75867-41-3

Usage

Uses

Used in Organic Synthesis:
Methyl 4-(2-(trimethylsilyl)ethynyl)benzoate is used as a building block for the synthesis of complex organic molecules, leveraging its reactivity to form a variety of chemical structures. Its presence in the synthesis process aids in creating new compounds with potential applications across different fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, methyl 4-(2-(trimethylsilyl)ethynyl)benzoate is used as a precursor for the preparation of pharmaceutical compounds. Its unique structure and reactivity contribute to the development of new drugs with specific therapeutic properties.
Used in Chemical Industry:
Methyl 4-(2-(trimethylsilyl)ethynyl)benzoate is employed in the chemical industry for the production of specialty chemicals and materials. Its versatility allows for its use in creating compounds with tailored properties for specific applications.
Used as a Protecting Group in Organic Synthesis:
The trimethylsilyl group in methyl 4-(2-(trimethylsilyl)ethynyl)benzoate is used as a protecting group for sensitive functional groups during organic synthesis. This protects the functional groups from unwanted reactions, ensuring the successful synthesis of the desired product.

Upstream product

• 619-42-1 4-methoxycarbonylphenyl bromide 
• 1066-54-2 trimethylsilylacetylene 
• 619-44-3 methyl 4-iodobenzoate 
• 3034-86-4 4-ethynylbenzoic acid methyl ester 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 
• 619-58-9 4-iodobenzoic acid 
• 60-29-7 diethyl ether 
• 586-76-5 4-Bromobenzoic acid 
• 78389-87-4 ((trimethylsilyl)ethynyl)zinc(II) chloride 
• 134856-58-9 1-iodo-4-(trimethylsilylethynyl)benzene 
• 67-56-1 methanol 

Downstream Products

• 110598-53-3 methyl 4-(1-(4-hydroxyphenyl)vinyl)benzoate 
• 110598-39-5 4-[(E)-1-(4-Hydroxy-phenyl)-2-trimethylsilanyl-vinyl]-benzoic acid methyl ester 
• 110598-46-4 4-[(Z)-2-(4-Hydroxy-phenyl)-2-trimethylsilanyl-vinyl]-benzoic acid methyl ester 
• 10602-00-3 4-Ethynyl-benzoic acid 
• 3034-86-4 4-ethynylbenzoic acid methyl ester 
• 275386-60-2 4-(hydroxymethyl)-1-(trimethylsilylethynyl)benzene 
• 870719-33-8 4-ethynylbenzyl 3,5-bis[3',4'-di(octan-1-yloxy)benzyloxy]benzoate 
• 870719-39-4 4-ethynylbenzyl 3,5-bis[3',4'-di((S)-3,7-dimethyloctan-1-yloxy)benzyloxy]benzoate 
• 870719-35-0 4-ethynylbenzyl 3,5-bis[3',4'-di(decan-1-yloxy)benzyloxy]benzoate 
• 474297-38-6 4-ethynylbenzyl 3,5-bis(3',4'-bis(dodecan-1-yloxy)benzyloxy)benzoate 
• 870719-59-8 4-ethynylbenzyl 3,5-bis[3',4'-di(tetradecan-1-yloxy)benzyloxy]benzoate 
• 10602-04-7 (4-ethynylphenyl)methanol 
• 229174-43-0 4-((4-methoxyphenyl)ethynyl)benzoic acid methyl ester 
• 16882-08-9 bis(4-(methoxycarbonyl)phenyl)acetylene 

Relevant academic research and scientific papers

Acetylenic Replacement of Albicidin's Methacrylamide Residue Circumvents Detrimental E/Z Photoisomerization and Preserves Antibacterial Activity

The natural product albicidin is a highly potent inhibitor of bacterial DNA gyrase. Its outstanding activity, particularly against Gram-negative pathogens, qualifies it as a promising lead structure in the search for new antibacterial drugs. However, as we show here, the N-terminal cinnamoyl moiety of albicidin is susceptible to photochemical E/Z isomerization. Moreover, the newly formed Z isomer exhibits significantly reduced antibacterial activity, which hampers the development and biological evaluation of albicidin and potent derivatives thereof. Hence, we synthesized 13 different variants of albicidin in which the vulnerable para-coumaric acid moiety was replaced; this yielded photostable analogues. Biological activity assays revealed that diaryl alkyne analogues exhibited virtually undiminished antibacterial efficacy. This promising scaffold will therefore serve as a blueprint for the design of a potent albicidin-based drug.

Field-induced single-ion magnets exhibiting tri-axial anisotropy in a 1D Co(ii) coordination polymer with a rigid ligand 4,4′-(buta-1,3-diyne-1,4-diyl)dibenzoate

Herein a 1D Co(ii) coordination polymer of formula [Co(η1-L1)(η2-L1)(py)2(H2O)]n (CoCP) has been synthesised using the rigid H2L1 proligand, containing a long spacer bearing two triple bonds. Single-crystal X-ray diffraction showed that Co(ii) adopts a distorted octahedral geometry. The state-averaged complete active self-consistent field (SA-CASSCF) calculation showed that the ground state of CoCP is a high spin quartet with a highly multiconfigurational character of its electronic structure. Due to the large intra- and intermolecular distances between the spin carriers, the magnetic interactions are negligible and the zero-field splitting (ZFS) effects of cobalt(ii) ions are predominant. This behavior was confirmed by direct current (DC) magnetic measurements and theoretical calculations using the broken-symmetry approach. Quantum chemical calculations indicate that CoCP has a negative axial component possessing mixed tri-axial anisotropy. The DC magnetic susceptibility data were fitted with a Griffith-Figgis Hamiltonian and the obtained parameters are in good agreement with those simulated by the ab initio calculation. Alternating current (AC) magnetic measurements showed a field induced slow magnetic relaxation in CoCP, which is attributed to the hyperfine interaction effects.

BODIPY compounds containing 8-(diphenylethynyl)-ester groups as well as synthesis and application thereof

The invention discloses BODIPY compounds containing 8-(diphenylethynyl)-ester groups as well as a preparation method and application thereof. The BODIPY compounds have a structure A. According to theinvention, BODIPY is used as a matrix, a diphenylacetylene rigid structure and an ester-based alkyl chain flexible structure are introduced to the No. 8 site through the Sonogashira coupling reaction,and a series of 8-(diphenylethynyl)-ester-based BODIPY dichroic dyes are designed and synthesized. The maximum emission wavelength of the compounds in dichloromethane is concentrated at about 518 nm,green fluorescence is shown, and good dichroic ratio and ordered parameters are shown in a liquid crystal E7; and the liquid crystal compounds provided by the invention have a liquid crystal mesophase within a temperature range of 50-100 DEG C, can be used for manufacturing liquid crystal display products, and particularly can be used as guest body dyes for guest-host mode liquid crystal displays; and when the compounds are added into the E7 liquid crystal and used in a guest-host display mode, response time can be prolonged, and the effect of quick response is achieved.

Design, synthesis and antitumor evaluations of nucleoside base hydroxamic acid derivatives as DNMT and HDAC dual inhibitors

DNA methyltransferase (DNMT) and histone deacetylase (HDAC) are well recognized epigenetic targets for discovery of antitumor agents. In this study, we designed and synthesized a series of nucleoside base hydroxamic acid derivatives as DNMT and HDAC dual inhibitors. MTT assays and enzymatic inhibitory activity tests indicated that compound 204 exhibited potent DNMT1 and HDAC1/6 inhibitory potency simultaneously in enzymatic levels and at cellular levels, inducing hypomethylation of p16 and hyperacetylation of histones H3K9 and H4K8. Besides, 204 remarkably inhibited proliferation against cancer cells U937 by prompting G0/G1 cell cycle arrest. Molecular docking models explained the functional mechanism of 204 inhibiting DNMT1 and HDAC. Preliminary studies on metabolic profiles revealed that 204 showed desirable stability in liver microsomes. Our study suggested that 204 inhibiting DNMT and HDAC concurrently can be a potential lead compound for epigenetic cancer therapy.

Polyacetylene derivatives in perovskite solar cells: From defect passivation to moisture endurance

The last decade has witnessed the exploration of exceptional optoelectronic and photovoltaic properties of perovskite solar cells (PSCs) at the laboratory scale. Unfortunately, their sensitivity to moisture causes bulk degradation, hindering the commercialization of PSC devices. Despite the numerous strategies that have been developed to date in this field, effective passivation against moisture remains highly challenging. Here, we report a novel approach based on the incorporation of polyacetylene derivatives into the perovskite active layer to yield perovskite films with larger grains, lower defect density, and excellent robustness with respect to moisture. Moreover, it is revealed that the reduced trap-state density of these films is most likely due to the efficient coordination between the carboxylate moieties in the polymer and the undercoordinated Pb2+ in the perovskite. Upon adopting the polymer-doped perovskite as an active layer in inverted planar heterojunction PSCs with all-inorganic charge extraction layers, the power conversion efficiency (PCE) is improved to 20.41%, which is the highest value reported to date for this type of PSC to the best of our knowledge. Most importantly, the optimized device retained 90% of its initial PCE after aging in ambient air for 60 days due to its dual mechanism of moisture resistance. This work highlights an approach for developing high-performance PSCs with improved moisture stability and paves the way for their potential commercialization. This journal is

Discovery of 5-{2-[5-Chloro-2-(5-ethoxyquinoline-8-sulfonamido)phenyl]ethynyl}-4-methoxypyridine-2-carboxylic Acid, a Highly Selective in Vivo Useable Chemical Probe to Dissect MCT4 Biology

Due to increased lactate production during glucose metabolism, tumor cells heavily rely on efficient lactate transport to avoid intracellular lactate accumulation and acidification. Monocarboxylate transporter 4 (MCT4/SLC16A3) is a lactate transporter that plays a central role in tumor pH modulation. The discovery and optimization of a novel class of MCT4 inhibitors (hit 9a), identified by a cellular screening in MDA-MB-231, is described. Direct target interaction of the optimized compound 18n with the cytosolic domain of MCT4 was shown after solubilization of the GFP-tagged transporter by fluorescence cross-correlation spectroscopy and microscopic studies. In vitro treatment with 18n resulted in lactate efflux inhibition and reduction of cellular viability in MCT4 high expressing cells. Moreover, pharmacokinetic properties of 18n allowed assessment of lactate modulation and antitumor activity in a mouse tumor model. Thus, 18n represents a valuable tool for investigating selective MCT4 inhibition and its effect on tumor biology.

Chemoselective Cleavage of Si-C(sp3) Bonds in Unactivated Tetraalkylsilanes Using Iodine Tris(trifluoroacetate)

Organosilanes are synthetically useful reagents and precursors in organic chemistry. However, the typical inertness of unactivated Si-C(sp3) bonds under conventional reaction conditions has hampered the application of simple tetraalkylsilanes in organic synthesis. Herein we report the chemoselective cleavage of Si-C(sp3) bonds of unactivated tetraalkylsilanes using iodine tris(trifluoroacetate). The reaction proceeds smoothly under mild conditions (-50 °C to room temperature) and tolerates various polar functional groups, thus enabling subsequent Tamao-Fleming oxidation to provide the corresponding alcohols. NMR experiments and density functional theory calculations on the reaction indicate that the transfer of alkyl groups from Si to the I(III) center and the formation of the Si-O bond proceed concertedly to afford an alkyl-λ3-iodane and silyl trifluoroacetate. The developed method enables the use of unactivated tetraalkylsilanes as highly stable synthetic precursors.

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.

Development of helical aromatic amide foldamers with a diphenylacetylene backbone

We designed and synthesized aromatic polyamides with a diphenylacetylene backbone, α-DPA and β-DPA, bearing (S)-α-and (S)-β-methyl-substituted triethyleneglycol (TEG) side chains, respectively, and examined their conformations in solution. Both polymers exhibit strong, solvent polarity-dependent circular dichroism spectra, which indicated that they take helical conformations in low-polarity solvents. The spectra were mirror images, depending on the chiral position of the side chains. Thus, the polyamide α-DPA bearing (S)-α-methyl-substituted TEG groups takes a left-handed helical conformation, while the polyamide β-DPA with (S)-β-methyl-substituted TEG groups takes a right-handed helical conformation. The difference in the screw sense of α-DPA and β-DPA would be caused by the steric interaction between the main chain and the side chain, as observed in poly(p-benzamide) possessing (S)-β-methyl-substituted TEG side chains (β-PA) because the large cavity of the helical structure of DPA would disturb the solvophobically induced helical folding. Detailed conformational analyses of the oligoamides 6-12 with β-methyl-substituted TEG groups were conducted. Theoretical calculations indicated that the oligoamides with β-methyl-substituted TEG groups exist in a helical conformation with a cavity of 7 ? in diameter. The 1H NMR spectra of the oligomers revealed interactions with small anions such as chloride and acetate anions and with pyridinium cations.

COMPOUND ACTING AS ANTIBIOTICS

The present invention provides a novel antibiotic compound represented by the following formula (I), a pharmaceutically acceptable salt thereof, an ester thereof, a prodrug thereof, a solvate thereof, or a deuterated analog thereof, or a stereoisomer thereof. The compound of the present invention exhibits excellent antibacterial activity, especially against Gram bacteria. wherein each group is defined as in the description.