A heterocyclic organic compound is a cyclic organic compound that has atoms of at least two different elements as members of its ring. Heterocycle chemistry is a branch of organic chemistry that deals with the synthesis, properties, and applications of these heterocycles. Heterocyclic organic compounds are of great importance in most pharmaceuticals, most of the biomass (cellulose and related materials), and many natural and synthetic dyes.
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Applications
Medical chemistry: Imidazole can be incorporated into many important biological molecules. The most common is histidine, an amino acid with an imidazole side chain. Histidine is present in many proteins and enzymes and plays an important role in the structure and binding function of hemoglobin. Imidazole has become a vital part of many drugs. Synthetic imidazoles are present in many fungicides and antifungals, antiprotozoals and antihypertensives. Imidazole is also part of theophylline molecule found in tea and coffee beans, which stimulates the central nervous system. It is present in the anti-cancer drug mercaptopurine and combats leukemia by interfering with DNA activity.
Organic chemistry: THF is water-miscible and can form a solid clathrate hydrate structure with water at very low temperatures. THF is a commonly used solvent in the laboratory. It is more fundamental than diethyl ether and forms a stronger complex with Mg2+, Li+, and borane. It is a common solvent for hydroboration reaction and for organometallic compounds such as organolithium and Grignard reagents. Thus, although diethyl ether is still the preferred solvent for some reactions such as the Grignard reaction, THF plays a role in many other solvents where strong coordination is desirable. Pyridine is used as a polar low-reactivity solvent, for example in Knoevenagel condensation. It is particularly suitable for the dehalogenation reaction, in which pyridine is the base for the elimination reaction, and forms a pyridinium salt. In esterification and acylation reactions, pyridine can activate carboxylic acid halides or anhydrides.
Biochemistry: Diazepanines are commonly used as photoreactive crosslinkers because carbenes can insert into C-H, N-H and O-H bonds upon irradiation with ultraviolet light. This would lead to proximity-dependent labeling of other species with diazoxide-containing compounds. Diazirines are widely used in receptor labeling studies. This is because it is possible to synthesize the diazanil-containing analogs of various ligands and then expose to light to produce a reactive carbene. The carbene will be covalently bonded to the residue of the receptor’s binding site. Carbene compounds can include bio-orthogonal labels or handle by which the protein of interest can be isolated. The protein can then be sequenced to determine the identity of the binding site in the receptor by mass spectrometry.
