103-03-7

Usage

Uses

Used in Pharmaceutical Industry:
1-Phenylsemicarbazide is used as a key intermediate for the synthesis of various alkyl(aryl/heteroaryl) substituted 3-trifluoromethyl-1H-1-phenylpyrazoles and alkyl 3-carboxylate analogs. These compounds have potential applications in the development of new drugs and therapeutic agents, making 1-Phenylsemicarbazide a valuable component in the pharmaceutical industry.
Used in the Synthesis of Antipyretic Dellepsoids D26:
1-Phenylsemicarbazide is used as a starting material in the production of Antipyretic Dellepsoids D26, a brand name for a group of compounds with antipyretic (fever-reducing) properties. The compound plays a crucial role in the development of these therapeutic agents, which can be used to alleviate symptoms of fever and inflammation in patients.

World Health Organization (WHO)

Phenicarbazide, which has analgesic and antipyretic activity, was introduced in the 1970s. It has been withdrawn in at least one country on grounds of its adverse effect profile and it appears to have fallen into disuse in others.

Purification Methods

Crystallise it from water and dry it in a vacuum over KOH. [Beilstein 15 H 287, 15 II 106, 15 III 184, 15 IV 180.]

InChI:InChI=1/C7H7N3O/c8-7(11)10-9-6-4-2-1-3-5-6/h1-5H,(H2,8,11)

Upstream product

• 934-48-5 3,5-dimethylpyrazole-1-carboxamide 
• 100-63-0 phenylhydrazine 
• 6268-32-2 N-phenyl-N-nitrosourea 
• 5877-04-3 acetone-(2-phenyl semicarbazone) 
• 590-28-3 potassium cyanate 
• 64-19-7 acetic acid 
• 57-13-6 urea 
• 684-93-5 1-methyl-1-nitrosourea 
• 5338-16-9 dicyanodiamidine sulfate 
• 51-79-6 urethane 
• 59-88-1 phenylhydrazine hydrochloride 
• 140-22-7 1,5-diphenylcarbazide 
• 39538-93-7 2-phenylsemicarbazide 
• 627-48-5 ethyl cyanate 

Downstream Products

• 19382-50-4 1,5-diphenyl-1,2-dihydro-[1,2,4]triazol-3-one 
• 76033-80-2 1-benzoyl-1-phenyl semicarbazide 
• 53723-90-3 1-acetyl-1-phenyl semicarbazide 
• 109047-22-5 1-chloroacetyl-1-phenyl semicarbazide 
• 151221-74-8 1-phenyl-5-styryl-1,2-dihydro-[1,2,4]triazol-3-one 
• 6942-46-7 1-phenylurazole 
• 4231-68-9 1-phenyl-1,2-dihydro-[1,2,4]triazol-3-one 
• 58748-26-8 1-dichloroacetyl-1-phenyl semicarbazide 
• 14500-23-3 1-phenyl-4-methylurazole 

Relevant academic research and scientific papers

Ammonium Chloride-Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation

Monosubstituted ureas are important scaffolds in organic chemistry. They appear in various biologically active compounds and serve as versatile precursors in synthesis. Monosubstituted ureas were originally prepared using toxic and hazardous phosgene equivalents. Modern methods include transamidation of urea and nucleophilic addition to cyanate salts, both of which suffer from a narrow substrate scope due to the need for a strong acid and prolonged reaction times. We hereby report that ammonium chloride can promote the reaction between amines and potassium cyanate to generate monosubstituted ureas in water. This method proceeds rapidly under microwave irradiation and tolerates a broad range of functional groups. Unlike previous strategies, it is compatible with other nucleophiles, acid-labile moieties, and most of the common protecting groups. The products precipitate out of solution, allowing facile isolation without column chromatography.

Microwave-assisted synthesis of N-monosubstituted urea derivatives

An easy and rapid procedure for the preparation of N-monosubstituted ureas via reaction between potassium cyanate and a wide range of amines is described. The procedure was performed under microwave irradiation using water as solvent. This methodology is particularly attractive since it provides ureas in high yield and purity. Georg Thieme Verlag Stuttgart · New York.

Synthesis of novel halobenzyloxy and alkoxy 1,2,4-triazoles and evaluation for their antifungal and antibacterial activities

A new class of halobenzyloxy or alkoxy 1,2,4-triazoles and their hydrochlorides were synthesized through cyclization starting from commercially available phenylhydrazine. The structures were characterized by MS, IR and 1H NMR spectra as well as elemental analyses. All the synthesized compounds were screened for their antibacterial activities in vitro against Staphylococcus aureus (ATCC29213), methicillin-resistant Staphylococcus aureus (N315), Bacillus subtilis, Escherichia coli (ATCC25922), Pseudomonas aeruginosa, Shigella dysenteriae, Eberthella typhosa, and antifungal activities against Candida albicans (ATCC76615), Aspergillus fumigatus by broth microdilution assay method. The results of preliminary bioassay indicated that 3-(2,4- difluorobenzyloxy)-1-phenyl-1H-1,2,4-triazole hydrochloride exhibited the best inhibitory activity with an MIC value of 56.25 μM against P. aeruginosa superior to Chloramphenicol, and showed comparable activity with Chloramphenicol against E. coli (ATCC25922).

Gene delivery compounds

Compounds having the structure: wherein R1, R2 and R3 are each independently a C0-12 substituent selected from the group consisting of: hydrogen, a heteroatom, alkyl, alkenyl, alkynyl, heteroatom substituted alkyl, heteroatom substituted alkenyl, heteroatom substituted alkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl; where the heteroatom is selected from the group consisting of: N, O and S; and where (A) is a single or double bond between N and R3. Further the C0-12 substituent is linear, branched or cyclic and optionally includes a pendant moiety selected from the group consisting of: carbonyl, hydroxyl, carboxyl, amine, thiol, thioester, thioether, phosphate, alkoxy, aryl, arylalkyl, sulfonamide and alkyl halide. Further, compounds 6883, 6898, 6975, 7036, 7064 and 8496 are provided. A process is provided for activating gene transfer in a subject by administering a pharmaceutically effective amount of a gene transfer activating compound to a subject and delivering pharmaceutically effective amount of a vector containing a nucleic so that the nucleic acid is transcribed in a target cell of the subject. A process for activating gene transfer to a cell is provided. A kit for activating gene transfer is provided.

Prostaglandins

Novel compounds have a formula (I) STR1 wherein STR2 represents a bicyclo[2,2,1]hept-2Z-ene, bicyclo[2,2,1]heptane, 7-oxabicyclo[2,2,1]hept-2Z-ene, 7-oxabicyclo[2,2,1]heptane, bicyclo[2,2,2]oct-2Z-ene or bicyclo[2,2,2]octane substituted at the 5-position by the group R1 and at the 6-position by the group C(R2)=NR, a 6,6-dimethyl-bicyclo[3,1,1]heptane substituted at the 5-position by the group R1 and at the 6-position by the group C(R2)=NR or at the 5-position by the group C(R2)=NR and at the 6-position by the group R1, a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R1 and at the 5-position by the group C(R2)=NR, or a 1-hydroxycyclopentane substituted at the 2-position by the group R1 and at the 2-position by the group C(R2)=NR, R1 is a 6-caboxyhex-2-enyl group or a modification thereof as defined herein, R2 is hydrogen, an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, and R is a group --OR3, --OR4, --A--R3 or -- N=R5 in which A is --NH--, --NH.CO--, --NH.CO.CH2 N(R6)--, --NH.SO2 --, --NH.CO.NH or --NH.CS.NH-- and wherein R3 is an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, R4 is an aliphatic hydrocarbon group which is substituted through an oxygen atom ay an aliphatic hydrocarbon group which is itself substituted by an aromatic group, R5 is an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, and R6 is hydrogen, an aliphatic hydrocarbon group, an aromatic group or an aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group, with the proviso that when R is a group --OR3, --NH.COR3 or --NH.CO.NHR3 then STR3 excludes bicyclo[2,2,1]hept-2Z-enes and bicyclo[2,2,1]heptanes. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.

Prostaglandins

Novel bicyclo [2,2,1] heptanes and hept-2-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by a grouping --C(R)=N--NHCO--(NH)a --R' in which R is hydrogen, an aliphatic hydrocarbon residue, an aromatic residue or an aliphatic hydrocarbon residue substituted by an aromatic residue, a is 0 or 1 and R' is an aliphatic hydrocarbon residue, an aromatic residue, or an aliphatic hydrocarbon residue substituted directly or through an oxygen or sulphur atom by an aromatic residue. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.