57-56-7

Usage

Uses

Used in Food Safety and Animal Breeding:
Semicarbazide is used as a detection agent for monitoring the presence of nitrofurazone in food-producing animals. This is due to the carcinogenic properties of nitrofurans, which are prohibited within the EU in animal breeding (Commission Regulation 37/2010). To harmonize the detection of semicarbazide, a Minimum Required Performance Limit (MRPL) of 1 μg/kg is set within the EU (Commission Decision 2003/181). This application helps ensure the safety and quality of food products by preventing the use of harmful substances in animal breeding.

Toxicology

Limited toxicological data are available for semicarbazide. It belongs, however, to a family of chemicals (hydrazines) which are known to cause cancer in animals. Semicarbazide is weakly genotoxic in some in vitro tests. The limited in vivo experimental data available are insufficient to assess whether the activity observed in vitro is also expressed in vivo. Semicarbazide appears to be only a weak carcinogen.

InChI:InChI=1/CH5N3O/c2-1(5)4-3/h3H2,(H3,2,4,5)

Upstream product

• 6055-71-6 acrolein semicarbazone 
• 684-93-5 1-methyl-1-nitrosourea 
• 556-89-8 nitrourea 
• 624-46-4 butan-2-one semicarbazone 
• 100-63-0 phenylhydrazine 
• 108-88-3 toluene 
• 110-20-3 acetone semicarbazone 
• 57-13-6 urea 
• 57383-89-8 C₇H₁₆N₄O₃ 
• 106737-90-0 C₈H₁₀ClN₃O₂ 
• 57383-91-2 C₁₂H₁₆N₄O₅ 
• 120445-74-1 furfural semicarbazone 
• 7647-01-0 hydrogenchloride 
• 26454-35-3 4-xanthen-9-yl semicarbazide 

Downstream Products

• 14106-51-5 p-tolyl-diazenecarboxylic acid amide 
• 19163-22-5 5-phenyl-thiophene-2-carbaldehyde-semicarbazone 
• 93003-32-8 5-benzyl-furan-2-carbaldehyde semicarbazone 
• 100318-34-1 cyclohexyl-[2]thienyl ketone semicarbazone 
• 92375-90-1 5-(4-methyl-benzyl)-furan-2-carbaldehyde semicarbazone 
• 100975-57-3 (2-methyl-5-phenyl-[3]furyl)-glyoxal disemicarbazone 
• 106842-33-5 2-methyl-3-(2-pyrrolidino-ethyl)-cyclohex-2-enone semicarbazone 
• 7356-95-8 NSC 49095 
• 111327-99-2 3-phenyl-benzofuran-2-carbaldehyde semicarbazone 
• 94460-26-1 (+/-)-trans-3-hydroxy-2-phenyl-chroman-4-one semicarbazone 

Relevant academic research and scientific papers

Synthesis, Antileishmanial Activity and In Silico Studies of Aminoguanidine Hydrazones (AGH) and Thiosemicarbazones (TSC) Against Leishmania chagasi Amastigotes

Background: Leishmaniasis is a worldwide health problem, highly endemic in developing countries. Among the four main clinical forms of the disease, visceral leishmaniasis is the most se-vere, fatal in 95% of cases. The undesired side-effects from first-li

Insight on a new indolinone derivative as an orally bioavailable lead compound against renal cell carcinoma

A series of novel 3-indolinone-thiazolidinones and oxazolidinones 4a-k was synthesized via molecular hybridization approach and sequentially evaluated to explore its cytotoxic activity. The cytotoxicity screening pointed toward the N-cyclohexyl thiazolidinone derivative 4f that revealed promising renal cytotoxicity against CAKI-1 and UO-31 renal cancer cell lines with IC50 values 4.74 and 3.99 μM, respectively, which were comparable to those of sunitinib along with good safety threshold against normal renal cells. Further emphasis on compound 4f renal cytotoxicity was achieved via different enzyme assays and CAKI-1 and UO-31 cell cycle analysis. The results were supported by in silico studies to explore its physicochemical, pharmacokinetic and drug-likeness properties. Finally, compound 4f was subjected to an in vivo pharmacokinetic study through two different routes of administration showing excellent oral bioavailability. This research represents compound 4f as a promising candidate against renal cell carcinoma.

A new coordination compound based on 4-amino-3-(tetrazol-5-yl)-furazan (HAFT): preparation, crystal structure, and thermal properties

The green nitrogen-rich coordination compound Cd(SCZ)2(AFT)2 (1) (AFT =4-amino-3-(5-tetrazolate)-furazan and SCZ = semicarbazide) was first synthesized and characterized by EA and Fourier Transform Infrared (FT-IR). The single crystal was cultivated and determined with X-ray diffraction. It revealed that 1 crystallizes in the monoclinic space group P21/c. A Cd2+ ion is coordinated by four N atoms and two O atoms to form a distorted octahedral structure. Among them, two nitrogen atoms are from the two AFT ions and the other four atoms are from two SCZ molecules. The thermal decomposition behavior of 1 was studied with DSC and TG-DTG methods. The apparent activation energy (E), thermal stability, and safety parameters (TSADT, TTIT, and Tb) were calculated for 1. Moreover, entropy of activation (ΔS≠), enthalpy of activation (ΔH≠), free energy of activation (ΔG≠), specific heat capacity (Cp), and impact sensitivity were also discussed in detail.

Chelates with π-stacking and hydrogen-bonding interactions as safer and structurally reinforced energetic materials

Three chelating energetic materials (CEM), [Co(SCZ)2(H2O)2](TNR)(H2O)2 (1), [Ni(SCZ)2(H2O)2](TNR)(H2O)2 (2) and [Zn(SCZ)2(H2/sub

Peptidomimetics comprising N-amino cyclic urea residues and uses thereof

Novel peptidomimetics comprising N-amino cyclic urea residues are disclosed. Use of such peptidomimetics for modulating the activity of CD36 or IL-1 receptor in a cell, and for treating CD36- or IL-1-related disease, disorder or condition is also described.

PEPTIDOMIMETICS COMPRISING N-AMINO CYCLIC UREA RESIDUES AND USES THEREOF

Novel peptidomimetics comprising N-amino cyclic urea residues are disclosed. Use of such peptidomimetics for modulating the activity of CD36 or IL-1 receptor in a cell, and for treating CD36- or IL-1-related disease, disorder or condition is also described

Synthesis, crystal structure, characterisation, and antifungal activity of 3-thiophene aldehyde semicarbazone (3STCH), 2,3-thiophene dicarboxaldehyde bis(semicarbazone) (2,3BSTCH2) and their nickel (II) complexes

The reaction of nickel (II) chloride and bromide with 3-thiophene aldehyde semicarbazone (3STCH) and 2,3-thiophene dicarboxaldehyde bis(semicarbazone) (2,3BSTCH2) leads to the formation of a series of new complexes: [NiCl2(3STCH)2], [NiBr2(3STCH)2], [NiCl(2,3BSTCH2)(H2O)]Cl, and [NiBr(2,3BSTCH 2)(H2O)]Br respectively. The crystal structures of the two ligands 3STCH, 2,3BSTCH2 and of the complex [NiBr(2,3BSTCH 2)(H2O)]Br have been determined by X-ray diffraction methods. For all these complexes, the central ion is coordinated through the oxygen atom of the carbonyle and the azomethine nitrogen atom of the semicarbazone. The antifungal activity of the complexes and their corresponding ligands was evaluated against some strains of respectively, Candida albicans, Candida glabrata and Aspergillus fumigatus. The complexes with 3STCH and 2,3BSTCH2 revealed interesting CMI80 values specifically against C. glabrata. Cytotoxicity assay was also carried out in vitro on MRC5 cells.

Study of the reaction between carbamoyl azides of α-N-protected amino acids and hydrazine monohydrate

Two simple and efficient synthetic methods for the preparation of semicarbazide amino acid derivatives are reported. The procedures involve reaction between the carbamoyl azides of α-N-protected amino acids and hydrazine monohydrate: 4-[(alkoxycarbonylamino)(alkyl)methyl]semicarbazides 1 are obtained when hydrazine is added to the separated tetrahydrofuran (THF) solution containing the carbamoyl azide at 0 °C, whereas 1-[(alkoxycarbonylamino)(alkyl)methyl-carbamoyl]-4-[(alkoxycarbonylamino)(alkyl) methyl]semicarbazides 4 are produced by adding hydrazine directly into the final THF/aqueous buffer (KH2PO4) biphasic mixture containing the prepared carbamoyl azide at 50 °C, respectively. NMR experimental data obtained from samples dissolved in [D6]dimethyl sulfoxide suggest a dimeric association for semicarbazides 4 with intermolecular hydrogen bonds. Moreover, the ESI-MS-MS spectra reveal some interesting common features.

HETEROCYCLIC ANTIVIRAL COMPOUNDS

The present invention relates to a method of treating an HIV-I infection with a compound according to formula I where R1, R2, R3, R4, R5, are as defined herein.

Synthesis and biological screening of novel thiadiazoles, selenadiazoles, and spirocyclic benzopyran by ultrasonic and microwave irradiation

We describe the synthesis of novel thiadiazole, selenadiazole, and spirocyclic benzopyrans via the semicarbazides 3 and thiosemicarbazides 3 of 2-ethyl-2-methyl-4H-chromen-4-ones 1 by conventional and nonconventional methods. The microwave and ultrasonic irradiation methods form the respective products in excellent yields in very short reaction time as compared to the conventional method. The synthesized compounds were tested for antimicrobial screening against bacteria and fungi show moderate activity. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Copyright Taylor & Francis Group, LLC.