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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 .
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.
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.
Naphthoylpyrroles: Any compound containing a 3-(1-naphthoyl)pyrrole structure with substitution at the nitrogen atom of the pyrrole ring by an alkyl, haloalkyl, alkenyl, cycloalkylmethyl, cycloalkylethyl, 1-(N-methyl-2-piperidinyl)methyl, or 2-(4-morpholinyl)ethyl group whether or not further substituted in the pyrrole ring to any extent and ...
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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.
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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