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1,2,5-oxadiazole

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1,2,5-oxadiazole Basic information

Product Name:
1,2,5-oxadiazole
Synonyms:
  • 1,2,5-oxadiazole
  • furazane
  • Azoxazole
  • Furazan
CAS:
288-37-9
MF:
C2H2N2O
MW:
0
Mol File:
288-37-9.mol
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1,2,5-oxadiazole Usage And Synthesis

Description

1,2,5-Oxadiazole is a five-membered, heteroaromatic, planar heterocycle comprised of one oxygen atom with two vicinal nitrogen atoms (N-O-N) and two carbon atoms at the 3- and 4-positions of the ring. It is a π-excessive heterocycle also referred to by its trivial name furazan and corresponding 2-N-oxide as furoxan. The ionization energy of oxadiazole is 11.79 eV and the dipole moment is 3.38 D greater than isoxazole. The π electron density of the nitrogen atom is greater than the oxygen and carbon atoms as depicted in the following scheme.

Physical properties

The parent 1,2,5-oxadiazole is a colorless liquid with an mp of ?28°C and a bp of 98°C, soluble in water and stable at room temperature. Its density is 1.168 g/cm.3

Application

1,2,5-Oxadiazole derivatives are found to be potent inhibitors of indoleamine 2,3-dioxygenase and are useful for the treatment of cancer and other disorders. They are also useful as a new class of SENP2 inhibitors and can be used for the development of novel therapeutic agents for various diseases targeting SENPs. 1,2,5-Oxadiazole-2-oxides are used as a source of NO in biological studies. 4-Amino-1,2,5-oxadiazole-2-oxide-3-carboxylic acid and azo derivatives have been studied for their vasodilating properties.

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