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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 .
Imidazole is a planar 5-membered ring, that exists in two equivalent tautomeric forms because hydrogen can be bound to one or another nitrogen atom. Imidazole is a highly polar compound, as evidenced by its electric dipole moment of 3.67 D, [12] and is highly soluble in water.
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
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.
Imidazole and other five-membered aromatic heterocyclic systems with two nitrogens are extremely common in nature and form the core of many biomolecules, such as histidine. Compound classes [ edit ]
The most important of these small molecules are pyrrole–imidazole polyamides. [3] Dervan is credited with influencing "the course of research in organic chemistry through his studies at the interface of chemistry and biology" as a result of his work on "the chemical principles involved in sequence-specific recognition of double helical DNA". [4]
Imidazo[1,2-a]pyridine—an example of imidazopyridine and a core structure of zolpidem and some compounds described below.. An imidazopyridine is a nitrogen containing heterocycle that is also a class of drugs that contain this same chemical substructure.