HOME

TheInfoList



Click Here for Items Related To - Benzamidine
OR:
Benzamidine on:   [Wikipedia]   [Google]   [Amazon]

Benzamidine is an
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 ...
with the formula C6H5C(NH)NH2. It is the simplest aryl
amidine Amidines are organic compounds with the functional group RC(NR)NR2, where the R groups can be the same or different. They are the imine derivatives of amides (RC(O)NR2). The simplest amidine is formamidine, HC(=NH)NH2. Examples of amidines includ ...
. The compound is a white solid that is slightly soluble in water. It is usually handled as the hydrochloride salt, a white, water-soluble solid.


Structure

Benzamidine has one short C=NH bond and one longer C-NH2 bond, which are respectively 129 and 135 pm in length, respectively. The triangular diamine group gives it a distinctive shape which shows up in difference density maps.


Applications

Benzamidine is a reversible competitive inhibitor of
trypsin Trypsin is an enzyme in the first section of the small intestine that starts the digestion of protein molecules by cutting long chains of amino acids into smaller pieces. It is a serine protease from the PA clan superfamily, found in the dig ...
, trypsin-like enzymes, and serine proteases. It is often used as a
ligand In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's el ...
in protein crystallography to prevent proteases from degrading a protein of interest. The benzamidine moiety is also found in some pharmaceuticals, such as
dabigatran Dabigatran, sold under the brand name Pradaxa among others, is an anticoagulant used to treat and prevent blood clots and to prevent stroke in people with atrial fibrillation. It is commonly used to prevent blood clots following hip or kn ...
. Condensation with various haloketones provides a synthetic route to 2,4-disubstituted imidazoles. :


References

{{reflist Phenyl compounds Amidines