Article
Biochemistry & Molecular Biology
Haojue Wang, Wanfei Shao, Xianyi Lu, Chunxia Gao, Ling Fang, Xiaojun Yang, Peizhi Zhu
Summary: A novel nano-drug delivery system, HA-MA-MTX, was developed in this study to enhance the accumulation of MTX in tumors and minimize toxicity to normal tissues. The system combines MTX as a tumor-targeting ligand, HA as another tumor-targeting ligand, and MA as an anti-inflammatory agent. In vitro experiments showed that HA-MA-MTX nanoparticles effectively inhibited K7 cancer cells while exhibiting lower toxicity to normal MC3T3-E1 cells compared to MTX.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
Review
Food Science & Technology
Lisi Li, Yujia Dong, Xifu Liu, Meng Wang
Summary: Mangiferin, a natural polyphenolic compound found in many plants, has shown remarkable pharmacological activities such as anti-inflammatory, anti-tumor, antioxidative stress, and antiviral effects. Evidence suggests that it has therapeutic benefits in treating various liver diseases, including liver injury, nonalcoholic fatty liver disease, alcoholic liver disease, liver fibrosis, and hepatocellular carcinoma. This review aims to summarize the potential signaling pathways and findings of mangiferin in liver disease treatment, highlighting its potential as a therapeutic agent for liver disease in humans.
Article
Chemistry, Applied
Qi Wang, Weiwei Cheng, Yifeng Zhang, Qingzheng Kang, Vemana Gowd, Yuanyuan Ren, Feng Chen, Ka-Wing Cheng
Summary: Differential solvent extraction and phytochemical profiling were used to identify potent inhibitors of PhIP formation in Chinese chive. The inhibitory mechanism was found to be related to phenylacetaldehyde scavenging rather than antioxidant activities. Organic synthesis and structural elucidation confirmed the proposed mode of action for the novel inhibitor.
Article
Multidisciplinary Sciences
Kyan A. D'Angelo, Carly K. Schissel, Bradley L. Pentelute, Mohammad Movassaghi
Summary: The study presents a concise total synthesis method for himastatin, a natural product with an unusual homodimeric structure. The final-stage dimerization strategy used in the synthesis was inspired by a detailed understanding of the compound's biogenesis. By combining this approach with a modular synthesis, a series of designed derivatives of himastatin, including synthetic probes to investigate its antibiotic activity, were efficiently accessed.
Article
Chemistry, Multidisciplinary
Ya-Kui Sun, Jin-Bao Qiao, Yu-Meng Xin, Qin Zhou, Zhi-Hua Ma, Hui Shao, Yu-Ming Zhao
Summary: In this paper, a concise and divergent synthesis of the complex hasubanan alkaloids metaphanine and oxoepistephamiersine from commercially available and inexpensive cyclohexanedione monoethylene acetal is reported. The synthesis involves a palladium-catalyzed cascade cyclization reaction, regioselective Baeyer-Villiger oxidation followed by a MeNH2 triggered skeletal reorganization cascade, and a strategically late-stage regio-/diastereoselective oxidative annulation of sp(3) C-H bond. Additionally, a highly enantioselective alkylation of cyclohexanedione monoethylene acetal was used for the asymmetric synthesis of the target molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Ya-Kui Sun, Jin-Bao Qiao, Yu-Meng Xin, Qin Zhou, Zhi-Hua Ma, Hui Shao, Yu-Ming Zhao
Summary: A concise and divergent synthesis of the complex hasubanan alkaloids metaphanine and oxoepistephamiersine from commercially available and inexpensive cyclohexanedione monoethylene acetal was reported. The synthesis includes a palladium-catalyzed cascade cyclization reaction, a regioselective Baeyer-Villiger oxidation followed by a MeNH2 triggered skeletal reorganization cascade, and a strategically late-stage regio-/diastereoselective oxidative annulation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Chi He, Yu Wang, Cheng Bi, David S. Peters, Timothy J. Gallagher, Johannes Teske, Jason S. Chen, Rachel Corsetti, Anthony D'Onofrio, Kim Lewis, Phil S. Baran
Summary: A modular total synthesis method for kibdelomycin has been disclosed, which allows for structure-activity relationship studies. This method uses simple building blocks and addresses lingering questions regarding its structural assignment and its relationship to amycolamicin. Initial antibacterial assays indicate that both C-22 epimers of the natural product exhibit similar activity, while structurally truncated analogs lose activity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yun-Peng Zou, Zheng-Lin Lai, Meng-Wei Zhang, Jianzhao Peng, Shuai Ning, Chuang-Chuang Li
Summary: The first total synthesis of (+/-)- and (-)-daphnilloninB, a daphnicyclidin-type alkaloid with a novel hexa-cyclic core, was achieved through a series of chemical reactions. The B/C/D ring system was efficiently constructed using a mild intramolecular cycloaddition and a GrubbsII catalyst-catalyzed radical cyclization. The E/F fused ring system was synthesized via a diastereo-selective intramolecular Pauson-Khand reaction. The challenging hexa-cyclic core was reassembled from a hexa-cyclic framework found in calyciphylline A-type Daphniphyllum alkaloids through a unique Wagner-Meerwein rearrangement.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Feng-Yuan Wang, Lei Jiao
Summary: An asymmetric total synthesis of cage-like indole alkaloid arborisidine is achieved using a new synthetic strategy that involves a catalytic parallel kinetic resolution based on ambident nucleophilicity of indole and a 5-exo-trig radical cyclization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Hao Yu, Zachary P. Sercel, Samir P. Rezgui, Jonathan Farhi, Scott C. Virgil, Brian M. Stoltz
Summary: This study describes a synthetic approach to aleutianamine and highlights its potent biological activity against human pancreatic cancer cells, making it a potential candidate for therapeutic development.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Vasil H. Vasilev, Lukas Spessert, Kuan Yu, Thomas J. Maimone
Summary: The large family of daphnane diterpene orthoesters (DDOs) represents a remarkable class of natural products both in terms of structure and function. They are potent lead compounds for the treatment of pain, neurodegeneration, HIV/AIDS, and cancer. However, the synthesis of DDO natural products remains rare.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Yang Wang, Yongjian Su, Yanxing Jia
Summary: In this research, the structurally intriguing diterpene (+)-aberrarone was synthesized in only 12 steps from commercially available (S,S)-carveol without protecting group manipulations. This concise synthesis includes a Cu-catalyzed asymmetric hydroboration to generate the chiral methyl group, a Ni-catalyzed reductive coupling to link two fragments, and a Mn-mediated radical cascade cyclization to construct the triquinane system.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Jiujian Ji, Jiajun Chen, Sixun Qin, Wanye Li, Jun Zhao, Guozhao Li, Hao Song, Xiao-Yu Liu, Yong Qin
Summary: This article reports the first total synthesis of vilmoraconitine using efficient ring-forming reactions. Key steps include an oxidative dearomatization-induced Diels-Alder cycloaddition, a hydrodealkenylative fragmentation/Mannich sequence, and an intramolecular Diels-Alder cycloaddition.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Stephan N. Hess, Xiaobin Mo, Conny Wirtz, Alois Fuerstner
Summary: Limaol, a marine-derived C40-polyketide, is unique in structure due to the nonthermodynamic array of four skipped methylene substituents on its hydrophobic tail. This distinctive segment was assembled using a two-directional approach and coupled to the polyether domain through an allyl/alkenyl Stille reaction under neutral conditions. The core region was prepared through several key steps, including asymmetric propargylation catalyzed by 3,3'-dibromo-BINOL, gold-catalyzed spirocyclization, and substrate-controlled allylation to introduce the southern sector.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Daria E. Kim, Yingchuan Zhu, Shingo Harada, Isaiah Aguilar, Abbigayle E. Cuomo, Minghao Wang, Timothy R. Newhouse
Summary: In this study, we successfully reported the total synthesis of the indole diterpenoid natural product shearilicine for the first time through an 11-step sequence using a generalizable precursor. The target molecule was obtained in an enantiospecific manner using a native chiral auxiliary strategy. The formation of the key carbazole substructure was achieved through a mild intramolecular Heck cyclization, which was promoted by noncovalent substrate-ligand and ligand-ligand interactions revealed by computational study.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)