40207-03-2

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-Methoxyphenyl)-3-thiosemicarbazide is used as an active pharmaceutical ingredient for its potential antifungal and antimicrobial properties. It can be formulated into medications to combat various fungal and bacterial infections.
Used in Agrochemical Industry:
In the agrochemical sector, 4-(4-Methoxyphenyl)-3-thiosemicarbazide is used as a bioactive compound with potential applications in the development of fungicides and bactericides to protect crops from diseases and enhance agricultural productivity.
Used in Materials Science:
4-(4-Methoxyphenyl)-3-thiosemicarbazide is utilized as a corrosion inhibitor in materials science, helping to protect metal surfaces from corrosion and extending the lifespan of various industrial equipment and structures.
Used in Coordination Chemistry:
As a ligand in coordination chemistry, 4-(4-Methoxyphenyl)-3-thiosemicarbazide is used to form coordination compounds with metal ions. These complexes have potential applications in catalysis, sensing, and other areas of chemistry and materials science.
With ongoing research, 4-(4-Methoxyphenyl)-3-thiosemicarbazide may discover additional uses in the future, further expanding its relevance and contribution to scientific and industrial applications.

InChI:InChI=1/C8H11N3OS/c1-12-7-4-2-6(3-5-7)10-8(13)11-9/h2-5H,9H2,1H3,(H2,10,11,13)

Upstream product

• 2284-20-0 4-Methoxyphenyl isothiocyanate 
• 1219-96-1 N-(p-methoxyphenyl)-N'-phenylthiourea 
• 75-15-0 carbon disulfide 
• 104-94-9 4-methoxy-aniline 
• 54379-86-1 -essigsaeure 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 90-04-0 2-methoxy-phenylamine 
• 15867-08-0 N-(p-methoxyphenyl)dithiocarbamic acid 
• 2293-07-4 1-(4-methoxyphenyl)thiourea 
• 3926-62-3 sodium monochloroacetic acid 
• 302-01-2 hydrazine 
• 15866-98-5 ammonium salt of N-p-anisylamino dithiocarbamic acid 
• 1142816-82-7 C₈H₈NOS₂^(1-)*K⁽¹⁺⁾ 

Downstream Products

• 92193-33-4 (E)-N-(4-methoxyphenyl)-2-(pyridin-2-ylmethylene)hydrazine-1-carbothioamide 
• 107682-76-8 pyridine-3-carbaldehyde-[4-(4-methoxy-phenyl)-thiosemicarbazone] 
• 107681-95-8 pyridine-4-carbaldehyde-[4-(4-methoxy-phenyl)-thiosemicarbazone] 
• 101353-09-7 1-(4-chloro-phenylcarbamoyl)-4-(4-methoxy-phenyl)-thiosemicarbazide 
• 740-86-3 4-methoxy-benzaldehyde 4-(4-methoxy-phenyl)-thiosemicarbazone 
• 738-81-8 2-(2-hydroxybenzylidene)-N-(4'-methoxyphenyl)hydrazinecarbothioamide 
• 21123-55-7 N-(4-methoxy-phenyl)-N'-phenyl-[1,3,4]thiadiazole-2,5-diamine 
• 90840-58-7 3-amino-2-(4-methoxy-phenylimino)-thiazolidin-4-one 
• 61955-51-9 (4-methoxy-phenyl)-[1,3,4]thiadiazol-2-yl-amine 
• 740-87-4 3-phenyl-propenal 4-(4-methoxy-phenyl)-thiosemicarbazone 
• 20158-25-2 2-methoxy-benzaldehyde 4-(4-methoxy-phenyl)-thiosemicarbazone 
• 82236-71-3 C₁₇H₁₆N₄O₂S 
• 79560-79-5 1-(N-methylisatin)-4-(4'-methoxyphenyl)-3-thiosemicarbazone 
• 68337-44-0 4-(4-Methoxyphenyl)-5-methyl-4H-1,2,4-triazole-3-thiol 

Relevant academic research and scientific papers

A new organometallic palladium(II) compound derived of 2,6-diacetylpyridine mono(thiosemicarbazone): Synthesis, spectroscopic properties and crystal structure of two solvatomorphic forms

Preparation and characterization of a novel 2,6-diacetylpyridine mono(4-methoxyphenyl-thiosemicarbazone), H2L, is described. Treatment of H2L with PdCl2(PPh3)2 gave the neutral mononuclear complex [Pd

New thiosemicarbazide-1,2,3-triazole hybrids as potent α-glucosidase inhibitors: Design, synthesis, and biological evaluation

A new series of thiosemicarbazide-1,2,3-triazole hybrids 10a-o has been synthesized, characterized by 1H NMR, 13C NMR, and screened for their in vitro α-glucosidase inhibitory activity. All of the synthesized compounds displayed excellent α-glucosidase inhibitory activity with IC50 values in the range of 75.0 ± 0.5 to 253.0 ± 0.5 μM, as compared to the standard drug acarbose (IC50 = 750.0 ± 1.5 μM). Among the synthesized compounds, compound 10h (IC50 = 75.0 ± 0.5)with 4-methoxy group at phenyl part of thiosemicarbazide moiety and 2,6-dichloro substituents at benzyl moiety was found to be the most potent compound. Kinetic analysis revealed that compound 10h is a competitive inhibitor for α-glucosidase. Docking study of compound 10h in the active site of α-glucosidase showed that this compound interacted with residues His239, His279, Glu304, Gly306, and Arg312.

Oxadiazol-based mTOR inhibitors with potent antiproliferative activities: synthetic and computational modeling

Series of N-aryl-1,3,4-oxadiazole-2-amines and 3-aryl-1,2,4-oxadiazole-5-carboxamides derivatives were synthesized as novel chemotherapeutic agents. Synthesized compounds were evaluated for their anticancer activities against several cancer cell lines. Many analogues of 1,3,4-oxadiazole scaffold showed potent antiproliferative activities against breast cancer cell lines, with higher activities toward the metastatic breast cancer cell line (MDA-MB-231). Active analogues were profiled using in-house pharmacophore database in search for molecular target. Active analogues (2j and 2k) were found to fit the pharmacophoric map of ATP-competitive inhibitors of mTOR. The mTOR inhibitory activities of the most active compounds were confirmed with IC50 values in nanomolar range. The N-aryl-1,3,4-oxadiazole-2-amines linked to a basic head is a novel ATP-competitive inhibitors of mTOR with potential activities for treatment of different types of cancer. Graphical abstract: [Figure not available: see fulltext.].

Diaryl-substituted thiosemicarbazone: A potent scaffold for the development of New Delhi metallo-β-lactamase-1 inhibitors

The superbug infection caused by New Delhi metallo-β-lactamase (NDM-1) has become an emerging public health threat. Inhibition of NDM-1 has proven challenging due to its shuttling between pathogenic bacteria. A potent scaffold, diaryl-substituted thiosemicarbazone, was constructed and assayed with metallo-β-lactamases (MβLs). The obtained twenty-six molecules specifically inhibited NDM-1 with IC50 0.038–34.7 μM range (except 1e, 2e, and 3d), and 1c is the most potent inhibitor (IC50 = 0.038 μM). The structure-activity relationship of synthetic thiosemicarbazones revealed that the diaryl-substitutes, specifically 2-pyridine and 2-hydroxylbenzene improved inhibitory activities of the inhibitors. The thiosemicarbazones exhibited synergistic antimycobacterial actions against E. coli-NDM-1, resulted a 2–512-fold reduction in MIC of meropenem, while 1c restored 16–256-, 16-, and 2-fold activity of the antibiotic on clinical isolates ECs, K. pneumonia and P. aeruginosa harboring NDM-1, respectively. Also, mice experiments showed that 1c had a synergistic antibacterial ability with meropenem, reduced the bacterial load clinical isolate EC08 in the spleen and liver. This work provided a highly promising scaffold for the development of NDM-1 inhibitors.

Synthesis and antimicrobial activities of new thiosemicarbazones and thiazolidinones in indole series

Abstract: New thiosemicarbazones were synthesized in excellent yield reaction of indole derivatives with thiosemicarbazides. These thiosemicarbazones were reacted with ethyl bromoacetate to produce original heterocyclic-substituted indole derivatives possessing a 4-oxo-thiazolidine group. Analytical IR and NMR spectra and elemental analysis were performed to reveal their structures. The antimicrobial activity of all synthesized compounds was evaluated for antibacterial activity in vitro against Gram-positive and Gram-negative bacteria. Antibacterial screening data showed that two compounds demonstrated activity against Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. These preliminary results indicate that some of these newly synthesized compounds show a promising antibacterial potency. Graphic abstract: [Figure not available: see fulltext.].

Synthesis and Antiproliferative Activity of New Thiosemicarboxamide Derivatives

To discover new anticancer agents, two series of thiosemicarboxamide derivatives were synthesized and evaluated for their antiproliferative activity against human cancer cells in vitro. Most target compounds (especially 3f, 3g, and 3h) exhibit potent antiproliferative activity against HeLa cells. Importantly, compound 3h, bearing a 4-methylphenyl substituent at N position of thiourea moiety, has significant and broad-spectrum inhibitory activities against cancer cells (HepG2, HeLa, MDA-MB231, A875, and H460 cells) with low IC50 values (5.0 μM) and shows low toxicity to normal LO2 and MRC-5 cells. Further studies show that compound 3h exerts high inhibitory activity in cancer cells by inducing the G2/M-phase arrest of cancer cells. Collectively, this study presents compound 3h as a new entity for the development of cell cycle arrest inducers for the treatment of cancer.

Preparation and application of thiosemicarbazone compound

The invention discloses a thiosemicarbazone compound, and biological activity analysis is carried out on the thiosemicarbazone compound. The invention also discloses application of the thiosemicarbazone compound in preparation of antibacterial drugs. According to the invention, important intermediates 6a-6h are synthesized from hydrazine hydrate and react with adamantane benzaldehyde respectivelyto synthesize eight adamantane aromatic aldehyde thiosemicarbazone compounds, the structures of the compounds can be confirmed by infrared, nuclear magnetic hydrogen spectrum, carbon spectrum and massspectrum methods, and the antibacterial activity of the compounds is tested in vitro. The result shows that the compound has a good antibacterial effect on escherichia coli and bacillus subtilis.

Carbazole-based semicarbazones and hydrazones as multifunctional anti-Alzheimer agents

With the aim to combat a multi-faceted neurodegenerative Alzheimer’s disease (AD), a series of carbazole-based semicarbazide and hydrazide derivatives were designed, synthesized and assessed for their cholinesterase (ChE) inhibitory, antioxidant and biometal chelating activity. Among them, (E)-2-((9-ethyl-9H-carbazol-3-yl)methylene)-N-(pyridin-2-yl)hydrazinecarbothioamide (62) and (E)-2-((9-ethyl-9H-carbazol-3-yl)methylene)-N-(5-chloropyridin-2-yl)hydrazinecarbothioamide (63) emerged as the premier candidates with good ChE inhibitory activities (IC50 values of 1.37 μM and 1.18 μM for hAChE, IC50 values of 2.69 μM and 3.31 μM for EqBuChE, respectively). All the test compounds displayed excellent antioxidant activity (reduction percentage of DPPH values for compounds (62) and (63) were 85.67% and 84.49%, respectively at 100 μM concentration). Compounds (62) and (63) conferred specific copper ion chelating property in metal chelation study. Molecular docking studies of compounds (62) and (63) indicate strong interactions within the active sites of both the ChE enzymes. Besides that, these compounds also exhibited significant in silico drug-like pharmacokinetic properties. Thus, taken together, they can serve as a starting point in the designing of multifunctional ligands in pursuit of potential anti-AD agents that might further prevent the progression of ADs. Communicated by Ramaswamy H. Sarma.

Synthesis and antibacterial activity of novel Schiff bases of thiosemicarbazone derivatives with adamantane moiety

Increased bacterial resistance to antibiotics is a major threat to human health, and it is particularly important to develop novel antibiotic drugs. Here, we designed a series of Schiff base thiosemicarbazone derivatives containing an adamantane moiety, and carried out the structural characterization of the compounds and in vitro antibacterial activity tests. Compound 7e was as effective as the commonly used antibiotic ampicillin against the Gram-negative bacterium Escherichia coli, and compound 7g had a good inhibitory effect against Gram-positive Bacillus subtilis. These findings provide data for the development of better thiosemicarbazone antibacterial agents.

1,3,4-thiadiazine compound and application thereof

The invention relates to a 1,3,4-thiadiazine compound, and the chemical structure of the compound is shown as a formula (I). The provided compound has a remarkable inhibition effect on human cervicalcancer cells Hela and human colon cancer cells HCT116, a