Article
Chemistry, Multidisciplinary
Haiting Yin, Qin Ma, Yushan Wang, Xiaoxia Gu, Zhijun Feng, Yunjun Wu, Ming Wang, Shaoyin Wang
Summary: The study presents a facile and efficient route to tetrahydro-beta-carbolines from 2-indolylmethyl azides and propargylic alcohols via acid-catalyzed dehydrative annulation reactions. The reaction involves a cascade sequence of Friedel-Crafts-type alkylation followed by intramolecular Click reaction, forming multiple chemical bonds in a single operation with excellent atom-economy and broad functional group tolerance.
Article
Chemistry, Physical
Jianxiong Zhao, Daniel Mendez-Sanchez, Rebecca Roddan, John M. Ward, Helen C. Hailes
Summary: The study demonstrates the use of wild-type NCS and selected variants with various ketones to access challenging non-natural THIAs. Some NCS variants were found to accept fused bicyclic ketones and diketones, providing new insights into the rational for this acceptance through in silico modeling.
Article
Chemistry, Organic
Qi-Wen Shen, Wei Wen, Qi-Xiang Guo
Summary: The first catalytic asymmetric cascade Heck-alkylation reaction of NH2-unprotected amino acid esters with N-(2-iodophenyl)allenamides is reported in this work. The reaction proceeds smoothly using a combining catalytic system comprising a chiral aldehyde, a chiral palladium complex, and the Lewis acid ZnCl2, giving optically active alpha-alkyl tryptophan derivatives in moderate to good yields and excellent enantioselectivities. The target products can be converted into other structurally complex chiral indoles without the loss of enantioselectivities.
Article
Chemistry, Multidisciplinary
Michael E. Pyne, Vincent J. J. Martin
Summary: This review outlines the increasing activity surrounding the production of natural, semisynthetic, and new-to-nature THIQ metabolites in engineered microbial systems, which has accelerated THIQ pathway discovery and engineering, and spurred the development of highly productive microbial strains.
CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY
(2022)
Article
Chemistry, Applied
Liu-Yang Pu, Fan Yang, Ji-Qiang Chen, Ying Xiong, Jian-Hua Xie, Qi-Lin Zhou
Summary: The enantioselective total synthesis of the pentacyclic proaporphine alkaloid (-)-misramine was achieved, featuring key reactions including Pictet-Spengler cyclization and Baeyer-Villiger oxidation. The absolute configuration of the pentacyclic framework was determined through X-ray single-crystal analyses.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Biotechnology & Applied Microbiology
Man Zhang, Zheng-Yu Huang, Ying Su, Fei-Fei Chen, Qi Chen, Jian-He Xu, Gao-Wei Zheng
Summary: By utilizing the improved biocatalyst and using condensation reactions as the main strategy, the synthesis of 1-aryl-tetrahydroisoquinoline alkaloids with significant biological and pharmaceutical activity was achieved, yielding products with high conversion rate and optical purity.
BIORESOURCES AND BIOPROCESSING
(2023)
Article
Chemistry, Organic
Fan Xiao, Shi-Ming Xu, Xiu-Qin Dong, Chun-Jiang Wang
Summary: The Ir-catalyzed asymmetric tandem allylation/iso-Pictet-Spengler cyclization reaction provides a direct and practical approach for accessing tetrahydro-gamma-carboline derivatives with multiple functional groups and stereogenic centers in good to high yields and excellent stereoselective control. The wide substrate generality, easily available substrates, and simple chiral catalytic system demonstrate the great potential practicality of this efficient protocol.
Article
Integrative & Complementary Medicine
Chen Bo-Ru, Gao Cheng-Long, Liu Jin, Guo Yue-Wei, Jiang Jian-Lan, Pang Tao, Li Xu-Wen
Summary: Diversity-oriented synthesis was used to design and synthesize a series of indole-containing marine natural product derivatives for evaluation of their anti-inflammatory activity. One of the newly synthesized derivatives showed promising activity by inhibiting cytokine release, suggesting the potential of marine indole alkaloids as leads for anti-inflammatory drug discovery.
CHINESE JOURNAL OF NATURAL MEDICINES
(2022)
Article
Chemistry, Medicinal
Ramil Y. Baiazitov, Hongyan Qi, Tamil Arasu, William Lennox, Liangxian Cao, Marla Weetall, Bansri Furia, Jin Zhuo, Soongyu Choi, Min Jung Kim, Josephine Sheedy, Thomas Davis, Young-Choon Moon
Summary: This paper describes a lead optimization campaign that led to the discovery of Emvododstat (PTC299), a highly potent DHODH inhibitor. Modulating the activity of this enzyme can be used to control diseases associated with rapid, out-of-control cell growth.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Jay Prakash Soni, Manda Sathish, Fabiane M. Nachtigall, Leonardo S. Santos, Nagula Shankaraiah
Summary: The Pictet-Spengler reaction is an efficient synthetic tool for constructing tetrahydro-beta-carbolines and tetrahydroisoquinolines, with a brown seaweed-derived alginic acid reported as an effective reusable catalyst. The protocol shows good yields with various aliphatic and aromatic aldehydes, and demonstrates sustainable synthesis of different compounds including a natural spirooxindole. The catalyst was found to be reusable with no significant deterioration in reaction yields observed up to the 6th cycle.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
G. F. Sakhautdinova, I. M. Sakhautdinov, I. S. Nazarov, A. G. Mustafin, V. Vinogradova, M. S. Yunusov
Summary: New synthetic benzylisoquinoline-alkaloid analogs based on the diaryl ether hernandial were prepared under Pictet-Spengler reaction conditions.
CHEMISTRY OF NATURAL COMPOUNDS
(2022)
Article
Chemistry, Inorganic & Nuclear
Bruna Paes, Andrea R. Aguirre, Bernardo L. Rodrigues, Isolda C. Mendes, Joao Paulo Ataide Martins, Rafael P. Vieira, Heloisa Beraldo
Summary: Attempts to obtain Schiff bases from the reactions of pyridoxal with L-histidine and L-tryptophan resulted in Pictet-Spengler cyclization, leading to the formation of specific cyclic compounds. The diastereoselectivity of the reactions was investigated and the cis isomer was found to be present in both cases. The theoretical calculations of the reactions' free energies and the formation of complexes with zinc indicated the thermodynamic preferences and the prevention of cyclization.
Article
Chemistry, Organic
Meng Wang, Ze-Hong Zheng, Mu-Qiu Chen, Gu Zhan, Jie Wang, Qian-Qian Yang, Wei Huang
Summary: A series of tetrahydro-beta-carbolin 1,3-diketone frameworks can be synthesized efficiently under mild conditions using azlactones and indole-2-amides. This reaction exhibits excellent compatibility and can be completed without a metal mediator.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Ahreum Kim, Aram Kim, Sunjung Park, Sangji Kim, Hongil Jo, Kang Min Ok, Sang Kook Lee, Jayoung Song, Yongseok Kwon
Summary: A novel chiral phosphoric acid-catalyzed atroposelective Pictet-Spengler reaction of N-arylindoles has been reported, resulting in highly enantioenriched N-aryl-tetrahydro-beta-carbolines with axial chirality. The introduction of a hydrogen bond donor on the bottom aromatic ring, forming a secondary interaction with the phosphoryl oxygen, is crucial for achieving high enantioselectivity. The transformation is tolerant to a wide variety of substituents and can provide products with up to 98% ee.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Marek Buchman, Elliot P. Farney, Stephen N. Greszler, Robert J. Altenbach, Gregory A. Gfesser, Eric A. Voight
Summary: This study presents operationally facile methods for synthesizing substituted dihydroisoquinolinones and tetrahydroisoquinolines from readily accessible substrates. Cyclized products as single regioisomers are efficiently produced from electronically diverse substrates, demonstrating a departure from traditional methods tailored to electron-rich precursors.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
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)