Synthesis, structure, and antifungal evaluation of some novel 1,2,4-triazolylmercaptoacetylthiosemicarbazide and 1,2,4-triazolylmercaptomethyl-1,3,4-thiadiazole analogs.

Novel 1-[[4-(4-bromophenyl)-5-(2-furyl)-4H-1,2,4-triazole-3-yl]mercaptoacetyl]-4-alkyl/aryl-3-thiosemicarbazides (5-12) were synthesized by the reaction of 4-(4-bromophenyl)-5-(2-furyl)-4H-1,2,4-triazole-3-ylmercaptoacetylhydrazide (4) with substituted isothiocyanates. Cyclodehydration of thiosemicarbazides with concentrated sulfuric acid yielded 2-[4-(4-bromophenyl)-5-(2-furyl)-4H-1,2,4-triazole-3-yl]mercaptomethyl-5-alkyl/arylamino-1,3, 4-thiadiazoles (13-17). The new compounds were evaluated for in vitro antifungal activity using the microdilution method.

rac-2-Hydroxy-2,8-dimethyl-4-morpho-linoethyl-1-thia-4-aza-spiro-[4.5]decan-3-one.

The title compound, C(16)H(28)N(2)O(3)S, is dimerized by inversion symmetry-related inter-molecular O-H⋯N hydrogen bonding, forming an R(2) (2)(16) motif. The dimers are also linked through inter-molecular C-H⋯O hydrogen bonding. The compound is chiral with a stereogenic centre located in the thia-zole ring, but in the crystal structure it forms a racemate.

8-Methyl-4-morpholinoethyl-1-thia-4-aza-spiro-[4.5]decan-3-one.

In the title compound, C(15)H(26)N(2)O(2)S, the cyclo-hexane and morpholine rings adopt chair conformations, while the thia-zole ring has a twist conformation. An intra-molecular C-H⋯S hydrogen-bond inter-action forms a five-membered ring. The crystal packing involves C-H⋯O=C inter-molecular inter-actions where carbonyl O atoms act as double acceptors to two symmetrically related H atoms.

8-Ethyl-2-hydr-oxy-2-methyl-4-morpholinoethyl-1-thia-4-aza-spiro-[4.5]decan-3-one.

Mol-ecules of the title spiro-[4.5]decane derivative, C(17)H(30)N(2)O(3)S, are linked by paired O-H⋯N hydrogen bonds into centrosymmetric R(2) (2)(16) dimers and these dimers are linked into a three-dimensional framework structure by C-H⋯O interactions.