Indazole-3-carboxylic Acid on:
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Indazole, also called isoindazole, is a 
heterocyclic
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...
aromatic
In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
. This bicyclic
In chemistry, a bicyclic molecule () is a molecule that features two joined rings. Bicyclic structures occur widely, for example in many biologically important molecules like α-thujene and camphor. A bicyclic compound can be carbocyclic (all o ...
compound consists of the fusion of benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
and pyrazole
Pyrazole is an organic compound with the formula C3H3N2H. It is a heterocycle characterized by a 5-membered ring of three carbon
Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent
...
.
Indazole is an amphoteric
In chemistry, an amphoteric compound () is a molecule or ion that can react both as an acid and as a base. What exactly this can mean depends on which definitions of acids and bases are being used.
One type of amphoteric species are amphiproti ...
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.
Indazole derivatives display a broad variety of biological activities.
Indazoles are rare in nature. The alkaloid
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...
s nigellicine, nigeglanine, and nigellidine are indazoles. Nigellicine was isolated from the widely distributed plant ''Nigella sativa
''Nigella sativa'' (black caraway, also known as black cumin, nigella, kalonji or siyahdaneh) is an annual flowering plant in the family Ranunculaceae, native to eastern Europe (Bulgaria and Romania) and Western Asia (Cyprus, Turkey, Iran and Ir ...
'' L. (black cumin). Nigeglanine was isolated from extracts of ''Nigella glandulifera
''Nigella'' is a genus of 18 species of annual plants in the family Ranunculaceae, native to Southern Europe, North Africa, South Asia, Southwest Asia and Middle East. Common names applied to members of this genus are nigella, devil-in-a-bush o ...
''.
The Davis–Beirut reaction
The Davis–Beirut reaction is ''N,N''-bond forming heterocyclization that creates numerous types of 2''H''-indazoles and indazolones in both acidic and basic conditions
The Davis–Beirut reaction is named after Mark Kurth and Makhluf Haddadin ...
can generate 2''H''-indazoles.
Indazole, C7H6N2, was obtained by E. Fischer (''Ann.'' 1883, 221,
p. 280) by heating ortho-hydrazine cinnamic acid,
:
Some derivatives
; indazole-3-carboxylic acid: Having acarboxylic acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...
group on carbon 3. Can be further modified to lonidamine
Lonidamine is a derivative of indazole-3-carboxylic acid, which for a long time, has been known to inhibit aerobic glycolysis in cancer cells. It seems to enhance aerobic glycolysis in normal cells, but suppress glycolysis in cancer cells. This is ...
.
See also
*Indole
Indole is an aromatic heterocyclic organic compound with the formula C8 H7 N. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indole is widely distributed in the natural environmen ...
, an analog with only one nitrogen
Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...
atom
Every atom is composed of a nucleus and one or more electrons bound to the nucleus. The nucleus is made of one or more protons and a number of neutrons. Only the most common variety of hydrogen has no neutrons.
Every solid, liquid, gas, and ...
in position 1.
* Benzimidazole
Benzimidazole is a heterocyclic aromatic organic compound. This bicyclic compound may be viewed as fused rings of the aromatic compounds benzene and imidazole. It is a colorless solid.
Preparation
Benzimidazole is produced by condensation of o- ...
, an analog with the nitrogen atoms in positions 1 and 3.
* Simple aromatic ring
Simple aromatic rings, also known as simple arenes or simple aromatics, are aromatic organic compounds that consist only of a conjugated planar ring system. Many simple aromatic rings have trivial names. They are usually found as substructures of ...
s
* 7-Nitroindazole
7-Nitroindazole, or 7-NI, is a heterocyclic small molecule containing an indazole ring that has been nitrated at the 7 position. Nitroindazole acts as a selective inhibitor for neuronal nitric oxide synthase, a hemoprotein enzyme that, in neuron ...
, an indazole-based nitric oxide synthase
Nitric oxide synthases () (NOSs) are a family of enzymes catalyzing the production of nitric oxide (NO) from L-arginine. NO is an important cellular signaling molecule. It helps modulate vascular tone, insulin secretion, airway tone, and perista ...
inhibitor
References
* Synthesis: W. Stadlbauer, in ''Science of Synthesis'' 2002, ''12'', 227, and W. Stadlbauer, in ''Houben-Weyl'', 1994, ''E8b'', 764. * Review: A. Schmidt, A. Beutler, B. Snovydovych, ''Recent Advances in the Chemistry of Indazoles'', ''Eur. J. Org. Chem.'' 2008, 4073 – 4095. {{Nitric oxide signaling Simple aromatic rings