- Synthesis and characterization of 1,2,3-triazoles-linked urea hybrid sensor for selective sensing of fluoride ion
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Two urea-linked 1,2,3-triazole based sensors (5a and 5b) have been synthesized by 1,3-dipolar cycloaddition between 1-(4-fluorophenyl)-3-(prop-2-yn-1-yl)urea (2) and phenyl azides (4a-4b) via copper(I)-catalyzed click reaction. The synthesized sensors 5a
- Rani, Poonam,Lal, Kashmiri,Aruna,Shrivastava, Rahul,Ghule, Vikas D.
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Read Online
- 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, antiproliferative, docking and DFT studies of benzimidazole derivatives as EGFR inhibitors
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In the present work, new benzimidazole linked 1,2,3-triazole hybrids have been synthesized and screened for antiproliferative and EGFR kinase inhibitory activities.The structures of these hybrids were elucidated using IR, NMR, mass spectrometry and elemen
- Alam, Mohammad Mahboob,Alzahrani, Hessah Abdullah,Elhenawy, Ahmed A.,Malebari, Azizah M.,Nazreen, Syed
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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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- 2-((1-Phenyl-1H-1,2,3-triazol-4-yl)methyl)-2-azabicyclo[3.2.1]octan-3-one derivatives: Simplification and modification of aconitine scaffold for the discovery of novel anticancer agents
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The molecular chaperone heat shock protein 90 (Hsp90) is a promising target for cancer therapy. Natural product aconitine is a potential Hsp90 inhibitor reported in our previous work. In this study, we designed and synthesized a series of 2-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-2-azabicyclo[3.2.1]octan-3-one derivatives as potent Hsp90 inhibitors by simplifying and modifying aconitine scaffold. Among these compounds, 14t exhibited an excellent antiproliferative activity against LoVo cells with an IC50 value of 0.02 μM and a significant Hsp90α inhibitory activity with an IC50 value of 0.71 nM. Molecular docking studies provided a rational binding model of 14t in complex with Hsp90α. The following cell cycle and apoptosis assays revealed that compound 14t could arrest cell cycle at G1/S phase and induce cell apoptosis via up-regulation of bax and cleaved-caspase 3 protein expressions while inhibiting the expressions of bcl-2. Moreover, 14t could inhibit cell migration in LoVo and SW620 cell lines. Consistent with in vitro results, 14t significantly repressed tumor growth in the SW620 xenograft mouse model.
- Zhang, Yi,Zhang, Ting-jian,Li, Xin-yang,Liang, Jing-wei,Tu, Shun,Xu, Hai-li,Xue, Wen-han,Qian, Xin-hua,Zhang, Zhen-hao,Zhang, Xu,Meng, Fan-hao
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- Design, Synthesis and Evaluation of a Series of 1,5-Diaryl-1,2,3-triazole-4-carbohydrazones as Inhibitors of the YAP-TAZ/TEAD Complex
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Starting from our previously reported hit, a series of 1,5-diaryl-1,2,3-triazole-4-carbohydrazones were synthesized and evaluated as inhibitors of the YAP/TAZ-TEAD complex. Their binding to hTEAD2 was confirmed by nanodifferential scanning fluorimetry, an
- Gibault, Floriane,Sturbaut, Manon,Coevoet, Mathilde,Pugnière, Martine,Burtscher, Ashley,Allemand, Frédéric,Melnyk, Patricia,Hong, Wanjin,Rubin, Brian P.,Pobbati, Ajaybabu V.,Guichou, Jean-Fran?ois,Cotelle, Philippe,Bailly, Fabrice
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p. 2823 - 2844
(2021/07/10)
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- Synthesis, antimicrobial evaluation, and in silico studies of quinoline—1H-1,2,3-triazole molecular hybrids
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Abstract: Antimicrobial resistance has become a significant threat to global public health, thus precipitating an exigent need for new drugs with improved therapeutic efficacy. In this regard, molecular hybridization is deemed as a viable strategy to afford multi-target-based drug candidates. Herein, we report a library of quinoline—1H-1,2,3-triazole molecular hybrids synthesized via copper(I)-catalyzed azide-alkyne [3 + 2] dipolar cycloaddition reaction (CuAAC). Antimicrobial evaluation identified compound 16 as the most active hybrid in the library with a broad-spectrum antibacterial activity at an MIC80 value of 75.39?μM against methicillin-resistant S. aureus, E. coli, A. baumannii, and multidrug-resistant K. pneumoniae. The compound also showed interesting antifungal profile against C. albicans and C. neoformans at an MIC80 value of 37.69 and 2.36?μM, respectively, superior to fluconazole. In vitro toxicity profiling revealed non-hemolytic activity against human red blood cells (hRBC) but partial cytotoxicity to human embryonic kidney cells (HEK293). Additionally, in silico studies predicted excellent drug-like properties and the importance of triazole ring in stabilizing the complexation with target proteins. Overall, these results present compound 16 as a promising scaffold on which other molecules can be modeled to deliver new antimicrobial agents with improved potency. Graphic abstract: [Figure not available: see fulltext.].
- Awolade, Paul,Cele, Nosipho,Kerru, Nagaraju,Singh, Parvesh
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p. 2201 - 2218
(2020/06/17)
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- Gold(I) complexes bearing ring-fused benzoxazine-derived triazolylidenes and their use in C–N bond-forming processes
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We report the synthesis and full characterization of a novel series of ring-fused benzoxazine-derived triazolium salts (1a–c) and their corresponding triazolylidene gold(I) complexes (2a–c). All new compounds were fully characterized by means of 1H and 13C NMR spectroscopy, elemental analyses, and mass spectroscopy and in the case of triazoliums 1a and 1b by single-crystal X-ray diffraction. The new triazolylidene gold complexes (2a–c) were tested as precatalysts in the hydroamination and hydrohydrazination of terminal alkynes employing aniline derivatives and hydrazine as nitrogen sources, respectively.
- Campos-Dominguez, Emmanuel,Vasquez-Perez, Jose,Rojas-Lima, Susana,Lopez-Ruiz, Heraclio,Mendoza-Espinosa, Daniel
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- Naproxen based 1,3,4-oxadiazole derivatives as EGFR inhibitors: Design, synthesis, anticancer, and computational studies
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A library of novel naproxen based 1,3,4-oxadiazole derivatives (8–16 and 19–26) has been synthesized and screened for cytotoxicity as EGFR inhibitors. Among the synthesized hy-brids, compound2-(4-((5-((S)-1-(2-methoxynaphthalen-6-yl)ethyl)-1,3,4-oxadiazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl)phenol(15) was the most potent compound against MCF-7 and HepG2cancer cells with IC50 of 2.13 and 1.63 μg/mL, respectively, and was equipotent to doxorubicin (IC50 1.62 μg/mL) towards HepG2. Furthermore, compound 15 inhibited EGFR kinase with IC50 0.41 μM compared to standard drug Erlotinib (IC50 0.30 μM). The active compound induces a high percentage of necrosis towards MCF-7, HePG2 and HCT 116 cells. The docking studies, DFT and MEP also supported the biological data. These results demonstrated that these synthesized naproxen hybrids have EGFR inhibition effects and can be used as leads for cancer therapy.
- Alam, Mohammad Mahboob,Alfaifi, Mohammad Y.,Alfaifi, Sulaiman Y. M.,Almalki, Abdulraheem S. A.,Alsenani, Nawaf I.,Alsharif, Meshari A.,Elbehairi, Serag Eldin I.,Elhenawy, Ahmed A.,Malebari, Azizah M.,Nazreen, Syed
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- Synthesis and biological evaluation of 1,2,3-triazole tethered thymol-1,3,4-oxadiazole derivatives as anticancer and antimicrobial agents
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A library of 1,2,3-triazole-incorporated thymol-1,3,4-oxadiazole derivatives (6–18) hasbeen synthesized and tested for anticancer and antimicrobial activities. Compounds 7, 8, 9, 10, and 11 exhibited significant antiproliferative activity. Among these act
- Ahmad, Abrar,Alam, Mohammad Mahboob,Alfaifi, Sulaiman Y. M.,Alghamdi, Abdullah A. A.,Ali, Nada M.,Almalki, Abdulraheem S. A.,Alsharif, Meshari A.,Elhenawy, Ahmed A.,Malebari, Azizah M.,Nazreen, Syed
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- Bioisosteric Replacement of Amide Group with 1,2,3-Triazoles in Acetaminophen Addresses Reactive Oxygen Species-Mediated Hepatotoxic Insult in Wistar Albino Rats
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Acetaminophen (AP) is a popularly recommended over-the-counter analgesic-antipyretic in clinical use. However, the drug is handicapped by the occurrence of hepatotoxic insult following acute ingestion. Consequently, AP-induced hepatotoxicity is often impl
- Agrawal, Ramkishore,Das, Debashree,Gajbhiye, Asmita,Mishra, Shweta,Sahu, Adarsh,Sahu, Preeti,Sakthivel, Ayyamperumal
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- Fluconazole analogues with metal-binding motifs impact metal-dependent processes and demonstrate antifungal activity in Candida albicans
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Abstract: Azole antifungals are an important class of antifungal drugs due to their low cost, ability to be administered orally, and broad-spectrum activity. However, their widespread and long-term use have given rise to adaptation mechanisms that render these compounds less effective against common fungal pathogens, including Candida albicans. New antifungals are desperately needed as drug-resistant strains become more prevalent. We recently showed that copper supplementation potentiates the activity of the azole antifungal fluconazole against the opportunistic fungal pathogen C. albicans. Here, we report eight new azole analogues derived from fluconazole in which one triazole group has been replaced with a metal-binding group, a strategy designed to enhance potentiation of azole antifungal activity by copper. The bioactivity of all eight compounds was tested and compared to that of fluconazole. Three of the analogues showed activity against C. albicans and two had lower levels of trailing growth. One compound, Flu-TSCZ, was found to impact the levels, speciation, and bioavailability of cellular metals. Graphic abstract: [Figure not available: see fulltext.]
- Franz, Katherine J.,Hunsaker, Elizabeth W.,McAuliffe, Katherine J.
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- Carbon isotope labeling of carbamates by late-stage [11C], [13C] and [14C]carbon dioxide incorporation
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A general procedure for the late-stage [11C], [13C] and [14C]carbon isotope labeling of cyclic carbamates is reported. This protocol allows the incorporation of carbon dioxide, the primary source of carbon-14 and carbon-11 radioisotopes, in a direct, cost-effective and sustainable manner. A disconnection/reconnection strategy, involving ring opening/isotopic closure, was also implemented.
- Del Vecchio, Antonio,Talbot, Alex,Caillé, Fabien,Chevalier, Arnaud,Sallustrau, Antoine,Loreau, Olivier,Destro, Gianluca,Taran, Frédéric,Audisio, Davide
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supporting information
p. 11677 - 11680
(2020/10/19)
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- Design, synthesis and biological evaluation of homoerythrina alkaloid derivatives bearing a triazole moiety as PARP-1 inhibitors and as potential antitumor drugs
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A series of homoerythrina alkaloid derivatives containing a 1,2,3-triazole moiety as PARP-1 inhibitors were designed and synthesized. And their anti-proliferative activity was further evaluated. Compound 10n had excellent activity to inhibit proliferation of A549 cells (IC50 = 1.89 μM), which was higher than harringtonine (IC50 = 10.55 μM), pemetrexed (IC50 = 3.39 μM), and rucaparib (IC50 = 4.91 μM). Furthermore, the selectivity index of compound 10n was higher than rucaparib and pemetrexed for lung cancer cells. Flow cytometry analysis showed that compound 10n significantly arrested the cell cycle in the S phase, then induced apoptosis of A549 cells (apoptosis rate is 46%), which effectively inhibited cell proliferation. Simultaneously, western blot analysis revealed that compound 10n could prevent the biosynthesis of PAR. Further analysis results revealed that compound 10n could inhibit the expression of cyclin A, down-regulate the expression of bcl-2/bax, activate caspase-3, and ultimately induce apoptosis of A549 cells. All the results indicated that compound 10n had potential research value as a novel PARP-1 inhibitor in antitumor, and it provided a new reference for further development of PARP-1 inhibitors.
- Li, Shuai,Li, Xin-yang,Zhang, Ting-jian,Kamara, Mohamed Olounfeh,Liang, Jing-wei,Zhu, Ju,Meng, Fan-hao
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- Design, synthesis and biological evaluation of erythrina derivatives bearing a 1,2,3-triazole moiety as PARP-1 inhibitors
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Inhibitors of poly (ADP-ribose) polymerase-1 (PARP-1) have shown to be promising in clinical trials against cancer, and many researchers are interested in the development of new PARP-1 inhibitors. Herein, we designed and synthesized 44 novel erythrina derivatives bearing a 1,2,3-triazole moiety as PARP-1 inhibitors. MTT assay results indicated that compound 10b had the most potent anti-proliferative activity against A549 cells among five cancer cells. The enzyme inhibitory activity in vitro of compound 10b was also significantly better than rucaparib. Furthermore, the selectivity index of compound 10b was higher than rucaparib for lung cancer cells. Flow cytometry analysis showed that compound 10b induced apoptosis of A549 cells by the mitochondrial pathway. Western blot analysis indicated that compound 10b was able to inhibit the biosynthesis of PAR effectively, and it was more potent than rucaparib. Also, compound 10b was able to up-regulate the ratio of bax/bcl-2, activate caspase-3, and ultimately induced apoptosis of A549 cells. The combined results revealed that the discovery of novel non-amide based PARP-1 inhibitors have great research significance and provide a better choice for the future development of drugs.
- Li, Shuai,Li, Xin-yang,Meng, Fan-hao,Qian, Xin-hua,Xue, Wen-han,Zhang, Ting-jian,Zhu, Ju
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supporting information
(2020/01/21)
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- Synthesis, antibacterial, and antioxidant activities of naphthyl-linked disubstituted 1,2,3-triazoles
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Here, click synthesis of 15 naphthyl-linked disubstituted 1,2,3-triazoles has been carried out by the reaction between 1-(prop-2-yn-1-yloxy)naphthalene and aromatic azides. The structure elucidation of the synthesized compounds was carried out by FTIR, s
- Kaushik, Chander Prakash,Luxmi, Raj
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p. 2400 - 2409
(2020/03/16)
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- Bio-isosteric replacement of amide group with 1,2,3-triazole in phenacetin improves the toxicology and efficacy of phenacetin-triazole conjugates (PhTCs)
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Aim: Inflammatory algesia and pyresia are common pathological consequences of physiological defense. Phenacetin introduced as effective analgesic anti-pyretic agent, was proscribed from therapeutic use because of associated systemic toxicity. The aim of t
- Sahu, Adarsh,Das, Debashree,Agrawal, Ram Kishore,Gajbhiye, Asmita
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p. 176 - 188
(2019/05/14)
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- Design, synthesis and anti-platelet aggregation activity study of ginkgolide-1,2,3-triazole derivatives
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Ginkgolides are the major active component of Ginkgo biloba for inhibition of platelet activating factor receptor. An azide-alkyne Huisgen cycloaddition reaction was used to introduce a triazole nucleus into the target ginkgolide molecules. A series of ginkgolide-1,2,3-triazole conjugates with varied functional groups including benzyl, phenyl and heterocycle moieties was thus synthesized. Many of the designed derivatives showed potent antiplatelet aggregation activities with IC50 values of 5~21 nM.
- Cui, Jian,Hu, Lean,Shi, Wei,Cui, Guozhen,Zhang, Xumu,Zhang, Qing-Wen
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- Probing the Existence of a Metastable Binding Site at the β2-Adrenergic Receptor with Homobivalent Bitopic Ligands
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Herein, we report the development of bitopic ligands aimed at targeting the orthosteric binding site (OBS) and a metastable binding site (MBS) within the same receptor unit. Previous molecular dynamics studies on ligand binding to the β2-adrenergic receptor (β2AR) suggested that ligands pause at transient, less-conserved MBSs. We envisioned that MBSs can be regarded as allosteric binding sites and targeted by homobivalent bitopic ligands linking two identical pharmacophores. Such ligands were designed based on docking of the antagonist (S)-alprenolol into the OBS and an MBS and synthesized. Pharmacological characterization revealed ligands with similar potency and affinity, slightly increased β2/β1AR-selectivity, and/or substantially slower β2AR off-rates compared to (S)-alprenolol. Truncated bitopic ligands suggested the major contribution of the metastable pharmacophore to be a hydrophobic interaction with the β2AR, while the linkers alone decreased the potency of the orthosteric fragment. Altogether, the study underlines the potential of targeting MBSs for improving the pharmacological profiles of ligands.
- Gaiser, Birgit I.,Danielsen, Mia,Marcher-R?rsted, Emil,R?pke J?rgensen, Kira,Wróbel, Tomasz M.,Frykman, Mikael,Johansson, Henrik,Br?uner-Osborne, Hans,Gloriam, David E.,Mathiesen, Jesper Mosolff,Sejer Pedersen, Daniel
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p. 7806 - 7839
(2019/09/07)
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- Leucine ureido derivatives as aminopeptidase N inhibitors using click chemistry. Part II
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Aminopeptidase N (APN) has been proved to be deeply associated with cancer angiogenesis, metastasis and invasion. Therefore, APN gains increasing attention as a promising anti-tumor target. In the current study, we report the design, synthesis, biological evaluation and structure-activity relationship of one new series of leucine ureido derivatives containing the 1,2,3-triazole moiety. Among them, compound 31f was identified as the best APN inhibitor with IC50 value being two orders of magnitude lower than that of the positive control bestatin. Compound 31f possessed selective cytotoxicity to several tumor cell lines over the normal cell line human umbilical vein endothelial cells (HUVECs). Notably, when combined with 5-fluorouracil (5-Fu), 31f exhibited synergistic anti-proliferation effect against several tumor cell lines. At the same concentration, 31f exhibited much better anti-angiogenesis activities than bestatin in the HUVECs capillary tube formation assay and the rat thoracic aorta rings test. In the in vitro anti-invasion assay, 31f also exhibited superior potency over bestatin. Moreover, considerable in vivo antitumor potencies of 31f alone or in combination with 5-Fu were observed without significant toxic signs in a mouse heptoma H22 tumor transplant model.
- Cao, Jiangying,Zang, Jie,Kong, Xiujie,Zhao, Chunlong,Chen, Ting,Ran, Yingying,Dong, Hang,Xu, Wenfang,Zhang, Yingjie
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p. 978 - 990
(2019/02/09)
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- Baicalein triazole prevents respiratory tract infection by RSV through suppression of oxidative damage
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Baicalein, an isolate of secutellaria baicalensis is known for its anti-inflammatory activity. In the present study, 12-triazole derivatives of baicalein were synthesized and evaluated against RSV infected BEAS-2B cells in vitro and in mice model in vivo.
- Zhang, Cuicui,Li, Na,Niu, Fang
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p. 227 - 233
(2019/04/17)
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- A convenient synthesis and crystal structure of disubstituted 1,2,3-triazoles having ether functionality
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A series of 27 ether-linked 1,4-disubstituted 1,2,3-triazoles (8a–8z1) has been synthesized by 1,3 dipolar cycloaddition of 1-substituted-4-(prop-2-yn-1-yloxy)benzene (3a–3c) and aromatic azides (5a–5c, 7a–7f). The synthesized compounds were ex
- Luxmi, Raj,Kaushik,Kumar, Devinder,Kumar, Krishan,Pahwa, Ashima,Sangwan, Jyoti,Chahal, Manisha
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supporting information
p. 3435 - 3441
(2019/11/11)
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- DBU-promoted Cu(OAc)2·H2O-catalysed coupling reactions of aryl iodides and sodium azide
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An efficient and simple protocol for the synthesis of aryl azides by the coupling of aryl iodides with sodium azide, in good to excellent yields in DMSO at 95°C under catalysis by Cu(OAc)2·H2O and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), has been established. The optimised loadings of Cu(OAc)2·H2O and DBU were 10 mol% and 15 mol% respectively.
- Jiang, Yuqin,Suo, Huajun,Zhao, Yaru,Li, Xiyong,Sun, Yamin,Li, Xingfeng,Dong, Wenpei,Li, Wei,Zhang, Weiwei,Xu, Guiqing
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p. 247 - 250
(2018/06/29)
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- Annulation-Induced Cascade Transformation of 5-Iodo-1,2,3-triazoles to 2-(1-Aminoalkyl)benzoxazoles
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Base-mediated cyclization of (5-iodo-1,2,3-triazolyl)phenols was proposed as a new synthetic strategy for the in situ generation of diazoimines via electrocyclic ring opening of the fused heterocycle. Cu-catalyzed amination of the intermediate diazoalkanes was employed to develop an efficient cascade approach to functionalized benzoxazoles.
- Kotovshchikov, Yury N.,Latyshev, Gennadij V.,Navasardyan, Mger A.,Erzunov, Dmitry A.,Beletskaya, Irina P.,Lukashev, Nikolay V.
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supporting information
p. 4467 - 4470
(2018/08/09)
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- METHOD FOR PRODUCING 2-AMINO-4-SUBSTITUTED PHENOL
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A compound represented by formula (3): (wherein R1 represents a C1-C6 alkyl group optionally having one or more halogen atoms, R2 represents a C1-C6 alkyl group, and m represents an integer of 0 to 3) can be produced by reacting a C1
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Paragraph 0102-0104
(2018/10/21)
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- Synthesis method for aryl azide compound
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The invention discloses a synthesis method for an aryl azide compound. The synthesis method includes the steps of: adding an iodo-aryl compound, sodium azide, 1,8-diazabicyclo[5.4.0]undecane-7-ene and a catalyst into a reaction container filled with a solvent, performing a stirring reaction to the reaction mixture at 60-105 DEG C with TLC tracing detection until the reaction is completed, adding ammonia water to the reaction mixture, extracting the reaction mixture for 3 times by ethyl acetate, washing the reaction mixture for 1 time by saturated salt water, drying an organic phase, performing suction filtration and spinning solvent removal, and performing column chromatographic purification to obtain a target product. The method employs easy-to-obtained raw materials and has wide selection range of copper source of the catalyst, has mild reaction condition, simple operation and high yield.
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Paragraph 0036; 0037
(2017/08/28)
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- Alkyne-azide cycloaddition analogues of dehydrozingerone as potential anti-prostate cancer inhibitors: Via the PI3K/Akt/NF-kB pathway
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Herein, we report the isolation and synthetic modification of dehydrozingerone (DHZ, 1), a secondary metabolite present in the rhizome of Zingiber officinale. We synthesized O-propargylated dehydrozingerone, which was subsequently coupled by alkyne-azide cycloaddition (3-20) using click chemistry. The compounds (1-20) were evaluated for their in vitro cytotoxic activity in a panel of three cancer cell lines. Among all the DHZ derivatives, 3, 6, 7, 8, 9 and 15 displayed potent cytotoxic potential with an IC50 value ranging from 1.8-3.0 μM in MCF-7, PC-3 and HCT-116 cell lines. Furthermore, compound 7 has proven to be the most potent cytotoxic compound in all the three distinct cancer cell lines and also demonstrated significant anti-invasive potential in prostate cancer. The mechanistic study of compound 7 showed that it not only suppressed the AKT/mTOR signalling which regulates nuclear transcription factor-NF-kB but also augmented the expression of anti-invasive markers E-cadherin and TIMP. Compound 7 significantly decreased the expression of pro-invasive markers vimentin, MMP-2 and MMP-9, respectively. This study underscores an efficient synthetic approach employed to evaluate the structure-activity relationship of dehydrozingerone (1) in search of potential new anticancer agents.
- Kumar, Chetan,Rasool, Reyaz Ur,Iqra, Zainab,Nalli, Yedukondalu,Dutt, Prabhu,Satti, Naresh K.,Sharma, Neha,Gandhi, Sumit G.,Goswami, Anindya,Ali, Asif
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p. 2115 - 2124
(2017/11/22)
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- Photochemical synthesis of 6-substituted 12-oxo-6,12-dihydroazepino[2,1-b]quinazolines
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[Figure not available: see fulltext.] A method for the synthesis of 6-substituted 12-oxo-6,12-dihydroazepino[2,1-b]quinazolines via a photoinitiated reaction of orthosubstituted aryl azides with sodium 2-aminobenzoate is proposed. Stepwise annulation of t
- Budruev, Andrei V.,Dzhons, Daria Yu.,Faerman, Vladimir I.,Fukin, Georgy K.,Shavyrin, Andrey S.
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p. 694 - 699
(2017/03/16)
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- Design and Synthesis of Novel Triazolyl Benzoxazine Derivatives and Evaluation of Their Antiproliferative and Antibacterial Activity
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A series of novel triazolyl benzoxazine derivatives have been synthesized via Cu(I)-catalyzed ‘Click’ cycloaddition. All of the compounds were fully characterized from their spectral data, and their antiproliferative activity was evaluated against three selected human cancer cell lines: cervical cancer cells (HeLa), colorectal adenocarcinoma (HT-29), and ovarian adenocarcinoma (SKOV-3). A few representative compounds have also been evaluated for their antibacterial potential against two bacterial strains Pseudomonas aeruginosa and Bacillus subtilis.
- Khan, Abdullah,Prasad, Suchita,Parmar, Virinder S.,Sharma, Sunil K.
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p. 1264 - 1275
(2016/07/29)
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- Handling Hazards Using Continuous Flow Chemistry: Synthesis of N1-Aryl-[1,2,3]-triazoles from Anilines via Telescoped Three-Step Diazotization, Azidodediazotization, and [3 + 2] Dipolar Cycloaddition Processes
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The conversion of commercially available anilines into triazole products was realized using a telescoped three-reactor flow diazotization, azidodediazotization, and [3 + 2] dipolar cycloaddition process. The diazotization-azidodediazotization sequence was
- Teci, Matthieu,Tilley, Michael,McGuire, Michael A.,Organ, Michael G.
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supporting information
p. 1967 - 1973
(2017/02/10)
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- Synthesis, pharmacological evaluation and molecular modeling studies of triazole containing dopamine D3 receptor ligands
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A series of 2-methoxyphenyl piperazine analogues containing a triazole ring were synthesized and their in vitro binding affinities at human dopamine D2 and D3 receptors were evaluated. Compounds 5b, 5c, 5d, and 4g, demonstrate high a
- Peng, Xin,Wang, Qi,Mishra, Yogesh,Xu, Jinbin,Reichert, David E.,Malik, Maninder,Taylor, Michelle,Luedtke, Robert R.,Mach, Robert H.
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supporting information
p. 519 - 523
(2015/03/05)
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- Synthesis of new generation triazolyl- and isoxazolyl-containing 6-nitro-2,3-dihydroimidazooxazoles as anti-TB agents: In vitro, structure-activity relationship, pharmacokinetics and in vivo evaluation
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The nitroimidazole scaffold has attracted great interest in the last decade, which ultimately led to the discovery of the successful drug Delamanid for multi-drug resistant tuberculosis (MDR-TB). Herein, we report medicinal chemistry on a 6-nitro-2,3-dihy
- Munagala, Gurunadham,Yempalla, Kushalava Reddy,Singh, Samsher,Sharma, Sumit,Kalia, Nitin Pal,Rajput, Vikrant Singh,Kumar, Sunil,Sawant, Sanghapal D.,Khan, Inshad Ali,Vishwakarma, Ram A.,Singh, Parvinder Pal
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supporting information
p. 3610 - 3624
(2015/03/30)
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- 6-NITRO-2,3-DIHYDROIMIDAZO[2,1-b]OXAZOLES AND A PROCESS FOR THE PREPARATION THEREOF
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The present invention relates to newer generation of triazoles, tetrazoles, isoxazoles, urea and sulphonamide functionalities containing 6-nitro-2, 3-dihydronitroimidazooxazoles agents of formula 1, their method of preparation, and their use as drugs for
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- HERBICIDAL SUBSTITUTED PYRIMIDINYLOXY BENZENE COMPOUNDS
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Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, (INSERT FORMULA 1 HERE) wherein each Y1, Y2, Y3, Y4, Z, R2, m and R3 are as defined in the di
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Page/Page column 48
(2015/06/25)
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- Arylhydrazones of barbituric acid: Synthesis, coordination ability and catalytic activity of their CoII, CoII/III and CuII complexes toward peroxidative oxidation of alkanes
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New ortho-substituted arylhydrazones of barbituric acid, 5-(2-(2-hydroxyphenyl)hydrazono) pyrimidine-2,4,6(1H,3H,5H)-trione (H4L1) and the sodium salt of 2-(2-(2,4,6-trioxotetra-hydropyrimidin-5(2H)-ylidene)hydrazinyl)benzenesulfonic
- Palmucci, Jessica,Mahmudov, Kamran T.,Guedes da Silva, M. Fátima C.,Martins, Luísa M. D. R. S.,Marchetti, Fabio,Pettinari, Claudio,Pombeiro, Armando J. L.
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p. 84142 - 84152
(2015/10/28)
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- Syntheses and structure-activity relationships for some triazolyl p38α MAPK inhibitors
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The design, synthesis and biological evaluation of novel triazolyl p38α MAPK inhibitors with improved water solubility for formulation in cationic liposomes (SAINT-O-Somes) targeted at diseased endothelial cells is described. Water-solubilizing groups wer
- Seerden, Jean-Paul G.,Leusink-Ionescu, Gabriela,Leguijt, Robin,Saccavini, Catherine,Gelens, Edith,Dros, Bas,Woudenberg-Vrenken, Titia,Molema, Grietje,Kamps, Jan A.A.M.,Kellogg, Richard M.
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p. 1352 - 1357
(2014/03/21)
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- PdCl2 catalyzed efficient assembly of organic azides, CO, and alcohols under mild conditions: A direct approach to synthesize carbamates
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A simple and readily available PdCl2 catalyzed carbamate synthesis method via isocyanate generation and application in situ has been developed. This chemistry provides an efficient and practical approach to synthesize carbamates from simple organic azides, CO atmosphere and alcohols. The broad scope, mild and neutral conditions, and only N2 as the byproduct make this transformation very useful. Moreover, simple examples of modification of bioactive molecules and construction of macrocycles were achieved through this protocol. This journal is the Partner Organisations 2014.
- Ren, Long,Jiao, Ning
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supporting information
p. 3706 - 3709
(2014/04/03)
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- A convergent synthesis of alkyne-azide cycloaddition derivatives of 4-α,β-2-propyne podophyllotoxin depicting potent cytotoxic activity
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A facile synthetic approach to construct the O-propargyl derivatives of 4α and 4β-(1,2,3-triazol-4-yl)-podophyllotoxin (9a-k & 10a-k) and 4′-Demethyl-4′-4β-(1,2,3-triazol-4-yl)-epipodophyllotoxin (12a-d) were synthesized by means of click chemistry. The c
- Zilla, Mahesh K.,Nayak, Debasis,Vishwakarma, Ram A.,Sharma, Parduman Raj,Goswami, Anindya,Ali, Asif
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- One pot synthesis of aromatic azide using sodium nitrite and hydrazine hydrate
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A simple, rapid, and efficient protocol for the synthesis of aryl azide using sodium nitrite and hydrazine hydrate at room temperature is discussed. The short reaction time, simple work-up procedure, and use of inexpensive reagents are advantages of this method.
- Siddiki, Afsar Ali,Takale, Balaram S.,Telvekar, Vikas N.
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p. 1294 - 1297
(2013/03/13)
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- Catalytic Staudinger/aza-Wittig sequence by in situ phosphane oxide reduction
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A Staudinger/aza-Wittig reaction sequence is described that is catalytic in phosphorus. Towards this end, the phosphane oxide is reduced in situ by diphenylsilane, which allows for substoichiometric amounts of the catalyst 5-phenyldibenzophosphole to be used. The substrate scope is investigated and benzoxazoles, benzodiazepine imidates and a 2-methoxypyrrole were successfully synthesized. These investigations show that a fast aza-Wittig reaction is required to obtain high yields. A catalytic Staudinger/aza-Wittig reaction sequence, involving in situ phosphane oxide reduction, was successfully developed. Benzoxazoles, benzodiazepine imidates and 2-methoxypyrrole were synthesized without phosphane oxide waste products. Copyright
- Van Kalkeren, Henri A.,Te Grotenhuis, Colet,Haasjes, Frank S.,Hommersom,Rutjes, Floris P. J. T.,Van Delft, Floris L.
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supporting information
p. 7059 - 7066
(2013/11/06)
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- A 1,4-diphenyl-1,2,3-triazole-based β-turn mimic constructed by click chemistry
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A series of 1,4-diphenyl-1,2,3-triazole-incorporated amide derivatives have been designed and prepared. X-ray crystallographic and (1D and 2D) 1H NMR studies reveal that these compounds fold into stable U-shaped conformations driven by three-center intramolecular C-H???O hydrogen-bonding formed between the triazole C-5 H atom and the two ether O atoms. Such folded structures make this 1,4-diphenyl-1,2,3-triazole skeleton a good candidate to be used as β-turn mimic. To prove this, the formation of a β-hairpin structure induced by this β-turn motif has been further demonstrated.
- Wu, Chun-Fang,Zhao, Xin,Lan, Wen-Xian,Cao, Chunyang,Liu, Jin-Tao,Jiang, Xi-Kui,Li, Zhan-Ting
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experimental part
p. 4261 - 4270
(2012/06/18)
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- Organophosphorus-catalysed Staudinger reduction
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The first Staudinger reduction that is catalytic in phosphine has been developed, showing excellent yields and functional group selectivity. To this end we utilised dibenzophosphole catalysts and mild in situ reduction of the intermediate iminophosphoranes. We could avoid the necessity of water during the reduction, obtained no phosphine oxides as waste and thus enabled facile purification of the product. A range of azides was converted into amines with good to excellent yields and high functional group tolerance. Copyright
- Van Kalkeren, Henri A.,Bruins, Jorick J.,Rutjes, Floris P. J. T.,Van Delft, Floris L.
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supporting information; experimental part
p. 1417 - 1421
(2012/07/03)
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- Design, synthesis, and in vitro biological evaluation of 1 H -1,2,3-triazole-4-carboxamide derivatives as new anti-influenza A agents targeting virus nucleoprotein
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The influenza virus nucleoprotein (NP) is an emerging target for anti-influenza drug development. Nucleozin (1) and its closely related derivatives had been identified as NP inhibitors displaying anti-influenza activity. Utilizing 1 as a lead molecule, we successfully designed and synthesized a series of 1H-1,2,3-triazole-4-carboxamide derivatives as new anti-influenza A agents. One of the most potent compounds, 3b, inhibited the replication of various H3N2 and H1N1 influenza A virus strains with IC 50 values ranging from 0.5 to 4.6 μM. Compound 3b also strongly inhibited the replication of H5N1 (RG14), amantidine-resistant A/WSN/33 (H1N1), and oseltamivir-resistant A/WSN/1933 (H1N1, 274Y) virus strains with IC 50 values in sub-μM ranges. Further computational studies and mechanism investigation suggested that 3b might directly target influenza virus A nucleoprotein to inhibit its nuclear accumulation.
- Cheng, Huimin,Wan, Junting,Lin, Meng-I,Liu, Yingxue,Lu, Xiaoyun,Liu, Jinsong,Xu, Yong,Chen, Jianxin,Tu, Zhengchao,Cheng, Yih-Shyun E.,Ding, Ke
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supporting information; experimental part
p. 2144 - 2153
(2012/05/04)
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- Triazole-based chromogenic and non-chromogenic receptors for halides
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We designed and synthesized a series of triazole-based receptors for anion recognition. Our studies demonstrated that an amide-linked triazole unit is a promising moiety for anion recognition. We synthesized various chromogenic and non-chromogenic recepto
- Haridas,Sahu, Srikanta,Praveen Kumar
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body text
p. 6930 - 6934
(2012/02/05)
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- Click-based synthesis and proteomic profiling of lipstatin analogues
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Using click chemistry to enable both structural diversity and proteome profiling within a natural product derived library, two out of nineteen lipstatin analogues showed similar activity to Orlistat against fatty acid synthase (FAS), but with an improved
- Ngai, Mun H.,Yang, Peng-Yu,Liu, Kai,Shen, Yuan,Wenk, Markus R.,Yao, Shao Q.,Lear, Martin J.
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supporting information; experimental part
p. 8335 - 8337
(2010/12/25)
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- Rates of thermolysis of azidobenzenes in solution: Large stabilizations of transition states by charge transfer from electron-donor substituents
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Introduction of +R type para substituents into azidobenzenes causes very large increases in rate of thermolysis, up to 225-fold. The rates of nitrobenzene solutions at 120°C follow a Hammett-type linear free energy relationship log k = -5.44 - 2.33σ1 - 1.48R+ which indicates conjugative stabilization of a nitrene-like transition state. ortho-Substituents of the +R type causes still larger rate enhancements, up to 456-fold for 2-amino, which identify a special resonance proximity effect. It is suggested that the very high rates reported for such α-azidoheterocycles as 2-azidothiophene are due to similar resonance stabilizations and not to ring-opening concerted with nitrogen loss.
- Dyall, Leonard K.,L'abbe, Gerrit,Dehaen, Wim
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p. 971 - 975
(2007/10/03)
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- Photochemistry of phenyl azides bearing 2-hydroxy and 2-amino groups studied by matrix-isolation spectroscopy: Generation and characterization of reactive o-quinoid compounds
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Broad-band irradiation (λ > 370 nm) of 2-hydroxyphenyl azide (1) in Ar at 10 K monitored by IR resulted in the formation of at least three major products, all of which were shown to be photointerconvertible under these conditions. The two products showing
- Tomioka, Hideo,Matsushita, Takeshi,Murata, Shigeru,Koseki, Shiro
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p. 1971 - 1980
(2007/10/03)
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