Article
Chemistry, Organic
Jantra Jantrapirom, Nitwaree Palavong, Jumreang Tummatorn, Charnsak Thongsornkleeb, Somsak Ruchirawat
Summary: Our research develops a divergent synthesis approach for the production of 3,4-dihydro-2H-benzo[h]chromen-2-one and fluorenone derivatives using ortho-alkynylarylketones as common precursors. The synthesis of 3,4-dihydro-2H-benzo[h]chromen-2-ones involves silver catalyzed ketonization, double intramolecular cyclization, and decarboxylation, while the preparation of fluorenone derivatives proceeds through the formation of indenone analogs and subsequent intramolecular cyclization.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Dinesh Singla, Vijay Luxami, Kamaldeep Paul
Summary: A palladium-catalyzed [4+2] oxidative annulation of coumarin-benzimidazoles with olefins has been successfully achieved for the synthesis of polycyclic aromatic hydrocarbons. This synthetic method provides access to structurally distinct imidazo[1,2-a]chromeno[3,4-c]pyridines in moderate to good yields with high functional group tolerance. Additionally, the photophysical properties of the annulated scaffolds have been examined, revealing interesting solvatochromic emission behaviors.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Stuart Aiken, Georgina K. Armitage, Orlando D. C. C. de Azevedo, Daniel L. Crossley, Rhianne Dobson, Christopher D. Gabbutt, B. Mark Heron, Denis Jacquemin, Craig R. Rice, Nicola Soltowska
Summary: A series of photochromic compounds were efficiently synthesized using two complementary strategies, with the presence of specific substituents on the benzene ring affecting their photochromic properties. Different combinations of substituents with varying electronic properties at specific positions resulted in distinct optical characteristics.
Article
Oncology
Samir M. Awad, Mosaad S. Mohamed, Marwa Abd El-Fattah Khodair, Rania H. Abd El-Hameed
Summary: The study focused on synthesizing new benzo[h]chromene derivatives and testing their anti-cancer activities. Compound 1c showed the highest anti-cancer activity among all tested compounds and may require further investigation for potential development as a new anti-cancer agent.
ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Devulapally Yogananda Chary, Minpoor Soumya Reddy, Chidrawar Ajay, Balasubramanian Sridhar, Basi V. Subba Reddy
Summary: An Ir(III)-catalyzed double C-H activation strategy was developed for the synthesis of highly rigid spiro frameworks. Ortho-functionalization of 2-aryl phthalazinediones and 2,3-diphenylcycloprop-2-en-1-ones was achieved using the Ir(III)/AgSbF6 catalytic system. Smooth cyclization of 3-aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxides with 2,3diphenylcycloprop-2-en-1-ones led to diverse spiro compounds with excellent selectivity. Similarly, 2arylindazoles yielded chalcone derivatives under similar reaction conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Deepak Ranjan Mishra, Bhabani Shankar Panda, Sabita Nayak, Seetaram Mohapatra, Chita Ranjan Sahoo, Rabindra Nath Padhy
Summary: An efficient synthesis of a series of 4-((2H-chromen-3-yl)/(2-phenyl-2H-chromen-3-yl)methylene)-3-methylisoxazol-5(4H)-ones has been developed. The compounds were synthesized via one-pot multicomponent addition of ethyl acetoacetate, hydroxylamine hydrochloride, and 2H-chromene-3-carbaldehydes using DABCO as the organocatalyst. The synthesized compounds showed potential inhibitory activity against E. coli.
Article
Chemistry, Organic
Jiahui Duan, Xinwei He, Pui Ying Choy, Qi Wang, Mengqing Xie, Ruxue Li, Keke Xu, Yongjia Shang, Fuk Yee Kwong
Summary: The study achieved a functionalized benzo[c]chromen-6-one core through a DBU-mediated cascade strategy, involving a sequence of reactions including 1,4-conjugate addition, lactonization, alkyne-allene isomerization, enol-keto tautomerization, 6p-electrocyclization, and aromatization. The resulting products exhibit fluorescence properties, showing potential for fluorescent material applications.
Article
Chemistry, Medicinal
Yinhu Wang, Rawaf Alenazy, Xinjie Gu, Steven W. Polyak, Panpan Zhang, Matthew J. Sykes, Na Zhang, Henrietta Venter, Shutao Ma
Summary: This study designed novel chromanone and 2H-benzo[h]chromene derivatives as potential efflux pump inhibitors targeting Escherichia coli AcrB. Results showed that compounds WK2, WL7, and WL10 exhibited broad-spectrum and high-efficiency efflux inhibitory activity, suggesting their potential as ideal AcrB inhibitors. Molecular modeling revealed that the strong pi-pi stacking interactions and hydrogen bond networks were key factors contributing to tight binding of AcrB.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
M. A. Polovinkina, V. P. Osipova, A. D. Osipova, I. V. Kanevskaya, A. L. Ivanova, N. V. Pchelintseva, N. T. Berberova
Summary: The moderate antiradical activity of 2H-chromen-2-one derivatives was confirmed in various assays. The compound 4-[(1,2,3,4-tetrahydro-1-oxonaphthalen-2-yl)(piperidin-1-yl)methyl]benzoic acid exhibited the highest activity against the superoxide radical anion (O-2(-)) generated during the enzymatic reduction of nitro blue tetrazolium. Similarly, the compound 4-(6-oxo-8,9-dihydro-6H,7H-benzo[h]-chromene[4,3-b]chromen7-yl)benzoic acid showed the highest activity in the non-enzymatic oxidation of epinephrine in an alkaline medium. Furthermore, all the tested derivatives demonstrated prolonged antioxidant effect in a model of long-lasting lipid peroxidation in tilapia liver.
RUSSIAN CHEMICAL BULLETIN
(2022)
Article
Biochemistry & Molecular Biology
Spyridon Dimitrakis, Efthymios-Spyridon Gavriil, Athanasios Pousias, Nikolaos Lougiakis, Panagiotis Marakos, Nicole Pouli, Katerina Gioti, Roxane Tenta
Summary: In this study, a series of pyrrolo[2,3-c]pyridines, pyrrolo[3,2-d]pyrimidines, and pyrazolo[4,3-d]pyrimidines were designed and synthesized as antiproliferative agents. The most potent analogues exhibited excellent cytotoxic activity against cancer cells while showing no toxicity to normal cells.
Article
Chemistry, Multidisciplinary
Trisha Ghatak, Ismail Althagafi, Mohit Chahal, Mahendra Nath, Ramendra Pratap
Summary: We have developed a simple oxidative method to synthesize C-4 functionalized 2-oxo-2H-benzo[h]chromenes. The precursors, 4-(methylthio)-2-oxo-5,6-dihydro-benzo[h]chromenes, were synthesized by reacting 1-tetralones and 2-cyano-3,3-bis(methylthio)acrylate under basic conditions, and could be further aminated with different secondary amines in refluxing ethanol. We also reported the oxidation of 5,6-dihydro-benzo[h]chromenes using NBS and AIBN, leading to the formation of 4-(substituted)-2-oxo-benzo[h]chromenes. The scope of dehydrohalogenation was extended to synthesize thiophene-fused chromenes. The reactivity of synthesized 4-(substituted)-2-oxo-benzo[h]chromenes with C- and S-nucleophiles was explored.
Article
Chemistry, Medicinal
Jaime Perez-Villanueva, Felix Matadamas-Martinez, Lilian Yepez-Mulia, Vadim Perez-Koldenkova, Martha Leyte-Lugo, Karen Rodriguez-Villar, Francisco Cortes-Benitez, Ana Perla Macias-Jimenez, Ignacio Gonzalez-Sanchez, Ariana Romero-Velasquez, Juan Francisco Palacios-Espinosa, Olivia Soria-Arteche
Summary: Cancer is the second leading cause of death, and chemotherapy remains the main treatment method with drug resistance being a major issue. The research focused on designing and synthesizing hybrid compounds to target cancer cells, showing promising cytotoxic activity.
Article
Chemistry, Physical
Amena Ali, Abuzer Ali, Mohammed Afroz Bakht, Mohamed Jawed Ahsan
Summary: A series of new N-(substituted phenyl)-2-(7-hydroxy-4-methyl-2H-chromen-2-ylidene)hydrazine-1-carboxamides were synthesized using environmentally friendly ultrasound irradiation, showing promising anticancer and antioxidant activities, indicating potential pharmaceutical value.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Medicinal
Xu-Xiu Lu, Yao-Yao Jiang, Yan-Wei Wu, Guang-Ying Chen, Chang-Lun Shao, Yu-Cheng Gu, Ming Liu, Mei-Yan Wei
Summary: Brefeldin A, a natural compound with potent cytotoxic activity, was synthesized from the medicinal mangrove Acanthus ilicifolius by a marine fungus Penicillium sp. In this study, a series of ester derivatives were designed and synthesized, and their cytotoxic activities against human chronic myelogenous leukemia K562 cells were evaluated. Among them, the monoester derivative 7 exhibited the strongest inhibitory effect on cell proliferation, inducing cell cycle arrest and promoting cell apoptosis. Furthermore, molecular modeling suggested that compound 7 could effectively bind to the target site. These findings highlight the potential of compound 7 as a promising antileukemia agent or lead compound for further exploration.
Article
Biochemistry & Molecular Biology
You-Guang Zheng, Xin Pei, De-Xin Xia, Yuan-Bo Wang, Ping Jiang, Lin An, Tong-Hui Huang, Yun-Sheng Xue
Summary: Novel 2H-imidazo [1, 2-c] pyrazolo [3, 4-e] pyrimidine derivative compound 9b exhibited high antiproliferative activities against K562 and U937 cells, suggesting it may be a potential anticancer agent that deserves further investigation.
BIOORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Abdul Rahim, Md Golam Mostofa, Md Golam Sadik, Md Aziz Abdur Rahman, Md Ibrahim Khalil, Toshifumi Tsukahara, Kyoko Nakagawa-Goto, A. H. M. Khurshid Alam
Summary: Two new compounds identified from leaves of Leea aequata showed significant inhibition of HeLa cell proliferation and may induce apoptosis to exhibit anticancer activity.
NATURAL PRODUCT RESEARCH
(2021)
Article
Endocrinology & Metabolism
Renato Naito, Hiroshi Kano, Takashi Shimada, Tomoyuki Makino, Suguru Kadomoto, Hiroaki Iwamoto, Hiroshi Yaegashi, Kouji Izumi, Yoshifumi Kadono, Hiroki Nakata, Yohei Saito, Masuo Goto, Kyoko Nakagawa-Goto, Atsushi Mizokami
Summary: The derivative 16MS7F1924 showed significant antitumor effects on prostate cancer cells by inhibiting AR activity, reducing PSA expression, inducing mitotic catastrophe and apoptosis, mediated through the Akt pathway. In vivo studies demonstrated that 16MS7F1924 effectively inhibited tumor growth in both androgen-sensitive and cabazitaxel-resistant PCa cells, suggesting its potential as a novel therapeutic agent for hormone- and chemoresistant PCas.
Article
Multidisciplinary Sciences
Tomoyuki Makino, Kouji Izumi, Kaoru Hiratsuka, Hiroshi Kano, Takashi Shimada, Taito Nakano, Suguru Kadomoto, Renato Naito, Hiroaki Iwamoto, Hiroshi Yaegashi, Kazuyoshi Shigehara, Yoshifumi Kadono, Hiroki Nakata, Yohei Saito, Kyoko Nakagawa-Goto, Norihiko Sakai, Yasunori Iwata, Takashi Wada, Atsushi Mizokami
Summary: Kahweol acetate and cafestol can synergistically inhibit cell proliferation and migration by inducing apoptosis and inhibiting epithelial-mesenchymal transition. They also inhibit Akt and ERK phosphorylation and downregulate the expression of C-C chemokine receptors 2, 5, and 6 as well as programmed death-ligand 1, indicating their effects on the tumor microenvironment.
SCIENTIFIC REPORTS
(2021)
Article
Chemistry, Multidisciplinary
Weiyu Zhao, Chunxi Zeng, Jingyue Yan, Shi Du, Xucheng Hou, Chengxiang Zhang, Wenqing Li, Binbin Deng, David W. McComb, Yonger Xue, Diana D. Kang, Yizhou Dong
Summary: The SOLAR and DOLAR mRNA probes are designed to encode fluorescent proteins with different organelle localization signals, allowing visualization of protein localizations at various organelles and investigation of protein trafficking from ribosomal machinery to specific organelles. The in vitro results show that SOLAR probes exhibit consistent organelle targeting capabilities, while DOLAR probes with different linkers display distinct targeting properties based on organelle localization signals. Additionally, these mRNA probes demonstrate organelle labeling ability in vivo when delivered by lipid nanoparticles, providing a unique tool to study cell organelles and potentially aid in the design of organelle-based therapies.
ADVANCED MATERIALS
(2021)
Review
Chemistry, Multidisciplinary
Yuebao Zhang, Changzhen Sun, Chang Wang, Katarina E. Jankovic, Yizhou Dong
Summary: RNA-based therapeutics have shown great promise in treating diseases through various mechanisms, with lipid nanoparticles being the most widely used delivery system. The study of lipids, lipid derivatives, and lipid-derived macromolecules for RNA delivery has also made significant progress in recent years.
Editorial Material
Chemistry, Multidisciplinary
Yizhou Dong, Daniel G. Anderson
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Review
Pharmacology & Pharmacy
Jingyue Yan, Diana D. Kang, Gillian Turnbull, Yizhou Dong
Summary: RNA-binding proteins (RBPs) are crucial in RNA metabolism and alterations in the RBP-RNA network are related to cancer development. Various strategies, including small-molecule inhibitors and CRISPR-Cas9 technology, have been applied for RBP-based cancer therapies.
ADVANCED DRUG DELIVERY REVIEWS
(2022)
Article
Plant Sciences
Sachika Hirazawa, Yohei Saito, Momoko Sagano, Masuo Goto, Kyoko Nakagawa-Goto
Summary: Natural products with enzymatic synthesis have a wide range of biological activities. Our study focuses on the antiproliferative activity of novel benzo[b]thiophenyl (BT) flavones, which have a 10 pi-electron BT ring B instead of the usual 6 pi-electron phenyl ring. We synthesized and evaluated 10 isoflavones, 29 chalcones, and 4 aurones, and found that certain BT-flavonoids displayed significant antiproliferative effects against human tumor cell lines. Furthermore, our studies demonstrate the importance of BT instead of phenyl as ring B for the isoflavone and chalcone derivatives.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Nanoscience & Nanotechnology
Yonger Xue, Rafia Baig, Yizhou Dong
Summary: Stem cells, used as 'living drugs' for decades, offer potential solutions for various diseases, but face challenges in clinical translation due to pathological environments. To address these challenges, researchers have developed biomaterial-based strategies to enhance stem cell therapies for the next generation.
Article
Pharmacology & Pharmacy
Meng-Ting Chang, Li-Chu Tsai, Kyoko Nakagawa-Goto, Kuo-Hsiung Lee, Lie-Fen Shyur
Summary: This study uncovers the abnormal upregulation of PUFAs and oxylipin metabolism in vemurafenib resistant melanoma cells. DET and DETD-35 induce cell death in sensitive and resistant BRAF(V600E) melanoma cells by reprogramming metabolism and causing mitochondrial damage, targeting GPX4 and ferroptosis.
PHARMACOLOGICAL RESEARCH
(2022)
Article
Chemistry, Organic
Ryosuke Shimoi, Yohei Saito, Yuta Miura, Kyoko Nakagawa-Goto
Summary: In our study, we isolated a unique quinolone alkaloid, Waltherione A (1), from a methanol extract of Melochia umbellata, along with related compounds, paliasanines A-E. Compound 1 exhibited selective cytotoxicity against A549 and MCF-7 cell lines. Through a 21-step total synthesis starting from commercially available benzosuberone, we successfully accomplished the first total synthesis of 1 and elucidated its absolute configuration.
Review
Pharmacology & Pharmacy
Diana D. Kang, Haoyuan Li, Yizhou Dong
Summary: The accelerated progress and approval of two mRNA-based vaccines for SARS-CoV-2 were unprecedented, thanks to the solid foundation of research on in vitro transcribed mRNA (IVT mRNA). Through decades of research, mRNA-based vaccines or therapeutics offer many advantages to rapidly address a broad range of applications. This article describes the advances in IVT mRNA technology, including optimization of structural components, synthesis, and different classes of IVT RNA, and emphasizes the importance of continuing to drive this technology.
ADVANCED DRUG DELIVERY REVIEWS
(2023)
Article
Multidisciplinary Sciences
Shuying Chen, Xiangang Huang, Yonger Xue, Ester Alvarez-Benedicto, Yesi Shi, Wei Chen, Seyoung Koo, Daniel J. Siegwart, Yizhou Dong, Wei Tao
Summary: mRNA vaccines have revolutionized the field of infectious disease and cancer research, offering rapid and precise immune responses. This study discusses the development and evaluation of biomaterials and nanotechnology in mRNA vaccines, highlighting their advantages over traditional vaccines. The use of nanoparticles and nanotechnology provides innovative solutions to overcome challenges in mRNA delivery and enhance the potency of vaccines.
NATURE REVIEWS METHODS PRIMERS
(2023)
Article
Chemistry, Multidisciplinary
Ayun Dwi Astuti, Budiman Yasir, Abdul Rahim, Rosdiana Natzir, Subehan Subehan, Kyoko Nakagawa-Goto, Gemini Alam
Summary: This study focused on the characterization of two phytosterols isolated from the ethyl acetate extract of Plectranthus scutellarioides var. color blaze dark star. Cytotoxicity evaluation revealed that fractions 15 and 17 significantly inhibited cell growth.
EGYPTIAN JOURNAL OF CHEMISTRY
(2022)
Review
Nanoscience & Nanotechnology
Chunxi Zeng, Xucheng Hou, Margaret Bohmer, Yizhou Dong
Summary: Nanomaterials play a crucial role in combating the COVID-19 pandemic, including the development of easy, fast, and low-cost diagnostic assays, rapid vaccine development, and research into drug treatments.
Article
Chemistry, Medicinal
Shibin Zhao, Julian Maceren, Mia Chung, Samantha Stone, Raphael Geiben, Melissa L. Boby, Bradley S. Sherborne, Derek S. Tan
Summary: Antibiotic resistance is a major threat to public health, with Gram-negative bacteria presenting unique challenges due to their low permeability and efflux pumps. Limited understanding of the chemical rules for overcoming these barriers hinders antibacterial drug discovery. Efforts to address this issue, such as screening compound libraries and using cheminformatic analysis, have led to the design of sulfamidoadenosines with diverse substituents, showing potential utility in accumulation in Escherichia coli.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Jichun Li, Qing Li, Shuai Xia, Jiahuang Tu, Longbo Zheng, Qian Wang, Shibo Jiang, Chao Wang
Summary: This study successfully developed a short peptide mimetic as a MERS-CoV fusion inhibitor by reproducing the key recognition features of the HR2 helix. The resulting 23-mer lipopeptide showed comparable inhibitory effect to the 36-mer HR2 peptide HR2P-M2. This has important implications for developing short peptide-based antiviral agents to treat MERS-CoV infection.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Krista Jaunsleine, Linda Supe, Jana Spura, Sten van Beek, Anna Sandstrom, Jessica Olsen, Carina Halleskog, Tore Bengtsson, Ilga Mutule, Benjamin Pelcman
Summary: Beta(2)-adrenergic receptor agonists can stimulate glucose uptake by skeletal muscle cells and are therefore potential treatments for type 2 diabetes. The chirality of compounds has a significant impact on the activity of these agonists. This study found that certain synthesized compounds showed higher glucose uptake activity. These findings provide important information for the design of novel beta(2)AR agonists for T2D treatment.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Xin Xu, Jia Chen, Guan Wang, Xiaojuan Zhang, Qiang Li, Xiaobo Zhou, Fengying Guo, Min Li
Summary: The study focuses on EZH2, a promising therapeutic target for various types of cancers. Researchers designed and synthesized a series of novel derivatives aiming to enhance the EZH2 inhibition activity. Among them, compound 28 displayed potent EZH2 inhibition activity and showed high anti-proliferative effects in lymphoma cell lines and xenograft mouse models. The study suggests that compound 28 has potential as a therapeutic candidate for EZH2-associated cancers.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Wei Zhang, Wei Liu, Ya-Dong Zhao, Li-Zi Xing, Ji Xu, Rui-Jun Li, Yun-Xiao Zhang
Summary: This study developed a series of aromatic amide derivatives based on Rhein and investigated their inhibitory activity against alpha-Syn aggregation. Two of these compounds showed promising potential in treating Parkinson's disease by stabilizing alpha-Syn's conformation and disassembling alpha-Syn oligomers and fibrils.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Mani Sharma, S. S. S. S. Sudha Ambadipudi, Neeraj Kumar Chouhan, V. Lakshma Nayak, Srihari Pabbaraja, Sai Balaji Andugulapati, Ramakrishna Sistla
Summary: Therapeutically active lipids in drug delivery systems can enhance the safety and efficacy of treatment. The liposome formulation created using synthesized biologically active lipids showed additive anti-cancer effects and reduced tumorigenic potential.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
