1-(Benzylideneamino)-3-phenylthiourea

Base Information

• Chemical Name: 1-(Benzylideneamino)-3-phenylthiourea
• CAS No.: 13456-63-8
• Molecular Formula: C14H13 N3 S
• Molecular Weight: 255.343
• NSC Number: 529369
• DSSTox Substance ID: DTXSID60419871
• Nikkaji Number: J570.735H

Synonyms:NSC529369;13456-63-8;DTXSID60419871;1-(benzylideneamino)-3-phenylthiourea;NSC-529369

Chemical Property of 1-(Benzylideneamino)-3-phenylthiourea

Chemical Property:

• Vapor Pressure: 2.56E-06mmHg at 25°C
• Boiling Point: 390.9°C at 760 mmHg
• Flash Point: 190.2°C
• Density: 1.14g/cm³
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 255.08301860
• Heavy Atom Count: 18
• Complexity: 279

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=NNC(=S)NC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)/C=N\NC(=S)NC2=CC=CC=C2
• General Description: Benzaldehyde N-phenylthiosemicarbazone, also known as benzaldehyde 4-phenyl-3-thiosemicarbazone, is a synthesized compound with demonstrated anti-Toxoplasma gondii and antimicrobial activities. It exhibits potent toxicity against intracellular parasites, with IC50 values ranging from 0.05 to 1 mM, and shows promising efficacy against various bacterial and fungal strains, in some cases outperforming standard antimicrobial drugs. benzaldehyde N-phenylthiosemicarbazone represents a potential candidate for developing less toxic and more effective treatments for toxoplasmosis and microbial infections, particularly in the context of rising drug resistance.

Technology Process of 1-(Benzylideneamino)-3-phenylthiourea

There total 16 articles about 1-(Benzylideneamino)-3-phenylthiourea which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

benzaldehyde (100-52-7) + phenyl isothiocyanate (103-72-0) + hydrazine (302-01-2,78206-91-4,119775-10-9,75013-58-0) → 1-benzylidene-4-phenylthiosemicarbazide (13456-63-8)

Guidance literature:

In methanol; for 24h; Reflux;

DOI:10.1016/j.tetlet.2009.02.134

Reference yield: 81.0%

benzaldehyde, hydrazone (5281-18-5) + phenyl isothiocyanate (103-72-0) → 1-benzylidene-4-phenylthiosemicarbazide (13456-63-8)

Guidance literature:

In ethanol; Heating; slightly acidic pH value;

Reference yield: 78.0%

2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-one (34025-58-6,56479-38-0,56613-79-7,57794-27-1,93921-25-6,104873-86-1) + 4-Phenyl-3-thiosemicarbazide (5351-69-9) → C27H28N4S (1309865-05-1) + 1-benzylidene-4-phenylthiosemicarbazide (13456-63-8)

Guidance literature:

In ethanol; chloroform; at 90 - 100 ℃; for 96h; Acidic conditions;

DOI:10.3109/14756366.2010.525508

upstream raw materials:

benzaldehyde

4-Phenyl-3-thiosemicarbazide

ethanol

benzaldehyde, hydrazone

Downstream raw materials:

5-Phenyl-2-phenylamino-1,3,4-thiadiazol

bis-{4,5-diphenyl-1,2,4-triazolyl-⁽³⁾}-disulfide

2-benzylidenehydrazono-3-phenyl-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester

4-Phenyl-5-{[1-phenyl-meth-(E)-ylidene]-hydrazono}-[1,2,4]dithiazolidin-3-one

Refernces

Synthesis, anti-Toxoplasma gondii and antimicrobial activities of benzaldehyde 4-phenyl-3-thiosemicarbazones and 2-[(phenylmethylene)hydrazono]-4-oxo-3-phenyl-5-thiazolidineacetic acids

10.1016/j.bmc.2007.09.025

The study focuses on the synthesis and evaluation of a series of benzaldehyde 4-phenyl-3-thiosemicarbazones (1a–p) and 2-[(phenylmethylene)hydrazono]-4-oxo-3-phenyl-5-thiazolidineacetic acids (2a–p) for their anti-Toxoplasma gondii and antimicrobial activities. These compounds were synthesized and characterized using techniques such as IR, 1H, and 13C NMR. The purpose of these chemicals was to assess their potential as treatments against the intracellular parasite Toxoplasma gondii, which causes toxoplasmosis, and to evaluate their antimicrobial properties against various bacteria and fungal species. The study aimed to discover new, less-toxic, and more effective drugs for the treatment of toxoplasmosis and to combat microbial infections, given the increasing resistance of pathogens to existing treatments. The compounds were tested for their ability to reduce the percentage of infected cells and the mean number of parasites per cell, as well as their toxicity against intracellular parasites. The results showed that most of the 4-thiazolidinones demonstrated effective toxicity against intracellular parasites with IC50 values ranging from 0.05 to 1 mM and also exhibited promising antimicrobial activity, with some compounds showing better activity than standard drugs against certain microbial strains.

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