459-38-1

Basic information

• Product Name: 4-fluorobenzaldehyde thiosemicarbazone
• Synonyms: (2E)-2-(4-Fluorobenzylidene)hydrazinecarbothioamide; 2-(4-fluorobenzylidene)hydrazine-1-carbothioamide
• CAS NO: 459-38-1
• Molecular Formula: C₈H₈FN₃S
• Molecular Weight: 197.2326
• Mol File: 459-38-1.mol

Chemical Properties

• Boiling Point: 311.45°C at 760 mmHg
• Flash Point: 142.16°C
• Density: 1.31g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.608
• CAS DataBase Reference: 4-fluorobenzaldehyde thiosemicarbazone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-fluorobenzaldehyde thiosemicarbazone(459-38-1)
• EPA Substance Registry System: 4-fluorobenzaldehyde thiosemicarbazone(459-38-1)

Safety Data

• Hazardous Substances Data: 459-38-1(Hazardous Substances Data)

Upstream product

• 155401-44-8 2,4-bis(4-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-one 
• 79-19-6 thiosemicarbazide 
• 4346-94-5 thiosemicarbazide hydrochloride 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 401-47-8 5-propyl-thiazolidine-2,4-dione-2-(4-fluoro-benzylidenehydrazone) 
• 351-76-8 2-(2-(4-fluorobenzylidene)hydrazinyl)thiazol-4(5H)-one 
• 1338084-29-9 C₁₈H₁₇FN₆O₃S 
• 1338083-74-1 C₁₃H₉FN₆O₂S 
• 1338084-08-4 C₁₃H₈FN₅O₂S 
• 1431555-43-9 4-[[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-ylimino]-methyl]phenol 

Relevant articles and documents

Synthesis and characterization of 4-fluorobenzaldehyde thiosemicarbazone derivatives as corrosion inhibitors

In this paper, we report the syntheses, characterization and studies on the inhibition efficiency in mild steel acidic corrosion of 4-fluorobenzaldehyde thiosemicarbazone, Hfbt, 4-fluorobenzaldehyde 2-methylthiosemicarbazone, Me-fbt, and their Zn(II) comp

Synthesis, anti-Trypanosoma cruzi activity and quantitative structure relationships of some fluorinated thiosemicarbazones

Synthesis and spectroscopic characterization of ten fluorinated thiosemicarbazones are reported. All synthesized compounds were evaluated for their anti-Trypanosoma cruzi activity, and the IC50values were obtained in the range of 5.64–29.19 μg

Synthesis, antimicrobial and antioxidant evaluation with in silico studies of new thiazole Schiff base derivatives

A series of nineteen thiazole Schiff base derivatives 2a-2s were synthesized (Scheme 1) and elucidated by spectral analyses (IR, 1H NMR and HRMS). The evaluation of their antimicrobial activities against two gram-positive, two gram-negative, an

Discovery of new coumarin-based lead with potential anticancer, cdk4 inhibition and selective radiotheranostic effect: Synthesis, 2d & 3d qsar, molecular dynamics, in vitro cytotoxicity, radioiodination, and biodistribution studies

Novel 6-bromo-coumarin-ethylidene-hydrazonyl-thiazolyl and 6-bromo-coumarin-thiazolylbased derivatives were synthesized. A quantitative structure activity relationship (QSAR) model with high predictive power r2 = 0.92, and RMSE = 0.44 predicted five compounds; 2b, 3b, 5a, 9a and 9i to have potential anticancer activities. Compound 2b achieved the best ?G of –15.34 kcal/mol with an affinity of 40.05 pki. In a molecular dynamic study 2b showed an equilibrium at 0.8 ? after 3.5 ns, while flavopiridol did so at 0.5 ? after the same time (3.5 ns). 2b showed an IC50 of 0.0136 μM, 0.015 μM, and 0.054 μM against MCF-7, A-549, and CHO-K1 cell lines, respectively. The CDK4 enzyme assay revealed the significant CDK4 inhibitory activity of compound 2b with IC50 of 0.036 μM. The selectivity of the newly discovered lead compound 2b toward localization in tumor cells was confirmed by a radioiodination biological assay that was done via electrophilic substitution reaction utilizing the oxidative effect of chloramine-t.131 I-2b showed good in vitro stability up to 4 h. In solid tumor bearing mice, the values of tumor uptake reached a height of 5.97 ± 0.82%ID/g at 60 min p.i.131 I-2b can be considered as a selective radiotheranostic agent for solid tumors with promising anticancer activity.

Experimental and theoretical study on triazole derivatives as chelating agents to remove Fe++ Ions from wastewater in oil field

In this study, we synthesized triazole derivatives as chelating agents (3-(p-methylphenyl)-5-(phenylsulfonyl)-4H-1,2,4-triazoline (MT), 3-phenyl-5-(phenylsulfonyl)-4H-1,2,4-triazoline (PT), and 3-(p-fluorophenyl)-5-(phenylsulfonyl)-4H-1,2,4-triazoline (FT) to remove Fe++ ions from wastewater in oil field. The effect of synthesized compounds on the removal of iron (II) from iron-contaminated samples (Lab. design) and an industrial wastewater sample studied using DR5000 UV-vis spectrophotometer technique. Removal of iron was studied at different concentrations of FeSO4 solution and field sample concentration. In addition, removal of iron (II) was investigated at different times. The performance of the derivative groups (methyl and fluoro) on chelating of Fe++ ions was studied. The prepared compounds show high efficiency in removing the iron ions from the water samples used. The removal efficiency of the title molecules (MT), (PT), and (FT) was investigated using DMol3 (Materials Studio v7.0) based on quantum descriptors such as EHOMO and ELUMO. Mulliken atomic charges distribution and Fukui indices were estimated to verify the local reactive sites of the molecules. The quantum chemical parameters were found to suitable to interpret the performance of the investigated molecules as a chelating agent for Fe++.

Design, synthesis, biological evaluation, QSAR analysis and molecular modelling of new thiazol-benzimidazoles as EGFR inhibitors

Heterocyclic rings such as thiazole and benzimidazole are considered as privileged structures, since they constitute several FDA-approved drugs for cancer treatment. In this work, a new set of 2-(2-(substituted) hydrazinyl)-4-(1-methyl-1H-benzo[d]imidazol-2-yl) thiazoles 4a-q were designed as epidermal growth factor receptor (EGFR) inhibitors and synthesized using concise synthetic methods. The new target compounds have been evaluated in vitro for their suppression activity against EGFR TK. Compounds 4n, 4h, 4i, 4a and 4d exhibited significant potency in comparison with erlotinib which served as a reference drug (IC50, 71.67–152.59 nM; IC50 erlotinib, 152.59 nM). Furthermore, MTT assay revealed that compounds 4j, 4a, 4f, 4h, 4n produced the most promising cytotoxic potency against the human breast cancer cell line (MCF-7) (IC50; 5.96–11.91 μM; IC50 erlotinib; 4.15 μM). Compound 4a showed promising activity as EGFR TK inhibitor as well as anti-breast cancer agent. In addition, 4a induced apoptotic effect and cell cycle arrest at G2/M phase preventing the mitotic cycle in MCF-7 cells. Moreover, 4a upregulated the oncogenic parameters; caspase-3, p53, Bax/Bcl-2 as well as it inhibited the level of PARP-1 enzyme. QSAR study was carried out for the new derivatives and it revealed the goodness of the models. Furthermore, molecular docking studies represented the binding modes of the promising compounds in the active pocket of EGFR.

Synthesis and evaluation of 1,3,4-oxadiazole derivatives for development as broad-spectrum antibiotics

The reality and intensity of antibiotic resistance in pathogenic bacteria calls for the rapid development of new antimicrobial drugs. In bacteria, trans-translation is the primary quality control mechanism for rescuing ribosomes arrested during translation. Because trans-translation is absent in eukaryotes but necessary to avoid ribosomal stalling and therefore essential for bacterial survival, it is a promising target either for novel antibiotics or for improving the activities of the protein synthesis inhibitors already in use. Oxadiazole derivatives display strong bactericidal activity against a large number of bacteria, but their effects on trans-translation were recently questioned. In this work, a series of new 1,3,4-oxadiazole derivatives and analogs were synthesized and assessed for their efficiency as antimicrobial agents against a wide range of gram-positive and gram-negative pathogenic strains. Despite the strong antimicrobial activity observed in these molecules, it turns out that they do not target trans-translation in vivo, but they definitely act on other cellular pathways.

Novel synthesized SLC-0111 thiazole and thiadiazole analogues: Determination of their carbonic anhydrase inhibitory activity and molecular modeling studies

In the presented work, we report the design and synthesis of novel SLC-0111 thiazole and thiadiazole analogues (11a–d, 12a–d, 16a–c and 17a–d). A bioisosteric replacement approach was adopted to replace the 4-fluorophenyl tail of SLC-0111 with thiazole and thiadiazole ones, which were thereafter extended with lipophilic un/substituted phenyl moieties. All the newly synthesized SLC-0111 analogues were evaluated in vitro for their inhibitory activity towards a panel of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) isoforms (hCA I, II, IX and XII), using a stopped-flow CO2 hydrase assay. All the examined isoforms were inhibited by the primary sulfonamide derivatives (11a–d and 12a–d) in variable degrees with the following KI ranges: 162.6–7136 nM for hCA I, 9.0–833.6 nM for hCA II, 7.9–153.0 nM for hCA IX, and 9.4–94.0 nM for hCA XII. In particular, compounds 12b and 12d displayed 5.5-fold more potent inhibitory activity (KIs = 8.3 and 7.9 nM, respectively) than SLC-0111 (KI = 45 nM) towards hCA IX. Molecular docking study was carried out for 12d within the hCA IX (PDB 3IAI) active site, to justify its inhibitory activity.

Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents

A series of 5-substituted-1,3,4-thiadiazole-based fluoroquinolone derivatives were designed as potential antibacterial and anticancer agents using a molecular hybridization approach. The target compounds 16–25 were synthesized by reacting the correspondin

2 - (2 - Animal pen asia jingjing base) -5 - acyl thiazole and its medical use (by machine translation)

The invention formula I shown by 2 - (2 - animal pen asia jingjing base) - 5 - acyl thiazole and its pharmaceutically acceptable salt, pharmaceutical composition and thereof in the preparation of influenza virus neuraminidase inhibitors in the application. Wherein R is selected from: methyl, ethyl, C3 - C4 Straight-chain or C3 - C4 Branched alkyl; R1 Is selected from: hydrogen, C1 - C2 Alkyl, C3 - C4 Straight-chain or C3 - C4 Branched alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, bromomethyl, [...], three bromine methyl, chloromethyl, dichloro methyl or trichloromethyl; X1 , X5 Is selected from: hydrogen, deuterium, C1 - C2 Alkyl, hydroxy, methoxy, ethoxy, fluoro, chloro, bromo, iodo, nitro, amino, methylamino, dimethylamino, acetyl, carboxy, methoxycarbonyl or ethoxycarbonyl; X2 , X4 Is selected from: hydrogen, deuterium, C1 - C2 Alkyl, C3 - C4 Straight or branched chain alkyl, hydroxy, methoxy, ethoxy, fluoro, chloro, bromo, iodo, nitro, amino, methylamino, dimethylamino, acetyl, carboxy, methoxycarbonyl or ethoxycarbonyl; X3 Is selected from: hydrogen, deuterium, C1 - C2 Alkyl, hydroxy, methoxy, ethoxy, fluoro, chloro, bromo, iodo, nitro, amino, methylamino, dimethylamino, acetyl, carboxy, methoxycarbonyl or ethoxycarbonyl. (by machine translation)