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Indazole

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From Wikipedia, the free encyclopedia

Indazole

Skeletal formula with numbering convention

Names

Preferred IUPAC name

1H-Indazole^[1]

Identifiers

CAS Number

271-44-3^Y

3D model (JSmol)

Interactive image

ChEBI

CHEBI:36670^Y

ChEMBL

ChEMBL86795^Y

ChemSpider

8866^Y

ECHA InfoCard

100.005.436

PubChem CID

9221

UNII

7C4VQE5C03^Y

CompTox Dashboard(EPA)

DTXSID4075374

InChI

InChI=1S/C7H6N2/c1-2-4-7-6(3-1)5-8-9-7/h1-5H,(H,8,9)^Y
Key: BAXOFTOLAUCFNW-UHFFFAOYSA-N^Y
InChI=1/C7H6N2/c1-2-4-7-6(3-1)5-8-9-7/h1-5H,(H,8,9)
Key: BAXOFTOLAUCFNW-UHFFFAOYAQ

SMILES

c2ccc1[nH]ncc1c2

Properties

Chemical formula

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 theirstandard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

Indazole, also called isoindazole, is aheterocyclic aromatic organic compound. Thisbicyclic compound consists of the fusion ofbenzene andpyrazole.

Indazole is anamphoteric molecule which can be protonated to an indazolium cation or deprotonated to an indazolate anion. The correspondingpKa 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. Thealkaloids nigellicine,nigeglanine, andnigellidine are indazoles. Nigellicine was isolated from the widely distributed plantNigella sativa L. (black cumin). Nigeglanine was isolated from extracts ofNigella glandulifera.

TheDavis–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

[edit]

Benzydamine, commonly branded as Tantum Verde and Difflam, is the most well known Indazole derivative. It is anonsteroidal anti-inflammatory, with localanaesthetic andanalgesic properties forpain relief andanti-inflammatory treatment ofinflammatory conditions of themouth andthroat.

References

[edit]

^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.
^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.
^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.
^Chisholm, Hugh, ed. (1911)."Indazoles" .Encyclopædia Britannica. Vol. 14 (11th ed.). Cambridge University Press. p. 371.
^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.
^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.

Simple aromatic rings

1 ring

Three-membered	Borirene Cyclopropenone
Five-membered	Furan Pyrrole Imidazole Thiophene Phosphole Pyrazole Oxazole Isoxazole Thiazole Isothiazole Triazole Tetrazole Pentazole
Six-membered	Benzene Pyridine Pyrazine Pyrimidine Pyridazine Triazine Tetrazine Pentazine Hexazine
Seven-membered	Borepin Tropone
Nine-membered	Azonine
18-membered	Cyclooctadecanonaene

2 rings

Five + Five	Diazapentalene Thienothiophene Trithiapentalene
Five + Six	Benzofuran Isobenzofuran Indole Isoindole Benzothiophene Benzo(c)thiophene Benzophosphole Benzimidazole Purine Indazole Benzoxazole Benzisoxazole Benzothiazole 5-Aza-7-deazapurine
Six + Six	Naphthalene Quinoline Isoquinoline Quinoxaline Quinazoline Cinnoline Phthalazine
Five + Seven	Azulene

Nitric oxide signaling modulators

Forms

Targets

sGC	Activators/stimulators:Ataciguat BAY 41-2272 BAY 41-8543 BAY 60-4552 BI-703704 Cinaciguat (BAY 58-2667) GSK-2181236A Praliciguat Riociguat Vericiguat Inhibitors:ODQ

NO donors
(prodrugs)

Nitrosyl compounds:Metal nitrosyl complexes:Roussin's black salt
Roussin's red salt
Sodium nitroprusside (SNP)

NONOates (diazeniumdiolates):Diethylamine/NO (DEA/NO)
Diethylenetriamine/NO (DETA/NO)
GLO/NO
JS-K
Methylamine hexamethylene methylamine/NO (MAHMA/NO)
PROLI/NO
Spermine/NO (SPER/NO)
V-PYRRO/NO

Heterocyclic compounds:Furoxans:Furoxan
REC15/2739;Sydnonimines:Feprosidnine
Linsidomine (SIN-1)
Molsidomine (SIN-10)
Sydnonimine

Unsorted:Cimlanod
FK-409
FR144220
FR146881
N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide

Enzyme
(inhibitors)

NOS

nNOS	3-Bromo-7-nitroindazole 3-Chloroindazole 3-Chloro-5-nitroindazole 5-Nitroindazole 6-Nitroindazole 7-Nitroindazole A-84643 Aminoguanidine (pimagedine) ARL-17477 Indazole N⁵-(1-Iminoethyl)-L-ornithine (L-NIO) N^ω-Methyl-L-arginine (L-NMA) N^ω-Propyl-L-arginine (L-NPA) Nitroarginine (NNA, NOARG) Pentamidine isethionate TRIM
iNOS	1-Amino-2-hydroxyguanidine 2-Ethylaminoguanidine 2-Iminopiperidine 1400W AEITU Aminoguanidine (pimagedine) AMT AR-C 102222 BYK-191023 Canavanine Cindunistat (SD-6010) EITU IPTU MITU N⁵-(1-Iminoethyl)-L-ornithine (L-NIO) N⁶-(1-Iminoethyl)-L-lysine (L-NIL) N^ω-Methyl-L-arginine (L-NMA) Ronopterin (VAS-203) TRIM
eNOS	Aminoguanidine (pimagedine) N⁵-(1-Iminoethyl)-L-ornithine (L-NIO) N^ω-Methyl-L-arginine (L-NMA) Nitroarginine (NNA, NOARG)
Unsorted	Asymmetric dimethylarginine (ADMA) CKD-712 Guanidinoethyldisulfide (GED) GW-273629 Indospicine KD-7040 Nitroarginine methyl ester (NAME) NCX-456 NXN-462 ONO-1714 VAS-2381

Arginase

CAMK

Others

Precursors:L-Arginine
N^ω-Hydroxy-L-arginine (NOHA)

Indirect/downstream NO modulators:ACE inhibitors/AT-II receptor antagonists (e.g.,captopril,losartan)
ET_B receptor antagonists (e.g.,bosentan)
L-Type calcium channel blockers (e.g.,dihydropyridines:nifedipine)
Nebivolol (beta blocker)
PDE5 inhibitors (e.g.,sildenafil)
non-selective PDE inhibitors (e.g.,caffeine)
PDE9 inhibitors (e.g.,paraxanthine)
cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)
Statins (e.g.,simvastatin)

See also:Receptor/signaling modulators

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