- Synthesis of diverse 3-azido-5-(azidomethyl)benzene derivatives via formal C-H azidation and functional group-selective transformations
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3-Azido-5-(azidomethyl)benzene derivatives are useful compounds for preparing diverse bistriazole compounds and photoaffinity probes for target identification of bioactive compounds. To more easily synthesize a diverse range of diazido compounds, a facile
- Nishiyama, Yoshitake,Misawa, Yoshihiro,Hazama, Yuki,Oya, Kazuhiro,Yoshida, Suguru,Hosoya, Takamitsu
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p. 1053 - 1072
(2019/07/31)
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- Chemoselective Organoclick-Click Sequence
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A highly chemoselective bis-triazole synthesis based on a sequence organocatalyzed click reaction/copper-catalyzed click reaction is described in this paper. A range of bis-azides react with various ketones using proline catalysis through the aryl azide moiety while the alkyl azide one remains available for a metal-catalyzed triazole synthesis.
- Belkheira, Mokhtaria,El Abed, Douniazad,Pons, Jean-Marc,Bressy, Cyril
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p. 4254 - 4262
(2018/11/23)
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- Novel leucine ureido derivatives as aminopeptidase N inhibitors using click chemistry
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The over-expression of aminopeptidase N on diverse malignant cells is associated with the tumor angiogenesis and metastasis. In this report, one new series of leucine ureido derivatives containing the triazole moiety was designed, synthesized and evaluated as APN inhibitors. Among them, compound 13v showed the best APN inhibition with an IC50 value of 0.089 ± 0.007 μM, which was two orders of magnitude lower than that of bestatin (IC50 = 9.4 ± 0.5 μM). Compound 13v also showed dose-dependent anti-angiogenesis activities. Even at the lower concentration (10 μM), compound 13v presented similar anti-angiogenesis activity compared with bestatin at 100 μM in both the human umbilical vein endothelial cells (HUVECs) capillary tube formation assay and the rat thoracic aorta rings test. Moreover, compared with bestatin, 13v exhibited comparable, if not better in vivo anti-metastasis activity in a mouse H22 pulmonary metastasis model.
- Cao, Jiangying,Ma, Chunhua,Zang, Jie,Gao, Shuai,Gao, Qianwen,Kong, Xiujie,Yan, Yugang,Liang, Xuewu,Ding, Qin'ge,Zhao, Chunlong,Wang, Binghe,Xu, Wenfang,Zhang, Yingjie
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p. 3145 - 3157
(2018/06/01)
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- Steering Siglec–Sialic Acid Interactions on Living Cells using Bioorthogonal Chemistry
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Sialic acid sugars that terminate cell-surface glycans form the ligands for the sialic acid binding immunoglobulin-like lectin (Siglec) family, which are immunomodulatory receptors expressed by immune cells. Interactions between sialic acid and Siglecs regulate the immune system, and aberrations contribute to pathologies like autoimmunity and cancer. Sialic acid/Siglec interactions between living cells are difficult to study owing to a lack of specific tools. Here, we report a glycoengineering approach to remodel the sialic acids of living cells and their binding to Siglecs. Using bioorthogonal chemistry, a library of cells with more than sixty different sialic acid modifications was generated that showed dramatically increased binding toward the different Siglec family members. Rational design reduced cross-reactivity and led to the discovery of three selective Siglec-5/14 ligands. Furthermore, glycoengineered cells carrying sialic acid ligands for Siglec-3 dampened the activation of Siglec-3+ monocytic cells through the NF-κB and IRF pathways.
- Büll, Christian,Heise, Torben,van Hilten, Niek,Pijnenborg, Johan F. A.,Bloemendal, Victor R. L. J.,Gerrits, Lotte,Kers-Rebel, Esther D.,Ritschel, Tina,den Brok, Martijn H.,Adema, Gosse J.,Boltje, Thomas J.
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supporting information
p. 3309 - 3313
(2017/03/17)
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- Synthesis and Biological Evaluation of 1,2,3-triazole tethered Pyrazoline and Chalcone Derivatives
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A series of pyrazoline derivatives and corresponding chalcone intermediates with substituents same as combretastatin-A4(CA-4) conjugated with triazole nucleus has been synthesized and evaluated for their anticancer potential. Sulphorhodamine B(SRB) assay indicated compound 12c to be the most active compound from the series with GI50 value of 6.7 μm against the human liver carcinoma cell line HepG2. Interestingly, the intermediate 11c exhibited more promising cytotoxicity demonstrating GI50 value of 1.3 μm against the prostate cancer cell line DU145. Compounds 11c and 12c caused accumulation of cells in G2/M phase and inhibited tubulin polymerization. Furthermore, these compounds reduce the mitochondrial membrane potential and activate caspases 3 and 9, thereby indicating their ability to trigger apoptosis.
- Hussaini, Syed Mohammed Ali,Yedla, Poornachandra,Babu, Korrapati Suresh,Shaik, Thokhir B.,Chityal, Ganesh Kumar,Kamal, Ahmed
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- New Series of BPL Inhibitors To Probe the Ribose-Binding Pocket of Staphylococcus aureus Biotin Protein Ligase
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Replacing the labile adenosinyl-substituted phosphoanhydride of biotinyl-5′-AMP with a N1-benzyl substituted 1,2,3-triazole gave a new truncated series of inhibitors of Staphylococcus aureus biotin protein ligase (SaBPL). The benzyl group presents to the
- Feng, Jiage,Paparella, Ashleigh S.,Tieu, William,Heim, David,Clark, Sarah,Hayes, Andrew,Booker, Grant W.,Polyak, Steven W.,Abell, Andrew D.
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supporting information
p. 1068 - 1072
(2016/12/18)
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- Formal C-H-azidation-based shortcut to diazido building blocks for the versatile preparation of photoaffinity labeling probes
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Short synthetic routes to diazido building blocks with different connectable groups were established on the basis of the sequential iridium-catalyzed C-H borylation and copper-catalyzed azidation of 1,3-disubstituted benzenes, followed by diverse azido-fr
- Yoshida, Suguru,Misawa, Yoshihiro,Hosoya, Takamitsu
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supporting information
p. 3991 - 3995
(2014/07/08)
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