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  1. Article ; Online: Palladium-catalyzed native α-amino acid derivative-directed arylation/oxidation of benzylic C-H bonds: synthesis of 5-aryl-1,4-benzodiazepin-2-ones.

    Jiang, Fengxuan / Xu, Menghua / Bei, Wenfeng / Cheng, Kai / Huang, Lehao

    Chemical communications (Cambridge, England)

    2022  Volume 58, Issue 69, Page(s) 9638–9641

    Abstract: A Pd-catalyzed, native α-amino acid derivative-directed benzylic C-H bond arylation/oxidation with aryl iodides was developed. The natural amino acid auxiliary could serve as a desired building block for formation of 5-aryl-1,4-benzodiazepin-2-ones after ...

    Abstract A Pd-catalyzed, native α-amino acid derivative-directed benzylic C-H bond arylation/oxidation with aryl iodides was developed. The natural amino acid auxiliary could serve as a desired building block for formation of 5-aryl-1,4-benzodiazepin-2-ones after removal of the trifluoroacetyl protecting group. The bifunctional reaction probably proceeded through a sequential benzylic arylation/oxidation process.
    MeSH term(s) Amino Acids/chemistry ; Benzodiazepines ; Catalysis ; Iodides/chemistry ; Molecular Structure ; Palladium/chemistry
    Chemical Substances Amino Acids ; Iodides ; Benzodiazepines (12794-10-4) ; Palladium (5TWQ1V240M)
    Language English
    Publishing date 2022-08-25
    Publishing country England
    Document type Journal Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/d2cc03266j
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Peroxiredoxin 1 of Procambarus clarkii govern immune responses during pathogen infection.

    Huang, Long / Liu, Yu / Zhang, Xinxin / Xu, Jie / Dai, Lu / Dai, Lishang / Huang, Lehao

    Fish & shellfish immunology

    2023  Volume 138, Page(s) 108828

    Abstract: Members of the peroxiredoxin family are involved in a wide variety of physiological processes, including the ability to combat the effects of oxidative stress and immune responses, among others. Here, we cloned the cDNA of Procambarus clarkii ... ...

    Abstract Members of the peroxiredoxin family are involved in a wide variety of physiological processes, including the ability to combat the effects of oxidative stress and immune responses, among others. Here, we cloned the cDNA of Procambarus clarkii Peroxiredoxin 1 (designated as PcPrx-1) and investigated its biological role in immune system functions in relation to microbial pathogens. The PcPrx-1 cDNA had 744 base pairs in an open reading frame that encoded 247 amino acid residues and contained a PRX_Typ2cys domain. The analysis of tissue specific expression patterns revealed that PcPrx-1 expression was ubiquitous in all tissues. In addition, the mRNA transcript of PcPrx-1 was found to be highest in the hepatopancreas. There was a significant upregulation of PcPrx-1 gene transcripts after exposure to LPS, PGN, and Poly I:C, but the transcription patterns were different after pathogen challenge. Double-stranded RNA was used to knockdown PcPrx-1, which resulted in a striking change in the expression of all the tested P. clarkii immune-associated genes, including lectin, Toll, cactus, chitinase, phospholipase, and sptzale. On the whole, these results suggest that PcPrx-1 is important to confer innate immunity against pathogens by governing the expression of critical transcripts that encode immune-associated genes.
    MeSH term(s) Animals ; Peroxiredoxins ; Astacoidea/genetics ; DNA, Complementary/genetics ; Immunity, Innate/genetics ; Oxidative Stress ; Arthropod Proteins
    Chemical Substances Peroxiredoxins (EC 1.11.1.15) ; DNA, Complementary ; Arthropod Proteins
    Language English
    Publishing date 2023-05-16
    Publishing country England
    Document type Journal Article
    ZDB-ID 1067738-0
    ISSN 1095-9947 ; 1050-4648
    ISSN (online) 1095-9947
    ISSN 1050-4648
    DOI 10.1016/j.fsi.2023.108828
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article: Palladium-catalyzed native α-amino acid derivative-directed arylation/oxidation of benzylic C–H bonds: synthesis of 5-aryl-1,4-benzodiazepin-2-ones

    Jiang, Fengxuan / Xu, Menghua / Bei, Wenfeng / Cheng, Kai / Huang, Lehao

    Chemical communications. 2022 Aug. 25, v. 58, no. 69

    2022  

    Abstract: A Pd-catalyzed, native α-amino acid derivative-directed benzylic C–H bond arylation/oxidation with aryl iodides was developed. The natural amino acid auxiliary could serve as a desired building block for formation of 5-aryl-1,4-benzodiazepin-2-ones after ...

    Abstract A Pd-catalyzed, native α-amino acid derivative-directed benzylic C–H bond arylation/oxidation with aryl iodides was developed. The natural amino acid auxiliary could serve as a desired building block for formation of 5-aryl-1,4-benzodiazepin-2-ones after removal of the trifluoroacetyl protecting group. The bifunctional reaction probably proceeded through a sequential benzylic arylation/oxidation process.
    Keywords amino acids ; arylation ; oxidation
    Language English
    Dates of publication 2022-0825
    Size p. 9638-9641.
    Publishing place The Royal Society of Chemistry
    Document type Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/d2cc03266j
    Database NAL-Catalogue (AGRICOLA)

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  4. Article ; Online: Curcumin-Piperlongumine Hybrid Molecule Increases Cell Cycle Arrest and Apoptosis in Lung Cancer through JNK/c-Jun Signaling Pathway.

    Zhang, Qianwen / Hui, Min / Chen, Guo / Huang, Huijing / Wang, Shiyu / Ye, Yanfei / Wang, Yan / Wang, Mengying / Zhang, Shuyuan / Huang, Lehao / Zhang, Fangjun / Liu, Zhiguo

    Journal of agricultural and food chemistry

    2024  Volume 72, Issue 13, Page(s) 7244–7255

    Abstract: The instability of curcumin's structure and the toxic side effects of piperlongumine have limited their potential applications in cancer treatment. To overcome these challenges, we designed and synthesized a novel curcumin-piperlongumine hybrid molecule, ...

    Abstract The instability of curcumin's structure and the toxic side effects of piperlongumine have limited their potential applications in cancer treatment. To overcome these challenges, we designed and synthesized a novel curcumin-piperlongumine hybrid molecule, 3-[(
    MeSH term(s) Humans ; Curcumin/pharmacology ; Lung Neoplasms/drug therapy ; Lung Neoplasms/genetics ; Cell Line, Tumor ; Cell Cycle Checkpoints ; Apoptosis ; Cell Proliferation ; MAP Kinase Signaling System ; Cell Cycle ; Benzodioxoles
    Chemical Substances Curcumin (IT942ZTH98) ; piperlonguminine (HN39MC8KIO) ; Benzodioxoles
    Language English
    Publishing date 2024-03-22
    Publishing country United States
    Document type Journal Article
    ZDB-ID 241619-0
    ISSN 1520-5118 ; 0021-8561
    ISSN (online) 1520-5118
    ISSN 0021-8561
    DOI 10.1021/acs.jafc.4c00882
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Discovery of a selective TRF2 inhibitor FKB04 induced telomere shortening and senescence in liver cancer cells.

    Qiu, Yin-da / Yan, Qi / Wang, Yi / Ye, Yan-Fei / Wang, Yan / Wang, Meng-Ying / Wang, Pei-Pei / Zhang, Shu-Yuan / Wang, Da-Long / Yan, Hao / Ruan, Jing / Zhao, Yun-Jie / Huang, Le-Hao / Cho, Namki / Wang, Kun / Zheng, Xiao-Hui / Liu, Zhi-Guo

    Acta pharmacologica Sinica

    2024  

    Abstract: Telomere repeat binding factor 2 (TRF2), a critical element of the shelterin complex, plays a vital role in the maintenance of genome integrity. TRF2 overexpression is found in a wide range of malignant cancers, whereas its down-regulation could cause ... ...

    Abstract Telomere repeat binding factor 2 (TRF2), a critical element of the shelterin complex, plays a vital role in the maintenance of genome integrity. TRF2 overexpression is found in a wide range of malignant cancers, whereas its down-regulation could cause cell death. Despite its potential role, the selectively small-molecule inhibitors of TRF2 and its therapeutic effects on liver cancer remain largely unknown. Our clinical data combined with bioinformatic analysis demonstrated that TRF2 is overexpressed in liver cancer and that high expression is associated with poor prognosis. Flavokavain B derivative FKB04 potently inhibited TRF2 expression in liver cancer cells while having limited effects on the other five shelterin subunits. Moreover, FKB04 treatment induced telomere shortening and increased the amounts of telomere-free ends, leading to the destruction of T-loop structure. Consequently, FKB04 promoted liver cancer cell senescence without modulating apoptosis levels. In corroboration with these findings, FKB04 inhibited tumor cell growth by promoting telomeric TRF2 deficiency-induced telomere shortening in a mouse xenograft tumor model, with no obvious side effects. These results demonstrate that TRF2 is a potential therapeutic target for liver cancer and suggest that FKB04 may be a selective small-molecule inhibitor of TRF2, showing promise in the treatment of liver cancer.
    Language English
    Publishing date 2024-03-04
    Publishing country United States
    Document type Journal Article
    ZDB-ID 1360774-1
    ISSN 1745-7254 ; 0253-9756 ; 1671-4083
    ISSN (online) 1745-7254
    ISSN 0253-9756 ; 1671-4083
    DOI 10.1038/s41401-024-01243-6
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article ; Online: Oxidative Aminoarylselenation of Maleimides via Copper-Catalyzed Four-Component Cross-Coupling.

    Gao, Xue / Tang, Liyang / Huang, Lehao / Huang, Zu-Sheng / Ma, Yunfei / Wu, Ge

    Organic letters

    2019  Volume 21, Issue 3, Page(s) 745–748

    Abstract: The first example of copper-catalyzed four-component coupling reaction of aryl iodides, Se powder, secondary amines, and maleimides is developed. This reaction provides an efficient and concise route to access aminoarylselenated maleimides via double C- ... ...

    Abstract The first example of copper-catalyzed four-component coupling reaction of aryl iodides, Se powder, secondary amines, and maleimides is developed. This reaction provides an efficient and concise route to access aminoarylselenated maleimides via double C-Se bonds and C-N bond formation. The appealing features of this transformation are the use of Se powder as a selenating reagent, a green catalytic system, a wide range of substrate scope, and late-stage selenation of bioactive compounds.
    Language English
    Publishing date 2019-01-14
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.8b03980
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  7. Article ; Online: cyy-287, a novel pyrimidine-2,4-diamine derivative, inhibits tumor growth of EGFR-driven non-small cell lung cancer via the ERK pathway.

    Zhang, Qianwen / Huang, Huijing / Zheng, Shuwen / Tang, Yelin / Zhang, Xiaodan / Zhu, Qianqian / Ni, Zefeng / Zheng, Xiaohui / Wang, Kun / Huang, Lehao / Zhao, Yunjie / Liu, Zhiguo / Qian, Jianchang

    Acta biochimica et biophysica Sinica

    2022  Volume 54, Issue 10, Page(s) 1540–1551

    Abstract: In recent decades, EGFR-targeted tyrosine kinase inhibitors (TKIs) have been proven to be an effective therapy for EGFR-mutant non-small cell lung cancer (NSCLC). However, resistance to EGFR-TKIs limits their clinical application. In the present study, ... ...

    Abstract In recent decades, EGFR-targeted tyrosine kinase inhibitors (TKIs) have been proven to be an effective therapy for EGFR-mutant non-small cell lung cancer (NSCLC). However, resistance to EGFR-TKIs limits their clinical application. In the present study, we investigate the antitumor effect and underlying mechanism of a novel pyrimidine-2,4-diamine derivative, cyy-287, in NSCLC. We find that cyy-287 has a high affinity for lung tissue and inhibits the proliferation of NSCLC cells. Interestingly, the significant suppression of migration and induction of apoptosis by cyy-287 are only observed in EGFR-driven but not in EGFR-wild-type (wt) cells. According to the RNA sequencing and KEGG enrichment analysis results, cyy-287 markedly inhibits the MAPK pathway in EGFR-driven PC9 cells, and western blot analysis results further indicate that cyy-287 selectively blocks the ERK pathway in EGFR-driven cells. Meanwhile, apoptosis induced by cyy-287 could be partially reversed by ERK pathway inhibition. Further experiment indicates that cyy-287 inhibits the EGFR pathway in both EGFR-driven and EGFR-overexpressing cells. Interestingly, it only induces apoptosis in EGFR-driven cells, not in EGFR-overexpressing cells. The growth of EGFR-driven cells is suppressed by cyy-287
    MeSH term(s) Humans ; Carcinoma, Non-Small-Cell Lung/drug therapy ; Carcinoma, Non-Small-Cell Lung/genetics ; Carcinoma, Non-Small-Cell Lung/pathology ; Lung Neoplasms/genetics ; MAP Kinase Signaling System ; ErbB Receptors ; Signal Transduction ; Protein Kinase Inhibitors/pharmacology ; Protein Kinase Inhibitors/therapeutic use ; Cell Line, Tumor ; Pyrimidines/pharmacology ; Drug Resistance, Neoplasm ; Cell Proliferation ; Apoptosis
    Chemical Substances ErbB Receptors (EC 2.7.10.1) ; Protein Kinase Inhibitors ; Pyrimidines ; EGFR protein, human (EC 2.7.10.1)
    Language English
    Publishing date 2022-09-27
    Publishing country China
    Document type Journal Article
    ZDB-ID 2175256-4
    ISSN 1745-7270 ; 0582-9879 ; 1672-9145
    ISSN (online) 1745-7270
    ISSN 0582-9879 ; 1672-9145
    DOI 10.3724/abbs.2022139
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  8. Article ; Online: cyy260 suppresses the proliferation, migration and tumor growth of osteosarcoma by targeting PDGFR-β signaling pathway.

    Qiu, Yinda / Yan, Hao / Zheng, Ruiling / Chen, Xiaojing / Wang, Yi / Yan, Qi / Ye, Yanfei / Zhang, Jianxia / Han, Haoyi / Wang, Kun / Zhao, Yunjie / Huang, Lehao / Li, Xiaokun / Liu, Zhiguo

    Chemico-biological interactions

    2022  Volume 367, Page(s) 110200

    Abstract: Osteosarcoma (OS) is a group of malignant tumors with high rates of malignancy and metastasis. OS most commonly affects adolescents and young individuals. However, owing to the lack of effective targeted treatments, the 5-year survival rate for OS is ... ...

    Abstract Osteosarcoma (OS) is a group of malignant tumors with high rates of malignancy and metastasis. OS most commonly affects adolescents and young individuals. However, owing to the lack of effective targeted treatments, the 5-year survival rate for OS is still around 20%. Thus, it is essential to develop effective drugs with low toxicity for OS treatment. In the present study, we investigated the antitumor effect and underlying mechanism of cyy260 in OS via suppressing PDGFR-β and its downstream pathway. We demonstrated that cyy260 inhibits OS cell proliferation and promotes apoptosis via inducing DNA damage and causing cell cycle arrest. More importantly, cyy260 also significantly inhibits tumor migration. Further analysis of molecular mechanisms confirmed that PDGFR-β and its downstream AKT, STAT3, and ERK were involved in the cyy260-mediated antitumor effect. Analysis of subcutaneously transplanted tumors in mice showed that cyy260 suppressed tumor cell growth and exhibited low toxicity in vivo. Collectively, these findings proved that cyy260 could serve as a promising PDGFR-β inhibitor for the treatment of OS.
    MeSH term(s) Animals ; Apoptosis ; Bone Neoplasms/metabolism ; Cell Line, Tumor ; Cell Movement ; Cell Proliferation ; Mice ; Osteosarcoma/metabolism ; Protein Kinase Inhibitors/pharmacology ; Proto-Oncogene Proteins c-akt/metabolism ; Signal Transduction
    Chemical Substances Protein Kinase Inhibitors ; Proto-Oncogene Proteins c-akt (EC 2.7.11.1)
    Language English
    Publishing date 2022-09-25
    Publishing country Ireland
    Document type Journal Article
    ZDB-ID 218799-1
    ISSN 1872-7786 ; 0009-2797
    ISSN (online) 1872-7786
    ISSN 0009-2797
    DOI 10.1016/j.cbi.2022.110200
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  9. Article: Palladium-Catalyzed C8 Alkylation of 1-Naphthylamides with Alkyl Halides via Bidentate-Chelation Assistance

    Huang, Lehao / Li Qian / Qi Chenze / Sun Xudong

    Journal of organic chemistry. 2014 July 18, v. 79, no. 14

    2014  

    Abstract: A Pd-catalyzed regioselective alkylation of C8–H bonds in 1-naphthylamides containing a quinolinamide or picolinamide moiety as a bidentate directing group with alkyl halides is reported. The amide directing group can be easily hydrolyzed under basic ... ...

    Abstract A Pd-catalyzed regioselective alkylation of C8–H bonds in 1-naphthylamides containing a quinolinamide or picolinamide moiety as a bidentate directing group with alkyl halides is reported. The amide directing group can be easily hydrolyzed under basic conditions. Various alkyl halides including alkyl iodides and benzyl bromide or chloride can be employed as coupling partners, exclusively providing 8-alkyl-1-naphthylamide derivatives.
    Keywords alkylation ; bromides ; catalytic activity ; chlorides ; iodides ; moieties ; organic chemistry ; palladium ; regioselectivity
    Language English
    Dates of publication 2014-0718
    Size p. 6720-6725.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021%2Fjo500932x
    Database NAL-Catalogue (AGRICOLA)

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  10. Article ; Online: Palladium-catalyzed C8 alkylation of 1-naphthylamides with alkyl halides via bidentate-chelation assistance.

    Huang, Lehao / Sun, Xudong / Li, Qian / Qi, Chenze

    The Journal of organic chemistry

    2014  Volume 79, Issue 14, Page(s) 6720–6725

    Abstract: A Pd-catalyzed regioselective alkylation of C8-H bonds in 1-naphthylamides containing a quinolinamide or picolinamide moiety as a bidentate directing group with alkyl halides is reported. The amide directing group can be easily hydrolyzed under basic ... ...

    Abstract A Pd-catalyzed regioselective alkylation of C8-H bonds in 1-naphthylamides containing a quinolinamide or picolinamide moiety as a bidentate directing group with alkyl halides is reported. The amide directing group can be easily hydrolyzed under basic conditions. Various alkyl halides including alkyl iodides and benzyl bromide or chloride can be employed as coupling partners, exclusively providing 8-alkyl-1-naphthylamide derivatives.
    MeSH term(s) Alkylation ; Amides/chemistry ; Catalysis ; Chelating Agents/chemistry ; Hydrocarbons, Halogenated/chemistry ; Molecular Conformation ; Naphthalenes/chemistry ; Organometallic Compounds/chemistry ; Palladium/chemistry
    Chemical Substances Amides ; Chelating Agents ; Hydrocarbons, Halogenated ; Naphthalenes ; Organometallic Compounds ; 2-naphthylamide (2243-82-5) ; Palladium (5TWQ1V240M)
    Language English
    Publishing date 2014-07-18
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/jo500932x
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