PRESS-NEWS.org - Press Release Distribution
PRESS RELEASES DISTRIBUTION

Transforming inexpensive quinolines into complex drug candidates

Scientists develop a cost-effective methodology to produce various biologically relevant organic compounds from simple feedstock chemicals

Transforming inexpensive quinolines into complex drug candidates
2024-06-19
(Press-News.org)

An innovative synthesis strategy opened up the way to 2D/3D fused frameworks using inexpensive quinolines as feedstock, report scientists from Tokyo Tech. By leveraging a light-sensitive borate intermediate, the scientists could transform quinoline derivatives into a great variety of 2D/3D fused frameworks in a straightforward and cost-effective manner. Their findings are expected to enable the synthesis of highly customizable drug candidates.  

Quinolines have garnered much attention from chemists wanting to synthesize compounds known as 2D/3D fused frameworks. These complex organic molecules have a lot of medical potential due to their highly customizable structure and functional groups. Quinolines make synthesis of such frameworks possible thanks to their unique electronic configuration. They consist of an electron-abundant benzene ring fused to an electron-deficient pyridine ring; these electronically distinct rings can be modified independently by adjusting reaction conditions.

One of the most attractive ways to use quinolines as feedstock for 2D/3D frameworks is through dearomative photocycloadditions. This process involves destabilizing one of the aromatic rings in quinoline, using light and sometimes a catalyst, so that a reactant can ‘latch’ onto the ring, forming the target compound. Despite many efforts, most studies have reported photocycloadditions happening on quinoline’s benzene ring side, while few have targeted the pyridine side. Thus, the full potential of quinolines remains untapped.     

Against this backdrop, a research team from Tokyo Institute of Technology, Japan, led by Assistant Professor Yuki Nagashima, in collaboration with scientists from The University of Tokyo, decided to step up to the challenge. In their latest study, which was published in Angewandte Chemie International Edition on 27 May 2024, they present a convenient methodology to access the pyridine side of quinolines and synthesize diverse 2D/3D frameworks. 

The key to their approach lies in the use of a molecule known as pinacolborane, also known as H–B(pin). The researchers discovered that this boron-containing compound was extremely effective at inducing dearomative photocycloaddition almost exclusively on the pyridine side of quinoline. Not only were the yields obtained high but also could a wide variety of quinoline derivatives and reactants be used to obtain all sorts of 2D/3D frameworks.

Seeking to shed light on the mechanisms underlying their newfound strategy, the team conducted a series of experiments and theoretical analyses. They determined that quinoline reacts with an organolithium compound first and then with H–B(pin) to form an intermediate borate complex. This intermediate step is crucial, as Nagashima remarks: “Our detailed mechanistic studies revealed that the photoexcited borate complex both accelerates the cycloaddition and suppresses the rearomatization that usually occurs in conventional photocycloaddition reactions.” These effects combined lead to fewer unreacted compounds and undesired aromatics.   

It is worth noting that the proposed methodology offers several advantages over competing techniques. For one, it requires less reaction time and steps than classic synthesis routes. Catalysts are not needed either, which reduces costs further. Moreover, multi-substituted starting molecules can be used, which provides access to countless target compounds. “To our knowledge, these transformations are the first boron-based photocycloadditions and unlock previously elusive organoboron compounds. The present strategy based around an intermediate borate complex should be useful for further functionalization of various types of multi-ringed aromatic hydrocarbons,” highlights Nagashima.

With any luck, this work will serve as the foundation for novel photoinduced cycloaddition strategies, which in turn will lead to more effective and affordable drugs for challenging diseases.

###

About Tokyo Institute of Technology

Tokyo Tech stands at the forefront of research and higher education as the leading university for science and technology in Japan. Tokyo Tech researchers excel in fields ranging from materials science to biology, computer science, and physics. Founded in 1881, Tokyo Tech hosts over 10,000 undergraduate and graduate students per year, who develop into scientific leaders and some of the most sought-after engineers in industry. Embodying the Japanese philosophy of “monotsukuri,” meaning “technical ingenuity and innovation,” the Tokyo Tech community strives to contribute to society through high-impact research.

https://www.titech.ac.jp/english/

END


[Attachments] See images for this press release:
Transforming inexpensive quinolines into complex drug candidates Transforming inexpensive quinolines into complex drug candidates 2 Transforming inexpensive quinolines into complex drug candidates 3

ELSE PRESS RELEASES FROM THIS DATE:

Unlocking heart health: advancing noninvasive monitoring in chimpanzees

Unlocking heart health: advancing noninvasive monitoring in chimpanzees
2024-06-19
Measuring the heart rate of great apes in captivity is essential for both health management and animal studies. However, existing most methods are either invasive or inaccurate. Now, researchers from Japan have investigated the potential of using millimeter-wave radar technology to estimate heart rate from subtle body movements in chimpanzees. Their efforts will hopefully pave the way to better practices and techniques for monitoring heart rates in wild and captive primates.        Just like in humans, heart rate is a critically important and informative vital sign in nonhuman primates. Heart diseases are among the main causes ...

Study uses powerful new ‘digital cohort’ method to understand vaping epidemic

Study uses powerful new ‘digital cohort’ method to understand vaping epidemic
2024-06-19
Tapping into the vast amount of data now available on social media, a new study from scientists at the University of California San Diego introduces a powerful new approach to understanding the nation’s health, in this case the vaping epidemic.  The study, published in the American Journal of Preventive Medicine on June 19, was led by John W. Ayers, Ph.D., from the Qualcomm Institute within UC San Diego.  “Researchers studying social media have tended to analyze the frequency and content of posts,” said Ayers, who is deputy director of informatics at the Altman Clinical and Translational Research Institute, vice chief of innovation in the Division of Infectious ...

A new tuberculosis vaccine candidate recombinant protein with additional post-translational modifications occurring in Mycobacterium tuberculosis cells

A new tuberculosis vaccine candidate recombinant protein with additional post-translational modifications occurring in Mycobacterium tuberculosis cells
2024-06-19
Niigata, Japan - Tuberculosis is still one of the deadliest infectious diseases, causing over one million deaths each year worldwide. Additionally, about one-fourth of the world's population carries Mycobacterium tuberculosis (M. tuberculosis) without showing any symptoms, and most of these carriers do not develop the disease. The current anti-tuberculosis vaccine, BCG, is administered worldwide. However, considering that more than 10 million new tuberculosis cases are reported each year, its effectiveness is deemed ...

Experts converge at USC Music, Health, and Policy workshop

2024-06-19
USC recently hosted its first Music, Health, and Policy workshop as part of Los Angeles County Arts and Health Week, filling Joyce J. Cammilleri Hall on the University Park Campus. Event organizer Assal Habibi, an associate professor at the Brain and Creativity Institute at the USC Dornsife College of Letters, Arts and Sciences who explores the intersection between music and the human brain, brought together a wide range of experts on the importance of art and its effect on human development and well-being. “The workshop aims to bring people together ...

Private school and/or ‘higher status’ university education linked to better mid-life health

2024-06-19
A private (fee-paying) school and/or a ‘higher status’ (Russell Group*) university education may be linked to better mid-life health—at least in the UK—suggests research published online in the Journal of Epidemiology & Community Health. Alongside the level of education achieved, the type of educational institution a person attends may also influence subsequent health outcomes, suggest the researchers. Published research to date indicates that educational attainment is associated with better subsequent health. But other aspects ...

Heavy resistance training around retirement preserves vital leg strength years later

2024-06-19
Twelve months of heavy resistance training—exercise that makes muscles work against a force—around retirement preserves vital leg strength years later, show the follow up results of a clinical trial, published online in the open access journal BMJ Open Sport & Exercise Medicine.   Depletion of leg muscle strength is regarded as a strong predictor of death in older people, so is important to maintain, say the researchers. Skeletal muscle mass and function naturally decline with advancing age, ultimately often interfering with mobility and autonomy in older people, note the researchers. Resistance training, which ...

Illinois-led study reveals stable soil moisture variability within fields and opens the door for satellite remote sensing for future measurements

Illinois-led study reveals stable soil moisture variability within fields and opens the door for satellite remote sensing for future measurements
2024-06-19
A multi-institutional study led by University of Illinois and Agroecosystem Sustainability Center (ASC) scientists concluded that, although soil moisture varies significantly both within a single field and from field to field due to varying soil properties and different management practices, soil moisture distribution relative to the field average remains consistent across time within each field.  Over three years, the team used sensor measurements and a high-density campaign to reveal that the drier areas remain the drier areas and the wetter areas remain the wetter areas. The study also deduced this finding, reliable estimations of ...

Shining light on mental health in space science community

Shining light on mental health in space science community
2024-06-19
The severity of anxiety and depressive symptoms in the planetary science community is greater than in the general U.S. population, according to a study led by a University of Hawai‘i at Mānoa scientist and published this week in Nature Astronomy.  “After reading about so much anxiety and depression in academia, and as someone who loves both planetary science and psychology, I felt like I needed to do something because there are so many people suffering,” said David Trang, an assistant researcher in the Hawai‘i Institute of Geophysics and Planetology in the UH Mānoa School of Ocean and Earth Science and Technology at the ...

Texas A&M researchers investigating the impacts of space travel on astronauts’ eye health

2024-06-19
As space travel becomes more common, it is important to consider the impacts of space flight and altered gravity on the human body. Led by Dr. Ana Diaz Artiles, researchers at Texas A&M University are studying some of those impacts, specifically effects on the eye. Gravitational changes experienced by astronauts during space travel can cause fluids within the body to shift. This can cause changes to the cardiovascular system, including vessels in and around the eyes.  As the commercialization of space flight becomes more common and individual space travel increases, astronauts will not be the ...

UCSB's Haewon Jeong receives an NSF Early CAREER Award

UCSBs Haewon Jeong receives an NSF Early CAREER Award
2024-06-18
(Santa Barbara, Calif.) — Haewon Jeong, an assistant professor in UC Santa Barbara’s Electrical and Computer Engineering (ECE) Department, experienced a pivotal moment in her academic career when she was a postdoctoral fellow at Harvard University. She was investigating how machine learning (ML) models can discriminate against students in education-related applications. Discrimination, or bias, occurs when a model used to train algorithms makes incorrect predictions that systematically disadvantage a group of people. Bias in ML models can lead to inaccurate or unfair predictions, which can have serious consequences in fields such as healthcare, finance and criminal justice. ...

LAST 30 PRESS RELEASES:

U.K. food insecurity is associated with mental health conditions

At least eight bat species commute or forage over pig farms in Northern Italy

Ancient teeth reveal mammalian responses to climate change in Southeast Asia

Targeting young adults beginning university may be especially effective for encouraging pro-environmental behaviors

This robotic skin allows tiny robots to navigate complex, fragile environments

‘Metabots’ shapeshift from flat sheets into hundreds of structures

Starting university boosts recycling and greener travel, a University of Bath study finds

How cilia choreograph their “Mexican wave”, enabling marine creatures to swim

Why women's brains face higher risk: scientists pinpoint X-chromosome gene behind MS and Alzheimer's

Ancient lead exposure shaped evolution of human brain

How the uplift of East Africa shaped its ecosystems: Climate model simulations reveal Miocene landscape transformation

Human Organ Chip technology sets stage for pan-influenza A CRISPR RNA therapies

Research alert: Bacterial chatter slows wound healing

American Society of Anesthesiologists names Patrick Giam, M.D., FASA, new president

High-entropy alloy nanozyme ROS biocatalyst treating tendinopathy via up-regulation of PGAM5/FUNDC1/GPX4 pathway

SwRI’s Dr. Pablo Bueno named AIAA Associate Fellow

Astronomers detect radio signals from a black hole tearing apart a star – outside a galactic center

Locking carbon in trees and soils could help ‘stabilize climate for centuries’ – but only if combined with underground storage

New research shows a tiny, regenerative worm could change our understanding of healing

Australia’s rainforests first to switch from carbon sink to source

First-trimester mRNA COVID-19 vaccination and risk of major congenital anomalies

Glucose-lowering medication classes and cardiovascular outcomes in patients with type 2 diabetes

Rising seas and sinking cities signal a coastal crisis in China

Discovery of hundreds of new human gut viruses provides a new approach to studying the gut microbiome

Study indicates dramatic increase in percentage of US adults who meet new definition of obesity

Astrocytes are superstars in the game of long-term memory

WSU study finds positive framing can steer shoppers toward premium products

Study finds ending universal free school meals linked to rising student meal debt and stigma

Innovations in organoid engineering: Construction methods, model development, and clinical translation

Rescheduling coca: Aligning global drug policy with science, tradition, and indigenous rights

[Press-News.org] Transforming inexpensive quinolines into complex drug candidates
Scientists develop a cost-effective methodology to produce various biologically relevant organic compounds from simple feedstock chemicals