Sydnone imine is a
mesoionic
In chemistry, mesoionic compounds are one in which a heterocyclic structure is dipolar and where both the negative and the positive charges are delocalized. A completely uncharged structure cannot be written and mesoionic compounds cannot be repre ...
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 ...
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
. Sydnone imine is the
imine
In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bo ...
of
sydnone where the keto
functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...
of sydnone (=O) has been replaced with an imine (=NH) group.
A sydnone imine substructure can be found in the drugs
feprosidnine,
mesocarb
Mesocarb (brand names Sidnocarb, Sydnocarb) is a drug that is currently being developed for Parkinson's disease.
The drug was originally developed in the USSR in the 1970s for a variety of indications including asthenia, apathy, adynamia and ...
,
molsidomine
Molsidomine (trade names Corvasal, Corvaton and many others) is an orally active, long acting vasodilating drug used to treat angina pectoris. Molsidomine is metabolized in the liver to the active metabolite linsidomine. Linsidomine is an unstabl ...
,
ciclosidomine, and
linsidomine
Linsidomine (3-morpholinosydnonimine or SIN-1) is a vasodilator. It is a metabolite of the antianginal drug molsidomine and acts by releasing NO from the endothelial cells nonenzymatically. It also hyperpolarizes the cell membrane through influen ...
.
Chemical structure
See also
*
Montréalone
Montréalone (synonyms: montrealone, phospha-münchnone) is a mesoionic heterocyclic compound, heterocyclic chemical compound. It is named for the city of Montreal, Montréal, Canada, which is the location of McGill University, where it was first d ...
*
Münchnone
Münchnone (synonyms: 1,3-oxazolium-5-oxide; 1,3-oxazolium-5-olate; anhydro-5-hydroxy-1,3-oxazolium hydroxide; 5-hydroxy-1,3-oxazolium hydroxide, inner salt; oxido-oxazolium) is a mesoionic heterocyclic aromatic chemical compound, with the molecula ...
*
Sydnone
External links
IUPAC Goldbook entryDictionary of Organic Compounds
Simple aromatic rings
Oxadiazoles
Imines