Researchers confirm benzene-like electron delocalization of important molecule

UO team's findings could pave way for synthetic compounds useful in drug discovery and materials science
Researchers in the lab of University of Oregon chemist Shih-Yuan Liu have successfully synthesized and structurally characterized boron-nitrogen compounds that are isoelectronic and isostructural to the fundamentally important benzene molecule. Given the appearance of benzene derivatives in biomedical research and materials science, the boron-nitrogen substituted analogues could potentially play a pivotal role in these areas.

In the Journal of the American Chemical Society, Liu's team reports that, by using a structural approach, benzene surrogates known as 1,2-dihydro-1,2-azaborines possess electron-delocalized structures consistent with aromaticity -- a core concept in chemistry. The paper already has drawn praise by other researchers in a story in this week's Chemical & Engineering News.

"The bottom line is that we have synthesized reference compounds designed to be non-aromatic, and through the comparisons of the aromatic molecule with the reference compounds, we were able to unambiguously say that this compound is really electron delocalized in a way consistent with aromaticity," Liu said. "With the results of other research in this field, our findings present a very strong case that 1,2-dihydro-1,2-azaborines are indeed aromatic."

Liu is among molecule-making chemists who are interested in manipulating heterocycles -- ring-like structures that contain various elements in addition to carbon. Aromatic heterocycles play a big role in pharmaceuticals, Liu said, noting that eight of the top ten selling molecules on the market today contain aromatic compounds.

For biomedical purposes, Liu said, boron-containing molecules disguised with other components readily accepted by living tissues could conceivably be used as markers to track the location of the drug. Eventually, he said, targeted drug therapies might deliver very specific tumor-destroying action that leaves healthy cells untouched.

"Our objective is really to first develop the synthetic chemistry of these boron-nitrogen heterocycles, make it accessible to other chemists to study, and ultimately go into applied research to create opportunities in cancer therapies and materials sciences," Liu said. "I believe that we have made substantial progress for expanding the scope of accessible molecules such as this. The methods we have developed here at the University of Oregon are beginning to be quite useful."

Source: University of Oregon

Related stories:

Scientists find quick method to make magnets
(PhysOrg.com) -- Ultra-strong, high-temperature, high-performance permanent magnet compounds, such as Samarium Cobalt, are the mainstay materials for several industries that rely on high-performance motor and power generation applications, including the Department of Defense (DOD) and the automotive industry.
Researchers unravel key mechanism of cellular damage in aging and disease
Researchers have taken a first snapshot of how a class of highly reactive molecules inflicts cellular damage as part of aging, heart disease, stroke, cancer, diabetes, kidney disease and Alzheimer's disease to name a few. According to a study published today in the journal Cell, researchers have discovered a tool that can monitor related damage and determine the degree to which antioxidant drugs effectively combat disease.
Cranberry juice creates energy barrier that keeps bacteria away from cells, study shows
For generations, people have consumed cranberry juice, convinced of its power to ward off urinary tract infections, though the exact mechanism of its action has not been well understood. A new study by researchers at Worcester Polytechnic Institute (WPI) reveals that the juice changes the thermodynamic properties of bacteria in the urinary tract, creating an energy barrier that prevents the microorganisms from getting close enough to latch onto cells and initiate an infection.
Newly described 'dragon' protein could be key to bird flu cure
(PhysOrg.com) -- Scientists and researchers have taken a big step closer to a cure for the most common strain of avian influenza, or "bird flu," the potential pandemic that has claimed more than 200 lives and infected nearly 400 people in 14 countries since it was identified in 2003.
New approach may render disease-causing staph harmless
Researchers at the University of Illinois helped lead a collaborative effort to uncover a completely new treatment strategy for serious Staphylococcus aureus (“Staph”) infections. The research, published Feb. 14 in Science Express comes at a time when strains of antibiotic-resistant Staph (known as MRSA, for methicillin-resistant S. aureus) are spreading in epidemic proportions in hospital and community settings.
Cranberry sauce: good for what ails you
Cranberry sauce is not the star of the traditional Thanksgiving Day meal, but when it comes to health benefits, the lowly condiment takes center stage. In fact, researchers at Worcester Polytechnic Institute (WPI) have found that compounds in cranberries are able to alter E. coli bacteria, which are responsible for a host of human illnesses (from kidney infections to gastroenteritis to tooth decay), in ways that render them unable to initiate an infection.
Cholesterol metabolism links early- and late-onset Alzheimer's disease
Although the causes of Alzheimer's disease are not completely understood, amyloid-beta (A-beta) is widely considered a likely culprit — the "sticky" protein clumps into plaques thought to harm brain cells.
An apple peel a day might keep cancer at bay
An apple a day keeps the doctor away? Or, what appears to be more accurate: An apple peel a day might help keep cancer at bay, according to a new Cornell study.

News discussion:

General Science news