Article
Chemistry, Organic
Swagata Baruah, Sabera Sultana, Pratiksha Bhorali, Pallabi Saikia, Sanjib Gogoi
Summary: A novel Ru(ii)-catalyzed decarbonylative annulation and direct C-H functionalization reaction of phthalic anhydrides with acrylates is reported, providing an efficient route for the synthesis of 3,7-disubstituted phthalides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ziyong Wang, Walid Lamine, Karinne Miqueu, Shih-Yuan Liu
Summary: We present a study on Pd/Senphos-catalyzed carboboration of 1,3-enynes using a combination of experimental and computational methods. The study involves DFT calculations, P-31 NMR analysis, kinetic study, Hammett analysis, and Arrhenius/Eyring analysis. Our findings provide evidence against the conventional inner-sphere beta-migratory insertion mechanism and support a syn outer-sphere oxidative addition mechanism involving a Pd-pi-allyl intermediate and coordination-assisted rearrangements.
Review
Chemistry, Multidisciplinary
Laura M. Wickham, Ramesh Giri
Summary: Alkene dicarbofunctionalization is a powerful organic synthesis method that utilizes transition metals and carbon sources to synthesize complex molecules. The strategy of cyclometalation and metallacycle contraction is employed to address the issue of beta-H elimination in alkene dicarbofunctionalization reactions.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Organic
Wei Chen, Wanzhi Chen, Miaochang Liu, Huayue Wu
Summary: The palladium-catalyzed Suzuki-Miyaura cross-couplings of nitroarenes and heteroarylboronate esters has been developed, leading to the synthesis of various heterobiaryl compounds. The practicality of this approach is demonstrated through the synthesis of druglike molecules.
Article
Chemistry, Organic
Junjie Ying, Jingrong Huang, Chenguang Liu, Fa-Jie Chen, Chunfa Xu, Fen-Er Chen
Summary: This study reports a copper-catalyzed arylation reaction using readily available arylboronic acids for S-tosyl peptides. The method features high yields and a wide variety of aryl groups, enabling efficient synthesis of S-arylated cysteines and peptides under mild conditions.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Organic
Akash. G. G. Tathe, Sagar. S. S. Saswade, Nitin. T. T. Patil
Summary: Multicomponent reactions (MCRs) are an important branch in organic synthesis, allowing the construction of complex molecular structures from multiple starting materials in a single reaction. Traditionally, transition metals have been used as catalysts for MCRs, and numerous reviews have been published on this topic. Gold, on the other hand, offers unique reactivity profiles, enabling the synthesis of previously inaccessible molecules. In recent years, gold catalysts have emerged as powerful contenders for achieving MCRs with distinct mechanisms. This comprehensive review provides an overview of the state-of-the-art in the development of gold-catalyzed MCRs, with a focus on recent advancements.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Barry M. Trost, Chuanle Zhu, Chloe Christine Ence
Summary: This study reports a palladium-catalyzed [3 + 2] cycloaddition using in situ generated sulfone-TMM species to construct various chiral cyclopentyl sulfones in a highly regio-, diastereo-, and enantioselective manner. The robust chiral diamidophosphite ligand is crucial for the reactivity and selectivities of this transformation, allowing for the construction of three chiral centers in a single step.
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, Organic
Shiji Xu, Qiang Wang, Jing Sun, Ying Han, Weiming Hu, Lei Wang, Chao-Guo Yan
Summary: In this study, Pd/Cu-catalyzed cascade Heck-type reactions between alkenyl halides and terminal alkynes have been developed. This research provides an efficient atom-economical approach to access a variety of highly substituted pyrrolidines in moderate to good yields. This protocol features readily available substrates, broad substrate scope, easy scale-up, high selectivities, and versatile transformations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Shichao Li, Muyao Li, Shu-Sen Li, Jianbo Wang
Summary: A palladium-catalyzed stereoselective synthesis method has been developed for obtaining trans-alkenyl MIDA boronates from N-Methyliminodiacetyl boronate (BMIDA)-substituted N-tosylhydrazone and benzyl bromides. The products show moderate yields and good functional group compatibility, with potential applications in the synthesis of other boron-containing compounds or in cross-coupling reactions.
CHEMICAL COMMUNICATIONS
(2022)
Article
Biochemistry & Molecular Biology
Aude Salame, Jordan Rio, Ilaria Ciofini, Lionel Perrin, Laurence Grimaud, Pierre-Adrien Payard
Summary: Understanding and controlling the Cu-catalyzed homocoupling reaction is essential for the development of efficient Cu-catalyzed cross-coupling reactions. The presence of coordinating bases facilitates transmetalation reactions, while organocopper(II) dimers undergo a coupled transmetalation-electron transfer process promoting the formation of bis-organocopper(III) complexes. Guiding principles are suggested to avoid the undesired formation of homocoupling products in Cu-catalyzed cross-coupling reactions.
Article
Chemistry, Organic
Tienan Jin, Shin Suzuki, Hon Eong Ho, Hidenori Matsuyama, Masaki Kawata, Masahiro Terada
Summary: A novel Pd-catalyzed cascade reaction has been developed to construct a cyclopenta-fused acenaphtho[1,2-b]indole (ANI) scaffold, which can be used to synthesize pi-extended ANI derivatives with relatively narrow energy gaps. The potential applications of these ANI molecules as pi-segments in low-band-gap materials are implied by their increased HOMOs and lowered LUMOs.
Article
Chemistry, Organic
Zheng Dong, Ren-Jie Tong, Lei Xu, Hua-Jian Xu, Jun Xu
Summary: The synthesis of (deuterated) 1,1-disubstituted alkenes via Pd-catalyzed decarboxylative hydroarylation of alkynyl carboxylic acids with arylboronic acids has been developed. The reaction features excellent regioselectivity, a broad substrate scope and gram-scale synthetic ability and offers a general synthetic method to synthesize 1,1-dideuterio olefins. Preliminary mechanism investigations indicate that 1,1-disubstituted alkenes are formed by hydroarylation of terminal alkynes generated by in situ decarboxylation of alkynyl carboxylic acids.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Jonathan P. Knowles, Hannah G. Steeds, Maria Schwarz, Francesca Latter, Kevin Booker-Milburn
Summary: This method transforms simple starting materials into complex tetracyclic products with potential medicinal chemistry applications through a sophisticated chemical catalysis process.
Article
Chemistry, Organic
Marco Manenti, Simone Gusmini, Leonardo Lo Presti, Alessandra Silvani
Summary: Utilizing isocyanide-based multicomponent reactions, unprecedented boron-containing small molecule peptidomimetics were efficiently synthesized, successfully applying the concept of molecular hybridization.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Pharmacology & Pharmacy
Yang Yang, Yalin Tu, Junfeng Lu, Qiuhe Chen, Zeyu Zhu, Weijia Peng, Wenbo Zhu, Shijun Wen, Ji Zhang, Wei Yin, Rongbiao Pi
Summary: This study discovered a novel multi-kinase inhibitor, PT109, which suppressed the proliferation, colony formation, and migration of GBM cells, and reprogrammed them into oligodendrocytes. Proteomic analysis showed that PT109 influenced energy metabolism, cell cycle, and immune system processes of GBM-associated proteins. Metabolomic analysis revealed that PT109 improved the aerobic respiration process in glioma cells. Overall, PT109 provided a new strategy for the development of anti-glioma drugs by reprogramming GBM and changing its metabolic pattern through the PTBP1/PKM1/2 pathway.
EUROPEAN JOURNAL OF PHARMACOLOGY
(2022)
Article
Chemistry, Medicinal
Tian Tian, Shengyi Zhang, Bingling Luo, Feng Yin, Wenhua Lu, Yiqing Li, Kezhi Huang, Qiao Liu, Peng Huang, G. Garcia-Manero, Shijun Wen, Yumin Hu
Summary: In this study, a benzoimidazole compound was identified as a selective treatment for FLT3/ITD leukemia. The compound HP1328, derived from the benzoimidazole scaffold, demonstrated desirable properties and significantly reduced leukemia burden and prolonged survival in mice.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Muhammad Nadeem-ul-Haque, Anila Bashir, Humira Karim, Sadiq Noor Khan, Zafar Ali Shah, Almas Jabeen, Shaista Qayyum, A. Ganesan, M. Iqbal Choudhary, Farzana Shaheen
Summary: This study investigated the synthesis of [1-8-N alpha C]-zanriorb A1 from the medicinal plant Zanthoxylum riedelianum. The solution-phase route produced a mixture of proline rotamers, while the on-resin cyclization was less successful. Analogues of zanriorb A1 were also synthesized, and one compound showed strong anti-inflammatory potential.
JOURNAL OF PEPTIDE SCIENCE
(2022)
Article
Chemistry, Organic
Hui Peng, Qian Liu, Yameng Sun, Bingling Luo, Tianyian Yu, Peng Huang, Daqian Zhu, Shijun Wen
Summary: In this study, it was demonstrated that linear unsymmetrical diaryliodoniums can undergo one-pot cyclization/arylation using a dual nickel/palladium metal system, and the in situ generated benzoxazole motifs can be utilized as directing groups for subsequent C-H activated arylation from the unwanted aryl iodide, exhibiting good atom economy and regioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Mohammed Aldholmi, Rizwan Ahmad, Daniel Carretero-Molina, Ignacio Perez-Victoria, Jesus Martin, Fernando Reyes, Olga Genilloud, Lea Gourbeyre, Thierry Gefflaut, Hanne Carlsson, Alexei Maklakov, Ellis O'Neill, Robert A. Field, Barrie Wilkinson, Maria O'Connell, A. Ganesan
Summary: The study discovered that euglenatides from Euglena gracilis can inhibit pathogenic fungi and cancer cells, and bear resemblance to nemamides in Caenorhabditis elegans. Molecular network analysis also revealed the presence of multiple euglenatide-like metabolites in Euglena species.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Oncology
Peiting Zeng, Wenhua Lu, Jingyu Tian, Shuang Qiao, Jiangjiang Li, Christophe Glorieux, Shijun Wen, Hui Zhang, Yiqing Li, Peng Huang
Summary: The study found that overexpressed wild-type IDH2 in AML promoted leukemia cell survival and proliferation by facilitating the conversion of alpha-KG to isocitrate/citrate for lipid synthesis. Inhibition of wild-type IDH2 resulted in reduced lipid synthesis, decreased c-Myc expression downregulated by alpha-KG, and inhibition of AML viability and proliferation. Pharmacological inhibition of IDH2 showed therapeutic effects in AML cells with wild-type IDH2, inducing downregulation of C-MYC in vivo.
JOURNAL OF HEMATOLOGY & ONCOLOGY
(2022)
Article
Chemistry, Medicinal
Zhirong Guo, Yameng Sun, Liyun Liang, Wenhua Lu, Bingling Luo, Zhouming Wu, Bitao Huo, Yumin Hu, Peng Huang, Qiang Wu, Shijun Wen
Summary: This study presents the design, synthesis, and biological evaluation of first-in-class dual EZH2/BRD4 inhibitors. The most promising compound, YM458, demonstrates potent inhibitory activity against EZH2 and BRD4 and remarkable antiproliferative capacity against various solid cancer cell lines. In vivo experiments validate the therapeutic potential of EZH2/BRD4 dual inhibitors in lung cancer and pancreatic cancer xenograft tumor models, highlighting their potential to target a broad scope of resistant solid tumors.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Fang Liu, Xuan Wang, Jianli Duan, Zhijie Hou, Zhouming Wu, Lingling Liu, Hanqi Lei, Dan Huang, Yifei Ren, Yue Wang, Xinyan Li, Junxiao Zhuo, Zijian Zhang, Bin He, Min Yan, Huiming Yuan, Lihua Zhang, Jinsong Yan, Shijun Wen, Zifeng Wang, Quentin Liu
Summary: This study introduces a PROTAC cocktail that effectively degrades AURKA in acute myeloid leukemia cells, inhibits AML stem cells, and induces AML regression in mouse models and primary patient cells. This spatial-temporal drug administration strategy shows promise in eliminating the multifaceted functions of oncoproteins and preventing cancer stem cell-mediated drug resistance.
Article
Biochemistry & Molecular Biology
Qingbin Cui, Wenwen Ding, Panpan Liu, Bingling Luo, Jing Yang, Wenhua Lu, Yumin Hu, Peng Huang, Shijun Wen
Summary: This study demonstrates that enhancing the mitochondria-targeting capacity of gold compounds can enhance their efficacy in eradicating cancer cells. Bi-gold compounds showed better suppression of cancer cell proliferation compared to mono-gold compounds, and the most potent compound, BGC2a, inhibited the antioxidant enzyme TrxR and increased cellular ROS. BGC2a accumulated within mitochondria, leading to mitochondrial dysfunction and inhibition of tumor growth.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Review
Chemistry, Multidisciplinary
Xiaopeng Peng, Abdur Rahim, Weijie Peng, Feng Jiang, Zhenhua Gu, Shijun Wen
Summary: This article summarizes the recent advances in the research field of cyclic aryliodoniums, including their design and synthetic applications. The general preparation of typical diphenyl iodoniums, construction of heterocyclic iodoniums and monoaryl iodoniums are described. The use of cyclic aryliodoniums as initiators for cascade reactions and the construction of complex structures such as polycycles and biaryls are discussed. Furthermore, the recent advance of cyclic aryliodoniums as halogen-bonding organocatalysts is described.
Article
Oncology
Ipek Bulut, Adam Lee, Buse Cevatemre, Dusan Ruzic, Roman Belle, Akane Kawamura, Sheraz Gul, Katarina Nikolic, A. Ganesan, Ceyda Acilan
Summary: The newly developed LSD1/HDAC6 dual inhibitor iDual can inhibit the growth of leukemia cells by simultaneously targeting HDAC6 and LSD1, and it can enhance drug-induced apoptosis when used in combination with doxorubicin.
Article
Pharmacology & Pharmacy
Dusan Ruzic, Bernhard Ellinger, Nemanja Djokovic, Juan F. Santibanez, Sheraz Gul, Milan Beljkas, Ana Djuric, Arasu Ganesan, Aleksandar Pavic, Tatjana Srdic-Rajic, Milos Petkovic, Katarina Nikolic
Summary: This report describes the design and discovery of two selective HDAC6 inhibitors and two non-selective HDAC inhibitors. Molecular modeling found that the linker chemistry of the inhibitors influences their potency. A novel non-selective HDAC inhibitor with a longer linker showed potent anti-tumor, anti-metastatic, and anti-angiogenic effects.
Article
Plant Sciences
Xiaozhuo Tan, Meiling Le, Haiwen Wang, Bitao Huo, Tiantian Yu, Peng Huang, Tiangang Luan, Shijun Wen
Summary: This study reports the design and synthesis of novel peptide-drug conjugates (PDCs) that bind to both the extracellular and intracellular domains of epidermal growth factor receptor (EGFR). One peptide motif interacts with the extracellular domain, while the other motif derived from an EGFR inhibitor occupies the intracellular kinase domain. Among the synthetic PDCs, compound 14c shows the best inhibition of EGFR phosphorylation and the ability to inhibit cell proliferation and colony formation in lung cancer cells. This study provides a novel strategy to develop more potent EGFR inhibitors by targeting both extracellular and intracellular domains simultaneously.
PHYTOCHEMISTRY LETTERS
(2023)
Article
Microbiology
Anna Claudia Silva, Daniel Clemente de Moraes, Denilson Costa do Carmo, Giselle Cristina Casaes Gomes, A. Ganesan, Rosangela Sabbatini Capella Lopes, Antonio Ferreira-Pereira, Claudio Cerqueira Lopes
Summary: Azoles are the main antifungal drugs used to treat invasive candidiasis, but their efficacy is limited by fungal resistance mechanisms like overexpression of efflux pumps. A potential strategy to overcome this resistance is to inhibit the efflux process. This study aimed to synthesize altissimacoumarin D and its analogues to evaluate their ability to reverse the resistance phenotype of Candida albicans.
Article
Chemistry, Organic
Paulo Eliandro da Silva Junior, Shaiani Maria Gil de Melo, Murilo Helder de Paula, Ricardo Vessecchi, Till Opatz, James E. H. Day, A. Ganesan, Flavio da Silva Emery
Summary: This article discusses the reactivity of 6-azaindazole and 2,6-naphthyridine, which are important in fragment-based drug discovery. The article introduces selective functionalization methods for pyridone and pyrazole, as well as a new method for selective functionalization of heterocycle 1.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
