thiosemicarbazone
{{Short description|Class of chemical compounds}}
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
In terms of their chemical structures, the CSN3 core atoms are coplanar.{{cite journal |doi=10.1107/S1600536812044066|title=Iodido[1-(propan-2-ylidene)thiosemicarbazide-κS]bis(triphenylphosphane-κP)copper(I)|year=2012|last1=Wattanakanjana|first1= Yupa|last2=Pakawatchai|first2=Chaveng|last3=Saithong|first3=Saowanit|last4=Piboonphon|first4 =Prapaporn|last5=Nimthong|first5=Ruthairat|journal=Acta Crystallographica Section E |volume=68|issue=11|pages=m1417–m1418|pmid=23284381|pmc=3515154}}
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.{{cite journal|doi=10.1016/S0010-8545(00)80276-3|title=Transition metal complexes of thiosemicarbazide and thiosemicarbazones|year=1975|last1=Campbell|first1=Michel J.M.|journal=Coordination Chemistry Reviews|volume=15|issue=2–3|pages=279–319}} The affinity of thiosemicarbazones for metal ions is exploited in controlling iron overload.{{cite journal |doi=10.1089/ars.2012.4540|title=Novel Chelators for Cancer Treatment: Where Are We Now?|year=2013|last1=Merlot|first1=Angelica M.|last2=Kalinowski|first2=Danuta S.|last3=Richardson|first3=Des R.|journal=Antioxidants & Redox Signaling|volume=18|issue=8|pages=973–1006|pmid=22424293}}