Photocatalytic Difunctionalization of [1.1.1]Propellane DOI Open Access
Tanmay Das, M. F. Mohär, Alakananda Hajra

et al.

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

The hunt for new molecular structures to improve the efficacy of biologically active molecules is at forefront pharmaceutical chemistry. So synthetic chemists have always been busy in last few decades synthesizing and testing frameworks which would work as more efficient bioisosteres present bioactive functional groups. In this area, bicyclo[1.1.1]pentane (BCP) framework has identified a promising candidate. It being utilized bioisostere aryl, tert-butyl, alkynes, etc. Now major precursor various BCP derivatives [1.1.1]propellane functionalization drawn widespread attention organic chemist community. Over past two decades, use visible light synthesis rapidly gained popularity, it represents one most approaches aligned with principles green sustainable chemistry, several interesting papers covering photocatalytic difunctionalization also published decade. This particular field really attracted That why we decided compile review article articles related under conditions. Here review, categorized discussed three categories, namely i) without using any catalyst, ii) organocatalysts, iii) metal catalysts deeper understanding key aspects these transformations.

Language: Английский

C−F bond activation enables synthesis of aryl difluoromethyl bicyclopentanes as benzophenone-type bioisosteres DOI Creative Commons
Mingshuo Chen,

Yuang Cui,

Xiaoping Chen

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Jan. 10, 2024

Abstract Bioisosteric design has become an essential approach in the development of drug molecules. Recent advancements synthetic methodologies have enabled rapid adoption this strategy into discovery programs. Consequently, conceptionally innovative practices would be appreciated by medicinal chemistry community. Here we report expeditous method for synthesizing aryl difluoromethyl bicyclopentane (ADB) as a bioisostere benzophenone core. This involves merger light-driven C−F bond activation and strain-release under catalysis newly designed N -anionic-based organic photocatalyst. defluorinative coupling methodology enables direct conversion wide variety commercially available trifluoromethylaromatic bonds (more than 70 examples) corresponding bicyclo[1.1.1]pentanes (BCP) arenes/difluoromethyl BCP boronates single step. The can also applied to [3.1.1]and [4.1.1]propellane systems, providing access analogues with different geometries. Moreover, successfully used protocol rapidly prepare ADB-substituted bioactive molecule Adiporon. Biological testing shown that ADB scaffold potential enhance pharmacological properties benzophenone-type candidates.

Language: Английский

Citations

32

Divergent Synthesis of Sulfur‐Containing Bridged Cyclobutanes by Lewis Acid Catalyzed Formal Cycloadditions of Pyridinium 1,4‐Zwitterionic Thiolates and Bicyclobutanes DOI
Yuanjiu Xiao, Feng Wu, Lei Tang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: May 31, 2024

Bridged cyclobutanes and sulfur heterocycles are currently under intense investigation as building blocks for pharmaceutical drug design. Two formal cycloaddition modes involving bicyclobutanes (BCBs) pyridinium 1,4-zwitterionic thiolate derivatives were described to rapidly expand the chemical space of sulfur-containing bridged cyclobutanes. By using Ni(ClO

Language: Английский

Citations

18

More Than Resveratrol: New Insights into Stilbene-Based Compounds DOI Creative Commons
Paulina Pecyna,

Joanna Warguła,

Marek Murias

et al.

Biomolecules, Journal Year: 2020, Volume and Issue: 10(8), P. 1111 - 1111

Published: July 27, 2020

The concept of a scaffold concerns many aspects at different steps on the drug development path. In medicinal chemistry, choice relevant “drug-likeness” is starting point for design structure dedicated to specific molecular targets. For years, chemical uniqueness stilbene has inspired scientists from fields such as biology, pharmacy, and medicine. this review, we present outstanding potential stilbene-based derivatives. Naturally occurring stilbenes, together with powerful synthetic chemistry possibilities, may offer an excellent approach discovering new structures identifying their therapeutic With scientific tools, sophisticated equipment, better understanding disease pathogenesis level, moved innovation in science. This paper mainly focuses compounds beyond resveratrol, which are particularly attractive due biological activity. Given “fresh outlook” about stilbenoids particular regard isorhapontigenin methoxy- hydroxyl- analogues, update combretastatins, very often overlooked underestimated benzanilide story remarkable structure.

Language: Английский

Citations

118

Room temperature 3D printing of super-soft and solvent-free elastomers DOI Creative Commons
Renxuan Xie, Sanjoy Mukherjee,

Adam E. Levi

et al.

Science Advances, Journal Year: 2020, Volume and Issue: 6(46)

Published: Nov. 13, 2020

Super-soft elastomers derived from bottlebrush polymers show promise as advanced materials for biomimetic tissue and device applications, but current processing strategies are restricted to simple molding. Here, we introduce a design concept that enables the three-dimensional (3D) printing of super-soft solvent-free at room temperature. The key advance is class inks comprising statistical self-assemble into well-ordered body-centered cubic sphere phases. These soft solids undergo sharp reversible yielding 20°C in response shear with yield stress can be tuned by manipulating length scale microphase separation. addition soluble photocrosslinker allows complete ultraviolet curing after extrusion form near-perfect recoverable elasticity well beyond strain. structure-property rules create exciting opportunities tailor performance 3D-printed ways not possible processes.

Language: Английский

Citations

112

Structure-related endocrine-disrupting potential of environmental transformation products of benzophenone-type UV filters: A review DOI

Lale Carstensen,

Stephan Beil,

Hilmar Börnick

et al.

Journal of Hazardous Materials, Journal Year: 2022, Volume and Issue: 430, P. 128495 - 128495

Published: Feb. 16, 2022

Language: Английский

Citations

54

Comparison between pollutants found in breast milk and infant formula in the last decade: A review DOI Creative Commons
Irene Martín-Carrasco,

Pilar Carbonero-Aguilar,

Bouchra Dahiri

et al.

The Science of The Total Environment, Journal Year: 2023, Volume and Issue: 875, P. 162461 - 162461

Published: March 1, 2023

Since ancient times, breastfeeding has been the fundamental way of nurturing newborn. The benefits breast milk are widely known, as it is a source essential nutrients and provides immunological protection, well developmental benefits, among others. However, when not possible, infant formula most appropriate alternative. Its composition meets nutritional requirements infant, its quality subject to strict control by authorities. Nonetheless, presence different pollutants detected in both matrices. Thus, aim present review make comparison between findings terms contaminants last decade, order choose convenient option depending on environmental conditions. For that, emerging including metals, chemical compounds derived from heat treatment, pharmaceutical drugs, mycotoxins, pesticides, packaging materials, other were described. While concerning found metals such materials outstanding. In conclusion, convenience using feeding diet based or either depends maternal circumstances. important take into account compared formula, possibility combination with fulfilled only intake milk. Therefore, more attention should be paid analyzing these conditions each case able proper decision, will vary newborn environment.

Language: Английский

Citations

29

A review of sources, pathways, and toxic effects of human exposure to benzophenone ultraviolet light filters DOI Creative Commons
Yan‐an Yao, You Wang,

Hengling Zhang

et al.

Eco-Environment & Health, Journal Year: 2023, Volume and Issue: 3(1), P. 30 - 44

Published: Oct. 19, 2023

Benzophenone ultraviolet light filters (BPs) are high-production-volume chemicals extensively used in personal care products, leading to widespread human exposure. Given their estrogenic properties, the potential health risks associated with exposure BPs have become a public concern. This review aims summarize sources and pathways of risks. Dermal exposure, primarily through use sunscreens, constitutes major pathway for BP At recommended application rate, dermal BP-3 via sunscreens may reach or exceed suggested reference dose. Other BPs, such as drinking water, seafood, packaged foods, contribute minimal overall Inhalation is minor exposure; however, its contribution cannot be ignored. Human an order magnitude higher North America than Asia Europe. Studies conducted on laboratory animals cells consistently demonstrated toxic effects elicit reproductive developmental toxicities. Furthermore, neurotoxicity, hepatotoxicity, nephrotoxicity, carcinogenicity been reported from chronic In addition animal cell studies, epidemiological investigations identified associations between couples' fecundity other disorders, well adverse birth outcomes. Further studies urgently needed understand posed by health.

Language: Английский

Citations

27

Palladium-Catalyzed Carbonylative Synthesis of Diaryl Ketones from Arenes and Arylboronic Acids through C(sp2)–H Thianthrenation DOI
Jiajun Zhang, Xiao‐Feng Wu

Organic Letters, Journal Year: 2023, Volume and Issue: 25(12), P. 2162 - 2166

Published: March 21, 2023

The development of mild methodology for converting inert C-H bonds to value-added molecules has been an attractive research topic during the last few decades as it offers efficient preparation. Meanwhile, diaryl ketones hold potent applications in antitumor drugs, agrochemical industry, and synthetic chemistry. Herein, we report versatile palladium-catalyzed carbonylative cross-coupling reactions aryl thianthrenium salts with arylboronic acids. Arenes were transformed site selectively via C(sp2)-H thianthrenation, various desired produced good excellent yields.

Language: Английский

Citations

26

Visible light-induced synthesis of 1,3-disubstituted bicyclo[1.1.1]pentane ketonesviacooperative photoredox and N-heterocyclic carbene catalysis DOI
Yan Gao,

Zicong Zheng,

Yu Zhu

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(10), P. 3909 - 3915

Published: Jan. 1, 2023

Visible light-induced highly efficient synthesis of 1,3-disubstituted bicyclo[1.1.1]pentane with mild conditions, high atom economy, and superior functional group tolerance.

Language: Английский

Citations

26

A comprehensive review on palladium nanocatalysts in carbonylative Suzuki-coupling reactions DOI
Peng Hu, Mosstafa Kazemi

Journal of Coordination Chemistry, Journal Year: 2024, Volume and Issue: 77(12-14), P. 1324 - 1348

Published: July 15, 2024

Carbonylative Suzuki–Miyaura coupling is an attractive and efficient strategy for preparation of diaryl ketones. reactions are difficult palladium complexes popular catalysts. The use as catalysts allows the reaction to be carried out under milder conditions ketone products prepared with good high yields. nanocatalysts has become effective performing complex especially carbonylative because have characteristics both homogeneous heterogeneous catalytic systems. In this review, we study application ketones through aryl halides, arylboronic acids carbonyl sources. Based on internet code survey research, paper first review in reactions. We believe will a valuable source chemists working field or

Language: Английский

Citations

9