27895-95-0

Upstream product

• 119-52-8 4,4'-dimethoxybenzoin 
• 67-66-3 chloroform 
• 7789-60-8 phosphorus tribromide 
• 100-66-3 methoxybenzene 
• 104-01-8 4-Methoxyphenylacetic acid 
• 120-44-5 1,4-di(4-methoxyphenyl)ethanone 

Downstream Products

• 64997-22-4 2,3-dihydro-5,6-bis(p-methoxyphenyl)imidazo[2,1-b]thiazole 
• 134789-92-7 3-[4,5-Bis-(4-methoxy-phenyl)-thiazol-2-yl]-pyridine 
• 134789-97-2 4,5-Bis-(4-methoxy-phenyl)-2-thiophen-2-yl-thiazole 
• 134789-94-9 2-[4,5-Bis-(4-methoxy-phenyl)-thiazol-2-yl]-6-methyl-pyridine 
• 134789-99-4 2-(5-Chloro-thiophen-2-yl)-4,5-bis-(4-methoxy-phenyl)-thiazole 
• 70529-38-3 4,5-bis-(p-methoxyphenyl)-thiazole 
• 62894-32-0 4,5-bis(4-methoxyphenyl)-2-(ethylthio)imidazole 
• 134789-98-3 4,5-Bis-(4-methoxy-phenyl)-2-(5-methyl-thiophen-2-yl)-thiazole 
• 134790-00-4 4,5-Bis-(4-methoxy-phenyl)-2-(3-methyl-thiophen-2-yl)-thiazole 
• 134790-04-8 4,5-Bis(4-methoxyphenyl)-2-(1,5-dimethyl-2-pyrrolyl)thiazole 
• 134789-96-1 2-[4,5-Bis-(4-methoxy-phenyl)-thiazol-2-yl]-6-methoxy-pyridine 
• 43045-26-7 4,5-Bis(4-methoxyphenyl)-thiazol-2-thiol 
• 134790-06-0 2-[4,5-Bis-(4-methoxy-phenyl)-thiazol-2-yl]-pyrazine 
• 24827-38-1 4,5-bis-(4-methoxyphenyl)-2-aminothiazole 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel pyrrolidone-based derivatives as potent p53-MDM2 inhibitors

Inhibition of the interactions of the tumor suppressor protein p53 with its negative regulators MDM2 in vitro and in vivo, representing a valuable therapeutic strategy for cancer treatment. The natural product chalcone exhibited moderate inhibitory activity against MDM2, thus based on the binding mode between chalcone and MDM2, a hit unsaturated pyrrolidone scaffold was obtained through virtual screening. Several unsaturated pyrrolidone derivatives were synthesized and biological evaluated. As a result, because the three critical hydrophobic pockets of MDM2 were occupied by the substituted-phenyl linked at the pyrrolidone fragment, compound 4 h demonstrated good binding affinity with the MDM2. Additionally, compound 4 h also showed excellent antitumor activity and selectivity, and no cytotoxicity against normal cells in vitro. The further antitumor mechanism studies were indicated that compound 4 h could successfully induce the activation of p53 and corresponding downstream p21 proteins, thus successfully causing HCT116 cell cycle arrest in the G1/M phase and apoptosis. Thus, the novel unsaturated pyrrolidone p53-MDM2 inhibitors could be developed as novel antitumor agents.

Synthesis, cytotoxic evaluation, and molecular docking study of 4,5-diaryl-thiazole-2-thione analogs of combretastatin A-4 as microtubule-binding agents

A series of combretastatin A-4 analogs in which cis-olefinic bond replaced by thiazole ring were prepared by reaction of α-bromo-1,2-(p-substituted) diaryl-1-ethanones and dithiocarbamate derivatives. The cytotoxicity of these compounds was determined against three cancer cell lines (HT-29), (MCF-7), (AGS) as well as fibroblastic cell line (NIH-3T3) using MTT assay. Inhibition of tubulin polymerization for some potent compounds was evaluated. These biological studies proved that 6j and 6o were the most potent compounds in this series. Furthermore 2-(methylthio)-substituted compounds show moderate or no activity. Docking studies involving 6j and 6o demonstrated that this analogs could be successfully docked in the colchicine binding site of α,β-tubulin.

Synthesis, spectral studies and biological evaluation of a novel series of 2-substituted-5,6-diarylsubstituted imidazo(2,1-b)-1,3, 4-thiadiazole derivatives as possible anti-tubercular agents

A novel series of 18 analogs of 2-substituted-5,6- diarylsubstituted imidazo(2,1-b)-1,3,4-thiadiazole 6a-r have been synthesized by the reaction of 2-amino-5-substituted- 1,3,4-thiadiazoles 5a-d and an appropriately substituted a-bromo-1,2-(p-substituted)diaryl-1-ethanones 4a-e. Structures of these compounds were established by physiochemical, elemental analysis and spectral data. All the title compounds were tested for their in-vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv using Alamar Blue susceptibility test and the activity expressed as the minimum inhibitory concentration (MIC) in lg/ml. Among synthesized compounds, compound 6h (MIC = 1.25 μg/ml) exhibited excellent anti-tubercular activity with respect to other synthesized compounds and reference drugs. Compounds 6c, 6f, and6g have also displayed an encouraging anti-tubercular activity profile. Further, some title compounds were also assessed for their cytotoxic activity (IC 50) against in a mammalian Vero cell line using MTT assay. The results reveal that these compounds exhibit anti-tubercular activity at non-cytotoxic concentrations. Springer Science+Business Media, LLC 2011.

Utilization of natural sunlight and air in the aerobic oxidation of benzyl halides

Chemical equations presented. A novel, efficient oxidation of α-aryl halogen derivatives to the corresponding α-aryl carbonyl compounds at room temperature has been disclosed. Natural sunlight and air are successfully utilized in this approach through the combination of photocatalysis and organocatalysis. A plausible mechanism was proposed on the basis of the mechanistic studies.

Synthesis and preliminary in-vitro cytotoxic activity of novel substituted diaryl-imidazo [2, 1, b]-benzothiazole derivatives

A novel series of substituted diaryl imidazo[2, 1-b]benzothiazole derivatives (8a-y) were synthesized by condensation reaction between 2-amino benzothiazole derivatives (3a-g) and substituted a-bromo-1, 2-(substituted) diaryl-1-ethanones (7a-i). The structures of the synthesized compounds were established by IR, 1H NMR, 13C NMR and mass spectroscopical data. The compounds (8a-y) were evaluated for their in-vitro cytotoxic activity on murine (B16F10) and human (MCF-7) cancer cells by using MTT assay. From the in vitro studies compounds 8p, 8u and 8y were found most effective with an IC50 range of 0.56-27.50 μM in MCF-7 and 2.57-36.54 μM in B16F10 cells.

Synthesis and preliminary in-vitro cytotoxic activity of novel substituted diaryl-imidazo [2,1,b]-benzothiazole derivatives

A novel series of substituted diaryl imidazo[2,1-b]benzothiazole derivatives (8a-y) were synthesized by condensation reaction between 2-amino benzothiazole derivatives (3a-g) and substituted α-bromo-1, 2-(substituted) diaryl-1-ethanones (7a-i). The structures of the synthesized compounds were established by IR, 1H NMR, 13C NMR and mass spectroscopical data. The compounds (8a-y) were evaluated for their in-vitro cytotoxic activity on murine (B16F10) and human (MCF-7) cancer cells by using MTT assay. From the in vitro studies compounds 8p, 8u and 8y were found most effective with an IC50 range of 0.56-27.50 μM in MCF-7 and 2.57-36.54 μM in B16F10 cells.

Novel bisaryl substituted thiazoles and oxazoles as highly potent and selective peroxisome proliferator-activated receptor δ agonists

The discovery, synthesis, and optimization of compound 1 from a high-throughput screening hit to highly potent and selective peroxisome proliferator-activated receptor δ (PPARδ) agonists are reported. The synthesis and structure-activity relationship in this series are described in detail. On the basis of a general schematic PPAR pharmacophore model, scaffold 1 was divided into headgroup, linker, and tailgroup and successively optimized for PPAR activation using in vitro PPAR transactivation assays. A (2-methylphenoxy)acetic acid headgroup, a flexible linker, and a five-membered heteroaromatic center ring with two hydrophobic aryl substituents were required for efficient and selective PPARδ activation. The fine-tuning of these aryl substituents led to an array of highly potent and selective compounds such as compound 38c, displaying an excellent pharmacokinetic profile in mouse. In an in vivo acute dosing model, selected members of this array were shown to induce the expression of pyruvate dehydrogenase kinase-4 (PDK4) and uncoupling protein-3 (UCP3), genes that are known to be involved in energy homeostasis and regulated by PPARδ in skeletal muscle.

Synthesis and antibacterial activity of a novel series of 2,3-diaryl-substituted-imidazo(2,1-b)-benzothiazole derivatives

Benzothiazole and imidazole compounds are extensively studied heterocyclics due to their wide spectrum of bioactivities. Among them, the imidazo(2,1-b)-benzothiazole derivatives are pharmacologically important because of their immunostimulant, anti-inflammatory, antifungal, antimicrobial, antitumor, and other activities. In the present research work, a novel series of 2,3-diaryl-substituted imidazo(2,1-b)-benzothiazoles 13a-o have been synthesized by reaction of substituted 2-aminobenzothiazoles 1-8 and an appropriately substituted a-bromo-1-(4″-substituted)-phenyl-2-(4′- substituted)-phenyl-1-ethanones 9-12 in the presence of anhydrous acetonitrile. They were characterized by physicochemical, elemental, and spectral (IR, 1H-NMR, and Mass) data. All the synthesized compounds were screened for their in-vitro antibacterial activity against Gram-positive, Gram-negative bacteria. The investigation of antibacterial screening data revealed that most of the compounds tested have demonstrated congruent activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa as compared with the standard ampicillin. Among the series, compounds 13d, 13h, and 13m exhibited excellent an antibacterial activity profile as compared with the standard. In summary, preliminary results indicate that some of the newly synthesized title compounds exhibited promising antibacterial activities and they warrant more consideration as prospective antimicrobials.

UREIDE DERIVATIVE AND USE THEREOF FOR MEDICAL PURPOSES

This invention relates to a pharmaceutical comprising, as an active ingredient, a ureide derivative represented by formula: or a pharmaceutically acceptable salt thereof. The ureide derivative or a pharmaceutically acceptable salt thereof according to the present invention is useful for relieving pain and treating or preventing neuropathic pain.

Synthesis and biological evaluation of 2-trifluoromethyl/sulfonamido-5,6-diaryl substituted imidazo[2,1-b]-1,3,4-thiadiazoles: A novel class of cyclooxygenase-2 inhibitors

A series of 2-trifluoromethyl/sulfonamido-5,6-diarylsubstituted imidazo[2,1-b]-1,3,4-thiadiazole derivatives 15a-j have been synthesized by the reaction of 2-amino-5-trifluoromethyl/sulfonamido-1,3,4-thiadiazoles 14a-b and appropriately substituted α-bromo-1,2-(p-substituted)diaryl-1-ethanones 13a-h. Structures of these compounds were established by IR, 1H NMR, 13C NMR, Mass, and HRMS data. The selected compounds were evaluated for their preliminary in vitro cyclooxygenase inhibitory activity against COX-2 and COX-1enzymes using colorimetric method. The compounds tested showed selective inhibitory activity toward COX-2 (80.6-49.4%) over COX-1 (30.6-8.6), amongst them compounds 15f and 15j showed appreciable COX-2 selective inhibitory activity. These compounds also exhibited significant anti-inflammatory activity (70.09-42.32%), which is comparable to that of celecoxib in the carrageenan-induced rat paw edema method.