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Bicyclic Isothioureas for Conjugation with Tubulin Targeted Anticancer Agents

Alexander A. Alexeev,Evgenia Nurieva, Ilia A. Elisseev,Elena R. Milaeva,Konstantin A. Lyssenko,Olga N. Zefirova

Mendeleev communications（2022）

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Abstract
Two bicyclic annulated isothiourea derivatives were synthesized using as a key stage either the reaction of isothiocyanate halide with sodium sulfide or cyclization of unsaturated thiourea in the presence of bromine. X-ray molecular structure of N-[(3aSR,7aRS,Z)-hexahydro-1,3-benzothiazol-2(3H)-ylidene]glycine was determined. The conjugate of colchicine with [(3aR,5S,6aS)-2-(tert-butylamino)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]thiazol-5-yl]methanol obtained demonstrated pronounced cytotoxic effect on cancer cells.
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Key words
non -aromatic heterocycles,annulated bicyclic isothiourea,thioureas,cyclization,zwitterions,tubulin,podophyllotoxin&nbsp,colchicine
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