Article
Parasitology
Ana Carolina Santana Vieira, Mariana da Silva Santos, Anderson Brandao Leite, Amanda Evelyn da Silva, Luiz Henrique Agra Cavalcante-Silva, Gabrielle de Souza Augusto Pereira, Sany Delany Gomes Marques, Barbara Viviana de Oliveira Santos, Alysson Wagner Fernandes Duarte, Aline Cavalcante de Queiroz, Kristerson Reinaldo de Luna-Freire, Magna Suzana Alexandre-Moreira
Summary: Leishmaniasis is a neglected disease with limited treatment options and adverse effects. This study evaluated the antileishmanial activity of several derivatives and found that one derivative (1G) showed activity against both promastigote and amastigote forms with low toxicity to macrophages.
PARASITOLOGY RESEARCH
(2022)
Article
Chemistry, Physical
Yinuo Li, Cuiyu Bao, Zhoutong Sun, Wuyuan Zhang, Bo Yuan
Summary: The oxidation of benzylic alcohols coupled with the Morita-Baylis-Hillman (MBH) reactions in biocatalytic compatible conditions was evaluated. One-pot cascades were described and compared, including a chemoenzymatic cascade with galactose oxidase (GOase M3-5) and 1,4-Diazabicyclo [2.2.2] octane (DABCO), a concurrent dual-enzyme cascade with GOase M3-5 and a computationally designed enzyme MBHase (BH32.14), and a whole cell biotransformation with co-expression modules of the two enzymes. The cascades showed high conversions and yields, with some products having high optical purity.
Article
Chemistry, Organic
Olfa Mhasni, Jalloul Bouajila, Farhat Rezgui
Summary: A highly α-regioselective N-nucleophilic allylic substitution reaction was conducted between cyclic MBH alcohols or acetates and imidazole or benzimidazole, using toluene as solvent and azeotropic distillation at reflux, resulting in good yields of N-substituted imidazole derivatives in the absence of catalysts or additives. On the other hand, the aza-Michael addition reaction of imidazole onto acyclic MBH alcohols was performed in refluxing toluene or methanol, with the presence of DABCO as an additive, leading to 1,4 adducts in yields of 70-84%.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xian-Zhou Zheng, Kai Chen, Jun-An Xiao, Jun Li, Sha-Sha Wang, Qing-Lan Zhao, Hao-Yue Xiang, Xiao-Qing Chen, Hua Yang
Summary: In a newly developed palladium-catalysed enantioselective nucleophilic substitution reaction, an unusual temperature-enantioselectivity relationship was observed where higher enantioselectivity was achieved at an abnormally high temperature (140 degrees C) in less than 5 minutes. Experimental and computational studies suggest that temperature-dependent changes in the rate-determining steps may be responsible for the abnormal effect of temperature on stereocontrol in this process.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Lin Jiang, Liu-Dong Yu, Pei-Ying Peng, Hong-Li Li, Deng-Bang Jiang, Yi-Dan Wang, Ming-Long Yuan, Ming-Wei Yuan
Summary: A two-step metal-free process has been developed for the stereoselective allylic 1,3-dienylation of Morita-Baylis-Hillman (MBH) carbonates under mild reaction conditions. This transformation involves allylic alkylation with MBH carbonates followed by denitration, resulting in allylic 1,3-dienyl MBH derivatives with exclusive (E)-selectivity.
SYNTHETIC COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Shutao Wang, Yongliang Gao, Shaoli Song, Xinze Li, Zhuoqi Zhang, Jinbao Xiang, Lianyou Zheng
Summary: This article describes a Lewis base catalyzed allylation reaction between N-aryl amides and various Morita-Baylis-Hillman (MBH) carbonates. The substrate scope of MBH carbonates and amides is comprehensively explored, making this approach useful for the synthesis of diversified branched tertiary N-allylic amides, with broad substrate scope, mild reaction conditions, and scalability.
Article
Chemistry, Organic
Niannian Ni, Jiawei Chen, Siyu Ding, Dongping Cheng, Xiaonian Li, Xiaoliang Xu
Summary: The Ru-catalyzed coupling reaction of Morita-Baylis-Hillman (MBH) adducts with tertiary amines and alpha-trimethylsilyl amines under visible light showed different chemical reaction characteristics when compared to MBH adducts with ester groups as withdrawing-electron groups. The universality of substrates has been extended, allowing for the synthesis of structurally complementary acrylonitriles in satisfied yields under mild conditions and providing an opportunity to discover new meaningful bioactive compounds.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Lei Zhang, Wangzhen Bao, Yuchen Liang, Wenjing Pan, Dongyang Li, Lichun Kong, Zhi-Xiang Wang, Bo Peng
Summary: This study demonstrates the reversal of stereoselectivity in MBH-type [3,3]-rearrangement by using a new pair of rearrangement partners, leading to the synthesis of different types of alpha-aryl alpha,beta-unsaturated carbonyl derivatives. Mechanistic studies provide insights into the reaction pathway and the opposite stereoselectivities observed.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Ru-Jie Yan, Bao-Xin Liu, Yuan Hu, Wei Du, Ying-Chun Chen
Summary: Zwitterionic N-allylic ylide species are generated from Morita-Baylis-Hillman carbonates of trifluoromethyl ketones and acrylonitrile under the catalysis of cinchona-derived tertiary amines, and participate in switchable asymmetric [3+2] or [4+1] annulations with 1-azadienes in chemo-, regio-, and stereodivergent manners to construct frameworks with trifluoromethylated all-carbon quaternary stereogenic centre or tetrasubstituted alkene moiety in good yields with excellent enantioselectivity.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Xing Guo, Boming Shen, Chang Liu, Hongyue Zhao, Xuechen Li, Peiyuan Yu, Pengfei Li
Summary: Based on the frontier molecular orbital theory, two types of modified enones have been designed and successfully applied in the chiral phosphine-catalyzed stereoselective [1 + 4]-annulation of MBH carbonates. The reaction proceeds smoothly under mild conditions, exhibiting excellent functional group tolerance and providing a broad scope of enantioenriched 2,3-dihydrofurans with high efficiency. DFT calculations have been used to guide the design of additional enones and understand the origin of stereoselectivity. Furthermore, this method explores the application scope of enones and enriches the chemistry of [1 + 4]-annulations of MBH carbonates for the preparation of optically active multifunctional 2,3-dihydrofurans.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Prashant Shukla, Ambika Asati, Devkumari Patel, Manorama Singh, Vijai K. K. Rai, Ankita Rai
Summary: This study reports on the Morita Baylis-Hillman (MBH) reaction using various aldehydes with acrylonitrile and methyl acrylate as electron-deficient alkenes. A novel catalyst, EDC.HCl, is utilized in the presence of CuI to synthesize the MBH adduct. The synthetic protocol shows excellent product yield (up to 99%), ambient reaction conditions, shorter reaction time, and no side product formation.
Article
Chemistry, Physical
Ricardo Lucas Gomes Pimentel, Rodolfo B. da Silva, Mario Luiz Araujo de Almeida Vasconcellos, Claudio Gabriel Lima-Junior, Fausthon F. da Silva
Summary: This study explores the synthesis and characterization of a mixed-metal copper-manganese iminodiacetate 1D coordination polymer (Cu/Mn-IDA) and its application as a catalyst for the Morita-Baylis-Hillman reaction. The results demonstrate that under optimized conditions, the catalyst can achieve yields of up to 87% for various aldehyde substrates. Additionally, the catalyst exhibits good recyclability.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Organic
Jianning Liao, Jipan Dong, Jiaqing Xu, Wei Wang, Yongjun Wu, Yuxia Hou, Hongchao Guo
Summary: A phosphine-catalyzed [3 + 2] annulation reaction has been developed in this study to synthesize multifunctional isoxazoles with moderate to good yields and diastereoselectivities. The use of a spirocyclic chiral phosphine catalyst resulted in up to 89% ee.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Marta Papis, Raffaella Bucci, Alessandro Contini, Maria Luisa Gelmi, Leonardo Lo Presti, Giovanni Poli, Gianluigi Broggini, Camilla Loro
Summary: A phosphine-catalyzed domino assembly of six units of 2-bromomethyl acrylates was developed to synthesize polyalkenyl adducts containing two cyclohexenyl rings. This method involves initial dimerization and subsequent trimerization of the substrate, resulting in the formation of seven carbon-carbon bonds and four stereocenters. The protocol has also been successfully scaled up to gram-scale experiments.
Article
Biochemistry & Molecular Biology
Yi-Lin He, Miao Zhong, Zi-Long Song, Yu-Kai Shen, Lanning Zhao, Jianguo Fang
Summary: This study reports the design and synthesis of a series of Baylis-Hillman adducts, among which a typical adduct showed superior cytotoxicity against HepG2 cells. The selected typical adduct was found to selectively target TrxR in HepG2 cells, leading to the disruption of intracellular redox homeostasis. It also arrested the cell cycle and significantly restrained the metastasis of HepG2 cells. These findings suggest that the selected typical adduct, as well as other Baylis-Hillman skeleton-bearing compounds, hold promise as candidate or ancillary agents for the treatment of various cancers.
BIOORGANIC & MEDICINAL CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Haibo Mei, Jianlin Han, Sarah White, Daniel J. Graham, Kunisuke Izawa, Tatsunori Sato, Santos Fustero, Nicholas A. Meanwell, Vadim A. Soloshonok
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Review
Chemistry, Multidisciplinary
Jianlin Han, Lorand Kiss, Haibo Mei, Attila Mario Remete, Maja Ponikvar-Svet, Daniel Mark Sedgwick, Raquel Roman, Santos Fustero, Hiroki Moriwaki, Vadim A. Soloshonok
Summary: This comprehensive review focuses on the effects of fluoride ions and organofluorine compounds on human health and the environment, as well as related topics including the reasons for the advancement of fluorine-containing pharmaceuticals and agrochemicals, metabolism of fluorinated drugs, withdrawn fluorinated drugs, natural sources of fluorine compounds in the environment, sources of fluoride intake, and biomarkers of fluoride exposure.
Article
Chemistry, Organic
Yupiao Zou, Ryosuke Takeda, Jianlin Han, Hiroyuki Konno, Hiroki Moriwaki, Hidenori Abe, Kunisuke Izawa, Vadim A. Soloshonok
Summary: Ni(II) complexes derived from glycine Schiff bases with chiral tridentate ligands have been used as powerful tools for synthesizing structurally diverse tailor-made amino acids. An asymmetric alkylation reaction between chiral nucleophilic glycine derived Ni-complex and 3-(chloromethyl)-1H-pyrrolo[2,3-b]pyridine has been developed under convenient conditions, yielding the alkylated Ni-complex in 74% yield with excellent diastereoselectivity. This reaction features convenient conditions and completely controlled diastereoselectivity, providing a valuable approach for asymmetric synthesis of 7-aza-tryptophan.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Biochemistry & Molecular Biology
Jianlin Han, Alicja Wzorek, Karel D. Klika, Vadim A. Soloshonok
Summary: This review emphasizes the necessity of conducting tests to gauge the magnitude of the self-disproportionation of enantiomers (SDE) phenomenon to ensure the accuracy of reported enantiomeric excess (ee) values. Care must be taken to handle SDE effects when subjecting scalemic samples to physicochemical processes, or even avoiding fractionation if possible.
Article
Multidisciplinary Sciences
Magdalena Kwiatkowska, Alicja Wzorek, Anna Kolbus, Mariusz Urbaniak, Jianlin Han, Vadim A. Soloshonok, Karel D. Klika
Summary: Flurbiprofen, a member of the nonsteroidal anti-inflammatory drug family, is currently available on the pharmaceutical market as a racemate. Various forms of chromatography and nuclear magnetic resonance testing revealed that its intermolecular associations are solvent dependent, influencing the rationalization and prediction of chromatographic outcomes. This study also explored the importance of scalemic samples of flurbiprofen and the implications of SDEvC and SDEvS for enantioenriched drug preparation and storage.
Editorial Material
Biochemistry & Molecular Biology
Jianlin Han, Roman Dembinski, Vadim A. Soloshonok, Karel D. Klika
Article
Chemistry, Organic
Ziyi Li, Nana Wang, Jiang Liu, Haibo Mei, Vadim A. Soloshonok, Jianlin Han
Summary: A new reactivity mode of tert-butanesulfinamide has been developed for rapid assembly of poly functionalized isothiazoles through C-S and O-S bond cleavage of N-propargyl tert-butanesulfinylamide. This intramolecular cyclization reaction is conducted under mild conditions and tolerates several fluoroalkyl and substituted phenyl groups with good chemical yields, providing an easy strategy for the synthesis of isothiazoles.
Review
Chemistry, Medicinal
Aiyao Liu, Jianlin Han, Arina Nakano, Hiroyuki Konno, Hiroki Moriwaki, Hidenori Abe, Kunisuke Izawa, Vadim A. Soloshonok
Summary: Amino acids play a crucial role in the modern health industry as key synthetic precursors for pharmaceuticals, biomaterials, biosensors, and drug delivery systems. In 2020, FDA approved 12 newly introduced pharmaceuticals derived from amino acids, covering various therapeutic areas.
Review
Biochemistry & Molecular Biology
Bo Fu, Jorge Escorihuela, Jianlin Han, Santos Fustero, Pablo Barrio, Mikiko Sodeoka, Shintaro Kawamura, Alexander Sorochinsky, Vadim A. Soloshonok
Summary: Incorporating fluorine into organic molecules is a well-established strategy in designing advanced materials, agrochemicals, and pharmaceuticals. Among various modern synthetic approaches, functionalizing unsaturated bonds with simultaneous addition of trifluoromethyl group is currently one of the most attractive methods in development. This review highlights significant contributions in the chloro-, bromo-, iodo-, fluoro-, and cyano-trifluoromethylation of alkenes and alkynes over the last decade (2012-2021).
Article
Multidisciplinary Sciences
Qian Wang, Xin Zhang, Alexander E. Sorochinsky, Greg Butler, Jianlin Han, Vadim A. Soloshonok
Summary: This review briefly discusses traditional methods for synthesizing CF3-O-containing compounds, as well as critically evaluates known trifluoromethoxylating reagents, focusing on their preparation, synthetic generality, and limitations.
Review
Chemistry, Medicinal
Qian Wang, Jianlin Han, Alexander Sorochinsky, Aitor Landa, Greg Butler, Vadim A. Soloshonok
Summary: Nowadays, the selective introduction of fluorine into bioactive compounds is a mature strategy in drug design. Amino acids, on the other hand, are a ubiquitous class of organic compounds and have great potential in the development of targeted drugs. In recent years, there has been a clear trend in combining the structural features of both amino acids and fluorine in pharmaceutical design.
Review
Biochemistry & Molecular Biology
Nana Wang, Haibo Mei, Gagan Dhawan, Wei Zhang, Jianlin Han, Vadim A. Soloshonok
Summary: The strategic fluorination in pharmaceutical drugs allows us to manipulate their stability, bio-absorption, and overall efficiency. Additionally, natural and tailor-made amino acids serve as essential frameworks for the development of bioactive molecules. This review article highlights these prevalent trends in recently approved drugs.
Article
Biochemistry & Molecular Biology
Ziyi Li, Hua Gao, Haibo Mei, Guangwei Wu, Vadim A. Soloshonok, Jianlin Han
Summary: Sclareolide was developed as an efficient C-nucleophilic reagent for an asymmetric Mannich addition reaction with N-tert-butylsulfinyl aldimines. The reaction exhibited high yields and diastereoselectivities, even on a gram scale. The resulting Mannich addition products could be deprotected to obtain sclareolide derivatives with a free N-H group, which showed considerable antifungal activity against forest pathogenic fungi in vitro.
Editorial Material
Biochemistry & Molecular Biology
Roman Dembinski, Vadim Soloshonok
Article
Chemistry, Analytical
Alicja Wzorek, Vadim A. Soloshonok, Karel D. Klika
Summary: a-Pinene is a unique monoterpene that undergoes the self-disproportionation of enantiomers (SDE) phenomenon in the gaseous phase, as shown by gas chromatography (GC). This study successfully replicated the SDE of a-pinene using evaporation off silica gel and foam fractionation methods, confirming the plausibility of the GC report. Molecular associations in 2D adsorbed monolayers, rather than conventional functional group-based interactions, are responsible for the observed SDE.
