Английская Википедия:Indazole

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Indazole, also called isoindazole, is a heterocyclic aromatic organic compound. This bicyclic compound consists of the fusion of benzene and pyrazole.

Indazole is an amphoteric molecule which can be protonated to an indazolium cation or deprotonated to an indazolate anion. The corresponding pKa values are 1.04 for the equilibrium between indazolium cation and indazole and 13.86 for the equilibrium between indazole and indazolate anion.[1]

Indazole derivatives display a broad variety of biological activities.

Indazoles are rare in nature. The alkaloids nigellicine, nigeglanine, and nigellidine are indazoles. Nigellicine was isolated from the widely distributed plant Nigella sativa L. (black cumin). Nigeglanine was isolated from extracts of Nigella glandulifera.

The Davis–Beirut reaction can generate 2H-indazoles.

Indazole, C7H6N2, was obtained by E. Fischer (Ann. 1883, 221, p. 280) by heating ortho-hydrazine cinnamic acid,[2]

Файл:Fischer indazole.png

Some derivatives

indazole-3-carboxylic acid
Having a carboxylic acid group on carbon 3. Can be further modified to lonidamine.

See also

References

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Шаблон:Simple aromatic rings Шаблон:Nitric oxide signaling