Indazole

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Indazole
Indazole 2D numbered.svg
Indazole 3D ball.png
Indazole 3D spacefill.png
Names
Preferred IUPAC name
1H-Indazole [1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.436 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C7H6N2/c1-2-4-7-6(3-1)5-8-9-7/h1-5H,(H,8,9) Yes check.svgY
    Key: BAXOFTOLAUCFNW-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C7H6N2/c1-2-4-7-6(3-1)5-8-9-7/h1-5H,(H,8,9)
    Key: BAXOFTOLAUCFNW-UHFFFAOYAQ
  • c2ccc1[nH]ncc1c2
Properties
C7H6N2
Molar mass 118.14 g/mol
Melting point 147 to 149 °C (297 to 300 °F; 420 to 422 K)
Boiling point 270 °C (518 °F; 543 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

Contents

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. [2]

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. [3]

Indazole, C7H6N2, was obtained by E. Fischer (Ann. 1883, 221, p. 280) by heating ortho-hydrazine cinnamic acid, [4]

Fischer indazole.png

Drugs made from Indazole

Benzydamine, commonly branded as Tantum Verde and Difflam, is the most well known Indazole derivative. It is a nonsteroidal anti-inflammatory, with local anaesthetic and analgesic properties for pain relief and anti-inflammatory treatment of inflammatory conditions of the mouth and throat.

Marsanidine [1034875-38-1] Marsanidine.svg
Marsanidine [1034875-38-1]

See also

References

  1. ↑ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 213. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
  2. ↑ Catalan, Javier; Elguero, Jose (1987). "Basicity and Acidity of Azoles". Advances in Heterocyclic Chemistry Volume 41. Vol. 41. Elsevier. pp. 187–274. doi:10.1016/s0065-2725(08)60162-2. ISBN   9780120206414.
  3. ↑ Zhu, Jie S.; Haddadin, Makhluf J.; Kurth, Mark J. (22 July 2019). "Davis–Beirut Reaction: Diverse Chemistries of Highly Reactive Nitroso Intermediates in Heterocycle Synthesis". Accounts of Chemical Research. 52 (8): 2256–2265. doi:10.1021/acs.accounts.9b00220. PMC   6702092 . PMID   31328502.
  4. ↑ Chisholm, Hugh, ed. (1911). "Indazoles"  . Encyclopædia Britannica . Vol. 14 (11th ed.). Cambridge University Press. p. 371.
  5. ↑ Saczewski F, Kornicka A, Rybczyńska A, Hudson AL, Miao SS, Gdaniec M, Boblewski K, Lehmann A. 1-[(Imidazolidin-2-yl)imino]indazole. Highly alpha 2/I1 selective agonist: synthesis, X-ray structure, and biological activity. J Med Chem. 2008 Jun 26;51(12):3599-608. doi: 10.1021/jm800112s. Epub 2008 Jun 3. PMID 18517187.
  6. ↑ Franciszek Saczewski, et al. WO2009071906 (to Ip2ipo Innovations Ltd, Medical University of Gdansk).
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