Article
Chemistry, Organic
Yan Chen, Vincent Gandon, Christophe Bour
Summary: Difluoromethylene-skipped enones can be readily synthesized from arylvinyltriflates and aryldifluoroenoxysilanes using a squaramide/Li+ catalyst. This strategy enables the reaction between a typically weak electrophile and a weak nucleophile, which is difficult to achieve with classical aldol/dehydration methods.
Article
Chemistry, Organic
Baris Temelli, Pinar Kapci
Summary: A copper triflate-mediated approach is described for the first time to access copper complexes of pyrrole-substituted corroles from the reaction of 1,9-diformyldipyrromethanes and an excess amount of pyrrole. This procedure provides a simple and efficient way to prepare corroles with a polymerizable substituent on meso-positions.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Vinita Yadav, Sayali G. Jagtap, Ekambaram Balaraman, Santosh B. Mhaske
Summary: A novel method for the synthesis of N-substituted indoles under additive and base-free conditions is reported. The method utilizes a one-pot cascade approach with water as the only stoichiometric byproduct. The catalytic system used in this transformation exhibits high efficiency. A diverse range of N-alkylated indoles can be synthesized using various substrates.
Article
Multidisciplinary Sciences
Hang Chen, Zhi-Zhong Wu, Dong-Yang Shao, Pei-Qiang Huang
Summary: The catalytic asymmetric geminal bis-nucleophilic addition to nonreactive functional groups is a highly desirable yet challenging transformation in organic chemistry. In this study, the first catalytic asymmetric reductive/deoxygenative alkynylation of secondary amides was reported. The method combines iridium/copper relay catalysis with organocatalysis and allows the efficient synthesis of a variety of chiral a-branched amines. The protocol also demonstrates excellent enantioselectivity, chemoselectivity, and functional group tolerance.
Article
Chemistry, Applied
Li-Sheng Wang, You Zhou, Shuang-Gui Lei, Bo-Cheng Tang, Zhi-Cheng Yu, Yong-Xing Tang, Yan-Dong Wu, An-Xin Wu
Summary: A one-pot multicomponent cascade cyclization reaction has been reported, involving the introduction of -OCD3 into pyrroles in situ using I-2-DMSO as a mediator. The reaction includes readily available substrates such as methyl ketones, aniline, ethyl benzoylacetate, and CD3OD, and forms one C-C bond, one C-O bond, and two C-N bonds. This process has demonstrated good substrate compatibility (62 examples) and eliminates the need for anhydrous and anaerobic conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Ruiqin Zhang, Yuxin Ding, Renchao Ma, Xuqiong Xiao, Rener Chen, Lei Wang, Yongmin Ma
Summary: An efficient synthesis method for multi-substituted pyridines and pyrroles from aryl methyl ketones with 1-amino-2-methylpropan-2-ol and 1,2-diamino-2-methylpropane has been developed. The reactions involve cleavage of a C-N bond and formation of two new bonds (C-C bond and C-N bond) through an oxidative cyclization process promoted by I-2/PhNO2. The selective cleavage occurs at the C-N bond adjacent to the primary carbon of 1,2-diamino-2-methylpropane.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Letter
Chemistry, Organic
Amol Prakash Pawar, Jyothi Yadav, Atul Jankiram Dolas, Yadav Kacharu Nagare, Eldhose Iype, Krishnan Rangan, Indresh Kumar
Summary: An operationally simple organocatalytic method has been developed to create functionality with a chiral tertiary/quaternary stereocenter at position C3 of pyrrole. The synthesized chiral C3-hydroxyalkylated N-alkyl/Ar/H-pyrroles showed good to high yields and excellent enantioselectivity.
Article
Chemistry, Multidisciplinary
Yong Yang, Zhuoyu Wen, Zixuan Zu, Dongliang Wang, Huairong Zhou, Dongqiang Zhang
Summary: Direct CO2 methylation with toluene has potential for CO2 utilization to produce para-xylene, but the tandem catalysis faces challenges of low conversion and selectivity. Thermodynamic analyses and comparison with catalytic results are conducted to investigate product distribution and optimize conditions for higher conversion and selectivity.
Article
Chemistry, Organic
Haijian Wu, Jing Gui, Manman Sun, Yongmin Ma, Jianguo Yang, Zhiming Wang
Summary: A palladium-catalyzed C-H allylation/annulation reaction was developed to synthesize 3,4-dihydroisoquinolones with a vinyl substituent. This cascade cyclization involving allylic alcohols has not been reported before. The use of commercially available allylic alcohols, water as the only by-product, and O2 as the terminal oxidant provides environmentally friendly advantages.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Matthew B. B. Williams, Matthew L. L. Martin, Steffen Wiedmann, Alistair Boyer
Summary: 1,1-Dibromoalkenes can be directly used as precursors for the synthesis of 5-substituted 1,2,3-triazoles. Three different approaches, dependent on the N1 substituent, were developed to access various 1,2,3-triazole products. Treatment of 1,1-dibromoalkenes with n-butyllithium and reaction with a sulfonyl azide yielded 5-substituted 1-sulfonyl-1,2,3-triazoles. Reaction of the lithium base with zinc followed by reaction with aryl azides provided access to 1-aryl-1,2,3-triazoles. Lastly, the use of EtMgBr as base and reaction with an alkyl azide afforded 1-alkyl-1,2,3-triazoles.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Inorganic & Nuclear
Akira Imaizumi, Akinobu Nakada, Takeshi Matsumoto, Toshiyuki Yokoi, Ho-Chol Chang
Summary: This study demonstrates a simple thermal synthesis of porous aluminosilicates from a single-source spiro-7-type molecular precursor. The synthesized aluminosilicates show low carbon content, large surface area, and improved catalytic activity.
INORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Saiprasad Nunewar, Sanjeev Kumar, Srilakshmi Talakola, Srinivas Nanduri, Vinaykumar Kanchupalli
Summary: Metal carbenes play a crucial role in transition-metal-catalyzed synthetic transfer reactions. Meanwhile, C-H functionalizations catalyzed by Co(III), Rh(III) & Ir(III) have been well established. The combination of C-H activation and carbene migratory insertion has gained significant attention in recent years.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Review
Chemistry, Organic
Ismail A. Abdelhamid, Mahmoud A. E. Hawass, Sherif M. H. Sanad, Ahmed H. M. Elwahy
Summary: Interest in pyrazole chemistry has increased significantly in the past decade due to the fascinating properties demonstrated by numerous pyrazole derivatives. Researchers have focused on creating hybrid molecules to enhance biological effectiveness and have explored various methods for constructing pyrazole-substituted heterocycles using pyrazole carboxaldehydes as effective precursors.
Article
Chemistry, Multidisciplinary
Amol Prakash Pawar, Jyothi Yadav, Nisar Ahmad Mir, Eldhose Iype, Krishnan Rangan, Sumati Anthal, Rajni Kant, Indresh Kumar
Summary: The study developed a simple multicomponent method for synthesizing beta-substituted pyrroles, using aqueous succinaldehyde, primary amines, and isatins. The research delved into the direct synthesis of beta-substituted free NH-pyrrole, and DFT calculations and preliminary mechanism investigation supported a possible reaction pathway.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Ravinder Kumar, Raj Kamal, Vipan Kumar
Summary: The present study demonstrates the synthetic applications of alpha-aryl-beta,beta-ditosylm ketones as versatile precursors for synthesizing underexplored pyrazoles. The regiochemistry and structure of the pyrazoles were confirmed using various analytical techniques. The strategy offers simplicity, high regioselectivity, and versatile reactivity. Furthermore, this methodology has potential applications in the synthesis of regioisomeric analogues of well-recognized drugs.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Hai-Hao Han, Han-Min Wang, Paramesh Jangili, Mingle Li, Luling Wu, Yi Zang, Adam C. Sedgwick, Jia Li, Xiao-Peng He, Tony D. James, Jong Seung Kim
Summary: Cancer is a major global health problem, with millions of people diagnosed each year. Current chemotherapy options lack selectivity for cancer cells, are prone to resistance, and have toxicities. Researchers have focused on developing prodrug-based strategies to overcome these limitations. This review discusses recently developed prodrug strategies for cancer therapy and highlights the importance of targeting specific biomarkers in the tumor microenvironment and overexpressed in cancer cells. The advantages and limitations of each approach are also discussed.
CHEMICAL SOCIETY REVIEWS
(2023)
Review
Chemistry, Inorganic & Nuclear
Zhiqiang Mao, Ji Hyeon Kim, Jieun Lee, Hao Xiong, Fan Zhang, Jong Seung Kim
Summary: In recent years, BODIPY-based theranostics have been increasingly utilized in cancer therapy with remarkable success. By modifying the chemical structure, the optical imaging and phototherapy properties of BODIPY-based dyes can be well-balanced and tailored. Additionally, molecular/nanoparticle engineering allows versatile functionalities and improved tumor-targeting ability, enhancing the therapeutic efficacy and minimizing side effects. This review focuses on the applications of BODIPY-based theranostics in tumor therapy, including fluorescence-guided chemotherapy, photodynamic therapy, photothermal therapy, and multi-modal imaging-guided therapies.
COORDINATION CHEMISTRY REVIEWS
(2023)
Review
Chemistry, Inorganic & Nuclear
Xiaorui Shi, Miae Won, Chu Tang, Qihang Ding, Amit Sharma, Fu Wang, Jong Seung Kim
Summary: The RNA splicing process is essential for gene expression, and monitoring and controlling it can help repair mutant genes and treat diseases. However, the lack of appropriate tools hampers the understanding of splicing regulation.
COORDINATION CHEMISTRY REVIEWS
(2023)
Review
Oncology
Zhe Yang, Di Gao, Jing Zhao, Gaojie Yang, Ming Guo, Ying Wang, Xuechun Ren, Jong Seung Kim, Lin Jin, Zhongmin Tian, Xingcai Zhang
Summary: Immunotherapy has revolutionized cancer treatment, but promoting antitumour immunity in patients with resistant tumours remains a challenge. Thermal therapies offer a promising approach by reprogramming the tumour microenvironment and promoting immune cell recruitment. This review summarizes the role of thermal therapies in combination with immunotherapies, as well as the development of thermal immuno-nanomedicines for cancer treatment.
NATURE REVIEWS CLINICAL ONCOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Yuling Xu, Chonglu Li, Jusung An, Xin Ma, Jingfang Yang, Lishi Luo, Yun Deng, Jong Seung Kim, Yao Sun
Summary: Researchers synthesized a novel Pt(II) metallacycle (Pt1110) that can be activated with a 980 nm laser for photodiagnosis/treatment in deep tissue. Pt1110 showed significantly improved photothermal conversion and O-1(2) generation compared to the ligand itself 1, and it was capable of light-induced sterilization under safe laser irradiation. Pt1110 also had little to no toxicity to cells. When incorporated into liposomes, Pt1110 NPs effectively promoted wound healing in infection and keratitis models upon laser irradiation, observed by NIR-II fluorescence imaging. This novel metal-coordinated supramolecular material has the potential to be a universal platform for phototherapy in deep tissue.
SCIENCE CHINA-CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Mingle Li, Jungryun Kim, Hyeonji Rha, Subin Son, Matthew S. Levine, Yunjie Xu, Jonathan L. Sessler, Jong Seung Kim
Summary: Pyroptosis is a programmed cell death process characterized by the release of pro-inflammatory cytokines. The recent focus on pyroptosis stems from its potential to induce host immunity, with interest in photon-controlled pyroptosis activation (PhotoPyro) emerging as a strategy for systemic immunity via photoirradiation. In this Perspective, we discuss the current state of PhotoPyro and its potential to trigger antitumor immunity, providing insights and highlighting cutting-edge breakthroughs for future contributions in this area.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Moyi Liu, Yunli Luo, Junyu Yan, Xiaolin Xiong, Xiwen Xing, Jong Seung Kim, Taotao Zou
Summary: Boronic acid (or ester) is commonly used in the development of anticancer prodrugs, but their application is hindered by low activation efficiency. In this study, a photoactivation approach was developed to convert the boronic acid-caged iridium complex into a bioactive form under hypoxic tumor microenvironments. The mechanism involves the photo-oxidation of phenyl boronate anion to generate a highly reactive phenyl radical, which can capture O2 even at low concentrations. This photoactivation approach shows potent antitumor activities in various experimental models. It can also be extended to activate prodrugs of other anticancer compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Minsu Park, Kyoung Sunwoo, Yoon-Jae Kim, Miae Won, Yunjie Xu, Jaewon Kim, Zhongji Pu, Mingle Li, Ji Young Kim, Jae Hong Seo, Jong Seung Kim
Summary: A study introduces a new method to selectively eliminate cancer stem cells by cutting off proton leaks on the inner mitochondrial membrane. A molecule channel blocker called Bo-Mt-Ge, derived from Gardenia jasminoides fruit extract, is developed. This study also identifies the mitochondrial uncoupling protein UCP2 as being closely correlated with the stemness of cancer stem cells, providing a new perspective for drug discovery targeting these cells.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
News Item
Chemistry, Multidisciplinary
Yunjie Xu, Jong Seung Kim, Mingle Li
Review
Chemistry, Multidisciplinary
Siyue Ma, Ji Hyeon Kim, Wei Chen, Lu Li, Jieun Lee, Junlian Xue, Yuxia Liu, Guang Chen, Bo Tang, Wei Tao, Jong Seung Kim
Summary: Targeted fluorescent prodrugs that efficiently accumulate in tumor cells in different organs have shown great potential in improving drug targeting efficacy for tumor therapy. In this review, the development of innovative targeted fluorescent prodrugs for lung cancer, liver cancer, cervical cancer, breast cancer, glioma, and colorectal cancer is highlighted. The latest progress in chemical design and synthetic considerations, as well as the activation of therapeutic efficacy and fluorescence by tumor-specific stimuli, are reviewed. Furthermore, novel perspectives on engineered nanoparticle platforms and their use in monitoring the delivery of therapeutic agents in preclinical models are provided.
Review
Chemistry, Multidisciplinary
Zhiqiang Mao, Hyeonji Rha, Jungryun Kim, Xinru You, Fan Zhang, Wei Tao, Jong Seung Kim
Summary: Near-infrared fluorescence imaging is crucial for studying the biological world. However, the short emissions and small Stokes shifts of current xanthene dyes have limited their biological applications. A new technique involving THQ structural modification has been developed, which allows for longer emission wavelengths and larger Stokes shifts in THQ-modified xanthene dyes. This opens up possibilities for various applications of THQ-xanthene in fluorescence probe-based sensing and imaging, cancer theranostics, and super-resolution imaging.
Article
Engineering, Biomedical
Zehra Zunbul, Jusung An, Hira Aziz, Jinwoo Shin, Sungsu Lim, Le Yu, Yun Kyung Kim, Jong Seung Kim
Summary: Fluorescence imaging of amyloid beta (A beta) polypeptide using a small-molecule fluorophore is a practical system for Alzheimer's disease (AD) diagnosis. A molecular designing strategy for a new fluorogenic probe is suggested, with redshifted fluorescence emission wavelength and optimized binding affinities for A beta fibrils. Thioflavin T (ThT)-derived fluorescent dyes are developed by adjusting the hydrophobicity of electron donor moiety, resulting in significantly sensitive fluorogenic probes for bioimaging in AD.
ADVANCED NANOBIOMED RESEARCH
(2023)
Review
Chemistry, Multidisciplinary
Nayeon Kang, Subin Son, Sunhong Min, Hyunsik Hong, Chowon Kim, Jusung An, Jong Seung Kim, Heemin Kang
Summary: Ferroptosis, an iron-dependent programmed cell death mechanism, can be regulated by intracellular iron supplementation and glutathione synthesis inhibition. Utilizing various endogenous and exogenous stimuli, such as tumor microenvironment conditions and external energy sources, can provide precise control and controllability for ferroptosis-based cancer therapy. The utilization of dual stimuli provides a new direction for efficient cancer therapy.
CHEMICAL SOCIETY REVIEWS
(2023)
Review
Materials Science, Biomaterials
Le Tu, Qian Li, Sheng Qiu, Meiqin Li, Jinwoo Shin, Pan Wu, Nem Singh, Junrong Li, Qihang Ding, Cong Hu, Xiaoxing Xiong, Yao Sun, Jong Seung Kim
Summary: This review article provides an overview of the recent development of carbon dots (CDs) in biomedical research. It highlights the crucial applications of CDs in biosensing, bioimaging, cancer therapy, and antibacterial applications. The challenges and future potential of CD-based biomedicine are also emphasized, enriching biomedical researchers' knowledge about the potential of CDs and the need for overcoming technical obstacles.
JOURNAL OF MATERIALS CHEMISTRY B
(2023)
Article
Chemistry, Multidisciplinary
Minhyeok Choi, Nem Singh, Subin Son, Ji Hyeon Kim, Minjung Kang, Su Hong Park, Dong Hoon Choi, Chang Seop Hong, Jong Seung Kim
Summary: The discharge of chemicals and textile waste into industrial effluents significantly pollutes water, making it unbearable for humans and other organisms. Conventional water treatment processes are efficient in degrading stable organic dye molecules. However, there is a continuous demand for sustainable technology to degrade toxic organic pollutants. In this study, a porphyrin-based porous organic polymer (PNP) modified with platinum clusters (Pt@PNP) was developed to enhance the photocatalytic degradation of toxic organic dyes in water. This modified catalyst effectively decomposed carcinogenic organic dyes by generating reactive oxygen species (ROS) under mild light irradiation, and it showed high efficiency and recyclability.
MATERIALS CHEMISTRY FRONTIERS
(2023)
