Protection of imidazoles as their β-trimethylsilylethoxymethyl (SEM) derivatives

Lipshutz, Bruce H.; Vaccaro, Wayne; Huff, Bret E.

doi:10.1016/s0040-4039(00)84919-9

Cited by 59 publications

(22 citation statements)

References 15 publications

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“…Finally, the preparation of the N -biphenylmethyl imidazole derivatives 30 and 32 is depicted in Scheme 4. Firstly, the imidazole ring was protected at the N -1 by the 2-(trimethylsilyl)ethoxymethyl (SEM) group using standard conditions [18,27,28]. Thus, treatment of the unsaturated methyl ester 6 with SEM-Cl in the presence of NaH in dry DMF, at ambient temperature for 2 h, led to 27 in 78% yield.…”

Section: Resultsmentioning

confidence: 99%

Facile and Efficient Syntheses of a Series of N-Benzyl and N-Biphenylmethyl Substituted Imidazole Derivatives Based on (E)-Urocanic acid, as Angiotensin II AT1 Receptor Blockers

et al. 2013

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Abstract:In the present work, a facile and efficient route for the synthesis of a series of N-substituted imidazole derivatives is described. Docking studies have revealed that N-substituted imidazole derivatives based on (E)-urocanic acid may be potential antihypertensive leads. Therefore, new AT1 receptor blockers bearing either the benzyl or the biphenylmethyl moiety at the N-1 or N-3 position, either the (E)-acrylate or the propanoate fragment and their related acids at the C-4 position as well as a halogen atom at the C-5 position of the imidazole ring, were synthesized. The newly synthesized analogues were evaluated for binding to human AT1 receptor. The biological results showed that this class of molecules possesses moderate or no activity, thus not always confirming high docking scores. Nonetheless, important conclusions can be derived for their molecular basis of their mode of action and help medicinal chemists to design and synthesize more potent ones. An aliphatic group as in losartan seems to be important for enhancing binding affinity and activity.

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Section: Resultsmentioning

confidence: 99%

Facile and Efficient Syntheses of a Series of N-Benzyl and N-Biphenylmethyl Substituted Imidazole Derivatives Based on (E)-Urocanic acid, as Angiotensin II AT1 Receptor Blockers

et al. 2013

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“…40 They commenced with lithiation of 1-SEM-2-phe-nylthioimidazole, which is made from imidazole in two synthetic steps, both of which require strictly anhydrous conditions. 41,42 We prepared p-methoxybenzyl isothiocyanate from p-methoxybenzylamine and thiophosgene on a large scale, based on the method of Threadgill and coworkers, 43 and added it to preformed tyrosine dianion (Scheme 4). Cyclization in sulfuric acid and acetone proceeded in low yield, but no chromatography was necessary and the reaction was amenable to the preparation of several grams of 10.…”

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confidence: 99%

Facile Conversion of Amino Acids into 1-Alkyl Imidazole-2-thiones, and Their Oxidative Desulfurization to Imidazoles with Benzoyl Peroxide

Wolfe¹,

Schreiner²

2007

Synthesis

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Glycine was acylated with isothiocyanates and condensed to 3-alkyl 2-thiohydantoins, which were reduced with a mixture of sodium borohydride and lithium chloride and dehydrated to 1-alkyl imidazole-2-thiones. These were oxidatively desulfurized to imidazoles with benzoyl peroxide. No chromatography was required for model compounds. The methods developed were used to elaborate tyrosine to 1,4-di(p-methoxybenzyl)imidazole, a common intermediate in the syntheses of three imidazoles from the sponge Leucetta.

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“…NMR assignments of isolated flavacol (5) S6. NMR assignments of isolated PZ-1 (6) S7. NMR assignments of isolated PZ-2 (7) S3.…”

Section: Supplementary Tablesmentioning

confidence: 99%

“…NMR assignments of isolated PZ-2 (7) S3. Mass spectra of isolated Leu-dPNO (1), Leu-PNO A (2), leucinazole (3), Leu-PNO B (4), flavacol (5), PZ-1 (6), and PZ-2 (7)…”

Section: Supplementary Tablesmentioning

confidence: 99%

Enzymatic Synthesis of Diverse Heterocycles by a Noncanonical Nonribosomal Peptide Synthetase

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Protection of imidazoles as their β-trimethylsilylethoxymethyl (SEM) derivatives

Cited by 59 publications

References 15 publications

Facile and Efficient Syntheses of a Series of N-Benzyl and N-Biphenylmethyl Substituted Imidazole Derivatives Based on (E)-Urocanic acid, as Angiotensin II AT1 Receptor Blockers

Facile and Efficient Syntheses of a Series of N-Benzyl and N-Biphenylmethyl Substituted Imidazole Derivatives Based on (E)-Urocanic acid, as Angiotensin II AT1 Receptor Blockers

Facile Conversion of Amino Acids into 1-Alkyl Imidazole-2-thiones, and Their Oxidative Desulfurization to Imidazoles with Benzoyl Peroxide

Enzymatic Synthesis of Diverse Heterocycles by a Noncanonical Nonribosomal Peptide Synthetase

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