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Indazole

Indazole
Skeletal formula with numbering convention
Ball-and-stick model
Space-filling model
Names
Preferred IUPAC name
1H-Indazole[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.436 Edit this at Wikidata
UNII
  • InChI=1S/C7H6N2/c1-2-4-7-6(3-1)5-8-9-7/h1-5H,(H,8,9) checkY
    Key: BAXOFTOLAUCFNW-UHFFFAOYSA-N checkY
  • 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.

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]

Drugs made from Indazole

Marsanidine [1034875-38-1][5][6]

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).
  • Synthesis: Stadlbauer, W. (2002). "Product Class 2: 1H- and 2H-Indazoles". In Neier; Bellus (eds.). Category 2, Hetarenes and Related Ring Systems. Science of Synthesis. Houben-Weyl. doi:10.1055/sos-SD-012-00277. ISBN 9783131122711.
  • Review: Schmidt, Andreas; Beutler, Ariane; Snovydovych, Bohdan (2008). "Recent Advances in the Chemistry of Indazoles". European Journal of Organic Chemistry. 2008 (24): 4073–4095. doi:10.1002/ejoc.200800227.
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