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Pyrrole–imidazole polyamides (PIPs) are a class of polyamides have the ability to bind to minor grooves found in the DNA helix. [ 1 ] [ 2 ] Scientists are experimenting with it as a drug-delivery mode that can switch genes on and off, as well as epigenetic modification in gene therapy .
The substituted imidazole derivatives are valuable in treatment of many systemic fungal infections. [21] Imidazoles belong to the class of azole antifungals, which includes ketoconazole, miconazole, and clotrimazole. For comparison, another group of azoles is the triazoles, which includes fluconazole, itraconazole, and voriconazole.
Pyrrole is an extremely weak base for an amine, with a conjugate acid pK a of −3.8. The most thermodynamically stable pyrrolium cation (C 4 H 6 N +) is formed by protonation at the 2 position. Substitution of pyrrole with alkyl substituents provides a more basic molecule—for example, tetramethylpyrrole has a conjugate acid pK a of +3.7.
For example, with the benzo-fused unsaturated nitrogen heterocycles, pyrrole provides indole or isoindole depending on the orientation. The pyridine analog is quinoline or isoquinoline, and the class of analogues with two nitrogen atoms is known as the benzodiazines. For azepine, benzazepine is the preferred name.
The compound can be synthesized on a laboratory scale by methylation of imidazole at the pyridine-like nitrogen and subsequent deprotonation. [4] Similarly, 1-methylimidazole may be synthesized by first deprotonating imidazole to form a sodium salt followed by methylation. [5] [6] H 2 C 2 N(NH)CH + CH 3 I → [H 2 C 2 (NH)(NCH 3)CH]I
utilizing pyrrole, imidazole, or indole compounds in place of the pyrazole rings²; the possibility of tripodal heptadentate ligands such as N 4 O 3 from the ligand tris[6-((2-N,N-diethylcarbamoyl)pyridyl)methyl]amine³; Sulfur donor groups such as those found in the Tm ligand or oxygen donor groups. [4]
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Azoles are a class of five-membered heterocyclic compounds containing a nitrogen atom and at least one other non-carbon atom (i.e. nitrogen, sulfur, or oxygen) as part of the ring. [1] Their names originate from the Hantzsch–Widman nomenclature .