Spirotryprostatin A
Encyclopedia
Spirotryprostatin A is an indolic
alkaloid
found in the Aspergillus fumigatus
fungus. Spirotryprostatin A and several other indolic alkaloids (including Spirotryprostatin B
, as well as other tryprostatins and cyclotryprostatins) have been found to have anti-mitotic
properties, and as such they have become of great interest as anti-cancer
drugs. Because of this, the total syntheses
of these compounds is a major pursuit of organic chemists, and a number of different syntheses have been published in the chemical literature.
One such total synthesis was published in 1999, which showed that the isopropylidene side chain was not necessary to the biological activity of the compound, leading to a number of new theorized analogues.
Indole
Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Indole is a popular component of fragrances and the precursor to many pharmaceuticals. Compounds that contain an...
alkaloid
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...
found in the Aspergillus fumigatus
Aspergillus fumigatus
Aspergillus fumigatus is a fungus of the genus Aspergillus, and is one of the most common Aspergillus species to cause disease in individuals with an immunodeficiency....
fungus. Spirotryprostatin A and several other indolic alkaloids (including Spirotryprostatin B
Spirotryprostatin B
Spirotryprostatin B is an indolic alkaloid found in the Aspergillus fumigatus fungus. Spirotryprostatin B and several other indolic alkaloids have been found to have anti-mitotic properties, and as such they have become of great interest as anti-cancer drugs...
, as well as other tryprostatins and cyclotryprostatins) have been found to have anti-mitotic
Mitosis
Mitosis is the process by which a eukaryotic cell separates the chromosomes in its cell nucleus into two identical sets, in two separate nuclei. It is generally followed immediately by cytokinesis, which divides the nuclei, cytoplasm, organelles and cell membrane into two cells containing roughly...
properties, and as such they have become of great interest as anti-cancer
Cancer
Cancer , known medically as a malignant neoplasm, is a large group of different diseases, all involving unregulated cell growth. In cancer, cells divide and grow uncontrollably, forming malignant tumors, and invade nearby parts of the body. The cancer may also spread to more distant parts of the...
drugs. Because of this, the total syntheses
Total synthesis
In organic chemistry, a total synthesis is, in principle, the complete chemical synthesis of complex organic molecules from simpler pieces, usually without the aid of biological processes. In practice, these simpler pieces are commercially available in bulk and semi-bulk quantities, and are often...
of these compounds is a major pursuit of organic chemists, and a number of different syntheses have been published in the chemical literature.
One such total synthesis was published in 1999, which showed that the isopropylidene side chain was not necessary to the biological activity of the compound, leading to a number of new theorized analogues.