Jingyao Li

University of Groningen

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Alexander Dömlingꝉ

Institute of Technology and Business

V. di Lorenzo

Budapest University of Technology and Economics

Pravin Patil

Temple University Hospital

Qiang Zheng

University of Groningen

Katarzyna Kurpiewska

Jagiellonian University

Justyna Kalinowska‐Tłuścik

Jagiellonian University

Ajay L. Chandgude

University of Groningen

Marco A. Velasco‐Velázquez

Universidad Nacional Autónoma de México

Angel J. Ruiz‐Moreno

University of Groningen

Huaming Sun

Shaanxi Normal University

Cooperative Institutions

University of Groningen

Chinese Academy of Sciences

Nagoya University

Universidade de São Paulo

Dialyse Centrum Groningen

University of Chinese Academy of Sciences

Dalian University of Technology

Tsinghua University

Centre National de la Recherche Scientifique

Kyoto University

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Innovative synthesis of drug-like molecules using tetrazole as core building blocks

Beilstein Journal of Organic Chemistry (2024)

Jingyao Li Ajay L. Chandgude Qiang Zheng Alexander Dömlingꝉ

Tetrazole is widely utilized as a bioisostere for carboxylic acid in the field of medicinal chemistry and drug development, enhancing the drug-like characteristics of various molecules. Typically, tetrazoles are introduced from their nitrile precursors through late-stage functionalization. In this work, we propose a novel strategy involving the use of diversely protected, unprecedented tetrazole aldehydes as building blocks. This approach facilitates the incorporation of the tetrazole group into multicomponent reactions or other chemistries, aiding in the creation of a variety of complex, drug-like molecules. These innovative tetrazole building blocks are efficiently and directly synthesized using a Passerini three-component reaction (PT-3CR), employing cost-effective and readily available materials. We further showcase the versatility of these new tetrazole building blocks by integrating the tetrazole moiety into various multicomponent reactions (MCRs), which are already significantly employed in drug discovery. This technique represents a unique and complementary method to existing tetrazole synthesis processes. It aims to meet the growing demand for tetrazole-based compound libraries and novel scaffolds, which are challenging to synthesize through other methods.

Tetrazole

Bioisostere

Moiety

10.3762/bjoc.20.85

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Scaffolding-Induced Property Modulation of Chemical Space

ACS Combinatorial Science (2020)

Jingyao Li V. di Lorenzo Pravin Patil Angel J. Ruiz‐Moreno Katarzyna Kurpiewska

Physicochemical property switching of chemical space is of great importance for optimization of compounds, for example, for biological activity. Cyclization is a key method to control 3D and other properties. A two-step approach, which involves a multicomponent reaction followed by cyclization, is reported to achieve the transition from basic moieties to charge neutral cyclic derivatives. A series of multisubstituted oxazolidinones, oxazinanones, and oxazepanones as well as their thio and sulfur derivatives are synthesized from readily available building blocks with mild conditions and high yields. Like a few other methods, MCR and cyclization allow for the collective transformation of a large chemical space into a related one with different properties.

Chemical space

Thio-

Chemical transformation

10.1021/acscombsci.0c00072

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Citations (11)

CCDC 2124066: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

Ya Wu Xinya Bu Yongqi Ke Huaming Sun Jingyao Li

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc299885

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Crystal structure of ethyl 2-amino-4-(2,6-dichlorophenyl)-7-methyl-5-oxo-4H,5H-pyrano [4,3-b]pyran-3-carboxylate, C₁₈H₁₅Cl₂NO₅

Zeitschrift für Kristallographie - New Crystal Structures (2018)

Jingyao Li

Abstract C 18 H 15 Cl 2 NO 5 , monoclinic, P 2 1 / c (no. 14), a = 7.423(5) Å, b = 27.798(3) Å, c = 9.550(2) Å, β = 117.62(4)°, V = 1746.0(14) Å 3 , Z = 4, R gt ( F ) = 0.0395, wR ref ( F 2 ) = 0.1030, T = 293(2) K.

Monoclinic crystal system

Pyran

Carboxylate

10.1515/ncrs-2018-0054

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ChemInform Abstract: Synthesis of a C₆₀ Functionalized Calix[4]‐spiro‐bis‐crown.

ChemInform (1998)

C. Chen Jingyao Li Gharsallah Neacute ji Qiang Zheng Dazhao Zhu

Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

10.1002/chin.199850198

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CCDC 1957561: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Jingyao Li V. di Lorenzo Pravin Patil Angel J. Ruiz‐Moreno Katarzyna Kurpiewska

10.5517/ccdc.csd.cc23q040

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Multicomponent Macrocyclic IL-17a Modifier

ACS Medicinal Chemistry Letters (2022)

Eman M. M. Abdelraheem Max Lubberink Wenja Wang Jingyao Li Atilio Reyes Romero

IL-17a is a major inflammation target, with several approved antibodies in clinical use. Small-molecule IL-17a antagonists are an emerging hot topic, with the recent advancement of three compounds into clinical trials. Here, we describe the design, discovery, synthesis, and screening of macrocyclic compounds that bind to IL-17a. We found that all currently described IL-17a modifiers belong to the same pharmacophore model, likely resulting in a similar receptor binding mode on IL-17a. A pipeline of pharmacophore analysis, virtual screening, resynthesis, and protein biophysics resulted in a potent IL-17a macrocyclic modifier.

10.1021/acsmedchemlett.2c00257

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PROTACs– a game-changing technology

Expert Opinion on Drug Discovery (2019)

Markella Konstantinidou Jingyao Li Bidong Zhang Zefeng Wang Shabnam Shaabani

Introduction: Proteolysis – targeting chimeras (PROTACs) have emerged as a new modality with the potential to revolutionize drug discovery. PROTACs are heterobifunctional molecules comprising of a ligand targeting a protein of interest, a ligand targeting an E3 ligase and a connecting linker. The aim is instead of inhibiting the target to induce its proteasomal degradation.Areas covered: PROTACs, due to their bifunctional design, possess properties that differentiate them from classical inhibitors. A structural analysis, based on published crystal aspects, kinetic features and aspects of selectivity are discussed. Specific types such as homoPROTACs, PROTACs targeting Tau protein and the first PROTACs recently entering clinical trials are examined.Expert opinion: PROTACs have shown remarkable biological responses in challenging targets, including an unprecedented selectivity over protein family members and even efficacy starting from weak or unspecific binders. Moreover, PROTACs are standing out from classical pharmacology by inducing the degradation of the target protein and not merely its inhibition. However, there are also challenges in the field, such as the rational structure optimization, the evolution of computational tools, limited structural data and the greatly anticipated clinical data. Despite the remaining hurdles, PROTACs are expected to soon become a new therapeutic category of drugs.

Linker

10.1080/17460441.2019.1659242

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Citations (133)

Identification of a non-competitive inhibitor of Plasmodium falciparum aspartate transcarbamoylase

Biochemical and Biophysical Research Communications (2018)

Sergey Lunev Soraya S. Bosch Fernando de Assis Batista Chao Wang Jingyao Li

Aspartate transcarbamoylase catalyzes the second step of de-novo pyrimidine biosynthesis. As malarial parasites lack pyrimidine salvage machinery and rely on de-novo production for growth and proliferation, this pathway is a target for drug discovery. Previously, an apo crystal structure of aspartate transcarbamoylase from Plasmodium falciparum (PfATC) in its T-state has been reported. Here we present crystal structures of PfATC in the liganded R-state as well as in complex with the novel inhibitor, 2,3-napthalenediol, identified by high-throughput screening. Our data shows that 2,3-napthalediol binds in close proximity to the active site, implying an allosteric mechanism of inhibition. Furthermore, we report biophysical characterization of 2,3-napthalenediol. These data provide a promising starting point for structure based drug design targeting PfATC and malarial de-novo pyrimidine biosynthesis.

Aspartate carbamoyltransferase

Pyrimidine metabolism

10.1016/j.bbrc.2018.02.112

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Citations (19)

Chemistry of photoproteins as interface between bioactive molecules and protein function

Pure and Applied Chemistry (1998)

Minoru Isobe Tomoyuki Fujii Sathorn Suwan Masaki Kuse Kazuhito Tsuboi

Abstract

Interface (matter)

10.1351/pac199870112085

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Citations (10)