- Combinatorial synthesis of new fluorescent scaffolds using click chemistry
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Azides and acetylenes are bio-orthogonal functional groups that can be readily coupled using copper(I)- or ruthenium(II)- catalyzed 1,3-dipolar cycloaddition reactions. Using non-fluorescent aromatic azides and aromatic acetylenes, covering a range of electron rich and poor building blocks, the Huisgen cycloaddition afford 1,4-disubstituted or 1,5-disubstituted 1,2,3-triazoles. Using a combinatorial approach by running reaction in parallel in polypropylene 96-well plates we discovered several new fluorescent 1,2,3-triazoles scaffolds. These compounds show diverse interactions with biomolecules that could find applications in biology in, for example, fluorescence microscopy or biomolecule quantification.
- Cleemann, Felix,Karuso, Peter,Kum-Cheung, Wendy Loa
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supporting information
(2021/12/08)
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- Synthesis and antitumor activity of 1-substituted 1,2,3-triazole-mollugin derivatives
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A new series of mollugin-1,2,3-triazole derivatives were synthesized using a copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction of corresponding O-propargylated mollugin with aryl azides. All the compounds were evaluated for their cytotoxicity on five human cancer cell lines (HL-60, A549, SMMC-7721, SW480, and MCF-7) using MTS assays. Among the synthesized series, most of them showed cytotoxicity and most of all, compounds 14 and 17 exhibited significant cytotoxicity of all five cancer cell lines.
- Hu, Jiang-Miao,Li, Hong-Mei,Liu, Shou-Jin,Luo, Han,Lv, Yong-Feng,Zhang, Hong
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- Triazole [5, 4-d] pyrimidone tricyclic compounds as well as preparation method and application thereof
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The invention relates to triazole [5, 4-d] pyrimidone tricyclic compounds as well as a preparation method and application thereof.The triazole [5, 4-d] pyrimidone tricyclic compounds are prepared by following steps: taking different substituted anilines a
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Paragraph 0064; 0067-0070; 0076
(2021/07/09)
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- Primary discovery of 1-aryl-5-substituted-1H-1,2,3-triazole-4-carboxamides as promising antimicrobial agents
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Three series of novel 1H-1,2,3-triazole-4-carboxamides: 1-aryl-5-alkyl/aryl-1H-1,2,3-triazole-4-carboxamides, 1-aryl-5-amino-1H-1,2,3-triazole-4-carboxamides and 1,2,3-triazolo[1,5-a]quinazoline-3-carboxamides were synthesized via base-mediated click azide reactions. Compounds were evaluated for their antimicrobial activities against primary pathogens: Gram-positive and Gram-negative bacterial strains Escherichia coli, Klebsiella pneumonia, Acinetobacter baumannii, Pseudomonas aeruginosa, Staphylococcus aureus, as well as fungal strain Cryptococcus neoformans var. grubii and Candida albicans. Compounds exhibiting moderate to good activities were selected for SAR analysis. Several 5-methyl-1H-1,2,3-triazole-4-carboxamides 4d, 4l, 4r, showed potent antibacterial effect against S. aureus. On the contrary, 5-amino-1H-1,2,3-triazole-4-carboxamide 8b and [1,2,3]triazolo[1,5-a]quinazoline-3-carboxamide 9a were active against pathogenic yeast C. albicans. Thus, compound 4l under 1 μM demonstrated 50% growth inhibition against S. aureus. At the same concentration, the compound 9a killed approx. 40% of C. albicans cells. In general, these compounds demonstrated selective action and no significant impact on the viability of human keratinocytes of HaCaT line.
- Finiuk, Nataliya,Klyuchivska, Olha,Manko, Nazar,Matiychuk, Vasyl,Obushak, Mykola,Pokhodylo, Nazariy,Stoika, Rostyslav
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- Synthesis, characterization and antibacterial activity of the thioether linked 1,2,3-triazoles
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A green synthetic approach for the expedite construction of thirty six thioether linked 1,2,3-triazoles was carried out using Cellulose supported CuI nanoparticles in water. The structure of synthesized triazoles was explicated by spectroscopic techniques
- Kaushik, Chander P.,Sangwan, Jyoti
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supporting information
p. 3403 - 3415
(2021/09/13)
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- Optimizing the aryl-triazole of cjoc42 for enhanced gankyrin binding and anti-cancer activity
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Gankyrin is an oncoprotein overexpressed in numerous cancer types and appears to play a key role in regulating cell proliferation, cell growth, and cell migration. These roles are largely due to gankyrin's protein-protein interaction with the 26S proteaso
- Almasri, Joseph,D'Souza, Amber,Dukhande, Vikas V.,Farrales, Pamela,Gnanmony, Manu,Gupta, Vivek,Juang, Daniel,Kabir, Abbas,Kanabar, Dipti,Muth, Aaron,Shukla, Snehal,Torrents, Nicolas
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supporting information
(2020/07/10)
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- Synergistic combination of visible-light photo-catalytic electron and energy transfer facilitating multicomponent synthesis of β-functionalized α,α-diarylethylamines
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A synthetic strategy with the visible-light photo-catalytic synergistic combination of electron and energy transfer processes has been developed. The mild reaction conditions allow the radical-radical cross-coupling phenomenon for the multicomponent synthesis of β-arylsulfonyl(diarylphosphinoyl)-α,α-diarylethyl-amines from readily available arylsulfinic acids (diarylphosphine oxides), 1,1-diarylethylenes and arylazides.
- Wu, Yanan,Zhang, Yipin,Jiang, Mingjie,Dong, Xunqing,Jalani, Hitesh B.,Li, Guigen,Lu, Hongjian
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supporting information
p. 6405 - 6408
(2019/06/07)
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- Design, synthesis and antibacterial evaluation of novel 15-membered 11a-azahomoclarithromycin derivatives with the 1, 2, 3-triazole side chain
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Macrolides are widely prescribed in clinic to treat various respiratory tract infections. However, due to their inappropriate use, the prevalence of macrolide-resistant strains among clinical isolates has become a concern for public health. Therefore, nov
- Qin, Yinhui,Teng, Yuetai,Ma, Ruixin,Bi, Fangchao,Liu, Zhiyang,Zhang, Panpan,Ma, Shutao
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p. 321 - 339
(2019/07/18)
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- Controlled Transformations of Aryl Halides in a Flow System: Selective Synthesis of Aryl Azides and Aniline Derivatives
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Copper-mediated nitrogenation of aryl halides with sodium azide can result in either aryl azides or aniline derivatives. The selectivity of the transformation is highly dependent on reaction time and temperature, which led to contradictory literature results with respect to product selectivity and the conditions applied. The advantages of a strictly controlled flow reactor environment were exploited in order to facilitate selective haloarene transformations. Reaction conditions were carefully investigated to understand their role on product selectivity. Aryl azides and aryl amines were successfully prepared from the same starting materials using the same auxiliaries by means of precise control over residence time and reaction temperature, thereby ensuring time-, cost- and atom-efficient syntheses. (Figure presented.).
- Georgiádes, ádám,?tv?s, Sándor B.,Fül?p, Ferenc
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p. 1841 - 1849
(2018/04/09)
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- Synthesis and evaluation of novel triazolyl quinoline derivatives as potential antileishmanial agents
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The high potential of quinoline containing natural products and their derivatives in medicinal chemistry led us to discover novel series of 25 compounds for the development of new antileishmanial agents. A series of triazolyl 2-methyl-4-phenylquinoline-3-carboxylate derivatives has been synthesized via click chemistry inspired molecular hybridization approach and evaluated against Leishmania donovani. Most of the screened derivatives exhibited significant in vitro anti-leishmanial activity against promastigote (IC50 ranging from 2.43 to 45.75 μM) and intracellular amastigotes (IC50 ranging from 7.06 to 34.9 μM) than the control, miltefosine (IC50 = 8.4 μM), with less cytotoxicity in comparison to the standard drugs. Overall results revealed that prototype signify a new structural lead for antileishmanial chemotherapy.
- Upadhyay, Akanksha,Kushwaha, Pragati,Gupta, Sampa,Dodda, Ranga Prasad,Ramalingam, Karthik,Kant, Ruchir,Goyal, Neena,Sashidhara, Koneni V.
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p. 172 - 181
(2018/05/25)
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- Tetrahydroxydiboron-Mediated Palladium-Catalyzed Transfer Hydrogenation and Deuteriation of Alkenes and Alkynes Using Water as the Stoichiometric H or D Atom Donor
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There are few examples of catalytic transfer hydrogenations of simple alkenes and alkynes that use water as a stoichiometric H or D atom donor. We have found that diboron reagents efficiently mediate the transfer of H or D atoms from water directly onto unsaturated C-C bonds using a palladium catalyst. This reaction is conducted on a broad variety of alkenes and alkynes at ambient temperature, and boric acid is the sole byproduct. Mechanistic experiments suggest that this reaction is made possible by a hydrogen atom transfer from water that generates a Pd-hydride intermediate. Importantly, complete deuterium incorporation from stoichiometric D2O has also been achieved.
- Cummings, Steven P.,Le, Thanh-Ngoc,Fernandez, Gilberto E.,Quiambao, Lorenzo G.,Stokes, Benjamin J.
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supporting information
p. 6107 - 6110
(2016/06/09)
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- Design, synthesis and biological evaluation of ciprofloxacin tethered bis-1,2,3-triazole conjugates as potent antibacterial agents
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A series of new bis-1,2,3-triazole linked ciprofloxacin conjugates was designed, synthesized and evaluated in?vitro antibacterial activity against a panel of clinically relevant bacteria. A significant part of the compounds displayed enhanced activity against both Gram-positive and Gram-negative species of bacteria as compared to the parent drug. Additionally, negligible toxicity profile of compounds indicates that they may act a good antibiotic in future. Despite relatively small number of synthesized conjugates, it was possible to observe important dependences between their structure and activity.
- Kant, Rama,Singh, Vishal,Nath, Gopal,Awasthi, Satish Kumar,Agarwal, Alka
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p. 218 - 228
(2016/09/09)
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- Design, synthesis and antimicrobial activity of novel benzothiazole analogs
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In an attempt to design and synthesize a new class of antimicrobials, dialkyne substituted 2-aminobenzothiazole was reacted with various substituted aryl azides to generate a small library of 20 compounds (3a-t) by click chemistry. Structures of the newly synthesized compounds were established on the basis of spectral data. These compounds were screened for their antibacterial activity against Gram+ bacteria (Staphylococcus aureus and Enterococcus faecalis), Gram- bacteria (Salmonella typhi, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Shigella boydii) and antifungal activity against Candida tropicalis, Candida albicans, Candida krusei, Cryptococcus neoformans) as well as molds (Aspergillus niger, Aspergillus fumigatus). The compound 3e showed maximum potency against all Gram+/gram- bacterial strains with MIC value 3.12 μg/ml, which is two fold more active as compared to standard drug ciprofloxacin (MIC 6.25 μg/ml). However, all compounds were found ineffective against S. boydii (clinical isolate). Further, only one compound 3n was found to be the most active against all fungal strains with MIC value in the range of 1.56 μg/ml-12.5 μg/ml while the remaining compounds showed moderate to weak antifungal activity.
- Singh, Manavendra K.,Tilak, Ragini,Nath, Gopal,Awasthi, Satish K.,Agarwal, Alka
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p. 635 - 644
(2013/07/27)
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- In situ "click" assembly of small molecule matrix metalloprotease inhibitors containing zinc-chelating groups
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(Chemical Equation Presented) A panel of small molecule-based MMP inhibitors containing rhodanine warheads was assembled using "one-pot" click chemistry. Upon biological screening, moderate inhibitors were identified which specifically targets MMP-7 and MMP-13 over other MMPs.
- Hu, Mingyu,Li, Junqi,Yao, Shao Q.
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supporting information; experimental part
p. 5529 - 5531
(2009/06/17)
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