540778-94-7

Upstream product

• 34841-06-0 3-bromo-4-methoxybenzylaldehyde 
• 578-57-4 2-bromoanisole 
• 140-88-5 ethyl acrylate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 

Downstream Products

• 540779-17-7 ethyl 3-(3-bromo-4-hydroxyphenyl)acrylate 
• 540778-95-8 ethyl (E)-3-[3-(1-adamantyl)-4-benzyloxyphenyl]-4-methoxycinnamate 
• 1234462-90-8 (E)-3-(m-bromo-p-methoxyphenyl)-2-propen-1-ol 

Relevant academic research and scientific papers

Nonracemic Antifolates Stereoselectively Recruit Alternate Cofactors and Overcome Resistance in S. aureus

While antifolates such as Bactrim (trimethoprim-sulfamethoxazole; TMP-SMX) continue to play an important role in treating community-acquired methicillin-resistant Staphylococcus aureus (CA-MRSA), resistance-conferring mutations, specifically F98Y of dihydrofolate reductase (DHFR), have arisen and compromise continued use. In an attempt to extend the lifetime of this important class, we have developed a class of propargyl-linked antifolates (PLAs) that exhibit potent inhibition of the enzyme and bacterial strains. Probing the role of the configuration at the single propargylic stereocenter in these inhibitors required us to develop a new approach to nonracemic 3-aryl-1-butyne building blocks by the pairwise use of asymmetric conjugate addition and aldehyde dehydration protocols. Using this new route, a series of nonracemic PLA inhibitors was prepared and shown to possess potent enzyme inhibition (IC50 values 50 nM), antibacterial effects (several with MIC values 1 μg/mL) and to form stable ternary complexes with both wild-type and resistant mutants. Unexpectedly, crystal structures of a pair of individual enantiomers in the wild-type DHFR revealed that the single change in configuration of the stereocenter drove the selection of an alternative NADPH cofactor, with the minor α-anomer appearing with R-27. Remarkably, this cofactor switching becomes much more prevalent when the F98Y mutation is present. The observation of cofactor site plasticity leads to a postulate for the structural basis of TMP resistance in DHFR and also suggests design strategies that can be used to target these resistant enzymes. (Chemical Equation Presented).

S,O-Ligand-Promoted Pd-Catalyzed C?H Olefination of Anisole Derivatives

The C?H olefination of substituted anisole derivatives by a Pd/S,O-ligand catalyst is reported. The reaction proceeds under mild conditions with a broad range of substituted aryl ethers bearing both electron donating and withdrawing substituents at ortho,

Cycloadditions by oxidative visible light photocatalysis

Photochemical reactions are remarkable for their ability to easily assemble cyclobutanes and other strained ring systems that are difficult to construct using other conventional synthetic methods. We have previously shown that Ru(bpy)32+ is an efficient photocatalyst that promotes the [2+2] cycloadditions of electron-deficient olefins with visible light. Here, we show that Ru(bpy)32+ is also an effective photocatalyst for the [2+2] cycloaddition of electron-rich olefins. This transformation is enabled by the versatile photoelectrochemical properties of Ru(bpy) 32+, which enables either one-electron reduction or one-electron oxidation of interesting organic substrates under appropriate conditions.

Induction of apoptosis in cancer cells

The present invention provides compounds that are inducers or inhibitors of apoptosis or apoptosis preceded by cell-cycle arrest. In addition, the present invention provides pharmaceutical compositions and methods for treating mammals with leukemia or other forms of cancer or for treating disease conditions caused by apoptosis of cells.