 1.50 g of the laurylated polymer in 50 ml absolute ethanol was added 0.80 g 4-(chloromethy1)-imidazole hydrochloride, which had been prepared from 4-( hydroxymethy1)-imidaole hydrochloride according to the procedure of Turner et al 9 This was followed by 0.08 g sodium iodide and 18 ml diisopropylethylamine. The reaction mixture was refluxed under nitrogen for 7 days.…”

Section: Polymer Preparationsmentioning

confidence: 99%

Effects of metal ions on the hydrolysis of p‐nitrophenyl caproate by modified poly(ethylenimine)s

Takagishi

Klotz

1979

Biopolymers

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SynopsisHydrolysis of nitrophenyl caproate by modified poly(ethy1enimine)s containing imidazole moieties is markedly enhanced in the presence of divalent metal ions. The order of effec-, with Cu increasing the rate about 20-fold. The acceleration by the metal ion is much greater in the presence of CH3COO-or C1-as counterions than in the presence of Clod-. Turnover experiments, in which moles of substrate cleaved were in substantial excess of moles of metal present, established the catalytic nature of the effects of the metals. The extent of binding of Cu(I1) by the polymers was measured. Maximum accentuation in rate of hydrolysis of nitrophenyl ester was observed for the imidazole-containing polymer when the ratio of imidazole:Cu(II) was 2.75. Some possible mechanisms for the rate enhancement by metal ions are described.

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Studies on Imidazole Compounds. I. 4-Methylimidazole and Related Compounds

Cited by 65 publications

References 0 publications

Conformationally Constrained Histidines in the Design of Peptidomimetics: Strategies for the χ-Space Control

Conformationally Constrained Histidines in the Design of Peptidomimetics: Strategies for the χ-Space Control

Synthesis and Enzymatic Incorporation of Modified Deoxyadenosine Triphosphates

Effects of metal ions on the hydrolysis of p‐nitrophenyl caproate by modified poly(ethylenimine)s

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