Thiosemicarbazone

A thiosemicarbazone is an organosulfur compound with the formula H2NC(S)NHN=CR2. Many variations exist, including those where some or all of the NH centers are substituted by organic groups. Thiosemicarbazones are usually produced by condensation of a thiosemicarbazide with an aldehyde or ketone:

H2NC(S)NHNH2 + O=CR2 → H2NC(S)NHN=CR2 + H2O
General chemical structure of a thiosemicarbazone

In terms of their chemical structures, the CSN3 core atoms are coplanar.[1]

Occurrence and applications

Some thiosemicarbazones have medicinal properties, e.g. the antiviral metisazone and the antibiotic thioacetazone. Thiosemicarbazones are also widely used as ligands in coordination chemistry.[2] The affinity of thiosemicarbazones for metal ions is exploited in controlling iron overload.[3]

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References
  1. Wattanakanjana, Yupa; Pakawatchai, Chaveng; Saithong, Saowanit; Piboonphon, Prapaporn; Nimthong, Ruthairat (2012). "Iodido[1-(propan-2-ylidene)thiosemicarbazide-κS]bis(triphenylphosphane-κP)copper(I)". Acta Crystallographica Section E. 68 (11): m1417–m1418. doi:10.1107/S1600536812044066. PMC 3515154. PMID 23284381.
  2. Campbell, Michel J.M. (1975). "Transition metal complexes of thiosemicarbazide and thiosemicarbazones". Coordination Chemistry Reviews. 15 (2–3): 279–319. doi:10.1016/S0010-8545(00)80276-3.
  3. Merlot, Angelica M.; Kalinowski, Danuta S.; Richardson, Des R. (2013). "Novel Chelators for Cancer Treatment: Where Are We Now?". Antioxidants & Redox Signaling. 18 (8): 973–1006. doi:10.1089/ars.2012.4540. PMID 22424293.
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