Rhodanine is a 5-membered
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 organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
possessing a
thiazolidine
Thiazolidine is a heterocyclic organic compound with the formula (CH2)3(NH)S. It is a 5-membered saturated ring with a thioether group and an amine group in the 1 and 3 positions. It is a sulfur analog of oxazolidine. Thiazolidine is a colorl ...
core. It was discovered in 1877 by
Marceli Nencki who named it ''"Rhodaninsaure"'' in reference to its synthesis from ammonium rhodanide (known as
ammonium thiocyanate
Ammonium thiocyanate is an inorganic compound with the formula . It is an ammonium salt of thiocyanic acid. It consists of ammonium cations and thiocyanate anions .
Uses
Ammonium thiocyanate is used in the manufacture of herbicides, thiourea, an ...
to modern chemists) and
chloroacetic acid
Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula . This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds are dichlo ...
in water.
Rhodanines can also be prepared by the reaction of
carbon disulfide
Carbon disulfide (also spelled as carbon disulphide) is an inorganic compound with the chemical formula and structure . It is also considered as the anhydride of thiocarbonic acid. It is a colorless, flammable, neurotoxic liquid that is used as ...
,
ammonia
Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...
, and
chloroacetic acid
Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula . This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds are dichlo ...
, which proceeds via an intermediate
dithiocarbamate
In organic chemistry, a dithiocarbamate is a chemical compound with the general formula . It contains the functional group with the Chemical structure, structure . It is the analog of a carbamate in which both oxygen atoms are replaced by sulfur ...
.
:
Derivatives
Some rhodanine
derivatives have pharmacological properties; for instance,
epalrestat
Epalrestat is a carboxylic acid derivative and a noncompetitive and reversible aldose reductase inhibitor used for the treatment of diabetic neuropathy, which is one of the most common long-term complications in patients with diabetes mellitus
...
is used to treat
diabetic neuropathy
Diabetic neuropathy includes various types of nerve damage associated with diabetes mellitus. The most common form, diabetic peripheral neuropathy, affects 30% of all diabetic patients. Studies suggests that cutaneous nerve branches, such as the s ...
. However, most are promiscuous binders with poor selectivity; as a result, this class of compounds is viewed with suspicion by medicinal chemists. Differing academic opinions exist concerning the correct use of
PAINS filters, the necessity of the experimental confirmations of such properties, and many useful features of rhodanine derivatives.
References
{{reflist
Thiazolidines
Lactams
Substances discovered in the 19th century