20234-13-3

Usage

General Description

2-[(E)-(3-chloro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]hydrazinecarbothioamide is a chemical compound with the molecular formula C8H8ClN3OS. It is a derivative of hydrazinecarbothioamide and is commonly used in organic synthesis and pharmaceutical research. 2-[(E)-(3-chloro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]hydrazinecarbothioamide has potential biological activity and may be used in the development of new drugs or therapies. The chlorine and oxocyclohexa-2,4-dien-1-ylidene functional groups make 2-[(E)-(3-chloro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]hydrazinecarbothioamide versatile for use in various chemical reactions and applications. However, further research is needed to fully understand its properties and potential uses in different fields.

Upstream product

• 4346-94-5 thiosemicarbazide hydrochloride 
• 635-93-8 5-chlorosalicyclaldehyde 
• 79-19-6 thiosemicarbazide 
• 2420-26-0 4-chlorosalicylaldehyde 

Downstream Products

• 105790-18-9 5-chloro-2-hydroxy-benzaldehyde (4-oxo-5-propyl-thiazolidin-2-ylidene)-hydrazone 
• 133296-85-2 5-chloro-2-hydroxy-benzaldehyde [5-(4-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 167864-48-4 Sn(CH₃)3Cl(C₈H₈N₃OSCl) 
• 899098-14-7 2-(2-(5-chloro-2-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one 
• 167864-49-5 Sn(C₆H₅)2Cl₂(C₈H₈N₃OSCl) 
• 676519-49-6 2-(2-hydroxy-5-chloro)benzaldehyde-[4-(3-methyl-3-mesitylcyclobutyl)-1,3-thiazol-2-yl]hydrazone 
• 108622-59-9 5-chloro-2-hydroxy-benzaldehyde (5-butyl-4-oxo-thiazolidin-2-ylidene)-hydrazone 

Relevant academic research and scientific papers

Aryl hydrazones linked thiazolyl coumarin hybrids as potential urease inhibitors

Aryl hydrazones bearing thiazolyl coumarin hybrids 1–32 were prepared by following 'one-pot' two-steps reaction scheme. Various arylaldehydes were reacted to thiosemicarbazide under acidic condition to form aryl thiosemicarbazone intermediates which in turn treated with 3-bromoacetyl coumarin under basic condition to afford thiazolyl coumarin hybrids 1–32. All hybrids were recognized by EI- and HREI-MS and 1H- and 13C-NMR spectroscopic techniques. Compounds 1–32 were screened for in vitro inhibitory activity against urease enzyme and displayed good to moderate inhibitory potential in the ranges of IC50 = 16.29 ± 1.1–256.30 ± 1.4?μM. Worth stating that compound 21 (IC50 = 16.29 ± 1.1?μM) was identified as more potent urease inhibitor than the standard acetohydroxamic acid (IC50 = 27.0 ± 0.5?μM). Derivatives 19 (IC50 = 77.67 ± 1.5?μM) and 30 (IC50 = 71.21 ± 1.6?μM) were found to be moderately active. Structure–activity relationship revealed that -F, -Cl, -OH, and -OMe groups and their respective positions on aryl ring are playing important role in urease enzyme inhibition. Molecular docking studies identified important interaction between the ligand (active hybrids) and urease active site.

Iron complex taking 5-chloro-2-hydroxybenzaldehyde thiosemicarbazone as ligand as well as synthesis method and application thereof

The invention discloses an iron complex taking 5-chloro-2-hydroxybenzaldehyde thiosemicarbazone as a ligand as well as a synthesis method and application of the iron complex. The method comprises thesteps: taking 4,4-dimethyl thiosemicarbazone, 4-methyl thiosemicarbazone or thiosemicarbazone and 5-chloro-2-hydroxybenzaldehyde are respectively as raw materials to synthesize a Schiff base ligand; and reacting the synthesized ligand with ferric trichloride to obtain the iron complex. The structures of the three iron complexes synthesized by the method are brand-new structures; and experiments show that the iron complex has good anti-tumor activity on human ovarian cancer cells SKOV3, can effectively inhibit proliferation of ovarian cancer cells, is suitable for preparing drugs for treating ovarian cancer, has a more remarkable treatment effect than existing clinical drugs cis-platinum, and can prevent proliferation of cancer cells in the S phase.

Synthesis, screening and biological activity of potent thiosemicarbazone compounds as a tyrosinase inhibitor

Tyrosinase plays an essential role in melanogenesis. Tyrosinase inhibition may not only be a means to alleviate skin hyperpigmentation, but also the most effective method for fruit and vegetable preservation. Thiosemicarbazone compounds have received enormous attention because of their potential therapeutic activities due to their antitumoral, antibacterial and antimalarial properties. In this study, we focused on the screening, toxicity, interaction and inhibitory activities of potent thiosemicarbazone compounds as novel tyrosinase inhibitors. The results showed that the inhibitor effectiveness was drastically reduced by the absence of the ortho-hydroxyl group and was improved by changing the substituents of benzaldehyde. To develop a pharmacophore model, we explored the binding mode of thiosemicarbazone compounds in the active site of tyrosinase. Docking analysis using an AUTODOCK program was conducted to explain the flexible thiosemicarbazone molecules binding with the active site of tyrosinase, because of their perfect match with both the active site and the substrate channel of tyrosinase in both size and hydrophobicity. Their binding was mainly stabilized via both the coordination of the sulfur and nitrogen atoms in the inhibitors to binuclear copper in the tyrosinase active site. Further complementary studies on these types of inhibitors, such as for potential drug candidates for treating abnormal melanin pigmentation and inhibiting food or fruit browning, are still needed.

Fluorescent probe adopting Schiff base type structure as well as preparation method and applications of fluorescent probe

The invention relates to a fluorescent probe adopting a Schiff base type structure. The structural formula of the fluorescent probe is shown in the description; and R is any one of H, Br and Cl. Thiosemicarbazide is dissolved in absolute ethyl alcohol, a

Design, Synthesis, and Evaluation of 3-((4-(t-Butyl)-2-(2-benzylidenehydrazinyl)thiazol-5-yl)methyl)quinolin-2(1H)-ones as Neuraminidase Inhibitors

A series of novel 3-((4-(t-butyl)-2-(2-benzylidenehydrazinyl)thiazol-5-yl)methyl)quinolin-2(1H)-ones (7a-7z) were designed, synthesized and evaluated for their ability of inhibiting neuraminidase (NA) of in?uenza H1N1 virus. Some compounds displayed moder

Synthesis and characterization of some new Cu(II), Ni(II) and Zn(II) complexes with salicylidene thiosemicarbazones: Antibacterial, antifungal and in vitro antileukemia activity

Thirty two new Cu(II), Ni(II) and Zn(II) complexes (1-32) with salicylidene thiosemicarbazones (H2L1-H2L10) were synthesized. Salicylidene thiosemicarbazones, of general formula (X)N-NH-C(S)-NH(Y), were prepared

Structure-activity relationship study of thiosemicarbazones on an African trypanosome: Trypanosoma brucei brucei

To explore the structure-activity relationships of thiosemicarbazones on African trypanosome: Trypanosoma brucei brucei, a series of thirty-five thiosemicarbazones (1-35) have been synthesized and characterized by their 1H NMR, 13C NMR, and FT-IR spectra. All compounds were tested for trypanocidal activity using the method "Lilit alamar blue". The comparison of trypanocidal power of thiosemicarbazones was performed considering their structures. This study that was done using acetophenone thiosemicarbazone (1) as basic model, showed that: (a) the presence of lipophilic substituents in para position on benzene ring, (b) substitution of benzene ring and (c) substitution of hydrogen of thioamide function by a phenyl, strongly influence trypanocidal activity. The various modifications to basic structure (1) allowed the synthesis of 1-(4-chlorophenyl) ethylidene-4-phenyl- thiosemicarbazide (34). With a trypanocidal activity of 3.97 μM, this compound is the most active of the series.

Synthesis and crystal structures of dioxomolybdenum(VI) complexes with ONS-donor ligands

Three dioxomolybdenum complexes namely dioxo(5-chlorosalicylaldehyde thiosemicarbazonato) dimethylsulfoxide molybdenum(VI) (C1), dioxo(5- chlorosalicylaldehyde 2-ethylthiosemicarbazonato) dimethylsulfoxide molybdenum(VI) (C2) and dioxo(5-chlorosalicylalde

Synthesis and in vitro evaluation of palladium(II) salicylaldiminato thiosemicarbazone complexes against Trichomonas vaginalis

Eight mononuclear Pd(II) complexes containing salicylaldiminato thiosemicarbazones (saltsc-R; where R = H (1), 3-OMe (2), 3-tBu (3) and 5-Cl (4)) as dinegative tridentate ligands were prepared by the reaction of the corresponding thiosemicarbazone with the precursor Pd(L)2Cl 2 (L = phosphatriazaadamantane or 4-picoline) in the presence of a weak base. These complexes (9-16) were characterised by a range of spectroscopic and analytical techniques including NMR spectroscopy and X-ray diffraction. These complexes along with four other Pd(II) analogues (5-8) were screened for activity in vitro against the Trichomonas vaginalis parasite. Preliminary results show that the type of ancillary ligand as well as the substituents on the aromatic ring of the salicylaldiminato thiosemicarbazone ligand influences the antiparasitic activity of these complexes.

Design, synthesis and biological evaluation of thiazolidinone derivatives as potential EGFR and HER-2 kinase inhibitors

Two series of thiazolidinone derivatives designing for potential EGFR and HER-2 kinase inhibitors have been discovered. Some of them exhibited significant EGFR and HER-2 inhibitory activity. Compound 2-(2-(5-bromo-2-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one (12) displayed the most potent inhibitory activity (IC50 = 0.09 μM for EGFR and IC50 = 0.42 μM for HER-2), comparable to the positive control erlotinib. Docking simulation was performed to position compound 12 into the EGFR active site to determine the probable binding model. Antiproliferative assay results indicating that some of the thiazolidinone derivatives own high antiproliferative activity against MCF-7. Compound 12 with potent inhibitory activity in tumor growth inhibition would be a potential anticancer agent.