307325-12-8

Basic information

• Product Name: (E)-4-(4-chlorophenyl)-2-(((E)-furan-2-ylmethylene)hydrazono)-2,3-dihydrothiazole
• Synonyms: (E)-4-(4-chlorophenyl)-2-(((E)-furan-2-ylmethylene)hydrazono)-2,3-dihydrothiazole
• CAS NO: 307325-12-8
• Molecular Formula: C₁₄H₁₀ClN₃OS
• Molecular Weight: 303.7667
• Mol File: 307325-12-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 471.9±48.0 °C(Predicted)
• Appearance: /
• Density: 1.40±0.1 g/cm3(Predicted)
• PKA: 11.35±0.10(Predicted)
• CAS DataBase Reference: (E)-4-(4-chlorophenyl)-2-(((E)-furan-2-ylmethylene)hydrazono)-2,3-dihydrothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-(4-chlorophenyl)-2-(((E)-furan-2-ylmethylene)hydrazono)-2,3-dihydrothiazole(307325-12-8)
• EPA Substance Registry System: (E)-4-(4-chlorophenyl)-2-(((E)-furan-2-ylmethylene)hydrazono)-2,3-dihydrothiazole(307325-12-8)

Safety Data

• Hazardous Substances Data: 307325-12-8(Hazardous Substances Data)

Upstream product

• 5419-96-5 furan-2-aldehyde thiosemicarbazone 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 98-01-1 furfural 

Relevant articles and documents

Synthesis, anti-HIV activity, molecular modeling study and QSAR of new designed 2-(2-arylidenehydrazinyl)-4-arylthiazoles

Taking into consideration the eminence of 1,3-thiazoles in medicinal chemistry and in a view of procuring more pronounced biological contour, the synthesis of 2-(2-arylidenehydrazinyl)-4-arylthiazoles 6–43 was made possible by the cyclization reaction of thiosemicarbazones and α-bromoacetophenones. The thiosemicarbazones 5a-m were in turn synthesized from substituted benzaldehydes or acetophenones and thiosemicarbazide. Optimization of the reaction conditions was carried out in order to attain the target molecules in good yields. All the new compounds were evaluated in vitro for their antiviral activity against the replication of HIV-1 and HIV-2 in MT4 cells using a MTT assay. Screening results indicated that compounds 32–34 are the only compounds in the series inhibiting HIV-1 and HIV-2 replication in cell cultures with IC50 of >2.71, >2.19 and > 1.71 μM, respectively. The molecular docking of compounds 32 and 34 with some amino acids of human immunodeficiency virus reverse transcriptase (HIV RT) were also studied. The preliminary quantum structure-activity relationship (QSAR) among the newly synthesized congeners was obtained by two methods, Multiple Linear Regression (MRL) and Genetic Function Approximation (GFA).

Synthesis of a novel series of thiazole-based histone acetyltransferase inhibitors

Acetylation, which targets a broad range of histone and non-histone proteins, is a reversible mechanism and plays a critical role in eukaryotic genes activation/deactivation. Acetyltransferases are very well conserved through evolution. This allows the use of a simple model organism, such as budding yeast, for the study of their related processes and to discover specific inhibitors. Following a simple yeast-based chemogenetic approach, we have identified a novel HAT (histone acetyltransferase) inhibitor active both in vitro and in vivo. This new synthetic compound, 1-(4-(4-chlorophenyl)thiazol-2- yl)-2-(propan-2-ylidene)hydrazine, named BF1, showed substrate selectivity for histone H3 acetylation and inhibitory activity in vitro on recombinant HAT Gcn5 and p300. Finally, we tested BF1 on human cells, HeLa as control and two aggressive cancer cell lines: a neuroblastoma from neuronal tissue and glioblastoma from brain tumour. Both global acetylation of histone H3 and specific acetylation at lysine 18 (H3AcK18) were lowered by BF1 treatment. Collectively, our results show the efficacy of this novel HAT inhibitor and propose the utilization of BF1 as a new, promising tool for future pharmacological studies.