Nav: Home

UTA to develop faster, cheaper methods to synthesize compounds used in drug discovery

January 04, 2017

Chemists at The University of Texas at Arlington are developing new methods to synthesize groups of chemical compounds to provide faster, less expensive routes to produce the compounds for subsequent use in medical drug discovery and development.

The project focuses on compounds containing carbon-silicon bonds, which are called organosilanes or organosilanols. These molecules are in increasingly high demand for use in a variety of applications, including pharmaceutical and other medical-related activities. They are also widely used in organic chemistry, particularly as protecting groups, reducing agents and synthetic intermediates.

"The goal of our research is to develop novel compounds from readily accessible, simple chemical building blocks," said Junha Jeon, UTA assistant professor of chemistry and biochemistry and leader of the project. "The synthetic methods developed in this research will provide broadly applicable, time- and cost-saving, synthetic routes to provide rapid access to compounds for subsequent use in drug discovery and development, thus contributing to the promotion of human health."

The project, titled "Catalytic Reductive C-H and C-C Silylation with Silyl Acetals," is funded by a three-year, $424,720 grant from the National Institute of General Medical Sciences, one of the National Institutes of Health.

Current methods to prepare these organosilanes utilize multi-step procedures which demand considerable time and effort. The project's goal is the design and application of single-pot, transition metal-catalyzed reductive C-H and C-C silylations for the synthesis of a new class of organosilanes.

A single-pot, or one-pot, synthesis improves the efficiency of a chemical reaction by subjecting a compound to successive chemical reactions using a single reactor. This method is preferred by chemists because it avoids a lengthy separation process and purification of the intermediate chemical compounds which saves time and resources while increasing chemical yield.

Jeon said the research will deliver several positive outcomes.

"There are three main aims of the research," he said. "In the first two, we will develop a new, simple, catalytic strategy for breaking an ubiquitous yet inert carbon-hydrogen bond and installing a new highly useful silicon moiety. This will allow for the rapid preparation of bio-medically important drugs.

"The third aim will provide a new tool to selectively break a strong carbon-carbon bond over adjacent, abundant carbon-hydrogen bonds and incorporate a silicon moiety. This method will be highly useful to prepare biologically active, secondary metabolites and pharmaceuticals."

The project has already yielded one paper, titled "Catalytic Reductive ortho-C--H Silylation of Phenols with Traceless, Versatile Acetal Directing Groups and Synthetic Applications of Dioxasilines", which was published in the Journal of the American Chemical Society in June. Jeon co-authored the paper with Yuanda Hua, a UTA postdoctoral researcher; and two of the graduate students who work in his laboratory, Parham Asgari and Thirupataiah Avullala.

Jeon explained that during the past three decades, significant advances have been made to the organic processes of selectively transforming ubiquitous yet inert carbon-hydrogen bonds to other useful chemical entities. One reliable strategy for selective carbon-hydrogen bond cleavage within an organic is the use of a transition metal catalyst and a directing group, Jeon said. However, such a directing group is often difficult to install and manipulate after processes are completed.

"In this paper we describe how we first developed a general strategy for transition metal catalyst-assisted, site-selective carbon-hydrogen bond cleavage and insertion of a silicon moiety to phenols with a traceless directing group," Jeon said. "We believe that our new carbon-hydrogen bond functionalization approach to exploit readily available phenols and silanes more efficiently and cleanly will ultimately allow the practical production of diverse, biomedically important phenol derivatives and silicon-based materials."

A traceless directing group means that after a specific group directs, or guides, a catalyst to a specific position of a carbon-hydrogen bond within phenol, the group disappears without a trace. Phenols are a group of organic compounds whose aromatic ring is bonded to an alcohol group. Because phenol contains an alcohol group, it is able to form a very strong hydrogen bond with other molecules and often displays significant biological activities. Silanes are the basic building blocks of silicon chemistry and are versatile materials used in a wide range of applications.

Fred MacDonnell, professor and chair of the UTA Department of Chemistry & Biochemistry, said that Jeon's research has the potential to provide major positive impact on health and the human condition, one of four main themes in UTA's Strategic Plan 2020: Bold Solutions | Global Impact.

"Dr. Jeon's work is really starting to get a lot of attention from the scientific community and speaks to his creativity in this very challenging research area," MacDonnell said.

Jeon joined UTA in 2011. He earned a bachelor's of science degree in Chemistry in 2000 and a master's degree in Organic Chemistry in 2002, both from Sungkyunkwan University in Seoul, South Korea. He then came to the United States and did doctoral work at the University of Minnesota, receiving his Ph.D. in Organic Chemistry in 2009. After a two-year stint as a postdoctoral fellow at the University of Pennsylvania, he came to UTA.
-end-
The University of Texas at Arlington

The University of Texas at Arlington is a Carnegie Research-1 "highest research activity" institution. With a projected global enrollment of close to 57,000 in AY 2016-17, UTA is the largest institution in The University of Texas System. Guided by its Strategic Plan Bold Solutions | Global Impact, UTA fosters interdisciplinary research within four broad themes: health and the human condition, sustainable urban communities, global environmental impact, and data-driven discovery. UTA was recently cited by U.S. News & World Report as having the second lowest average student debt among U.S. universities. U.S. News & World Report also ranks UTA fifth in the nation for undergraduate diversity. The University is a Hispanic-Serving Institution and is ranked as the top four-year college in Texas for veterans on Military Times' 2017 Best for Vets list.

University of Texas at Arlington

Related Chemistry Articles:

Coordination chemistry and Alzheimer's disease
It has become evident recently that the interactions between copper and amyloid-β neurotoxically impact the brain of patients with Alzheimer's disease.
Can ionic liquids transform chemistry?
Table salt is a commonplace ingredient in the kitchen, but a different kind of salt is at the forefront of chemistry innovation.
Principles for a green chemistry future
A team led by researchers from the Yale School of Forestry & Environmental Studies recently authored a paper featured in Science that outlines how green chemistry is essential for a sustainable future.
Sugar changes the chemistry of your brain
The idea of food addiction is a very controversial topic among scientists.
Reflecting on the year in chemistry
A lot can happen in a year, especially when it comes to science.
Better chemistry through tiny antennae
A research team at The University of Tokyo has developed a new method for actively controlling the breaking of chemical bonds by shining infrared lasers on tiny antennae.
Chemistry in motion
For the first time, researchers have managed to view previously inaccessible details of certain chemical processes.
Researchers enrich silver chemistry
Researchers from Russia and Saudi Arabia have proposed an efficient method for obtaining fundamental data necessary for understanding chemical and physical processes involving substances in the gaseous state.
The chemistry behind kibble (video)
Have you ever thought about how strange it is that dogs eat these dry, weird-smelling bits of food for their entire lives and never get sick of them?
Top 10 chemistry start-ups
Starting a new chemistry-based company is one part discovery, one part risk.
More Chemistry News and Chemistry Current Events

Trending Science News

Current Coronavirus (COVID-19) News

Top Science Podcasts

We have hand picked the top science podcasts of 2020.
Now Playing: TED Radio Hour

Listen Again: Reinvention
Change is hard, but it's also an opportunity to discover and reimagine what you thought you knew. From our economy, to music, to even ourselves–this hour TED speakers explore the power of reinvention. Guests include OK Go lead singer Damian Kulash Jr., former college gymnastics coach Valorie Kondos Field, Stockton Mayor Michael Tubbs, and entrepreneur Nick Hanauer.
Now Playing: Science for the People

#562 Superbug to Bedside
By now we're all good and scared about antibiotic resistance, one of the many things coming to get us all. But there's good news, sort of. News antibiotics are coming out! How do they get tested? What does that kind of a trial look like and how does it happen? Host Bethany Brookeshire talks with Matt McCarthy, author of "Superbugs: The Race to Stop an Epidemic", about the ins and outs of testing a new antibiotic in the hospital.
Now Playing: Radiolab

Dispatch 6: Strange Times
Covid has disrupted the most basic routines of our days and nights. But in the middle of a conversation about how to fight the virus, we find a place impervious to the stalled plans and frenetic demands of the outside world. It's a very different kind of front line, where urgent work means moving slow, and time is marked out in tiny pre-planned steps. Then, on a walk through the woods, we consider how the tempo of our lives affects our minds and discover how the beats of biology shape our bodies. This episode was produced with help from Molly Webster and Tracie Hunte. Support Radiolab today at Radiolab.org/donate.