Article
Chemistry, Organic
Xian Feng, Jianjun Wang, Dexiu Liu, Hui Shi, Wenjing Lu, Daqing Shi
Summary: A novel three-component reaction was developed for the flexible and practical synthesis of pyrazolo-[3,4-b]-pyrrolo-[3,4-d]-pyridine derivatives from phenylglyoxal, beta-ketoamide, and 5-aminopyrazole using acetic acid as the solvent. Various dihydropyrazolo-[3,4-b]-pyrrolo-[3,4-d]-pyridin-6-(3H)-one compounds were obtained with moderate to good yields and broad functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Lu Wang, Yin Zhang, An-Qi Miao, Tian-Shu Zhang, Xiang Wang, Wen-Juan Hao, Shu-Jiang Tu, Bo Jiang
Summary: A novel metal-free nitrative bicyclization reaction of 1,7-diynes with (BuONO)-Bu-t in the presence of H2O is reported, which produces three skeletally diverse tricyclic pyrroles by tuning the linkers of the 1,7-diynes. This domino protocol shows remarkable compatibility regarding 1,7-diynes with different linkers.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Inorganic & Nuclear
Zeyu Li, Ying Liu, Yiping Zhang, Wenwen Duan, Yifan Wang, Min Zhang, Hongmei Deng, Liping Song
Summary: A series of poly-heterocycles containing hemi-aminal moieties were efficiently synthesized using different reactions, and their structures were confirmed by various methods.
JOURNAL OF FLUORINE CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
F. H. Mahmoud Naglaa, Sameh A. Rizk, A. Elsayed Galal, Ali Kh Ali
Summary: A rapid and efficient microwave-promoted one-pot strategy was utilized to synthesize differentially functionalized spiro[indoline-3,4'-pyrazolo[3,4-b] pyridine derivatives. The catalyst-free microwave-assisted fusion process has been proved to be the strategy with desirable traits to give good-to-excellent yields of the target compounds. The obtained compounds were characterized by elemental analyses, mass, H-1-NMR, and C-13-NMR spectrometry.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Medicinal
Areum Park, Jieon Hwang, Joo-Youn Lee, Eun Ji Heo, Yoon-Ju Na, Sein Kang, Kyu-Sung Jeong, Ki Young Kim, Sang Joon Shin, Hyuk Lee
Summary: In this study, 1H-pyrazolo[3,4-b]pyridine derivatives were synthesized as DYRK1A and 1B inhibitors, among which compound 8h showed excellent inhibitory activity towards colon cancer cells and bound to DYRK1B through various interactions. The compound also exhibited strong inhibitory activities in patient-derived colon cancer organoids model and 3D spheroid assay model of SW480 and SW620.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Medicinal
Shihe Hu, Cuihua Jiang, Meng Gao, Dongjian Zhang, Nan Yao, Jian Zhang, Qiaomei Jin
Summary: A series of pyrazolo[3,4-b]pyridine-based compounds were investigated as new Mps1 inhibitors through virtual screening, chemical synthesis, and biological evaluation. The representative compound, 31, showed strong inhibitory potency against Mps1 and significantly inhibited the proliferation of cancer cells, especially MDA-MB-468 and MV4-11 cells. Compound 31 also exhibited reasonable kinome selectivity and promising pharmacokinetic and pharmacodynamic profiles. Furthermore, it displayed good antitumor efficacy in a xenograft model without obvious toxicity. Compound 31 is identified as a potential Mps1 inhibitor for cancer therapy and warrants further research.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Joana L. S. Ribeiro, Julio C. A. Soares, Gisele B. Portapilla, Maiara Providello, Camilo H. S. Lima, Estela M. F. Muri, Sergio de Albuquerque, Luiza R. S. Dias
Summary: The study revealed that two new synthesized compounds containing 1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine showed promising in vitro activity against T. cruzi and are more suitable for in vivo activity.
BIOORGANIC & MEDICINAL CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Nian Liu, Xin Wang, Qinglin Fu, Qiaohua Qin, Tianxiao Wu, Ruicheng Lv, Dongmei Zhao, Maosheng Cheng
Summary: In this study, 38 pyrazolo[3,4-b]pyridine derivatives were synthesized based on scaffold hopping and computer-aided drug design. The activities of these derivatives in inhibiting TRKA were evaluated, and compound C03 showed promising activity with good selectivity and plasma stability, making it a potential candidate for further exploration.
RSC MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Yating Guo, Xiaoding Jiang, Qi Chang, Zhihong Xiao, Zhuo Chen, Dejian Jiang, Gaoyun Hu, Qianbin Li
Summary: A series of novel pyrazolo[3,4-b]pyridine derivatives were synthesized and evaluated for their anti-lung cancer activity. Compound 9d showed improved potency for A549 cell growth inhibition, and it induced G2/M cell cycle arrest by regulating the AMPK/70S6K pathway. This study provides a new lead for the discovery of anti-lung cancer agents.
ARCHIV DER PHARMAZIE
(2022)
Article
Chemistry, Organic
Ahmed A. O. Abeed, Talaat I. El-Emary, Mohamed S. K. Youssef, Ibrahim Hefzy, Ahmed M. A. Ibrahim
Summary: A precursor was utilized to synthesize various heterocyclic compounds, which were then tested for larvicidal activity against mosquito larvae. Five of these compounds exhibited significant insecticidal activity, and some compounds were found to inhibit digestive enzymes in the larvae. These findings suggest the potential importance of these synthesized compounds in enhancing agricultural productivity and managing diseases transmitted by insects.
CURRENT ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Eman M. Othman, Amany A. Bekhit, Mohamed A. Anany, Thomas Dandekar, Hanan M. Ragab, Ahmed Wahid
Summary: The study synthesized new purine bioisosteres with high cytotoxic activity against cancer cell lines, showing potential anticancer effects by inhibiting cancer cell proliferation.
Article
Chemistry, Multidisciplinary
Hai Truong Nguyen, Phu Hoang Dang, Phuong Hoang Tran
Summary: Among various catalysts, amorphous carbon-supported sulfonic acid (AC-SO3H) has emerged as a highly efficient solid catalyst due to its superior catalytic activity. The presence of -SO3H groups improves the surface properties of the carbon catalyst, making its activity much higher than that of sulfuric acid. AC-SO3H exhibits advantages such as low cost, non-toxicity, porosity, stability, and adjustable chemical surface. In this study, we introduce a new method for synthesizing pyrazolo[3,4-b]pyridine-5-carboxylate scaffolds using AC-SO3H as the catalyst in ethanol at room temperature. The reaction proceeds with good yields and involves a sequential opening/closing cascade reaction, offering advantages of room temperature conditions, short reaction time, and operational simplicity.
Article
Biochemistry & Molecular Biology
Xiao-Yu Miao, Yong-Ji Hu, Fu-Rao Liu, Yuan-Yuan Sun, Die Sun, An-Xin Wu, Yan-Ping Zhu
Summary: A cascade 6-endo-dig cyclization reaction has been developed for the switchable synthesis of halogen and non-halogen-functionalized pyrazolo[3,4-b]pyridines. This reaction demonstrated wide substrate scope, good functional group tolerance, and excellent regional selectivity.
Article
Biochemistry & Molecular Biology
Amena Ali, Magda H. Abdellattif, Abuzer Ali, Ola AbuAli, Mohd Shahbaaz, Mohamed Jawed Ahsan, Mostafa A. Hussien
Summary: Various computational techniques were used to identify potent compounds against TRAP1 kinase, leading to the development of a statistically significant QSAR model. Molecular docking and MD simulations validated the results, while virtual screening identified potential compounds with similar binding interactions. ADME analysis also highlighted the potential value of the study.
Article
Chemistry, Multidisciplinary
A. Smolobochkin, A. S. Gazizov, A. R. Garifzyanov, A. R. Burilov, M. A. Pudovik
Summary: This review covers comprehensive data on synthetic strategies and approaches to 1H-pyrazolo[3,4-b]pyridine derivatives reported from 2017 to 2021, categorizing the synthesis methods based on the assembly of the pyrazolopyridine system and discussing their advantages and drawbacks.
RUSSIAN CHEMICAL BULLETIN
(2022)
Article
Chemistry, Multidisciplinary
Meng-Fan Li, Shao-Qing Shi, Ting Xu, Qian Zhang, Wen-Juan Hao, Shu-Liang Wang, Jianyi Wang, Shu-Jiang Tu, Bo Jiang
Summary: A new method for the synthesis of tricyclic bridged-fused benzo[d]azepines has been developed through an organocatalytic double annulation cascade. The reaction involves the scission/recombination of N-O bonds of nitrones and has demonstrated moderate to good yields and complete diastereoselectivity. Density functional theory calculations were used to gain insight into the formation of diradical intermediates.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Organic
Jia-Yin Wang, Guigen Li, Wen-Juan Hao, Bo Jiang
Summary: In this study, two catalytic benzannulation/1,4-addition cascades of available enynones with indoles or tetronic acid-derived enamino lac tones as C-nucleophiles were reported, resulting in the synthesis of heterocycle-incorporating diarylmethanes. The reactions exhibited high atom utilization and mild reaction conditions, providing complementary approaches for the direct synthesis of new heterocycle-containing diarylmethanes.
Article
Chemistry, Organic
Tian-Shu Zhang, Si-Qing Song, Meng-Jiao Qi, Wen-Juan Hao, Bo Jiang
Summary: A concise photocatalytic strategy was developed for the synthesis of 1-indanones containing vinyl ether and CF3 groups from trifluoromathanesulfonyl chloride, low-cost alcohols, and easily available 1,6-enynes. The protocol enables trifluoromethylation/5-exo-dig-cyclization/etherification cascade in one-pot operation with moderate to good yields. It offers the advantages of constructing two C-C and one C-O bonds without the use of any oxidant.
TETRAHEDRON LETTERS
(2023)
Review
Chemistry, Organic
Tian-Shu Zhang, Shuai Liu, Wen-Juan Hao, Bo Jiang
Summary: ortho-Alkynyl aryl ketones have been widely used in organic synthesis in the past decade due to their high reactivity and structural diversity. Four common intramolecular annulative patterns based on Baldwin's rule, including oxo-cyclization and carbocyclization, have been employed with the help of various catalysts or photocatalysis. With recent developments, ortho-alkynyl aryl ketones have become important building blocks for the construction of various scaffolds. This review provides an overview of the chemistry, reactivities, mechanisms, and applications of ortho-alkynyl aryl ketones.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Applied
Lu Wang, Yi-Ting Shen, Yu-Xin Wang, Hai-Ying Wang, Wen-Juan Hao, Bo Jiang
Summary: A metal-free radical multicomponent bicyclization of heteroatom-linked 1,7-diynes with aryl diazonium tetrafluoroborates and DABCO-bis(sulfurdioxide) (DABSO) is reported, enabling the production of two types of skeletally diverse tricyclic sulfones, namely, thieno[3,4-c]quinoline 2,2-dioxides and thieno[3,4-c]chromene 2,2-dioxides, with moderate to good yields by simply tuning the linkers of the 1,7-diynes. This protocol demonstrates remarkable compatibility regarding N- and O-linked 1,7-diynes with different substitution patterns and aryl diazonium tetrafluoroborates.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Ling-Qi Chen, Chi-Fan Zhu, Su Zhang, Bao-Yang Liu, Shu-Jiang Tu, Wen-Juan Hao, Bo Jiang
Summary: A new palladium-catalyzed annulative allylic alkylation reaction has been developed for the regioselective synthesis of tetracyclic cyclic ethers with bridged aryl-indole scaffolds.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Organic
Zi-Xuan Ma, Shi-Chao Wang, Xin-Yu Gu, Shu-Liang Wang, Wen-Juan Hao, Bo Jiang
Summary: A concise and operationally simple photocatalysis strategy for the annulative cyanoalkyletherification of 1,6-enynes with cyclic oxime esters and alcohols is reported, producing a set of functionalized 1-indanones bearing an all-carbon quaternary center with generally good yields. In this process, single electron reduction of cyclic oxime esters drives deconstructive carbon-carbon s-bond cleavage to yield a key cyanopropyl radical poised for addition-cyclization. This reaction is redox-neutral and demonstrates good functional group compatibility and a wide substrate scope, in which diversified alcohols can be engaged in the annulation reaction to prepare exocyclic vinyl ethers.
Article
Chemistry, Applied
Yin Zhang, An-Qi Bao, Ming Wu, Qian Rao, Man-Su Tu, Wen-Juan Hao, Bo Jiang
Summary: A Bronsted acid-catalyzed dearomative skeletal rearrangement of azofurans with indoles is reported, which enables the regioselective synthesis of indolylated pyrrol-2-ones with a cyclic tetrasubstituted stereocenter. The reaction shows remarkable compatibility and complete regioselectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Tian-Shu Zhang, Jing Li, Hua Sun, Shuai Liu, Jing Li, Yan Chen, Wen-Juan Hao, Bo Jiang
Summary: An efficient synthetic approach for the synthesis of cyclopentenones containing a C-C stereocenter using gold(I)-catalyzed Nazarov-type cyclization/1,6-addition of 1,3-enyne esters with p-quinone methides (p-QMs) is described. This tandem transformation showed satisfactory substrate scope and acceptable functional group compatibility, providing a novel protocol for the rapid assembly of cyclopentenones in good to excellent yields under mild reaction conditions.
Article
Chemistry, Physical
Qian Rao, Yan Zhang, Xin-Yu Gu, Yin-Ping Liu, Bo Jiang, Wen-Juan Hao
Summary: This paper reports a new gold self-relay catalysis method, enabling intramolecular annulation and intermolecular Michael addition of 3-yne-1,2-diols with aurone-derived azadienes (or para-quinone methides), efficiently producing a range of unsymmetrical furanized triarylmethanes with substituent diversity in good yields. The overall process is governed by the & pi;- and & sigma;-Lewis acid capability of gold complexes, providing a catalytic strategy for constructing triarylmethane skeletons.
Article
Chemistry, Organic
Dong-Fang Jiang, Zhenjie Qi, Dengfeng Li, Si-Miaomiao Wen, Zhao Liu, Wen-Juan Hao, Bo Jiang
Summary: This study presents a metal-free protocol for the direct construction of C(sp(2))-N and C-O bonds via a PhI(OAc)(2)-mediated dehydrogenative aminoacyloxylation of β,γ-unsaturated hydrazones with Togni reagent II. The reaction is initiated by the carboxyl-containing species generated in situ from Togni reagent II, offering a new solution for regioselective functionalization at a remote site on β,γ-unsaturated hydrazones and providing a straightforward method for the synthesis of acyloxyl-substituted pyridazines. The reaction exhibits a broad substrate scope and can be carried out under mild conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Qian Rao, Yin Zhang, Yin-Ping Liu, Bo Jiang, Xiang Wang, Shu-Jiang Tu, Wen-Juan Hao
Summary: A novel gold(i)/Bronsted acid relay catalysis enables the annulative rearrangement of 3-yne-1,2-diols and aryldiazonium tetrafluoroborates, resulting in furan-2-yl-substituted pyrrol-2-ones with a quaternary carbon center in good yields. By using azofuran as a substitute for aryldiazonium tetrafluoroborate, similar furan-2-yl-containing pyrrol-2-ones with diverse substituents can be obtained, indicating the crucial role of azofuran activation and annulative rearrangement by gold/Bronsted acid relay catalysis.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Qian Rao, Yin Zhang, Yin-Ping Liu, Bo Jiang, Xiang Wang, Tu Shu-Jiang, Wen-Juan Hao
Summary: A novel gold(I)/Bronsted acid relay catalysis enables the activation of azofuran and induces annulative rearrangement from 3-yne-1,2-diols and aryldiazonium tetrafluoroborates, resulting in the formation of furan-2-yl-substituted pyrrol-2-ones bearing a quaternary carbon center with good yields. Substituting aryldiazonium tetrafluoroborate with azofuran yields structurally identical but substituent-diverse furan-2-yl-containing pyrrol-2-ones with good yields, providing support for the crucial role of azofuran activation and annulative rearrangement by gold/Bronsted acid relay catalysis.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Meng-Ying Hao, Yin Zhang, Na Lin, Rong Fu, Xiao-Shuang Ji, Bo Jiang, Shu-Jiang Tu, Wen-Juan Hao
Summary: A new gold(i) self-relay catalysis reaction has been reported, which enables the annulative oxygenation of propargylic alcohols with various O-nucleophiles, producing functionalized benzofurans in moderate to good yields under mild conditions. This protocol boasts the pi- and sigma-Lewis acid capability of gold complexes, showcasing high molecular convergence, broad substrate flexibility, high functional group compatibility, and mild conditions.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Peng Zhou, Wei-Tao Yang, Wen-Juan Hao, Bo Jiang
Summary: A copper-(II)/DBU relay catalyzed annulation of alpha-carbonyl-gamma-alkynyl sulfoxonium ylides with sulfonyl hydrazides is reported, resulting in the formation of a series of N-sulfonamido 2H-isoindoles. The reaction combines the Cu-(II)-catalyzed oxo-cyclization with the DBU-catalyzed skeletal rearrangement, leading to the formation of multiple new chemical bonds.
