Article
Chemistry, Organic
Bedadyuti Vedvyas Pati, Prateep Singh Sagara, Asit Ghosh, Smruti Ranjan Mohanty, Ponneri Chandrababu Ravikumar
Summary: The ruthenium(II)-catalyzed cross dehydrogenative annulation of N-(7-azaindole)benzamides with maleimides has been successfully demonstrated as a new method. By utilizing N-amino-7-azaindole as a directing group, a variety of pharmacologically useful 7-azaindole-based isoquinolones were efficiently synthesized with wide functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Hong-Li Wu, Wei-Kang Zhang, Can-Can Zhang, Ling-Tao Wang, Wen-Hui Yang, Wen-Chan Tian, Guo-Ping Ge, Long-Yong Xie, Rongnan Yi, Wen-Ting Wei
Summary: Chemodivergent tandem radical cyclization was achieved for the synthesis of mono- and di-alkylated ring-fused quinazolinones. This process involved the generation of alkyl radicals through oxidant-induced α-C(sp(3))-H functionalization, leading to selective synthesis of the compounds. Mechanistic investigations revealed the key steps of 1,2-hydrogen shift, resonance, and proton transfer in the formation of these compounds. This protocol represents the first example of remote second alkylation on the aromatic ring through α-C(sp(3))-H functionalization and difunctionalization in radical cyclization.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Jinlei Wang, Haohua Chen, Lingheng Kong, Fen Wang, Yu Lan, Xingwei Li
Summary: This report describes a method for introducing distally disposed axial and central chirality via rhodium-catalyzed C-H alkylation of benzamides using N-arylmaleimide as the alkylating reagent. The process features excellent enantio- and diastereoselectivity, broad substrate scope, and mild reaction conditions. Chiral induction is achieved through the judicious choice of a chiral rhodium cyclopentadienyl catalyst.
Article
Chemistry, Organic
Zhucheng Zhang, Qian He, Xiaofei Zhang, Chunhao Yang
Summary: A method of direct C-4 selective alkylation of pyridines under visible light irradiation at room temperature is reported. The method uses simple maleate-derived pyridinium salts as pyridine precursors and readily available carboxylic acid-derived N-(acyloxy)phthalimides as alkyl radical precursors, affording good to excellent yields without using stoichiometric oxidants and acids.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Manotosh Bhakat, Bitasik Khatua, Joyram Guin
Summary: In this study, we demonstrate a nonconventional photo-catalytic method for generating Cl-center dot using dichloroethane as a common chlorinated solvent. The generated Cl-center dot is utilized for the cross-dehydrogenative coupling of alkanes and azaarenes through hydrogen atom transfer. This process is free from chloride salt, toxic oxidant, and UV light, and is applicable to a wide range of substrates.
Article
Chemistry, Organic
Fang-Ting Xiong, Bin-Hong He, Yu Liu, Quan Zhou, Jian-Hong Fan
Summary: An iron-promoted oxidative tandem alkylation/cyclization reaction has been developed for the efficient synthesis of 2-alkylated indenones. The reaction involves oxidative homolysis of a C-C Sigma-bond in 1,4-dihydropyridines to generate an alkyl radical, which then adds to the C-C triple bond in ynones and undergoes intramolecular cyclization. The reaction offers a mild and selective method for the synthesis of a series of 2-alkylated indenones.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Le Yang, Zhihong Qiu, Jintao Wu, Jianyou Zhao, Tong Shen, Xuan Huang, Zhong-Quan Liu
Summary: This study successfully achieved direct and site-specific alkylation of the (sp(3))C-H bond, leading to the synthesis of various unnatural alpha-amino acids and peptides in good yields under specific reaction conditions.
Article
Chemistry, Multidisciplinary
Wan-Xu Wei, Yuke Li, Ya-Ting Wen, Ming Li, Xue-Song Li, Cui-Tian Wang, Hong-Chao Liu, Yu Xia, Bo-Sheng Zhang, Rui-Qiang Jiao, Yong-Min Liang
Summary: This study reports a method for the synthesis of highly strained spirocyclobutane-pyrrolines via a palladium-catalyzed tandem reaction, with the key step involving the activation of the δ-C-H bond to form a five-membered spiro-palladacycle intermediate. The CMD process, rate-determining step, and energy barrier of the entire reaction were explored through DFT calculations. Control experiments were conducted to investigate the rate-determining step and reversibility of the C(sp(3))-H activation step.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Austin D. Marchese, Andrew G. Durant, Mark Lautens
Summary: A simple and modular approach using palladium catalysis to synthesize bis-heterocyclic spirocycles is reported. The method leverages a Mizoroki-Heck-type reaction to generate neopentylpalladium species, allowing for intramolecular C-H activation on a wide array of C-H bonds to produce a variety of spirocycles. The reaction is scalable, allowing for easy incorporation of biologically relevant heterocycles without the need for flash column chromatography.
Article
Chemistry, Organic
Bai-Yu Xue, Chen-Ying Hou, Xiao-Bing Wang, Ming-Sheng Xie, Hai-Ming Guo
Summary: A regio- and enantioselective Friedel-Crafts alkylation/N-hemiacetalization and dehydration sequence using N-methyl-4-aminoindole as the 1,4-bisnucleophile and beta,gamma-unsaturated alpha-ketoesters was reported. The reaction was catalyzed by 5 mol% Ni(ii)-PyBPI complex and resulted in the formation of diverse chiral 7-membered-ring-bridged 3,4-fused tricyclic indoles with good yields (up to 91%) and high enantioselectivity (up to 97% ee). The by-products obtained were 6-membered-ring-bridged 4,5-fused tricyclic indoles.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Nikoleta Spiliopoulou, Christoforos G. Kokotos
Summary: A new photochemical approach for the synthesis of symmetrical and non-symmetrical disulfides is described, utilizing mild, inexpensive and green conditions. The method involves the use of phenylglyoxylic acid as the photoinitiator, household bulbs as the light source, and a simple inorganic salt as the additive, resulting in excellent yields of the products.
Article
Chemistry, Organic
Wen-Qin Yu, Jian-Hong Fan, Pu Chen, Bi-Quan Xiong, Jun Xie, Ke-Wen Tang, Yu Liu
Summary: This study describes the transition-metal-free alkylation/cyclization of activated alkenes using Hantzsch ester derivatives as effective alkyl reagents. A wide variety of valuable oxindoles can be constructed in a single step with excellent selectivity. The reaction proceeds via the formation of alkyl radical species followed by tandem addition/annulation of olefins under oxidative conditions. This protocol is expected to inspire the development of novel and efficient applications of Hantzsch esters in organic synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Jinyuan Jiang, Jidan Liu, Zhenke Yang, Jieying Zheng, Xin Tian, Liyao Zheng, Zhao-Qing Liu
Summary: An efficient method has been developed for the direct C-H oxidative annulation of isoquinolones with allyl alcohols, leading to the synthesis of structurally diverse isoindolo[2,1-b]isoquinolin-5(7H)-ones with high atom economy. This protocol is tolerant of a broad spectrum of functionalities and can be conducted in one-pot operation using readily available N-methoxybenzamides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Akanksha Singh Baghel, Anjali Aghi, Amit Kumar
Summary: The regioselective ortho-alkenylation of primary benzamides with activated olefins using a Ru(II) catalyst has been achieved, allowing the controlled introduction of olefin motifs at the ortho-position of benzamides. The success of this strategy relies on fine-tuning reaction conditions and involves a base-assisted internal electrophilic-type substitution step in the reaction mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Pragati Biswal, Tanmayee Nanda, Namrata Prusty, Smruti Ranjan Mohanty, Ponneri C. Ravikumar
Summary: A rhodium-catalyzed oxidative C-H/N-H dehydrogenative[3 + 2] annulation strategy has been developed for the synthesis of 2-methylindole scaffolds by reacting anilines and N-allylbenzimidazole. This transformation involves the cleavage of the thermodynamically stable C-N bond of allylamine and proceeds through a cascade of C(sp(2))-H alkylation followed by intramolecular cyclization. Detailed mechanistic studies have been performed to identify a key intermediate.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Analytical
Lirong Jiang, Huan Ye, Dini Ma, Joao Rodrigues, Ruilong Sheng, Douyong Min
Summary: A fluorescent probe was developed for determining the freshness of fish-based foods. The probe showed good specificity and high sensitivity, and could rapidly respond to cadaverine. Cheap and portable sensing tags were fabricated for visually detecting gaseous cadaverine, and they were successfully used for non-contact and visual monitoring of cadaverine in fish.
Review
Chemistry, Medicinal
Yuebin Liu, Ruilong Sheng, Junting Fan, Ruihua Guo
Summary: Pentacyclic triterpenoids are natural active substances that can be classified into four subgroups, with oleanane being the most popular. 18 beta-Glycyrrhetinic acid, extracted from licorice, possesses diverse bioactivities and has significant importance in medicinal chemistry research.
MINI-REVIEWS IN MEDICINAL CHEMISTRY
(2022)
Article
Materials Science, Biomaterials
Zhao Wang, Wenli Song, Ruilong Sheng, Xinyu Guo, Lingyun Hao, Xiaojuan Zhang
Summary: A new series of cholesterol-bearing poly(methacrylate)s with pendant cationic (l-)-lysine (Chol-PHML) were synthesized. These polymeric vectors efficiently bound/load pDNA and formed nanoparticles. The gene transfection efficiency and cytotoxicity depended on the molecular weight of the polymer.
INTERNATIONAL JOURNAL OF POLYMERIC MATERIALS AND POLYMERIC BIOMATERIALS
(2023)
Article
Chemistry, Analytical
Huan Ye, Seyoung Koo, Beitong Zhu, Yingjun Ke, Ruilong Sheng, Ting Duan, Lintao Zeng, Jong Seung Kim
Summary: In this study, a series of fluorescent probes were constructed for rapid and non-destructive monitoring of meat freshness. Among them, JDCN showed outstanding sensing performance and enabled the two-color visualization of cadaverine vapor, providing a promising platform for real-time evaluation of meat freshness.
ANALYTICAL CHEMISTRY
(2022)
Article
Chemistry, Applied
Huan Ye, Yingjun Ke, Chenyang Yue, Peng Xie, Ruilong Sheng, Lintao Zeng
Summary: Researchers have developed a sensitive fluorescent sensing platform, Nap-NH2, for the detection of formaldehyde and phosgene. The platform utilizes different emission channels to quickly and accurately detect the presence of these toxic compounds. The sensor can be integrated into portable test strips and paired with a smartphone for data recording and analysis.
Review
Chemistry, Medicinal
Xiaojing Sun, Binyu Shen, Hui Yu, Wenhui Wu, Ruilong Sheng, Yiwen Fang, Ruihua Guo
Summary: This paper comprehensively summarizes the pharmacological activities of demethylzeylasteral, a compound extracted from Tripterygium wilfordii Hook. f., which exhibits various pharmacological effects including anticancer, anti-inflammatory, immune suppression, anti-fertility, antivirus, and antimicrobial activities. These findings highlight the potential application of demethylzeylasteral as a therapeutic agent.
Article
Chemistry, Physical
Zhao Wang, Xinyu Guo, Lingyun Hao, Xiaojuan Zhang, Qing Lin, Ruilong Sheng
Summary: A biocompatible drug delivery system with long circulation times, high cellular endocytosis efficiency, and targeted drug release was designed and synthesized. The system showed smart surface charge conversion and accelerated drug release under the tumor microenvironment, leading to enhanced cellular uptake and inhibition of tumor cell proliferation. This system has the potential to serve as a multifunctional nanoplatform for effective oncology treatment.
Article
Biochemistry & Molecular Biology
Na Li, Xinyu Li, Meidi Deng, Feifei Zhu, Zian Wang, Ruilong Sheng, Wenhui Wu, Ruihua Guo
Summary: In this study, a series of isosteviol derivatives were synthesized and evaluated for their inhibitory activity on PTP1B. Most derivatives showed moderate inhibitory activities, but derivatives 10, 13, 24, and 27 exhibited remarkable bioactivities. Among them, derivative 24 showed the best inhibitory activity against PTP1B with high selectivity. Molecular docking studies suggested that the hydrogen bond interaction between 24 and LYS-116 residue in PTP1B is essential for its inhibitory activity. These findings indicate that derivative 24 has great potential as a drug candidate for the treatment of obesity and type II diabetes.
BIOORGANIC & MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Xiaojing Sun, Lin Xing, Jieying Yuan, Enxiao Wang, Yuxin Ding, Ruilong Sheng, Fang Wang, Wenhui Wu, Xiuwei H. Yang, Ruihua Guo
Summary: In this study, a new series of DEM derivatives were synthesized by modifying active groups in the chemical structure of DEM. Among them, derivative 7 showed remarkable inhibitory effect on three human cancer cell lines (A549, HCT116, and HeLa) and induced apoptosis in tumor cells.
Review
Chemistry, Medicinal
Yifan Shen, Ruilong Sheng, Ruihua Guo
Summary: Developing natural product-based anti-cancer drugs is a promising approach to overcome the side effects and toxicity of traditional chemotherapeutics. However, evaluating the in vivo anti-cancer activities of natural products is challenging. Zebrafish models have been utilized to address this issue and have shown great potential in assessing the in vivo activities of natural compounds.
Article
Biophysics
Jian Chen, Hui Wang, Li Zhang, Wanying Yan, Ruilong Sheng
Summary: This study developed stealth mPEG5k-PEI25k polymers as vaccine carriers for cancer immunotherapy. The polymers exhibited reduced cytotoxicity and improved IL-2 secretion compared to the control. The study also demonstrated that the cell biological features could be optimized by selecting suitable grafting ratios and weight ratios of the polymers.
COLLOIDS AND SURFACES B-BIOINTERFACES
(2023)
Review
Chemistry, Applied
Xichao Hu, Yingjun Ke, Huan Ye, Beitong Zhu, Joao Rodrigues, Ruilong Sheng
Summary: In this review, the recent progress of various fluorescent probes for phosgene and mustard gas detection is introduced, including recognition sites, sensing mechanisms, and structure-function relationships. Furthermore, the challenges and perspectives of fluorescent probes for chemical warfare agents are briefly stated. We hope this review will provide constructive information for the development of the most advanced fluorescent probes towards CWAs.
Article
Polymer Science
Zhao Wang, Jiajian Shi, Mengyao Gu, Xiaojuan Zhang, Ruilong Sheng
Summary: Developing facile, green, and efficient synthetic methodology for preparing surface-functionalized nanogels has attracted tremendous attention in the field of polymer chemistry and biomaterials engineering. This study successfully prepared clickable P(MAA-PMA) nanogels with reactive alkyne groups and characterized their physicochemical properties. The nanogels exhibited pH/redox responsiveness and were easily modified with thiol-containing functional ligands via thiol-yne photo click reaction. The folic acid-functionalized nanogels loaded with doxorubicin showed higher tumor cell proliferation inhibition effect compared to the non-functionalized counterparts.
JOURNAL OF APPLIED POLYMER SCIENCE
(2023)
Review
Chemistry, Multidisciplinary
Jinkai Zhang, Yu Zhuang, Ruilong Sheng, Helena Tomas, Joao Rodrigues, Guangyin Yuan, Xudong Wang, Kaili Lin
Summary: This review provides an overview of recent progress in the functionalization of titanium implants using smart stimuli-responsive (SSR) strategies. It discusses the material design and fabrication, responsive mechanisms, and in vitro and in vivo evaluations of these implants. The limitations, challenges, and future directions of SSR titanium implants are also discussed.
MATERIALS HORIZONS
(2023)
Article
Chemistry, Multidisciplinary
Sheng-Lin Pei, Jin Zhang, Wanyun Ge, Chao Liu, Ruilong Sheng, Lintao Zeng, Ling-Hui Pan
Summary: In this study, a resorufin-based fluorescence probe was reported for sensing various BAs. The probe showed rapid response, good selectivity, and low detection limit, and demonstrated good performance in visualizing BAs in living cells and zebrafish.
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
