Article
Chemistry, Medicinal
Yumin Dai, Jose A. Santiago-Rivera, Stefan Hargett, Joseph M. Salamoun, Kyle L. Hoehn, Webster L. Santos
Summary: We report new mitochondrial uncouplers derived from the conversion of [1,2,5]oxadiazolo[3,4-b]pyrazines to 1H-imidazo[4,5-b]pyrazines. Functionalization on the 2-position of the imidazole ring through a selection of orthoesters allowed the synthesis of a variety of imidazopyrazine derivatives. Our studies suggest that both a 2-trifluoromethyl group and N-methylation are crucial for mitochondrial uncoupling capacity.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Biochemistry & Molecular Biology
Ida Bocek Pavlinac, Katarina Zlatic, Leentje Persoons, Dirk Daelemans, Mihajlo Banjanac, Vedrana Radovanovic, Kristina Butkovic, Marijeta Kralj, Marijana Hranjec
Summary: A series of cyano- and amidino-substituted imidazo[4,5-b]pyridines were synthesized and evaluated for their biological activity. The compounds showed strong antiproliferative activity against colon carcinoma, with compound 10 and 14 displaying the most pronounced activity. Compound 14 also exhibited moderate antibacterial activity against E. coli, while other compounds lacked antibacterial activity. Derivatives 7 and 17 showed selective but moderate antiviral activity against respiratory syncytial virus (RSV).
Review
Biochemistry & Molecular Biology
Karim Jarmoni, Khalid Misbahi, Vincent Ferrieres
Summary: This review firstly discusses the synthetic methods of imidazo[4,5-b]pyridine derivatives and then provides examples of their potential, with a focus on protein inhibition abilities, opening up possibilities for their application as anti-cancer or antimicrobial agents.
CURRENT MEDICINAL CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Saradindu Debnath, Syaleena Parveen, Priyankar Pradhan, Ipsita Das, Tapas Das
Summary: Nitrogen heterocycles are vital compounds found in nature or synthesized, playing essential roles in living systems and having potential applications in drugs and materials.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Deyu Wu, Zhengqiang Liu, Yiting Chang, Jiajing Chen, Haixiang Qi, Yi Dong, Heng Xu
Summary: A synthetic protocol for the Cp*Co-III-catalyzed C-H amidation/annulation of 2-aryl-1H-imidazoles with 1,4,2-dioxazol-5-ones has been developed, affording imidazo[1,2-c]quinazoline derivatives with broad substrate scope and moderate to good yields. This method shows promising applications in the synthesis of imidazo[1,2-c]quinazoline drugs.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Sona Krajcovicova, Radek Jorda, David Vanda, Miroslav Soural, Vladimir Krystof
Summary: An efficient synthetic approach for trisubstituted imidazo [4,5-c]pyridines as BTK inhibitors was reported, with high tolerance of C6 substitutions observed. Cellular experiments indicated selective BTK targeting, suggesting the inhibitors could be potential options after ibrutinib failure.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Ida Bocek Pavlinac, Mirna Dragic, Leentje Persoons, Dirk Daelemans, Marijana Hranjec
Summary: A series of novel 2,6-diphenyl substituted imidazo[4,5-b]pyridines were synthesized and evaluated for their biological activity. Certain compounds showed strong antiproliferative activity against cancer cells, with a dose-dependent cell cycle-phase-specific mechanism of action. However, most of the tested compounds showed no antiviral activity.
Article
Chemistry, Organic
Ting Cui, Yanling Zhan, Changhui Dai, Jun Lin, Ping Liu, Peipei Sun
Summary: An electrochemical oxidative regioselective C-H cyanation of imidazo[1,2-a]pyridines was developed utilizing TMSCN as the cyano source, with the KH2PO4/K2HPO4 buffer being essential for the transformation. This protocol was compatible with a broad range of substituted imidazo[1,2-a]pyridines and provided the C3 cyanated products in moderate to excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Haiyan Liu, Zheng Li
Summary: This paper presents a method for the synthesis of benzo[4,5]imidazo[2,1-a]isoquinolines using calcium carbide as a solid alkyne source, 2-(2-bromophenyl)benzimidazoles as starting materials, and copper as a catalyst through Sonogashira cross-coupling/nucleophilic addition tandem reactions. The target products can also be synthesized through one-pot three-component reactions of o-phenylenediamines, o-bromobenzaldehydes, and calcium carbide, and both reaction routes can be scaled up to gram scale.
Article
Chemistry, Multidisciplinary
Vipin K. Pandey, Sangita Sahoo, Arnab Rit
Summary: AgSbF6 has been established as an effective catalyst for the hydroboration of diverse isocyanates, yielding selective N-boryl formamides or N-boryl methylamines under different conditions. Additionally, this catalyst system selectively hydroborates various N-heterocycles, with pyridine derivatives preferentially undergoing 1,4 hydroboration and quinolines observed to undergo complete heterocycle hydrogenation to form tetrahydroquinoline (after hydrolysis).
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Javeed Ahmad Tali, Ravi Shankar
Summary: Here, we report an unprecedented protocol using ruthenium-catalyzed annulation for the synthesis of 6H-chromeno[4 ',3 ':4,5]imidazo[1,2-a]pyridin-6-one, and a new method for intramolecular chelation-assisted C-H activation to produce functionalized 2-(3-formylimidazo[1,2-a]pyridin-2-yl)phenyl acetate. Furthermore, a one-pot approach using ruthenium catalysis and formic acid has been developed for the gram-scale synthesis of bis(2-phenylimidazo[1,2-a]pyridin-3yl)methane (BIP) and the late-stage functionalization of zolimidine, a marketed drug, with good yield.
Article
Chemistry, Organic
Xin Chen, Peng Sun, Baichuan Mo, Chunxia Chen, Jinsong Peng
Summary: An efficient synthesis of fused azapolycycles based on (benz)imidazole and pyridine scaffolds has been developed. These compounds show blue or green fluorescence with high quantum yields both in solution and solid states.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Linhua Wang, Xuesong Zheng, Qinze Zheng, Zhenlong Li, Jian Wu, Ge Gao
Summary: A Cu-catalyzed regioselective C5-H arylation of imidazo[1,5-a]pyridines with aryl iodides was achieved with the assistance of an ethylthio group at the C3 position. This directing group could be easily removed to produce a range of 5-(hetero)arylimidazo[1,5-a]pyridine derivatives. The reaction tolerates various functionalities and is compatible with sterically hindered substrates.
Article
Chemistry, Organic
Lucia Veltri, Roberta Amuso, Tommaso Prestia, Paola Vitale, Bartolo Gabriele
Summary: In this study, a direct and multicomponent approach to synthesize important fused-ring heterocycles was reported. The reaction employs readily available building blocks and shows high yields of the desired products under mild conditions. The reaction proceeds through a sequence of ordered steps.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Maofu Pang, Le-Le Shi, Yufang Xie, Tianyi Geng, Lan Liu, Rong-Zhen Liao, Chen-Ho Tung, Wenguang Wang
Summary: Selective transfer hydrogenation of pyridines to N-H 1,4-dihydropyridines has been achieved by cobalt-amido cooperative catalysis using H3NmiddotBH3 as a dihydrogen source. The reactions exhibit high chemo- and regioselectivity under mild conditions, providing a practical method to regenerate Hantzsch analogues after H2 delivery.
Article
Biochemistry & Molecular Biology
Clayton A. Whitmore, Mariam I. Boules, William J. Behof, Justin R. Haynes, Dmitry Koktysh, Adam J. Rosenberg, Mohammed N. Tantawy, Wellington Pham
Summary: This study reports the design and synthesis of a novel [C-11]promethazine PET radioligand for future in vivo studies, with high radiochemical purity and molar activity. The specificity of the probe was demonstrated through autoradiography using human hippocampal tissues.
Article
Multidisciplinary Sciences
William J. Behof, Clayton A. Whitmore, Justin R. Haynes, Adam J. Rosenberg, Mohammed N. Tantawy, Todd E. Peterson, Fiona E. Harrison, Robert B. Beelman, Wellington Pham
Summary: This study successfully demonstrated the biodistribution of ERGO in vivo using a [C-11]ERGO PET radioligand, showing significant accumulation in the brain, eyes, and small intestine of the mice. The radioligand also remained strong in the brain 30 minutes post-injection, marking the first preclinical demonstration of ERGO's biodistribution in a highly sensitive and non-invasive manner.
SCIENTIFIC REPORTS
(2021)
Article
Chemistry, Organic
Min Zhang, Jiqiang Gao, Jinbo Zhao, Tingtian Qiu, Zhongjuan Li, Ziteng Guo, Chunhui Liu, Yu Liu
Summary: An unprecedented Fe-catalyzed ring-opening reaction of simple cyclobutanones has been developed, allowing for the synthesis of conjugated enones with good functional group tolerance in high yields under mild conditions. Product derivatization and gram-scale experiments further demonstrated the synthetic utility of the reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Tengyun Chen, Yunkai Wu, Peilin Han, Jiqiang Gao, Yuanqi Wu, Jinbo Zhao, Haotian Liang, Yongsheng Liu, Yu Liu
Summary: We have developed a nickel catalyzed C-C bond reconstruction method using H2O as a hydrogen donor, which enables the conversion of o-bromophenylcyclobutanones into indanones and further synthesis of benzene-fused cyclic compounds.
HELVETICA CHIMICA ACTA
(2022)
Article
Chemistry, Organic
Jie Zhang, Peng Yan, Zhichao Wang, Jinbo Zhao, Qin Chen, Ping Lu
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Chao Hou, Yan Ma, Yongqi Zhang, Huiling Xu, Yuanqi Wu, Jinbo Zhao, Yuchao Wang, Yu Liu
Summary: In this paper, an efficient system based on inexpensive nickel catalyst and phosphine ligand for the cyclotrimerization of various internal esteryl alkynes is described. The regioselectivity of the protocol can be precisely controlled, providing a series of polysubstituted benzene rings mainly composed of 1,2,4-isomers.
HELVETICA CHIMICA ACTA
(2022)
Article
Biochemical Research Methods
Adam J. Rosenberg, Yiu-Yin Cheung, Fei Liu, Todd E. Peterson, James Silverman, Ciaran M. Considine, Daniel O. Claassen
Summary: In this study, a fully automated synthesis procedure for [F-18]MH.MZ radiotracer was developed using commercially available materials. The synthesis time was 100 min with a radiochemical yield of 7 +/- 0.9% (n = 3), and the radiochemical purity and molar activity met the relevant release criteria.
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS
(2022)
Article
Chemistry, Organic
Bowen Liu, Lei Wang, Yunfei Qin, Xianxiu Xu, Jinbo Zhao
Summary: In this study, a Lewis-base-catalyzed three-component electrophilic thiofunctionalization was developed for the synthesis of trisubstituted chromanes. This metal-free protocol offers high trans-diasteroselectivity and a unique substitution pattern, enabling access to the otherwise inaccessible chromane chemical space that is important for medicinal chemistry campaigns.
Article
Chemistry, Medicinal
Clayton A. Whitmore, Justin R. Haynes, William J. Behof, Adam J. Rosenberg, Mohammed N. Tantawy, Brian C. Hachey, Brian E. Wadzinski, Benjamin W. Spiller, Todd E. Peterson, Krista C. Paffenroth, Fiona E. Harrison, Robert B. Beelman, Printha Wijesinghe, Joanne A. Matsubara, Wellington Pham
Summary: The study assessed the effects of ERGO consumption on the progression of Alzheimer's disease in young 5XFAD mice. The results showed that ERGO could reduce amyloid plaques, oxidative stress, and restore glucose metabolism. The study also highlights the importance of imaging technology in evaluating treatment response.
Article
Chemistry, Organic
Xiao Yu, Zhihong Ma, Wenjing Zhu, Hongyan Liu, Zenghui Zhang, Yi Liu, Mei Zhang, Jinbo Zhao, Pengfei Zhang, Chengcai Xia
Summary: A novel route for the synthesis of derivatives of benzothiadiazine/1-(phenylsulfonyl)-1H-benzimidazole has been developed, utilizing a SnCl2-promoted tandem reduction, ammonolysis, condensation, and deamination reaction. The method offers convenient operation, good functional group tolerance, and employs unsensitive and inexpensive SnCl2/i-PrOH as the reaction reagent, providing a direct approach for the synthesis of pharmaceutically important targets.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Yi Liu, Wenjing Zhu, Xiao Yu, Hongyan Liu, Zenghui Zhang, Mei Zhang, Jinbo Zhao, Yacong Wang, Chengcai Xia
Summary: A method for synthesizing dihydropyrazoles has been developed, featuring mild reaction conditions and good functional group tolerance.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Na Li, Biqiong Hong, Jinbo Zhao, Zhenhua Gu
Summary: This study developed a practical method for the synthesis of phenanthridines through ring-expansion reaction, and successfully synthesized optically active planar chiral ferrocenyl phenanthridines.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Mei Zhang, Xiao Yu, Wenjing Zhu, Yi Liu, Zenghui Zhang, Jinbo Zhao, Chengcai Xia, Ke Li
Summary: A novel iron-catalyzed tandem sulfonylation, C(sp2)-H activation, cyclization reaction has been developed to synthesize derivatives of (Z)-2-phenyl-4-((phenylsulfonyl)methylene)-3,4-dihydro-2H-benzo[e][1,2]thiazine 1,1-dioxide using N-phenyl-N-(prop-2-yn-1-yl)benzenesulfonamide and benzenesulfonylhydrazide. This method offers convenient operation, good functional group tolerance, and utilizes inexpensive FeSO4 as the catalyst, providing a direct approach for the preparation of benzothiazides.
Article
Chemistry, Organic
Chuang Zhao, Ah-Ying Dong, Dongyan Ju, Jianhong Huang, Ran Jia, Yu Liu, Jinbo Zhao
Summary: This paper presents the Pd-catalyzed coupling cyclization of delta,epsilon-alkenyl oxime with (hetero)aryl and halides, which results in the synthesis of seven-membered N,O-heterocycles, tetrahydro-1,2-oxezapines, in moderate to good yields. DFT calculation supports an outer-sphere anti-oxypalladation pathway and provides important insights into the reaction mechanism. This reaction represents an unprecedented example of heterocyclization leading to the formation of a seven-membered ring.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Adam J. Rosenberg, Yiu-Yin Cheung, Fei Liu, Carina Sollert, Todd E. Peterson, Jonathan A. Kropski
Summary: The study presents a developed method to utilize liquid-target cyclotron-produced gallium-68 to prepare [Ga-68]Ga-FAPI-46. A fully-automated manufacturing process was developed, which successfully produced sufficient activity levels of [Ga-68]Ga-FAPI-46 for clinical research doses. The final product met all release criteria and the process consistently provided high radiochemical yield.
EJNMMI RADIOPHARMACY AND CHEMISTRY
(2023)
