Article
Chemistry, Organic
Yakun Wang, Shuaifei Wang, Yufeng Wu, Ting Zhao, Jie Liu, Junlin Zheng, Lin Wang, Jieli Lv, Tao Zhang
Summary: We have developed a highly efficient enantioselective fluorination reaction of 4-substituted pyrazolones using amide-based Cinchona alkaloids catalysts. The reaction affords tetrasubstituted fluorine-attached chiral center products in high yields (up to 99%) and excellent enantioselectivities (up to 98% ee). Our method features low catalyst loading, short reaction times, and wide substrate scope. Furthermore, the reaction can be carried out under sustainable conditions for 10 cycles, and the optically pure product (>99.5% ee) can be easily obtained on a multigram scale through simple extraction and recrystallization. Controlled experiments and DFT studies revealed that the multiple hydrogen bonding interactions and steric hindrance contribute to the high enantioselectivity and reactivity. This transformation provides a practical method for the preparation of chiral fluorine-containing compounds with a simple operational protocol and low catalyst loading.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Mahmoud A. Abdelkawy, Christopher Davin, El-Saied A. Aly, Mahmoud A. El-Badawi, Shinichi Itsuno
Summary: Repetitive Mizoroki-Heck (MH) coupling polymerization was employed to synthesize novel chiral polyureas containing cinchona alkaloids in the main chain. Some chiral polyureas were successfully polymerized through self polycondensation to serve as catalysts for the asymmetric Michael addition reaction. Phenolic-based chiral polymers demonstrated high catalytic activity and excellent enantioselectivities as heterogeneous catalysts for the enantioselective Michael reaction, with the ability to be recycled and reused.
Article
Chemistry, Organic
Yiqun Zeng, Chao Fei, Xiao Zhou, Jisheng Luo, Li Deng
Summary: A newly developed betaine catalyst was used for an asymmetric isomerization of beta,gamma-unsaturated butenolides at a lower loading (0.2-2 mol%) compared to available methods (0.5-2.0 mol%).
Article
Chemistry, Applied
Nick Wannenmacher, Martin Heberle, Xin Yu, Ayseguel Demircan, Daniel M. Wanner, Camilla Pfeffer, Rene Peters
Summary: This paper reports a diastereospecific enantiodivergent allylation of pyrazolones using a planar chiral pentaphenylferrocene based palladacycle as the catalyst. Both product enantiomers can be selectively obtained with the same catalyst batch. The method is applicable to structurally diverse substrates and gives products with high enantiomeric excesses. Additionally, the paper shows the transformation of pyrazolones into beta-aminoamides.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Yakun Wang, Shuaifei Wang, Yingying Wang, Yufeng Wu, Jie Liu, Kedi Zhou, Qichen Sun, Lizhen Fang, Tao Zhang
Summary: We have successfully developed an enantioselective trifluoromethylthiolation reaction of 4-substituted pyrazolones using amide-based Cinchona alkaloids catalyzed by N-trifluoromethylthiosaccharin. A variety of chiral CF3S-pyrazolones were obtained with excellent yields and high enantioselectivities. Control experiments revealed that multiple hydrogen bonding interactions and steric hindrance at the NH-position were crucial for achieving high enantioselectivity and reactivity. Moreover, these amide-based phase transfer catalysts could be easily recovered and reused with almost unchanged reactivity and enantioselectivity.
MOLECULAR CATALYSIS
(2023)
Article
Chemistry, Organic
Mingyu Zhang, Yuting Yan, Hexin Sun, Xuegang Fu, Jianhui Huang
Summary: This article reviews the use of Sparteine or its analogues as ligands in transition metal-involved asymmetric transformations and proposes further design and perspectives for similar ligands.
CURRENT ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
David Svestka, Jan Otevrel, Pavel Bobal
Summary: Here we report an asymmetric organocatalyzed method for the Friedel-Crafts reaction between activated phenols and trihaloacetaldehydes. A screening of 41 compounds identified a catalyst structure based on 3,5-dinitrobenzamide of 9-amino-epi-cinchonidine as the lead catalytic molecule. Under optimized conditions, the catalyst provided trihalohydroxyalkylated adducts in good yields and with high enantiomeric ratios. The reaction scope was determined on 29 entries and several follow-up transformations of the enantioenriched products were accomplished.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Mariola Zielinska-Blajet, Joanna Najdek
Summary: An efficient approach to synthesizing chiral selenoureas derived from Cinchona alkaloid scaffolds was described in this study. These selenoureas were evaluated as bifunctional organocatalysts in asymmetric Michael addition reactions, with the best results achieved by those containing the 4-fluorophenyl group, showing enantioselectivities up to 96% ee. Additionally, the catalytic performance of thiourea and selenourea counterparts was compared.
Article
Chemistry, Organic
Deniz Tozendemir, Cihangir Tanyeli
Summary: Cinchona alkaloid-derived organocatalysts have been widely utilized in asymmetric transformations, resulting in products with high enantiopurity. A bifunctional quinine-derived sulfonamide organocatalyst was developed for catalyzing the asymmetric sulfa-Michael reaction, achieving high enantioselectivity with low catalyst loading. The enriched sulfa-Michael addition products were successfully oxidized to obtain the corresponding sulfones.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Xin Huang, Wei Zhang
Summary: Organocatalysis offers unique activation modes, mild reaction conditions, and good catalyst adaptability, making it more efficient with the integration of green techniques. This article focuses on recyclable cinchona alkaloid-catalyzed reactions in the asymmetric synthesis of functionalized compounds of biological interest.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Norio Shibata, Dominique Cahard
Summary: From 2000, our two research groups independently and simultaneously designed and developed a novel family of electrophilic fluorinating reagents based on the use of Cinchona alkaloids. The chiral N-fluoro ammonium salts demonstrated the highest efficiency compared to prior art in enantioselective electrophilic fluorination for a wide range of substrates. In this account, we tell our respective stories, how the same idea germinated in our laboratories, the characterization of the chiral reagents, the use in stoichiometric quantity then the development of a catalytic version, the application to the synthesis of chiral fluorinated molecules of pharmaceutical interest, and finally the exploitation of our reagents by other teams and for other applications.
Article
Chemistry, Organic
Francesco Trenti, Kotaro Yamamoto, Benke Hong, Christian Paetz, Yoko Nakamura, Sarah E. O'Connor
Summary: Transcriptomic data led to the discovery of three enzymes involved in the biosynthesis of quinine, with a medium-chain alcohol dehydrogenase and an esterase being key in producing the biosynthetic intermediate dihydrocorynantheal from strictosidine aglycone. Additionally, the specific O-methyltransferase for 6'-hydroxycinchoninone suggested the final step order to be cinchoninone hydroxylation, methylation, and keto-reduction.
Review
Chemistry, Organic
Eric R. Miller, Karl A. Scheidt
Summary: This article summarizes the research on the total synthesis of bioactive alkaloids, highlighting the importance and achievements of catalytic asymmetric methods in this field, and providing new inspiration for future synthesis of these important natural products.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Shiqiang Wei, Wenyao Wang, Aiqi Xue, Shah Nawaz, Jingping Qu, Baomin Wang
Summary: The 4-isothiocyanatopyrazolones are utilized as efficient synthons for the construction of triazoline derivatives through asymmetric [3+2] annulation with azodicarboxylates, yielding a wide range of structurally diverse multi-nitrogen-containing spirocycles in excellent yields (up to 97%) with excellent enantioselectivities (up to 97% ee).
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Wenjing Gong, Xin Du, Wenyao Wang, Wande Zhang, Baomin Wang
Summary: The cascade Michael addition/cyclization reaction of 4-isothiocyanato pyrazolones with ethyl /3-benzoylacrylates was explored using asymmetric organocatalysis, resulting in spiro[pyrazolone-pyrrolidinethione] cores with three contiguous stereogenic centers in excellent enantioselectivities (up to 95% ee) and yields (up to 91%). This process showed a broad substrate scope and the advantage of simple operation.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Feng Zhang, Wei Liu, Jian Huang, Qi-long Chen, Dan-dan Wang, Li-wei Zou, Yong-fang Zhao, Wei-dong Zhang, Jian-guang Xu, Hong-zhuan Chen, Guang-bo Ge
Summary: Jingyin granules, an antiviral herbal medicine, are commonly used to treat viral infections. Research shows that the herbal extract of Jingyin granules can inhibit human drug-metabolizing enzymes and modulate the plasma exposure and half-life of certain drugs.
ACTA PHARMACOLOGICA SINICA
(2022)
Article
Biochemistry & Molecular Biology
Xing-Kai Qian, Jing Zhang, Pei-Fang Song, Yi-Su Zhao, Hong-Ying Ma, Qiang Jin, Dan-Dan Wang, Xiao-Qing Guan, Shi-Yang Li, XiaoZe Bao, Li-Wei Zou
Summary: Carboxylesterase 2 (CES2) is a crucial Phase I drug metabolizing enzyme with significant roles in mediating the effects of certain anticancer drugs. Through synthesizing a series of pyrazolones and analyzing their inhibitory effects against CES2, researchers identified compound 27 as a potent inhibitor with the ability to also inhibit adipocyte adipogenesis. These findings suggest compound 27 could serve as a valuable lead compound for developing more powerful CES2 inhibitors and exploring CES2's biological functions in humans.
BIOORGANIC & MEDICINAL CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Yun-Qing Song, Qiang Jin, Dan-Dan Wang, Jie Hou, Li-Wei Zou, Guang-Bo Ge
Summary: This review summarizes recent advances in the discovery of hCES inhibitors from clinically available medications and their impact on CES-associated drug metabolism. The potential risks of hCES inhibitors to trigger drug/herb-drug interactions (DDIs/HDIs) and future concerns in this field are also highlighted.
CHEMICO-BIOLOGICAL INTERACTIONS
(2021)
Review
Biochemistry & Molecular Biology
Xing-Kai Qian, Jing Zhang, Xiao-Dong Li, Pei-Fang Song, Li-Wei Zou
Summary: This article summarizes the structural characteristics, functions, and metabolism of the prolyl-specific peptidases or proteases family, as well as their importance in human physiology and drug metabolism.
CURRENT MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Peifang Song, Quisha Pan, Zhaohui Sun, Liwei Zou, Ling Yang
Summary: FAP-alpha is an enzyme associated with tumors, which is underexpressed in normal tissues but significantly increased in diseased states. This review provides an overview of the discovery and latest advances in FAP-alpha, including its structural characteristics, inhibitors, and detection methods.
CHEMICO-BIOLOGICAL INTERACTIONS
(2022)
Article
Biochemistry & Molecular Biology
Jing Zhang, Qiu-Sha Pan, Xing-Kai Qian, Xiang-Lu Zhou, Ya-Jie Wang, Rong-Jing He, Le-Tian Wang, Yan-Ran Li, Hong Huo, Cheng-Gong Sun, Lei Sun, Li-Wei Zou, Ling Yang
Summary: In this study, two triterpenoid derivatives with strong inhibitory effects on both pancreatic lipase (PL) and human carboxylesterase 1A (hCES1A) were discovered, showing potential as promising lead compounds for drug development.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2022)
Article
Materials Science, Biomaterials
Dan-Dan Wang, Xing-Kai Qian, Hong-Xin Li, Gui-Hua Jia, Qiang Jin, Xin Luan, Ya-Di Zhu, Yi-Nan Wang, Jian Huang, Li-Wei Zou, Guang-Bo Ge, Ling Yang
Summary: This study successfully constructed a novel enzyme-activatable fluorescent substrate for real-time detection and imaging of CD26 activity in various biological systems, revealing its relevance to tumorigenesis.
MATERIALS SCIENCE AND ENGINEERING C-MATERIALS FOR BIOLOGICAL APPLICATIONS
(2021)
Article
Engineering, Multidisciplinary
Qiusha Pan, Peifang Song, Zhenhua Ni, Xingkai Qian, Anqi Wang, Liwei Zou, Yong Liu, Ping Wang, Weidong Zhang, Hong Ma, Ling Yang
Summary: Accurately assessing and tracking the progression of liver-specific injury is a challenge in biomarker research. This study characterizes liver-specific damage caused by ANIT using serum and tissue biomarkers. CES1 and DPP-IV reflect different pathophysiologies of liver damage and can be used to identify liver damage and inflammation. CES1 is specifically able to determine liver cell destruction or damage without interference from inflammation. CES1 and DPP-IV can be combined to evaluate and track liver-specific injury.
Review
Chemistry, Analytical
Qiang Jin, Li-Lin Song, Le-Le Ding, Jing Zhang, Dan-Dan Wang, Yun-Qing Song, Li-Wei Zou, Guang-Bo Ge
Summary: This review summarizes the latest advances in the design and development of specific optical substrates for mammalian SHs and related high-throughput optical assays, as well as their applications in bioanalytical and biomedical fields.
TRAC-TRENDS IN ANALYTICAL CHEMISTRY
(2022)
Article
Plant Sciences
Ci-Qin Li, Jin-Hui Shi, Jie Mu, An-Qi Wang, Li-Wei Zou, Guang-Bo Ge
Summary: A set of 22 analogs of licochalcone A was designed and synthesized to explore their potentials as dipeptidyl peptidase 4 (DPP4) inhibitors with anti-inflammatory effects. The most potent activity was exhibited by the nitro-substituted analogue 27. The structure-activity relationship investigation revealed the importance of 4-hydroxyl and 5-chloro substituents for DPP4 inhibition, while the 3'-nitro substituent improved both DPP4 inhibition and microsomal stability. Furthermore, compound 27 showed good selectivity for DPP4 over other proteases and demonstrated no toxicity to normal cells and weak toxicity to cancer cells.
JOURNAL OF NATURAL PRODUCTS
(2023)
Article
Environmental Sciences
Zhenhua Ni, Honghong Ma, Xiaodong Li, Liwei Zou, Zongjun Liu, Xiongbiao Wang, Hong Ma, Ling Yang
Summary: Wogonin can alleviate the cytotoxicity induced by BaP in human airway epithelial cells by dual inhibition of CYP1A1 activity and expression, which involves the inhibition of CDK7 and CDK9 activity.
ENVIRONMENTAL TOXICOLOGY
(2023)
Article
Chemistry, Applied
An-Qi Wang, Ya-Jie Wang, Jing Zhang, Yi-Ming Fan, Shi-Yang Li, Li-Wei Zou
Summary: The inhibitory effects of twenty-six ginsenosides on human pancreatic lipase (hPL) and porcine pancreatic lipase (pPL) were studied. It was found that nine ginsenosides have moderate inhibitory effects on hPL, with good selectivity over pPL. In contrast, (S)-Rh2 exhibited good inhibitory effects on pPL over hPL. SAR analysis indicated that the introduction of the O-glycosyl group(s) at the C-3/C-7 site is not beneficial for hPL inhibition, and ginsenosides with the A-skeleton are more beneficial compared to those with the B-/C-skeleton. Inhibition kinetic analysis revealed that Rg3 and (S)-Rh2 inhibit hPL-catalyzed DDAO-ol hydrolysis in a mixed manner. Molecular docking studies confirmed that Rg3 and (S)-Rh2 inhibit hPL by forming multiple Pi-hydrogen interactions and hydrogen bonds with catalytic residues of hPL. These findings highlight the importance of using hPL rather than pPL to evaluate the inhibitory effect of PL.
NATURAL PRODUCT RESEARCH
(2023)
Article
Spectroscopy
Jianing Zhao, Ciqin Li, Sihan Wei, Chengwei Lu, Li-Wei Zou
Summary: In this study, three Schiff-based fluorescent probes with aggregation-induced emission (AIE) and excited intra-molecular proton transfer (ESIPT) characters were synthesized. A rare tri-responsive fluorescent probe (SN-Cl) was developed and could selectively identify Pb2+, Ag+ and Fe3+. The LOD values for the three ions were as low as 0.059 μM, 0.012 μM and 8.92 μM, respectively. SN-Cl showed satisfactory performance in real water samples detection and test paper experiments for three ions, and could be used as an excellent imaging agent for Fe3+ in HeLa cells.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
(2023)
Article
Biochemistry & Molecular Biology
Fang-Yuan Wang, Gui-Lin Wei, Yu-Fan Fan, Dong-Fang Zhao, Ping Wang, Li-Wei Zou, Ling Yang
Summary: In this study, oleanic acid, betulinic acid, and celastrol were identified as potent inhibitors of COMT with the ability to specifically recognize and bind with the enzyme, while reducing the risk of liver toxicity. These findings could lead to the development of new lead compounds and derivatives for further testing.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Analytical
Jing Zhang, Xing-Kai Qian, Pei-Fang Song, Xiao-Dong Li, An-Qi Wang, Hong Huo, Jing-Chun Yao, Gui-Min Zhang, Li-Wei Zou
Summary: This study established and optimized a high-throughput screening method for DPP-IV inhibitors using human plasma, demonstrating that GP-BAN has better specificity and affinity for enzymes, and has the potential to replace expensive human recombinant DPP-IV in detection.
ANALYTICAL METHODS
(2021)
