6028-93-9

Usage

Chemical Structure

A compound with a thienyl group at the 1-position, a 4-methoxyphenyl group at the 3-position, and a ketone group at the 2-position of a propene molecule.

Physical State

Yellow solid

Molecular Weight

198.22 g/mol

Uses

a. Manufacturing of various pharmaceuticals and organic compounds
b. Potential antioxidant and anti-inflammatory properties
c. Investigated as a potential treatment for various diseases and conditions

Unique Properties

Its unique chemical structure and properties make it a valuable ingredient in the production of medications and other chemical compounds.

Upstream product

• 88-15-3 2-Acetylthiophene 
• 123-11-5 4-methoxy-benzaldehyde 
• 98-03-3 thiophene-2-carbaldehyde 

Downstream Products

• 128342-41-6 4-(4-methoxyphenyl)-6-(thiophen-2-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile 
• 136786-72-6 5-(4-Methoxy-phenyl)-3-thiophen-2-yl-4,5-dihydro-1H-pyrazole 
• 957761-00-1 5-(4-methoxyphenyl)-3-(thiophen-2-yl)-4,5-dihydropyrazole-1-carbothioamide 
• 154419-89-3 1-(chloroacetyl)-3-(2-thienyl)-5-(4-methoxyphenyl)-2-pyrazoline 
• 1126639-64-2 C₂₀H₁₆ClNOS₂ 
• 1126639-68-6 C₂₂H₂₁NO₂S₂ 
• 1126639-66-4 C₂₁H₁₉NOS₂ 
• 1126639-63-1 2,5-dihydro-8-fluoro-2-(4-methoxyphenyl)-4-(2-thienyl)-1,5-benzothiazepine 
• 1126639-67-5 C₂₁H₁₉NO₂S₂ 
• 1182077-91-3 4-(4-methoxyphenyl)-6-(thiophen-2-yl)-2,2'-bipyridine 
• 1281979-82-5 C₁₅H₁₅N₃O₂S 
• 20264-73-7 3-(4-methoxy-phenyl)-1-phenyl-5-thiophen-2-yl-4,5-dihydro-1H-pyrazole 
• 852538-50-2 C₂₀H₁₆N₄O₅S 
• 59035-74-4 3-(4-Methoxy-phenyl)-5-thiophen-2-yl-4,5-dihydro-1H-pyrazole 

Relevant academic research and scientific papers

Synthesis, Characterization, Biological Evaluation and Molecular Docking Studies of Some Oxazinyl-Thiazolidinone Derivatives

A series of new 4-thiazolidinone derivatives of 2-(4-chlorophenyl)-3-(6-(thiophen-2-yl)-4-p-tolyl-4H-1,3-oxazin-2-yl)-thiazolidin-4-one (7h-m) are synthesized because of its wide range of biological activities.1H & 13C NMR, IR studie

Discovery of Novel Approach for Regioselective Synthesis of Thioxotriaza-Spiro Derivatives via Oxalic Acid

A vital approach for the synthesis of a range of novel thioxotriaza-spiro derivatives is described. These new heterocyclic systems are obtained via oxalic acid catalyzed reaction of α,β-unsaturated ketones in the presence of 5,6-diamino-2-mercaptopyrimidi

Investigating the Anticancer Activity of Isatin/Dihydropyrazole Hybrids

A series of isatin-dihydropyrazole hybrids have been synthesized in order to assess their potential as anticancer agents. In particular, 12 compounds were evaluated for their antiproliferative activity toward A549, IGR39, U87, MDA-MB-231, MCF-7, BT474, Bx

Application of Polyphosphoric Acid-Mediated Acyl Migration for Regiospecific Synthesis of Diverse 2-Acylpyrroles from Chalcones

A metal-free approach for the synthesis of 2-acylpyrroles is reported in this paper. Synthesis of the target molecule started from chalcones and was carried out in two steps. Initial step involved the conversion of chalcones to corresponding 4-substituted-3-acylpyrroles by reaction with TosMIC. In the subsequent step, target molecules were obtained in modest to good yields by polyphosphoric acid-mediated acyl rearrangement of 3-acylpyrroles to their 2-acyl congeners. The crucial final step was amenable to diverse substitutions on pyrrole ring. Preliminary experiment for the determination of mechanism indicated the involvement of acylium ion.

Synthesis, molecular modeling, and biological evaluation of 4-[5-aryl-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl] benzenesulfonamides toward acetylcholinesterase, carbonic anhydrase I and II enzymes

In this study, 4-[5-aryl-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl] benzenesulfonamides were synthesized, and inhibition effects on AChE, hCA I, and hCA II were evaluated. Ki values of the compounds toward hCA I were in the range of 24.2?±?4.6-49.8?±?12.8?nm, while they were in the range of 37.3?±?9.0-65.3?±?16.7?nm toward hCA II. Ki values of the acetazolamide were 282.1?±?19.7?nm and 103.60?±?27.6?nm toward both isoenzymes, respectively. The compounds inhibited AChE with Ki in the range of 22.7?±?10.3-109.1?±?27.0?nm, whereas the tacrine had Ki value of 66.5?±?13.8?nm. Electronic structure calculations at M06-L/6-31?+?G(d,p)//AM1 level and molecular docking studies were also performed to enlighten inhibition mechanism and to support experimental findings. Results obtained from calculations of molecular properties showed that the compounds obey drug-likeness properties. The experimental and computational findings obtained in this study might be useful in the design of novel inhibitors against hCA I, hCA II, and AChE.

Fighting against alzheimer’s disease: Synthesis of new pyrazoline and benzothiazole derivatives as new acetylcholinesterase and MAO inhibitors

Background: Alzheimer’s Disease (AD) is a complicated neurodegenerative disorder with a multifaceted pathogenesis.AD, characterized by gradual memory loss, falling in language ability and other cognitive deterioration, and has been a prominent risk to ageing population. This means that there is an urgent need to find new lead compounds for controlling and fighting against (AD). In this way, a new thiophene-2-pyrazoline derivatives (A1-A5) and benzothiazole derivatives (A6-A13) have been synthesized to give beneficial compounds to controlling and battling against (AD). Results: Compounds A5 and A13 showed the most remarkable activity with an 18.53 μM and 15.26 μM IC50 values against AChE enzyme. In like manner, compound A4 was active with a 20.34 μM IC50 value against MAO-A. These active compounds are in fact non-toxic making them very attractive for additional future studies. Enzyme kinetic was analyzed and the Lineweaver-Burk plot reveals that compound A13 was typically mixed AChE inhibitors, which showed significant similarity to donepezil. In addition, the best docking pose was done by analyzing the docking pattern of the most active compound A13 which was very compatible with the gorge and in interaction with both CAS and PAS. Conclusion: The synthesis of new thiophene-2-pyrazoline and benzothiazole derivatives targeting AChE/(MAO-A)/(MAO-B) enzymes was described. The selection of enzyme-kinetic analysis, molecular docking and toxicity test was led to good understanding to the therapeutic potential for the active derivatives. Therefore, these compounds may be accepted as promising leads for future research efforts in fighting against AD.

An improved synthesis of pyrido[2,3-: D] pyrimidin-4(1 H)-ones and their antimicrobial activity

The screening of a small library of diverse chemical structures resulted in the identification of 2-thioxodihydropyrido[2,3-d]pyrimidine 10a as having broad spectrum antibacterial activity (MIC 0.49-3.9 μg mL-1), and reasonable antifungal activity (MIC 31.25 μg mL-1). An expeditious synthesis of 10a was optimized by varying solvents, catalysts and the use of microwave irradiation with the best conditions using DMF as a solvent, I2 (10 mol%) and a 30 minutes reaction time compared to 15 h for classic conventional heating. The pharmacokinetic properties and calculation of drug likeness of 10a suggested good traditional drug-like properties and led to the synthesis of a small library with seven compounds 10a and 10d-i showing broad antimicrobial activity (MIC = 0.49-7.81 μg mL-1) and selectivity indices of more than 5.6 against the normal colon cell line (CCD-33Co). The antifungal activity of compounds 10d-i was moderate to strong with MIC values of 1.95-15.63 μg mL-1.

Facile one pot multicomponent synthesis of novel 4-(benzofuran-2-yl)-2-(3-(aryl/heteryl)-5-(aryl/heteryl)-4,5-dihydro-1H-pyrazol-1yl)thiazole derivatives

An efficient base catalyzed one pot multicomponent reaction of aryl/hetryl chalcones, thiosemicarbazide and 1-(benzofuran-2-yl)-2-bromoethan-1-one was developed to synthesize the novel 4-(benzofuran-2-yl)-2-(3-(aryl/heteryl)-5-(aryl/heteryl)-4,5-dihydro-1H-pyrazol-1yl)thiazole derivatives.

Luminescent PtII Complexes of Tridentate Cyclometalating 2,5-Bis(aryl)-pyridine Ligands

Bis-cyclometalated PtII complexes of dianionic 2,5-bis(aryl)-pyridine ligands (L1–6)2–, carrying various cyclometalating or pending aryl groups, are synthesised in two steps. The reactions of H2L protoligands with K2[PtCl4] in acetic acid give the mono-cyclometalated complexes [Pt(HL)Cl]2. Heating these complexes in hot DMSO (dimethyl sulfoxide) yields the double-cyclometalated DMSO complexes [Pt(L1–6)(DMSO)]. The reaction of [Pt(L4)(DMSO)] with N,N-dimethylimidazolium iodide in the presence of KOtBu as the base gives the carbene complex [Pt(L4)(Me2Imd)]. Detailed photophysical studies reveal the intense orange luminescence of these complexes in CH2Cl2 solution, with quantum yields up to 0.22, and increased quantum yields of up to 1.00 in glassy frozen CH2Cl2/MeOH (1:1) and up to 0.44 in PMMA matrices. Detailed electrochemistry (including spectroelectrochemistry) reveals reversible ligand-based first reductions at –2.1 to –2.3 V, irreversible Pt-centred oxidations at around 0.8 V and electrochemical band gaps of 2.8–3.0 eV. Further reduction waves at very negative potentials interfere with the solvent (THF with traces of water) discharge and can be traced, with UV/Vis spectroelectrochemistry, to Pt-centred reductions for the DMSO complexes and to a second ligand-centred reduction for the Me2Imd complex from. The photo/electrochemical properties can be roughly correlated with the ligand pattern and suggest their use in optoelectronic applications.

Synthesis and cytotoxicity evaluation of new 3-substituted 4-(4-methyloxy phenyl)-1H-pyrrole derivatives

A new series of 3-substituted 4-(4-methyloxy phenyl)-1H-pyrrole derivatives were synthesized and biologically evaluated for potential anticancer activity. Fifteen targeted compounds showed high selectivity toward normal cells and cancer cells: that is, al