Production Method 1

18856-63-8

93693-01-7

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Dichloromethane ;  3 h, reflux

Reference

Novel indol-3-yl-thiosemicarbazone derivatives: Obtaining, evaluation of in vitro leishmanicidal activity and ultrastructural studies

da Silva, Paula Roberta; de Oliveira, Jamerson Ferreira; da Silva, Anekecia Lauro; Queiroz, Camila Marques; Feitosa, Ana Paula Sampaio; et al, Chemico-Biological Interactions, 2020, 315,

Production Method 2

2414962-98-2

93693-01-7

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) ;  30 °C

Reference

N-substituted benzaldehyde thiosemicarbazone derivative, and its preparation method and application in preparing antifungal material

, China, , ,

Production Method 3

18856-63-8

93693-01-7

Reaction Conditions

1.1 Reagents: Hydrazine Solvents: Dichloromethane ;  2 h, 25 °C

Reference

Novel 4-quinoline-thiosemicarbazone derivatives: Synthesis, antiproliferative activity, in vitro and in silico biomacromolecule interaction studies and topoisomerase inhibition

Ribeiro, Amelia Galdino; Vitalino de Almeida, Sinara Monica; Ferreira de Oliveira, Jamerson; Souza, Tulio Ricardo Couto de Lima; Lima dos Santos, Keriolaine; et al, European Journal of Medicinal Chemistry, 2019, 182,

Production Method 4

18856-63-8

93693-01-7

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Dichloromethane ;  rt; 2 h, rt

Reference

Synthesis of thiophene-thiosemicarbazone derivatives and evaluation of their in vitro and in vivo antitumor activities

Ferreira de Oliveira, Jamerson; Lauro da Silva, Anekecia; Vendramini-Costa, Debora Barbosa; Amorim, Cezar Augusto da Cruz; Campos, Julia Furtado ; et al, European Journal of Medicinal Chemistry, 2015, 104, 148-156

Production Method 5

18856-63-8

93693-01-7

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Ethanol ;  0 °C; overnight, 0 °C

Reference

Synthesis, molecular modeling and antiviral activity of novel 5-fluoro-1H-indole-2,3-dione 3-thiosemicarbazones

Sevincli, Zekiye Seyma; Duran, Gizem Nur; Ozbil, Mehmet; Karali, Nilgun, Bioorganic Chemistry, 2020, 104,

Production Method 6

18856-63-8

93693-01-7

Reaction Conditions

1.1 Reagents: Hydrazine Solvents: Ethanol ;  rt; 3 h, cooled

Reference

Design, synthesis and biological evaluation of novel tetralone/indanone containing thiosemicarbazone derivatives with selective COX-2 inhibition as anticancer agents

Kuran, Ebru Didem ; Dincel, Efe Dogukan ; Biltekin, Sevde Nur ; Akalin-Ciftci, Gulsen; Ulusoy-Guzeldemirci, Nuray, Journal of Molecular Structure, 2023, 1286,

Production Method 7

18856-63-8

93693-01-7

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Methanol ;  1 h, rt

Reference

Structural revision of the Mcl-1 inhibitor MIM1: synthesis and biological studies on ovarian cancer cells with evaluation of designed analogues

Paysant, Hippolyte; Hedir, Siham; Justaud, Frederic; Weiswald, Louis Bastien; El Dine, Assaad Nasr; et al, Organic & Biomolecular Chemistry, 2021, 19(41), 8968-8987

Production Method 8

589-16-2

93693-01-7

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Dimethylformamide ;  4 h, rt
1.2 Reagents: Hydrazine hydrate (1:1) ;  rt → 65 °C; 2 h, 65 °C

Reference

Synthesis, cytotoxicity, and in vivo antitumor activity study of parthenolide semicarbazones and thiosemicarbazones

Jia, Xinxin; Liu, Qi; Wang, Shiyi; Zeng, Binglin; Du, Guohua; et al, Bioorganic & Medicinal Chemistry, 2020, 28(13),

Production Method 9

18856-63-8

93693-01-7

Reaction Conditions

1.1 Reagents: tert-Butyl carbazate
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Synthesis and structure-activity evaluation of isatin-β-thiosemicarbazones with improved selective activity toward multidrug-resistant cells expressing P-glycoprotein

Hall, Matthew D.; Brimacombe, Kyle R.; Varonka, Matthew S.; Pluchino, Kristen M.; Monda, Julie K.; et al, Journal of Medicinal Chemistry, 2011, 54(16), 5878-5889

4-(4-Ethylphenyl)-3-thiosemicarbazide Raw materials

• Acetic acid, 2-[[[(4-ethylphenyl)amino]thioxomethyl]thio]-, sodium salt (1:1)
• 4-Ethylphenyl isothiocyanate
• 4-Ethylaniline

4-(4-Ethylphenyl)-3-thiosemicarbazide Preparation Products

• 4-(4-Ethylphenyl)-3-thiosemicarbazide (93693-01-7)

• 1. Evidence of pre-micellar aggregates in aqueous solution of amphiphilic PDMS–PEO block copolymer?
  Domenico Lombardo,Gianmarco Munaò,Pietro Calandra,Luigi Pasqua,Maria Teresa Caccamo Phys. Chem. Chem. Phys., 2019,21, 11983-11991
• 2. Dissociative electron attachment to HGaF4 Lewis–Br?nsted superacid
  Marcin Czapla,Jack Simons Phys. Chem. Chem. Phys., 2018,20, 21739-21745
• 3. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
  Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203
• 4. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788
• 5. Excitation energies from ground-state density-functionals by means of generator coordinates
  A. B. F. da Silva,K. Capelle Phys. Chem. Chem. Phys., 2009,11, 4564-4569

Chemical Profile of 4-(4-Ethylphenyl)-3-thiosemicarbazide (CAS No. 93693-01-7)

4-(4-Ethylphenyl)-3-thiosemicarbazide, identified by the Chemical Abstracts Service Number (CAS No.) 93693-01-7, is a significant compound in the field of medicinal chemistry. This heterocyclic thiosemicarbazide derivative has garnered attention due to its unique structural properties and potential biological activities. The compound features a phenyl ring substituted with an ethyl group at the para position, linked to a thiosemicarbazide core. This structural configuration imparts distinct electronic and steric characteristics, making it a valuable scaffold for further chemical modifications and biological evaluations.

The thiosemicarbazide moiety in 4-(4-Ethylphenyl)-3-thiosemicarbazide is known for its versatile reactivity and biological relevance. Thiosemicarbazides have been extensively studied for their antimicrobial, antiviral, anti-inflammatory, and anticancer properties. The sulfur atom in the thiosemicarbazide group can participate in various interactions with biological targets, including metal ions and biomolecules, which contributes to the compound's pharmacological potential. The presence of the ethyl substituent on the phenyl ring may influence the compound's solubility, metabolic stability, and binding affinity to biological receptors.

Recent research has highlighted the importance of 4-(4-Ethylphenyl)-3-thiosemicarbazide in developing novel therapeutic agents. Studies have demonstrated that derivatives of thiosemicarbazide can exhibit inhibitory effects on enzymes such as monoamine oxidase (MAO) and xanthine oxidase (XO). These enzymes are implicated in various pathological conditions, including neurodegenerative diseases like Parkinson's disease and gout, respectively. The structural features of 4-(4-Ethylphenyl)-3-thiosemicarbazide make it a promising candidate for modulating these enzymes' activity.

In addition to its enzyme inhibition properties, 4-(4-Ethylphenyl)-3-thiosemicarbazide has shown promise in anticancer research. Preclinical studies have indicated that thiosemicarbazide derivatives can induce apoptosis in cancer cells by disrupting mitochondrial function and inhibiting key signaling pathways involved in cell proliferation. The ethyl-substituted phenyl ring may enhance the compound's ability to interact with specific cancer cell targets, improving its selectivity over normal cells. Further investigation into the mechanisms of action of 4-(4-Ethylphenyl)-3-thiosemicarbazide could lead to the development of novel chemotherapeutic strategies.

The synthesis of 4-(4-Ethylphenyl)-3-thiosemicarbazide involves multi-step organic reactions, typically starting from commercially available precursors such as 4-ethylbenzaldehyde and thiourea. The reaction sequence often includes condensation steps followed by cyclization to form the thiazolidine ring system. Optimization of synthetic routes is crucial to achieve high yields and purity, which are essential for subsequent biological evaluations. Advances in synthetic methodologies have enabled the preparation of complex derivatives with tailored properties for drug discovery applications.

The pharmacokinetic profile of 4-(4-Ethylphenyl)-3-thiosemicarbazide is another critical aspect that influences its potential as a therapeutic agent. Factors such as absorption, distribution, metabolism, and excretion (ADME) need to be carefully evaluated to determine the compound's bioavailability and duration of action. Computational modeling techniques, including molecular docking and pharmacokinetic simulations, have been employed to predict how 4-(4-Ethylphenyl)-3-thiosemicarbazide interacts with biological targets and distributes within the body.

Current research trends suggest that 4-(4-Ethylphenyl)-3-thiosemicarbazide could be a valuable tool in drug discovery efforts targeting neurological disorders. The compound's ability to cross the blood-brain barrier and interact with central nervous system (CNS) receptors makes it an attractive candidate for treating conditions such as Alzheimer's disease and epilepsy. Investigating its effects on neuroprotective pathways and oxidative stress markers may provide insights into its therapeutic potential.

In conclusion, 4-(4-Ethylphenyl)-3-thiosemicarbazide (CAS No. 93693-01-7) represents a fascinating compound with diverse biological activities and synthetic versatility. Its unique structural features make it a promising candidate for further development in medicinal chemistry. Continued research into its pharmacological effects, synthetic optimization, and pharmacokinetic properties will be essential in determining its potential as a therapeutic agent.

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