An Update of the Use of Thiocarbohydrazides and Thiosemicarbazides in the Preparation of Heterocycles and Their Biological Importance

Abstract

The inherent reactivity of thiocarbohydrazides and thiosemicarbazides makes them valuable as building blocks for the synthesis of other heterocyclic motifs. This review article discusses the recent applications of classes of compounds in syntheses of five‐membered to seven‐membered heterocycles of biological activities and remarkable number of metal complexes. Many previous reviews dealt with the reactivity of either thiosemicarbazides or thiocarbohydrazides. However, a large number of publications have recently dealt with the reactivity of thiosemicarbazides and thiocarbohydrazides. Consequently, we have found that it is of importance to shed new light on these interesting molecules.

One‐Pot Synthesis and Anticancer Activity of Novel Pyrazole Hybrids

“…Furthermore, a singlet signal at δ 2.35 ppm due to the four protons of the methylene groups appeared in its 1 HNMR besides NH 2 and NH protons' absence. The 13 CNMR showed a characteristic signal at δ 14.84 ppm belonging to 2 À CH 2 À carbon atoms. MS spectrum of pyrazole 3 indicated a molecular ion peak at m\z 362 that was compatible with the molecular formula (C 19 H 14 N 4 O 2 S) of pyrazole 3.…”

“…IR spectra showed characteristic signals at 3211, 3250 cm À 1 (NH 2 group for pyrazole 8), and additional band due to the coumarin C=O group at 1720 cm À 1 for compound 9. Additionally, their 1 HNMR and 13 CNMR spectral measurements showed the methyl (CH3) groups' singlet signals at δ 2.30, 2.33, and 2.33 ppm, respectively. On the other hand, this one-pot condensation with 2-amino-4-nitrobenzophenone afforded the unexpected triazepinyl pyrazole 10 via losing of H 2 S gas.…”

“…The latter include five-membered rings (e. g., pyrazoles, imidazoles, thiazoles, thiadiazole, triazoles, thiatriazole, dithiadiazole) and six-membered rings (e. g., pyridazines, pyrimidines, thiazines, triazines, oxadiazines, thiadiazines, and tetrazines) as well as seven-membered rings (e. g., triazepines, thiadiazepines, tetrazepines, and oxatriazepines) and eight-membered rings (e. g., thiadiazoctines). [12][13][14][15] We herein report the synthesis of novel pyrazole hybrids using thiocarbohydrazide. The newly synthesized pyrazoles will be tested for their cytotoxicity against HepG2 liver cancer cells as well as different breast cancer cells (e. g., 4T1, MDA-MB-231, and MCF-7).…”

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Novel pyrazole hybrids (3-17) were synthesized via one-pot reaction of thiocarbonyldihydrazide (1), ethyl 3-phenyl-3oxopropanoate (2), and different carbonyl reagents in good yields (68-98 %). Their structures were confirmed using IR, 1 HNMR, 13 CNMR, and Mass spectroscopy (MS), as well as elemental analysis. Pyrazole hybrids (3-17) were screened for their cytotoxicity against three different breast cancer cell lines (e. g., MDA-MB-231, MCF-7, and 4T1) and HepG2 liver cancer cells.

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New Paracyclophanylthiazoles with Anti-Leukemia Activity: Design, Synthesis, Molecular Docking, and Mechanistic Studies

“…Recently, we have an interest in the preparation of heterocycles of similar structural features [15][16][17][18][19][20][21][22][23]. In addition, we prepared metal complexes of thiosemicarbazones with Cu(I) and Cu(II) and the tridentate and bidentate structures of the paracyclophanyl-thiosemicarbazone-metal complexes were elucidated [24].…”