Article
Chemistry, Inorganic & Nuclear
Abebu A. Kassie, Ila Y. Castro De la Torre, Matthew S. Remy, Sukrit Mukhopadhyay, Jeff Kampf, Fengrui Qu, Melanie S. Sanford
Summary: This manuscript investigates the impact of different metals (ruthenium, iron, and manganese) on the PNP pincer complex-catalyzed dehydrogenative coupling reaction. The study reveals that the structures and reactivities of the intermediates vary depending on the metal used. It is found that the manganese pincer complex is an effective catalyst for the conversion of formamides and alcohols to carbamates under specific conditions.
Article
Chemistry, Organic
Sabrina Giofre, Camilla Loro, Letizia Molteni, Carlo Castellano, Alessandro Contini, Donatella Nava, Gianluigi Broggini, Egle M. Beccalli
Summary: A useful aminohalogenation reaction for the cyclization of O-alkynyl carbamates under copper catalysis has been developed in this study. N-Halosuccinimides were used as the halogen source, leading to selective intramolecular C-N bond formation and the generation of haloalkylidene substituted heterocycles. The mechanism for the two alternative reaction pathways was investigated by modeling the corresponding transition states at the DFT level.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Song-Ning Wang, Guo-Yu Zhang, Adedamola Shoberu, Jian-Ping Zou
Summary: A new method for the preparation of carbamates using copper-catalyzed cross-coupling reaction is described, which is environmentally friendly and compatible with a wide range of amines.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yang Yang, Dong Xing
Summary: In this study, an iridium-catalyzed branched-selective hydroacylation of 1-aryl 1,3-dienes with salicylaldehydes was successfully conducted under mild conditions without the need for phosphine ligands. The protocol yielded a series of alpha-branched beta,gamma-unsaturated o-hydroxyacetophenones with biological potentials in high efficiency and excellent regioselectivities. Exclusive linear-selective hydroacylation products were obtained when simple 1,3-butadiene or isoprene were used instead of 1-aryl 1,3-dienes.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Jichao Xiao, John Montgomery
Summary: A simple procedure for the nickel-catalyzed defluorinative alkylation of unactivated aliphatic aldehydes is reported. The protocol exhibits broad substrate scope, mild conditions, and a simple catalytic setup.
Article
Chemistry, Organic
Lingyun Yang, Yangfei Huang, Weijie Yu, Lijia Fan, Tao Wang, Junkai Fu
Summary: Organic carbamates are important structures in both organic chemistry and industry, but the synthesis of hydroxamic acid-based carbamates has received less attention due to the nucleophilicity of both O and N atoms in hydroxamic acids. In this study, a copper-catalyzed oxidative coupling reaction of quinazoline-3-oxides and formamides was reported for the efficient synthesis of O-quinazolinic carbamates. The protocol is practical, and involves simple starting materials and easy operation.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Samata E. Shetgaonkar, Aleena Raju, Hideyasu China, Naoko Takenaga, Toshifumi Dohi, Fateh V. Singh
Summary: Transition metal-catalyzed direct oxidative coupling reactions via C-H bond activation have become a convenient strategy for constructing complex molecules in organic synthesis. By directly transforming C-H bonds into carbon-carbon and carbon-heteroatom bonds, these reactions offer a more efficient alternative to traditional cross-coupling reactions. Hypervalent iodine compounds, with their excellent oxidizing nature and versatile reactivity, have emerged as mainstream reagents in this field.
FRONTIERS IN CHEMISTRY
(2022)
Article
Chemistry, Organic
Manoj Kumar Vala, Chithaluri Sudhakar, Suryakumari Adurthi, Shekhar Vanam
Summary: The carbamate group is commonly found in approved drugs and pro-drugs, and its use is increasing in medicinal chemistry and agrochemical industry. A method for synthesizing phenylcarbamate products by directly coupling simple phenols with mono- and di-alkyl formamides is presented.
SYNTHETIC COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Shuang Yang, Xiao-Yan Chen, Ming-Feng Xiong, Hao Zhang, Lei Shi, Dong-Zi Lin, Hai-Yang Liu
Summary: Copper porphyrin-catalyzed construction of C(sp(2))-O bond via coupling formamides with phenols was achieved for the first time, providing various carbamates in moderate to good yields with good functional group tolerance at low catalyst loading. Intermolecular competing kinetic isotope effect experiment revealed that the generation of formamide radical is the rate-determining step of the current cross-dehydrogenative coupling (CDC) reaction. This research extends the application of metalloporphyrin in CDC reaction.
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
(2021)
Article
Chemistry, Applied
Chongyang Shi, Boxia Xu, Xiaolan Fang, Xiaochun Yu, Huile Jin, Shun Wang
Summary: A copper-catalyzed oxidative dehydrogenative coupling of nitrosobenzenes with anilines was developed for the synthesis of unsymmetrical azoxybenzenes. This approach uses O-2 as the oxidant and provides diverse products different from those obtained in the Mills reaction. The use of an inexpensive copper catalyst, a broad substrate scope, and mild reaction conditions make this protocol an atom-economic and step-economic procedure for preparing unsymmetrical azoxy compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Multidisciplinary Sciences
Mahboubeh Asadi, M. Reza Naimi-Jamal, Leila Panahi
Summary: In this study, a new nano-scale Cu@salicylaldehyde-modified-chitosan (Cu@Sal-CS) catalyst was synthesized through a green, eco-friendly and cost-effective technique, and showed efficient performance in oxidative coupling reactions for organic compound synthesis.
SCIENTIFIC REPORTS
(2021)
Article
Chemistry, Organic
Camilla Loro, Julie Oble, Francesca Foschi, Marta Papis, Egle M. Beccalli, Sabrina Giofre, Giovanni Poli, Gianluigi Broggini
Summary: Treatment of O-allyl N-tosyl carbamates with aromatic compounds in the presence of Cu(OTf)(2) or TMSOTf as promoters results in the formation of N-substituted 1-arylpropan-2-amines, 1,2-diarylpropanes, 1,1-diarylpropanes, or indanes, depending on the nature of the promoter and aryl substrates. A proposed mechanism explains the outcome of these C-H based cascades, involving initial acid promoted decarboxylative/deamidative Friedel-Crafts allylation followed by protonation of the allylated arene.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Nidhi Mishra, Sumit K. Singh, Anoop S. Singh, Anand K. Agrahari, Vinod K. Tiwari
Summary: Glycosyl triazoles are efficient ligands for Cu-catalyzed Sonogashira reaction, overcoming challenges of sideways homocoupling reactions. High product yields can be achieved at 130 degrees C for various substrates, showing versatility of this catalytic system.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Long Zheng, Xueying Guo, Ying-Chao Li, Yichen Wu, Xiao-Song Xue, Peng Wang
Summary: In this study, the coupling of alkynes with Fischer-type copper carbene species bearing an alpha-siloxyl group is reported. The copper carbene species can be in situ generated from acylsilanes under photoirradiation and redox-neutral conditions. The side-arm modified bisoxazoline (SaBox) ligands play a crucial role in this coupling reaction, providing the corresponding alkynyl alcohol in high yields with remarkable heterocycle tolerance and broad substrate scope.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Atsuhisa Mitsui, Kazunori Nagao, Hirohisa Ohmiya
Summary: This study presents a novel approach for the chemoselective synthesis of alpha-hydroxy ketones through a reductive cross-coupling reaction between aromatic aldehydes and arylnitriles using a copper catalyst and a silylboronate as a reductant.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Mohana Reddy Mutra, Jing Li, Yu-Ting Chen, Jeh-Jeng Wang
Summary: In this study, time-atom economic regio- and chemoselective sulfonyl radical triggered 5-exo-dig cyclization of unactivated 1,6-enynes with sulfonyl halides was developed under metal, additive-free reaction conditions to obtain highly substituted five-membered heterocyclic compounds. This transformation involves the formation of three new bonds, including C-SO2, C-C, and active C-I/Br bonds. Importantly, the one-pot protocols allow for direct synthesis of desired products from sodium sulfinates and have additional advantages such as reducing chemical waste, saving time, and simplifying practical aspects compared to existing protocols.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Medicinal
Chi-Jen Tai, Atallah F. Ahmed, Chih-Hua Chao, Chia-Hung Yen, Tsong-Long Hwang, Fang-Rong Chang, Yusheng M. Huang, Jyh-Horng Sheu
Summary: Three new 5,5,6,6,5-pentacyclic spongian diterpenes were isolated from a Red Sea sponge. They exhibited inhibitory activity against superoxide anion generation, antibacterial properties, and anti-inflammatory effects, with one compound showing higher inhibition against Staphylococcus aureus.
Article
Biochemistry & Molecular Biology
Chi-Jen Tai, Chih-Hua Chao, Atallah F. Ahmed, Chia-Hung Yen, Tsong-Long Hwang, Fang-Rong Chang, Yusheng M. Huang, Jyh-Horng Sheu
Summary: Chemical investigation of the Red Sea sponge Spongia sp. resulted in the discovery of four new compounds, secodinorspongins A-D (1-4), as well as a known compound sponginolide (5). The structures of these compounds and their absolute configurations were elucidated using spectroscopic methods and a comparison of calculated and experimental CD spectra. A possible biosynthetic pathway for compounds 1-4 was proposed. The cytotoxic, antibacterial, and anti-inflammatory activities of compounds 1-5 were also evaluated, with compound 1 showing inhibitory activity against Staphylococcus aureus growth, and compounds 4 and 5 suppressing superoxide-anion generation and elastase release in human neutrophils.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Plant Sciences
Yen Chi Loo, Hao-Chun Hu, Szu-Yin Yu, Yi-Hong Tsai, Michal Korinek, Yang-Chang Wu, Fang-Rong Chang, Ying-Jung Chen
Summary: In this study, the anti-aging potential of Cosmos caudatus Kunth (CC) extracts and fractions was investigated. It was found that these extracts and fractions inhibited collagenase, MMP-1, and MMP-3 activities in human dermal fibroblasts and contained flavonoid glycosides as the major compounds. These findings suggest that CC has the potential to be developed as anti-aging products.
Review
Oncology
Ya-Ting Chuang, Jen-Yang Tang, Jun-Ping Shiau, Ching-Yu Yen, Fang-Rong Chang, Kun-Han Yang, Ming-Feng Hou, Ammad Ahmad Farooqi, Hsueh-Wei Chang
Summary: Cancer cells produce exosomes to regulate cell functions for tumor progression, and the modulation of exosome processing by natural products is not well understood. This review focuses on the organization of cancer-derived exosomal miRNAs and their processing and cell functions modulation by natural products. It provides a comprehensive understanding of the potential mechanisms and targets for exosome processing and cancer cell functions by natural products.
Article
Chemistry, Applied
Mohana Reddy Mutra, Yu-Ting Chen, Jeh-Jeng Wang
Summary: We have developed a photoinduced sulfonyl radical-triggered cyclization of 1,6-dynes without metals, oxidants, or additives. The reaction forms three new bonds (-SO2-C, C-C, and C-I/C-Se-) under mild conditions with excellent selectivity. The conversion is economically and atomically efficient, and can be easily scaled up. Mechanistic studies reveal that the reaction proceeds through a radical pathway. Subsequent synthetic transformations of the products result in various substituted compounds. Notably, a selective C-C single bond cleavage with boronic acid insertion was observed under Suzuki reaction conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Biochemistry & Molecular Biology
Jun-Ping Shiau, Ya-Ting Chuang, Ching-Yu Yen, Fang-Rong Chang, Kun-Han Yang, Ming-Feng Hou, Jen-Yang Tang, Hsueh-Wei Chang
Summary: This review aims to elucidate the relationship between natural products, miRNAs, and the AKT pathway in cancer cell development. By identifying the connections between miRNAs and the AKT pathway, as well as miRNAs and natural products, an miRNA/AKT/natural product axis was established to facilitate a better understanding of their anticancer mechanisms.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Medicine, Research & Experimental
Hsien-Kuo Chin, Mei-Chin Lu, Kai-Cheng Hsu, Mohamed El-Shazly, Tsen-Ni Tsai, Tzu-Yung Lin, Shou-Ping Shih, Tony Eight Lin, Zhi-Hong Wen, Yu-Chen S. H. Yang, Yi-Chang Liu
Summary: 13-AC is a compound derived from coral that can induce apoptosis in human acute lymphoblastic leukemia cells. It acts as a dual inhibitor of heat shock protein 90 and topoisomerase IIa, leading to its cytotoxic effects.
KAOHSIUNG JOURNAL OF MEDICAL SCIENCES
(2023)
Review
Oncology
Ya-Ting Chuang, Jun-Ping Shiau, Jen-Yang Tang, Ammad Ahmad Farooqi, Fang-Rong Chang, Yi-Hong Tsai, Ching-Yu Yen, Hsueh-Wei Chang
Summary: Cancer cells release exosomes containing tumor-promoting effects, and natural products can block exosome processing and inhibit cancer progression. However, the correlation between exosomal lncRNAs and natural product treatments is not well understood. By using bioinformatics, this study fills the gap by exploring the interaction between exosomal lncRNAs, miRNAs, and exosomal processing genes, and summarizes their roles in cancer progression and the anticancer effects of natural products.
Article
Biochemistry & Molecular Biology
Wei-Cheng Yuan, Tung-Ying Wu, Pei-Yi Chu, Fang-Rong Chang, Yang-Chang Wu
Summary: An efficient method for preparing bioactive ingredient 3S,3 ' S-astaxanthin (3S,3 ' S-AST) from genetically modified yeast was developed. The combination of enzyme-assisted extraction and salt-assisted liquid-liquid extraction (SALLE) resulted in a high yield of 3S,3 ' S-AST with over 99% purity. The antioxidant capacity of the purified 3S,3 ' S-AST products was found to be 18.3 times higher than that of the original raw material extract. This new method has the potential to replace previous methods and can be scaled up for the production of high-purity 3S,3 ' S-AST with lower cost and simpler equipment in the food and/or drug industries.
Review
Biochemistry & Molecular Biology
Jen-Yang Tang, Ya-Ting Chuang, Jun-Ping Shiau, Ching-Yu Yen, Fang-Rong Chang, Yi-Hong Tsai, Ammad Ahmad Farooqi, Hsueh-Wei Chang
Summary: This review focuses on the regulating effects of natural products on miRNAs to assess the potential impacts of radiomodulation and exosome biogenesis for both the radiosensitization of cancer cells and the radioprotection of non-cancer cells.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Jeh-Jeng Wang
Summary: Here, we report a photoinduced energy-transfer catalysis reaction of tethered conjugated dienes, enabling the synthesis of bridged cyclopropanes. This single-step reaction efficiently generates complex tricyclic compounds with multiple stereocenters from readily accessible starting materials. The reaction demonstrates a broad substrate scope, atom-economy, excellent selectivity, and satisfactory yield, including facile scale-up synthesis and synthetic transformation. An in-depth mechanistic study reveals that the reaction proceeds via an energy-transfer pathway.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Mohana Reddy Mutra, Jing Li, Jeh-Jeng Wang
Summary: We efficiently synthesized tetrasubstituted olefins in a highly selective and stereoselective manner using sulfonyl iodides from ynamides and internal alkynes under blue LED irradiation in just a few minutes. This metal-free, user-friendly, and environmentally friendly approach showed broad applicability, as demonstrated by the successful gram-scale experiment and subsequent transformation of the sulfonyl-iodinated products into diverse compounds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Lin-Wei Pan, Jun-Hao Lin, Yi-Chi Luo, Jeh-Jeng Wang
Summary: Here, we report a visible light-promoted intramolecular radical cascade reaction for the construction of fluorenol and naphthalene-fused cyclopropyl carbaldehyde derivatives. This method offers mild reaction conditions, a broad substrate scope, excellent step efficiency, and scalability, without the need for external chemical oxidants. The novelty of this protocol was demonstrated by synthesizing chrysene analogs and performing late-stage functionalizations.
Review
Chemistry, Medicinal
Heba A. S. El-Nashar, Mohamed Taleb, Mohamed EL-Shazly, Chao Zhao, Mohamed A. Farag
Summary: This review comprehensively discusses the antidiabetic effects and mechanisms of action of major soluble dietary fibers (SDF), which can aid in the development of novel natural antidiabetic drugs from SDF.
PHYTOTHERAPY RESEARCH
(2023)
