1-(1,3-Benzothiazol-2-yl)-3-(4-chlorobenzoyl)thiourea

This review provides an overview of the chemistry, structure and potential applications of 1-(acyl/aroyl)-3-(mono-substituted) and 1-(acyl/aroyl)-3,3-(di-substituted) thioureas, with general formula R 1 C(O)N (1) HC(S)N (3) R 2 R 3 . In recent years, the title compounds have found extensive applications as ligands in coordination chemistry. The effect that nitrogen substituents exert on the intra-and intermolecular hydrogen-bonding interactions is discussed, including their role on the coordination properties displayed by these ligands. Novel applications of transition metal complexes bearing 1-(acyl/aroyl)-3-(mono-and di-substituted) thioureas are introduced. Biological aspects are also highlighted. As recently demonstrated, high-throughput screening assay and structure-activity analyses are feasible for this class of compounds. The chemical versatility of 1-(acyl)-3-(substituted) thiourea molecules and the derived metal complexes, together with the possibility of determining detailed structural properties, join biological applications in a promising interdisciplinary approach. The bibliography includes 382 references with emphasis on the literature appearing after 2007.

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A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

Saeed

Flörke

Erben

2013

Journal of Sulfur Chemistry

198

123

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N-(4-Chlorobenzoyl)-N′-(3-fluorophenyl)thiourea

2010

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Crystal structure of 1-(1,3-benzothiazol-2-yl)-3-(4-bromobenzoyl)thiourea

Sow,

Thiam,

Odame

et al. 2024

Acta Cryst E

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The chemical reaction of 4-bromobenzoylchloride and 2-aminothiazole in the presence of potassium thiocyanate yielded a white solid formulated as C15H10BrN3OS2, which consists of 4-bromobenzamido and 2-benzothiazolyl moieties connected by a thiourea group. The 4-bromobenzamido and 2-benzothiazolyl moieties are in a trans conformtion (sometimes also called s-trans due to the single bond) with respect to the N—C bond. The dihedral angle between the mean planes of the 4-bromophenyl and the 2-benzothiazolyl units is 10.45 (11)°. The thiourea moiety, —C—NH—C(=S) —NH— fragment forms a dihedral angle of 8.64 (12)° with the 4-bromophenyl ring and is almost coplanar with the 2-benzothiazolyl moiety, with a dihedral angle of 1.94 (11)°. The molecular structure is stabilized by intramolecular N—H...O hydrogen bonds, resulting in the formation of an S(6) ring. In the crystal, pairs of adjacent molecules interact via intermolecular hydrogen bonds of type C—H...N, C—H...S and N—H...S, resulting in molecular layers parallel to the ac plane.

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1-(1,3-Benzothiazol-2-yl)-3-(4-chlorobenzoyl)thiourea

Cited by 3 publications

References 11 publications

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

N-(4-Chlorobenzoyl)-N′-(3-fluorophenyl)thiourea

Crystal structure of 1-(1,3-benzothiazol-2-yl)-3-(4-bromobenzoyl)thiourea

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