- Synthesis, inhibition properties against xanthine oxidase and molecular docking studies of dimethyl N-benzyl-1H-1,2,3-triazole-4,5-dicarboxylate and (N-benzyl-1H-1,2,3-triazole-4,5-diyl)dimethanol derivatives
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This study focused on synthesis various dimethyl N-benzyl-1H-1,2,3-triazole-4,5-dicarboxylate and (N-benzyl-1H-1,2,3-triazole-4,5-diyl)dimethanol derivatives under the conditions of green chemistry without the use of solvent and catalysts. Their inhibition properties were also investigated on xanthine oxidase (XO) activity. All dimethanol and dicarboxylate derivatives exhibited significant inhibition activities with IC50 values ranging from 0.71 to 2.25 μM. Especially, (1-(3-bromobenzyl)-1H-1,2,3-triazole-4,5-diyl)dimethanol (5c) and dimethyl 1-(4-chlorobenzyl)-1H-1,2,3-triazole-4,5-dicarboxylate (6 g) compounds were found to be the most promising derivatives on the XO enzyme inhibition with IC50 values 0.71 and 0.73 μM, respectively. Moreover, the double docking procedure was to evaluate compound modes of inhibition and their interactions with the protein (XO) at atomic level. Surprisingly, the docking results showed a good correlation with IC50 [correlation coefficient (R2 = 0.7455)]. Also, the docking results exhibited that the 5c, 6f and 6 g have lowest docking scores ?4.790, ?4.755, and ?4.730, respectively. These data were in agreement with the IC50 values. These results give promising beginning stages to assist in the improvement of novel and powerful inhibitor against XO.
- Yagiz, Güler,Noma, Samir Abbas Ali,Altundas, Aliye,Al-khafaji, Khattab,Taskin-Tok, Tugba,Ates, Burhan
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- Synthesis, Docking, and Biological activities of novel Metacetamol embedded [1,2,3]-triazole derivatives
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ERα controls the breast tissue development and progression of breast cancer. In our search for novel compounds to target Estrogen Receptor Alpha Ligand-Binding Domain, we identified “N-(3-((1H-1,2,3-triazol-4-yl)methoxy)phenyl)acetamide” derivatives as lead compounds. The Docking studies indicated good docking score for Metacetamol derivatives when docked into the 1XP6. A series of metacetamol derivatives have been synthesized, characterized and evaluated for cytotoxicity, anti bacterial and anti oxidant activities. Among the tested twelve hybrid compounds, “7a, 7g, 7h and 7i” derivatives showed promising cytotoxicity with IC50 value of 50 value of 30 μM, whereas Compounds “7a, 7b, 7c, 7d, 7g, 7j, 7k and 7l” showed moderate anti bacterial activity with the MIC value of 300 μM.
- Battu, Satyanarayana,Joolakanti, Hima Bindhu,Kamepalli, Ramanjaneyulu,Miryala, Jeevanreddy
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- NOVEL DIBENZOOXAPHOSPHININE OXIDE DERIVATIVE COMPOUNDS AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING DEGENERATIVE DISEASE COMPRISING THE SAME AS AN ACTIVE INGREDIENT
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The present invention relates to a novel dibenzooxininin oxide derivative compound having various nitrogen-containing substituents introduced at 6-position of a dibenzooxaphosphorin oxide mononuclear, and to the use thereof. The present invention relates to a pharmaceutical composition for preventing or treating degenerative diseases and a health supplement food composition for preventing or treating degenerative diseases, comprising the dibenzooxaphosphorin oxide derivative compound of the present invention.
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Paragraph 0117-0120
(2021/03/23)
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- Design, synthesis, and evaluation of metronidazole-1,2,3-triazole derivatives as potent urease inhibitors
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A new series of metronidazole-1,2,3-triazole derivatives 6a–o was synthesized and evaluated as Helicobacter pylori urease inhibitors. All the synthesized compounds were more potent than standard inhibitor thiourea against urease. Among the synthesized compounds, compound 6f (IC50 = 1.975 ± 0.25?μM) with inhibitory activity around 11-fols more than thiourea (IC50 = 22.00 ± 0.14?μM) was the most potent compound. Kinetic study of this compound revealed that compound 6f inhibited urease in an uncompetitive mode. Based on molecular modeling study, compound 6f pointed toward the bi-nickel center and stabilized by H-bond and T-shape π–π hydrophobic interactions with the critical residues His492 and Asp633. Moreover, it anchored to the helix-turn-helix motif in the active site cavity through interaction with His593 and Arg609. Consequently, it proposed that compound 6f through stabilization of active site flap inhibited urease activity.
- Rezaei, Elham Babazadeh,Abedinifar, Fahimeh,Azizian, Homa,Montazer, Mohammad Nazari,Asadi, Mehdi,Hosseini, Samanesadat,Sepehri, Saghi,Mohammadi-Khanaposhtani, Maryam,Biglar, Mahmood,Larijani, Bagher,Amanlou, Massoud,Mahdavi, Mohammad
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p. 4217 - 4226
(2021/04/26)
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- Synthesis of 1,2,3,triazole modified analogues of hydrochlorothiazide via click chemistry approach and in-vitro α-glucosidase enzyme inhibition studies
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The current study was aimed to discover potent inhibitors of α-glucosidase enzyme. A 25 membered library of new 1,2,3-triazole derivatives of hydrochlorothiazide (1) (HCTZ, a diuretic drug also being used for the treatment of high blood pressure) was synt
- Baheej, M. A. A.,Choudhary, M. Iqbal,Haniffa, Haroon M.,Iqbal, Shazia,Rizvi, Fazila,Siddiqui, Hina,Ullah, Saeed,Wahab, Atia-tul
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- Anti-Lung Cancer Activities of 1,2,3-Triazole Curcumin Derivatives via Regulation of the MAPK/NF-κB/STAT3 Signaling Pathways
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In this study, a series of curcumin derivatives containing 1,2,3-triazole were designed and synthesized, and their inhibitory activities against the proliferation of lung cancer cells were studied. Compound 5 k (3,4-dichlorobenzyltriazole methyl curcumin)
- Cai, Kun Yi,He, Xin Hua,Li, Zhen Wang,Liu, Kai Qiang,Sun, Xian Yu,Wang, Xin,Zhao, Yu Chao,Zhi, Tai Xin
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- Discovery of a Series of Theophylline Derivatives Containing 1,2,3-Triazole for Treatment of Non-Small Cell Lung Cancer
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Chemotherapy is the most common clinical treatment for non-small cell lung cancer (NSCLC), but low efficiency and high toxicity of current chemotherapy drugs limit their clinical application. Therefore, it is urgent to develop hypotoxic and efficient chemotherapy drugs. Theophylline, a natural compound, is safe and easy to get, and it can be used as a modified scaffold structure and hold huge potential for developing safe and efficient antitumor drugs. Herein, we linked theophylline with different azide compounds to synthesize a new type of 1,2,3-triazole ring-containing theophylline derivatives. We found that some theophylline1,2,3-triazole compounds showed a good tumor-suppressive efficacy. Especially, derivative d17 showed strong antiproliferative activity against a variety of cancer cells in vitro, including H460, A549, A2780, LOVO, MB-231, MCF-7, OVCAR3, SW480, and PC-9. It is worth noting that the two NSCLC cell lines H460 H and A549 are sensitive to compound d17 particularly, with IC50 of 5.929 ± 0.97?μM and 6.76 ± 0.25?μM, respectively. Compound d17 can significantly induce cell apoptosis by increasing the ratio of apoptotic protein Bax/Bcl-2 by downregulating the expression of phosphorylated Akt protein, and it has little toxicity to normal hepatocyte cells LO2 at therapeutic concentrations. These data indicate that these theophylline acetic acid-1,2,3-triazole derivatives may be potential drug candidates for anti-NSCLC and are worthy of further study.
- Li, Qingjiao,Liu, Yulin,Mao, Longfei,Peng, Lizeng,Xie, Luoyijun,Yang, Jianxue,Ye, Jiahui,Yuan, Miaomiao,Zhang, Rongjun
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- TDP-43 Modulation by Tau-Tubulin Kinase 1 Inhibitors: A New Avenue for Future Amyotrophic Lateral Sclerosis Therapy
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Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease without any effective treatment. Protein TDP-43 is a pathological hallmark of ALS in both sporadic and familiar patients. Post-translational modifications of TDP-43 promote its aggre
- Chaikuad, Apirat,De Lago, Eva,Gil, Carmen,Gomez-Almeria, Marta,Gonzalo-Consuegra, Claudia,Knapp, Stefan,Lietha, Daniel,Martinez, Ana,Monti, Barbara,Nozal, Vanesa,Palomo, Valle,Petralla, Sabrina,Santana, Paula,Martín-Requero, Angeles,Martínez-González, Loreto,Pérez-Cuevas, Eva,Ramírez, David
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- Synthesis and muscarinic acetylcholine receptor (mAChR) antagonist activity of substituted piperazine-triazoles
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This study describes synthesis of a series of piperazine-triazole derivatives and their ex vivo evaluation for preliminary muscarinic acetylcholine receptor (mAChR) blocking activity on rat ileum model. A molecule based on benzonitrile piperazine triazole scaffold showed good tissue relaxation and blocking of neurotransmitter ACh in the ex vivo experiment. Graphic abstract: [Figure not available: see fulltext.]
- Acharya, Badri Narayan,Ghorpade, RamaRao,Singh, Kshetra Pal,Kumar, Deo,Nayak, Sabita
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p. 357 - 366
(2021/03/16)
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- New 1,2,3-triazole–(thio)barbituric acid hybrids as urease inhibitors: Design, synthesis, in vitro urease inhibition, docking study, and molecular dynamic simulation
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A new series of 1,2,3-triazole–(thio)barbituric acid hybrids 8a–n was designed and synthesized on the basis of potent pharmacophores with urease inhibitory activity. Therefore, these compounds were evaluated against Helicobacter pylori urease. The obtained result demonstrated that all the synthesized compounds, 8a–n, were more potent than the standard urease inhibitor, hydroxyurea. Moreover, among them, compounds 8a, 8c–e, 8g,h, and 8k,l exhibited higher urease inhibitory activities than the other standard inhibitor used: thiourea. Docking studies were performed with the synthesized compounds. Furthermore, molecular dynamic simulation of the most potent compounds, 8e and 8l, showed that these compounds interacted with the conserved residues Cys592 and His593, which belong to the active site flap and are essential for enzymatic activity. These interactions have two consequences: (a) blocking the movement of a flap at the entrance of the active site channel and (b) stabilizing the closed active site flap conformation, which significantly reduces the catalytic activity of urease. Calculation of the physicochemical and topological properties of the synthesized compounds 8a–n predicted that all these compounds can be orally active. The ADME prediction of compounds 8a–n was also performed.
- Asgari, Mohammad S.,Azizian, Homa,Nazari Montazer, Mohammad,Mohammadi-Khanaposhtani, Maryam,Asadi, Mehdi,Sepehri, Saghi,Ranjbar, Parviz R.,Rahimi, Rahmatollah,Biglar, Mahmood,Larijani, Bagher,Amanlou, Massoud,Mahdavi, Mohammad
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- P-benzoquinone diazide core skeleton derivative as well as preparation method and application thereof
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The invention relates to a p-benzoquinone diazide core skeleton derivative and a preparation method and application, thereof, belongs to. the field of organic chemistry, and can effectively treat-ovarian-ovarian cancer-carcinoma STAT3-ovarian, cancer-ATG4
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Paragraph 0046; 0104-0108
(2020/03/17)
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- 1,2,3-Triazole-linked 5-benzylidene (thio)barbiturates as novel tyrosinase inhibitors and free-radical scavengers
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In this study, benzyl-1,2,3-triazole-linked 5-benzylidene (thio)barbiturate derivatives 7a–d and 8a–h were designed as potential tyrosinase inhibitors and free-radical scavengers. The twelve derivatives were synthesized via the [3+2] cycloaddition reactio
- Ranjbar, Sara,Shahvaran, Parisa-sadat,Edraki, Najmeh,Khoshneviszadeh, Mahsima,Darroudi, Mahdieh,Sarrafi, Yaghoub,Hamzehloueian, Mahshid,Khoshneviszadeh, Mehdi
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- Synthesis of Novel Triazole Incorporated Thiazolone Motifs Having Promising Antityrosinase Activity through Green Nanocatalyst CuI-Fe3O4@SiO2 (TMS-EDTA)
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In the present work, novel 5-((1-benzyl-1,2,3-triazol-4-yl)methoxybenzylidene)-2-(arylamino)thiazol-4-one thiazolone incorporated triazole derivatives have been designed as tyrosinase inhibitors. The compounds were synthesized through click reaction in good yield. Moreover, the antityrosinas activity of the synthesized derivatives was evaluated. In the search for establishing a click copper-catalyzed azide/alkyne cycloaddition (CuAAC) reaction under strict conditions, in terms of a novel air-stable, a recyclable and efficient magnetic catalyst was planned for new triazole derivatives as a well-organized copper iodide supported on the functionalized Fe3O4@SiO2 core-shell (CuI/Fe3O4@SiO2(TMS-EDTA) nanoparticles). The engineered nanocatalyst synthesized for the first time and characterized by different methods, including FT-IR spectroscopy, XRD, FESEM, EDX, TEM, TGA, and BET analysis. The excellent catalytic performance in ethanol with high surface area (351.7 m2g?1) and short reaction time for diverse functional groups (120–200 min), no use of toxic solvents, reusability of the catalyst, and using eco-friendly conditions are the advantageous of this work. Moreover,the nanocatalyst can be used at least five times without any significant decrease in the yield of the reaction. The thiazolidine-triazole derivatives 9a, 9c, 9e, and 9 g showed promising tyrosinase inhibitory activity with IC50 values in the range of 5.90–9.81 μM. The compounds were found to be considerably more potent tyrosinase inhibitors than the reference inhibitor kojic acid (IC50 = 18.36 μM).
- Darroudi, Mahdieh,Ranjbar, Sara,Esfandiar, Mohammad,Khoshneviszadeh, Mahsima,Hamzehloueian, Mahshid,Khoshneviszadeh, Mehdi,Sarrafi, Yaghoub
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- Design, synthesis and antibacterial activity evaluation of novel 2-(4-((1-aryl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)2-(2-oxoazetidin-1-yl)acetamide derivatives
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In this paper, a novel series of 2-(4-((1-aryl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)2-(2-oxoazetidin-1-yl)acetamide derivatives are synthesized in two steps. The first step involved Ugi multicomponent reaction of β-alanine, o-(propargyl)benzaldehyde and i
- Zarei, Samaneh,Komeili, Golzar,Bahadorikhalili, Saeed,Yahya-Meymandi, Azadeh,Karami-Zarandi, Morteza,Larijani, Bagher,Biglar, Mahmood,Sadat Ebrahimi, Seyed Esmaeil,Mahdavi, Mohammad
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p. 4254 - 4261
(2020/09/21)
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- Design, synthesis, biological evaluation, and docking study of new acridine-9-carboxamide linked to 1,2,3-triazole derivatives as antidiabetic agents targeting α-glucosidase
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A new series of acridine-9-carboxamide-1,2,3-triazole derivatives 7a-m were designed, synthesized, and evaluated as novel α-glucosidase inhibitors. Acridine-9-carboxamide-1,2,3-triazole scaffold has been designed by combination of effective moieties from potent α-glucosidase inhibitors. Most of the synthesized compounds were more potent than standard inhibitor acarbose. Among the title compounds, the most potent compounds were compounds 7j, 7k, and 7a with IC50 values of 120.2 ± 1.0, 151.1 ± 1.4, and 157.6 ± 1.6 μM, respectively (IC50 value of acarbose = 750.0 ± 10.0 μM). Docking study of the most potent compounds demonstrated that these compounds formed stable complexes with α-glucosidase active site. Anti-α-amylase assay of compounds 7j, 7k, and 7a was performed and no activity was observed. in vitro cytotoxicity assay of the latter compounds revealed that these compounds were not cytotoxic toward human normal (HDF) and cancer (MCF-7) cell lines. ADME and toxicity prediction of compounds 7j, 7k, and 7a were also performed.
- Asgari, Mohammad S.,Tahmasebi, Behnam,Mojtabavi, Somayeh,Faramarzi, Mohammad A.,Rahimi, Rahmatollah,Ranjbar, Parviz R.,Biglar, Mahmood,Larijani, Bagher,Rastegar, Hossein,Mohammadi-Khanaposhtani, Maryam,Mahdavi, Mohammad
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p. 4348 - 4357
(2020/10/12)
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- Design and synthesis of C-ring quinoxaline-substituted sinomenine 1,2,3-triazole derivatives via click reactions
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The synthesis of C-ring quinoxaline-substituted sinomenine 1,2,3-triazole derivatives at the 4-OH via click reactions is accomplished, and a total of 16 novel sinomenine double N-heterocyclic derivatives are obtained in 74%–95% yields. The C-ring is first transformed into a 1,2-diketone structure under the action of hydrochloric acid, and then reacted with o-phenylenediamine to obtain a C-ring quinoxaline-substituted structure. The 4-OH of sinomenine reacts with chloropropyne to give an alkynyl sinomenine, and then reacts with sodium azide and various benzyl chlorides to give the target compounds. All the synthesized derivatives are characterized by Fourier-transform infrared spectrometry, high resolution mass spectrometry, 1H NMR, and 13C NMR spectroscopy.
- Chen, Xia,Dong, Ling,Gu, Chengwen,Jin, Jie,Lu, Tong,Pan, Hongmei,Tao, Naili,Wang, Ao,Wu, Xuedan,Zhang, Kehua
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p. 699 - 704
(2020/06/03)
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- Synthesis and evaluation of novel purple acid phosphatase inhibitors
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Transgenic studies in animals have demonstrated a direct association between the level of expression of purple acid phosphatase (PAP; also known as tartrate-resistant acid phosphatase) and the progression of osteoporosis. Consequently, PAP has emerged as
- Hussein, Waleed M.,Feder, Daniel,Schenk, Gerhard,Guddat, Luke W.,McGeary, Ross P.
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- Naphthoquinone-fused triazole core skeleton derivative compound, preparation method and application thereof
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The invention relates to a naphthoquinone-fused triazole core skeleton derivative compound, relates to a preparation method and application of the naphthoquinone-triazole core skeleton derivative compound, and belongs to the field of organic chemistry. Th
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Paragraph 0043; 0109-0113; 0198-0202; 0312-0316
(2019/10/01)
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- Identification of highly potent and selective Cdc25 protein phosphatases inhibitors from miniaturization click-chemistry-based combinatorial libraries
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Cell division cycle 25 (Cdc25) protein phosphatases play key roles in the transition between the cell cycle phases and their association with various cancers has been widely proven, which makes them ideal targets for anti-cancer treatment. Though several Cdc25 inhibitors have been developed, most of them displayed low activity and poor subtype selectivity. Therefore, it is extremely important to discover novel small molecule inhibitors with potent activities and significant selectivity for Cdc25 subtypes, not only served as drugs to treat cancer but also to probe its mechanism in transitions. In this study, miniaturized parallel click chemistry synthesis via CuAAC reaction followed by in situ biological screening were used to discover selective Cdc25 inhibitors. The bioassay results showed that compound M2N12 proved to be the most potent Cdc25 inhibitor, which also act as a highly selective Cdc25C inhibitor and was about 9-fold potent than that of NSC 663284. Moreover, M2N12 showed remarkable anti-growth activity against the KB-VIN cell line, equivalent to that of PXL and NSC 663284. An all-atom molecular dynamics (MD) simulation approach was further employed to probe the significant selectivity of M2N12 for Cdc25C relative to its structural homologs Cdc25A and Cdc25B. Overall, above results make M2N12 a promising lead compound for further investigation and structural modification.
- Jing, Lanlan,Wu, Gaochan,Hao, Xia,Olotu, Fisayo A.,Kang, Dongwei,Chen, Chin Ho,Lee, Kuo-Hsiung,Soliman, Mahmoud E.S.,Liu, Xinyong,Song, Yuning,Zhan, Peng
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- Carcarinic acid-1, 2, 3- based triazole compound as well as preparation method and application thereof (by machine translation)
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The method comprises the following steps: firstly 1, 2, 3 - oxidizing and opening the carbon- carbon double bond of the, carcarinic acid into methylene to, obtain carcarinic acid (not shown, in the technical field of, organic 3 - synthesis), Wolf - Kishner - 1, 2, 3 - 1, 2, 3 - 1, 2, 3 - 3 . (by machine translation)
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-
Paragraph 0109-0111
(2019/12/25)
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- Waste-minimised copper-catalysed azide-alkyne cycloaddition in Polarclean as a reusable and safe reaction medium
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Herein we report the first example of a generally useful organic reaction, namely the copper-catalysed azide-alkyne cycloaddition, performed in a Polarclean/water mixture as a reaction medium. The process is very efficient, affording in 24 out of the 26 tested cases the desired triazole in quantitative yields. Product isolation is also very convenient, since the triazoles either precipitate or form a separate liquid phase, without the need to perform chromatographic separations. Moreover, since the metal catalyst is retained in the Polarclean/water phase, the catalyst/reaction medium can be easily reused for consecutive reaction runs, without an apparent loss in efficiency. This methodology is associated with very limited waste production, as evidenced by calculated E-factors in the range 2.6-3.7.
- Luciani, Lorenzo,Goff, Emily,Lanari, Daniela,Santoro, Stefano,Vaccaro, Luigi
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supporting information
p. 183 - 187
(2018/01/17)
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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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- Targeting the entrance channel of NNIBP: Discovery of diarylnicotinamide 1,4-disubstituted 1,2,3-triazoles as novel HIV-1 NNRTIs with high potency against wild-type and E138K mutant virus
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Inspired by our previous efforts on the modifications of diarylpyrimidines as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTI) and reported crystallography study, novel diarylnicotinamide derivatives were designed with a “triazole tail” occupying the entrance channel in the NNRTI binding pocket of the reverse transcriptase to afford additional interactions. The newly designed compounds were then synthesized and evaluated for their anti-HIV activities in MT-4 cells. All the compounds showed excellent to good activity against wild-type HIV-1 strain with EC50 of 0.02–1.77 μM. Evaluations of selected compounds against more drug-resistant strains showed these compounds had advantage of inhibiting E138K mutant virus which is a key drug-resistant mutant to the new generation of NNRTIs. Among this series, propionitrile (3b2, EC50(IIIB) = 0.020 μM, EC50(E138K) = 0.015 μM, CC50 = 40.15 μM), pyrrolidin-1-ylmethanone (3b8, EC50(IIIB) = 0.020 μM, EC50(E138K) = 0.014 μM, CC50 = 58.09 μM) and morpholinomethanone (3b9, EC50(IIIB) = 0.020 μM, EC50(E138K) = 0.027 μM, CC50 = 180.90 μM) derivatives are the three most promising compounds which are equally potent to the marketed drug Etravirine against E138K mutant strain but with much lower cytotoxicity. Furthermore, detailed SAR, inhibitory activity against RT and docking study of the representative compounds are also discussed.
- Tian, Ye,Liu, Zhaoqiang,Liu, Jinghan,Huang, Boshi,Kang, Dongwei,Zhang, Heng,De Clercq, Erik,Daelemans, Dirk,Pannecouque, Christophe,Lee, Kuo-Hsiung,Chen, Chin-Ho,Zhan, Peng,Liu, Xinyong
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p. 339 - 350
(2018/04/10)
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- Discovery of Natural Product Derived Labdane Appended Triazoles as Potent Pancreatic Lipase Inhibitors
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Obesity contributes to the genesis of many metabolic disorders including dyslipidemia, coronary heart disease (CHD), nonalcoholic fatty liver, type 2 diabetes, etc. Pancreatic lipase plays a vital role in food fat digestion and absorption. Therefore, to c
- Jalaja, Renjitha,Leela, Shyni G.,Valmiki, Praveen K.,Salfeena, Chettiyan Thodi F.,Ashitha, Kizhakkan T.,Krishna Rao, Venkata Rao D.,Nair, Mangalam S.,Gopalan, Raghu K.,Somappa, Sasidhar B.
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supporting information
p. 662 - 666
(2018/06/27)
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- An efficient synthesis of novel triazoles incorporating barbituric motifs via [3+2] cycloaddition reactions: An experimental and theoretical study
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In this work, the synthesis of novel triazole derivatives with barbituric motifs in good yields is described. The alkyne was prepared through the Knoevenagel reaction of barbituric derivatives with ortho and para O-propargylated hydroxybenzaldehyde. The m
- Darroudi, Mahdieh,Sarrafi, Yaghoub,Hamzehloueian, Mahshid
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p. 821 - 835
(2018/08/21)
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- Discovery of phenylalanine derivatives as potent HIV-1 capsid inhibitors from click chemistry-based compound library
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The HIV-1 capsid (CA) protein plays essential roles in both early and late stages of HIV-1 replication and is considered an important, clinically unexploited therapeutic target. As such, small drug-like molecules that inhibit this critical HIV-1 protein h
- Wu, Gaochan,Zalloum, Waleed A.,Meuser, Megan E.,Jing, Lanlan,Kang, Dongwei,Chen, Chin-Ho,Tian, Ye,Zhang, Fangfang,Cocklin, Simon,Lee, Kuo-Hsiung,Liu, Xinyong,Zhan, Peng
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p. 478 - 492
(2018/09/25)
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- Natural phosphate-supported Cu(ii), an efficient and recyclable catalyst for the synthesis of xanthene and 1,4-disubstituted-1,2,3-triazole derivatives
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Cu(NO3)2 supported on natural phosphate, Cu(ii)/NP, was prepared by co-precipitation and applied as a heterogeneous catalyst for synthesizing xanthenes (2-3 h, 85-97%) through Knoevenagel-Michael cascade reaction of aromatic aldehydes with 1,3-cyclic diketones in ethanol under refluxing conditions. It was further used for regioselective synthesis of 1,4-disubstituted-1,2,3-triazoles (1-25 min, 95-99%) via a three-component reaction between organic halides, aromatic alkynes and sodium azide in methanol at room temperature. The proposed catalyst, Cu(ii)/NP, was characterized using X-ray fluorescence, X-ray diffraction, Fourier-transform infrared spectroscopy, scanning electron microscopy, Brunauer-Emmett-Teller, Barrett-Joyner-Halenda and inductively coupled plasma analyses. Compared to other reports in literature, the reactions took place through a simple co-precipitation, having short reaction time (85%), and high recyclability of catalyst (>5 times) without significant decrease in the inherent property and selectivity of catalyst. The proposed protocols provided significant economic and environmental advantages.
- Amini, Abbas,Fallah, Azadeh,Cheng, Chun,Tajbakhsh, Mahmood
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p. 41536 - 41547
(2019/01/03)
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- Design, synthesis and biological mechanisms research on 1,2,3-triazole derivatives of Jiyuan Oridonin A
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Two series of derivatives with 1,2,3-triazole as heterocyclic moiety of Jiyuan Oridonin A, a new ent-kaurene diterpenoid which was isolated from genus Isodon rubescens, were synthesized and biologically evaluated. All the derivatives possessed good anti-proliferative activities. Among them, compound 8g was found to significantly induce cell apoptosis and cell cycle arrest in MGC-803 via a series of signals activated by the increased intracellular ROS levels.
- Ke, Yu,Wang, Wang,Zhao, Long-Fei,Liang, Jian-Jia,Liu, Ying,Zhang, Xiao,Feng, Kai,Liu, Hong-Min
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supporting information
p. 4761 - 4773
(2018/08/25)
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- Synthesis of Novel Triazole-incorporated Isatin Derivatives as Antifungal, Antitubercular, and Antioxidant Agents and Molecular Docking Study
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A library of 1,2,3-triazoles efficiently prepared via click chemistry and evaluated for their antifungal, antitubercular, antioxidant, cytotoxicity, molecular docking and ADME prediction.
- Shaikh, Mubarak H.,Subhedar, Dnyaneshwar D.,Khan, Firoz A. Kalam,Sangshetti, Jaiprakash N.,Nawale, Laxman,Arkile, Manisha,Sarkar, Dhiman,Shingate, Bapurao B.
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p. 413 - 421
(2017/02/03)
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- Leishmanicidal and cytotoxic activity of hederagenin-bistriazolyl derivatives
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Aiming to obtain new potent leishmanicidal and cytotoxic compounds from natural sources, the triterpene hederagenin was converted into several new 1,2,3-triazolyl derivatives tethered at C-23 and C-28. For this work hederagenin was isolated from fruits of
- Rodríguez-Hernández, Diego,Barbosa, Luiz C.A.,Demuner, Antonio J.,Nain-Perez, Amalyn,Ferreira, Sebasti?o R.,Fujiwara, Ricardo T.,de Almeida, Raquel M.,Heller, Lucie,Csuk, René
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supporting information
p. 624 - 635
(2017/10/13)
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- A 1, 2, 3 - the triazole is joint 1, 3, 4 - oxdiazole compound and use thereof
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The invention discloses a 1, 2, 3-triazole-linked 1, 3, 4-oxadiazole compound and application thereof. The 1,2,3-triazole-linked 1,3,4-oxadiazole compound is shown in a formula (I): 2-R-(5-(1-(2-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-yl)-1,3,4-oxadiazole-2-sulfide), wherein a substituent R is C1-C12 alkyl, -COOR1, -R2COOR3 or -CH(R4)COR5, R1 can be H, a branched chain or C1-C4 alkyl or benzyl of the branched chain, R2 can be a linear chain or C1-C4 alkylidene of a branched chain, R3 can be H or C1-C4 alkyl of the linear chain or the branched chain, R4 is selected from H or 1H-1,2,4-triazolyl; R5 is selected from C1-C4 alkyl of the linear chain or the branched chain or a substituted phenyl, the amount of the substituent on the substituted phenyl is one or more, and the substituents are respectively and independently selected from halogens or 3-chlorophenoxy. The 2-R-(5-(1-(2-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-yl)-1,3,4-oxadiazole-2-sulfide) can be applied to preparation of antibacterial agents, has inhibition action on various bacteria (including bacillus subtilis, Escherichia coli and aspergillus fumigatus) and is simple in synthetic process and can be put into industrial production easily.(The formula of the compound is shown in the specification).
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Paragraph 0027; 0028
(2017/10/13)
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- Synthesis and antibacterial activity of novel 4″-O-(1-aralkyl-1,2,3-triazol-4-methyl-carbamoyl) azithromycin analogs
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Three novel structural series of 4″-O-(1-aralkyl-1,2,3-triazol-4-methyl-carbamoyl) azithromycin analogs were designed, synthesized and evaluated for their in vitro antibacterial activity. All the target compounds exhibited excellent activity against erythromycin-susceptible Streptococcus pyogenes, and significantly improved activity against three phenotypes of erythromycin-resistant Streptococcus pneumoniae compared with clarithromycin and azithromycin. Among the three series of azithromycin analogs, the novel series of 11,4″-disubstituted azithromycin analogs 9a–k exhibited the most effective and balanced activity against susceptible and resistant bacteria. Among them, compound 9j showed the most potent activity against Staphylococcus aureus ATCC25923 (0.008?μg/mL) and Streptococcus pyogenes R2 (1?μg/mL). Besides, all the 11,4″-disubstituted azithromycin analogs 9a–k except 9f shared the identical activity with the MIC value 0.002?μg/mL against Streptococcus pyogenes S2. Furthermore, compounds 9g, 9h, 9j and 9k displayed significantly improved activity compared with the references against all the three phenotypes of resistant S. pneumoniae. Particularly, compound 9k was the most effective (0.06, 0.03 and 0.125?μg/mL) against all the erythromycin-resistant S. pneumoniae expressing the erm gene, the mef gene and the erm and mef genes, exhibiting 2133, 133 and 2048-fold more potent activity than azithromycin, respectively.
- Wang, Yinhu,Cong, Chao,Chern Chai, Wern,Dong, Ruiqian,Jia, Li,Song, Di,Zhou, Ziteng,Ma, Shutao
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supporting information
p. 3872 - 3877
(2017/07/27)
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- Design and synthesis of new triazoles linked to xanthotoxin for potent and highly selective anti-gastric cancer agents
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Two series of xanthotoxin-triazole derivatives were designed, synthesized, and studied for their antiproliferative properties. The in vitro cytotoxicity of the compounds in the AGS cancer cell line and the L02 normal cell line was evaluated via MTT assay. Among the synthesized compounds, 9-((1-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)-7H-furo[3,2-g]chromen-7-one (6p) was found to have the greatest antiproliferative activity against AGS cells (IC50 = 7.5 μM) and showed better activity than the lead compound (xanthotoxin, IC50 > 100 μM) and the reference drug (5-fluorouracil, IC50 = 29.6 μM) did. The IC50 value of 6p in L02 cells was 13.3 times higher than that in the AGS cells. Therefore, the compound exhibited better therapeutic activity and specificity compared with the positive control 5-fluorouracil. Cell cycle analysis revealed that compound 6p inhibited cell growth via the induction of S/G2 phase arrest in AGS cells. Compound 6p was identified as a promising lead compound for the further development and identification of 1,2,3-triazole-based anticancer agents.
- Shen, Qing-Kun,Liu, Chuan-Feng,Zhang, Hong-Jian,Tian, Yu-Shun,Quan, Zhe-Shan
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supporting information
p. 4871 - 4875
(2017/09/27)
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- Synthesis and bioactivity of novel triazole incorporated benzothiazinone derivatives as antitubercular and antioxidant agent
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In search of new active molecules against Mycobacterium tuberculosis (MTB) H37Ra and M. bovis BCG, a small focused library of benzothiazinone based 1,2,3-triazoles has been efficiently prepared via click chemistry approach. Several derivatives were found to be promising inhibitors of MTB and M. bovis BCG characterized by lower MIC values (27.34-29.37 μg/mL). Among all the synthesized compounds, 6c and 6e is the most active compound against MTB and M. bovis BCG. The compounds were further tested for anti-proliferative activity against HeLa, A549 and A431 cell lines using MTT assay and showed no significant cytotoxic activity at the maximum concentration evaluated. Further, the synthesized compounds were found to have potential antioxidant activity with IC50 range = 14.14-47.11 μg/mL. Furthermore, to rationalize the observed biological activity data, the molecular docking study also been carried out against a potential target MTB DprE1, which revealed a significant correlation between the binding score and biological activity for these compounds. The results of the in vitro and in silico study suggest that the triazole incorporated benzothiazinone may possess the ideal structural requirements for further development of novel therapeutic agents.
- Shaikh, Mubarak H.,Subhedar, Dnyaneshwar D.,Arkile, Manisha,Khedkar, Vijay M.,Jadhav, Nandadeep,Sarkar, Dhiman,Shingate, Bapurao B.
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p. 561 - 569
(2016/01/09)
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- 1,2,3-Triazole incorporated coumarin derivatives as potential antifungal and antioxidant agents
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A series of novel ethyl-7-((1-(benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-2-oxo-2H-chromene-3-carboxylates 8a-h as potential antifungal agents were synthesized via click chemistry. The antifungal activity was evaluated against five human pathogenic fungal strains, such as Candida albicans, Fusarium oxysporum, Aspergillus flavus, Aspergillus niger and Cryptococcus neoformans. Compound 8c, 8d, 8e and 8h were found to be equipotent against C. albicans when compared with miconazole and compound 8f was found to be two-fold more active compared with miconazole and equipotent to fluconazole against C. albicans. The coumarin-based triazole derivatives were also evaluated for antioxidant activity and compound 8a was found to be potent antioxidant when compared with standard drug. Furthermore, molecular docking study of the newly synthesized compounds was performed and results showed good binding mode in the active site of fungal C. albicans enzyme P450 cytochrome lanosterol 14α-demethylase. Moreover, the synthesized compounds were also analyzed for ADME properties and showed potential to build up as good oral drug candidates.
- Shaikh, Mubarak H.,Subhedar, Dnyaneshwar D.,Khan, Firoz A. Kalam,Sangshetti, Jaiprakash N.,Shingate, Bapurao B.
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p. 295 - 301
(2018/03/22)
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- Novel hederagenin-triazolyl derivatives as potential anti-cancer agents
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A series of novel aryl-1H-1,2,3-triazol-4-yl methylester and amide derivatives of the natural product hederagenin was synthesized aiming to develop new antitumor agents, using Huisgen 1,3-dipolar cycloaddition reactions, with yields between 35% and 95%. T
- Rodríguez-Hernández, Diego,Demuner, Antonio J.,Barbosa, Luiz C.A.,Heller, Lucie,Csuk, René
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p. 257 - 267
(2016/04/05)
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- TRIAZOLO[4,5-D]PYRIMIDINES AS AGONISTS OF THE CANNABINOID RECEPTOR 2
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The invention relates to a compound of formula (I) wherein R1to R4and n are defined as in the description and in the claims. The present invention relates to organic compounds useful for therapy and/or prophylaxis in a mammal, and in
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Page/Page column 18
(2016/06/01)
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- Discovery of 7-Methyl-10-Hydroxyhomocamptothecins with 1,2,3-Triazole Moiety as Potent Topoisomerase I Inhibitors
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Homocamptothecin is emerging as an important topoisomerase I inhibitor originating in natural product camptothecin. We report the modifications and SAR of homocamptothecin on position C10 to develop potent topoisomerase I inhibitors for anticancer drug di
- Xu, Xiguo,Wu, Yuelin,Liu, Wenfeng,Sheng, Chuanquan,Yao, Jianzhong,Dong, Guoqiang,Fang, Kun,Li, Jin,Yu, Zhiliang,Min, Xiao,Zhang, Huojun,Miao, Zhenyuan,Zhang, Wannian
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p. 398 - 403
(2016/10/19)
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- One-pot synthesis of oxoisoindoline-1,2,3-triazole hybrid by a Ugi–click reaction
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1,2,3-Triazole-3-oxoisoindoline-1-carboxamide system was successfully synthesized by using a combination of Ugi and click reactions. This two-step, one-pot synthesis was started by the reaction of 2-formyl benzoic acid, propargyl amine, and cyclohexyl iso
- Akrami, Sara,Firoozpour, Loghman,Goli-Garmroodi, Fereshteh,Moghimi, Setareh,Mahdavi, Mohammad,Zonouzi, Afsaneh,Foroumadi, Alireza
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p. 1708 - 1712
(2016/10/21)
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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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- Containing 1, 2, 3-triazole 2, 4, 6-trisubstituted pyrimidine compound, preparation method and its application
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The invention discloses 2,4,6-trisubstituted pyrimidine compounds containing 1,2,3-triazole, a preparation method and application thereof in preparation of medicine and belongs to the field of medicinal chemistry. A pyrimidine parent nucleus and a 1,2,3-triazole activity unit are combined by using classical click chemistry to simply and efficiently synthesize the 2,4,6-trisubstituted pyrimidine compounds containing 1,2,3-triazole in an environment-friendly manner. The 2,4,6-trisubstituted pyrimidine compounds containing 1,2,3-triazole have a structure general formula as shown in the specification. In vitro anticancer activity tests show that the compounds have a certain inhibition effect on many tumor cells including EC-109, MCF-7, MGC-803 and B16 and can be applied to preparation of an antitumor medicine, as a further developed candidate or lead compound.
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Paragraph 0046; 0068; 0122
(2016/10/10)
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- Efficient synthesis of new antiproliferative steroidal hybrids using the molecular hybridization approach
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A series of steroidal hybrids with different terminal bioactive scaffolds were synthesized using the molecular hybridization approach and further evaluated for their antiproliferative activity against several cancer cell lines of different origins using t
- Yu, Bin,Qi, Ping-Ping,Shi, Xiao-Jing,Huang, Ruilei,Guo, Hao,Zheng, Yi-Chao,Yu, De-Quan,Liu, Hong-Min
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p. 241 - 255
(2016/04/26)
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- Clay-Supported Cu(II) Catalyst: An Efficient, Heterogeneous, and Recyclable Catalyst for Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Alloxan-Derived Terminal Alkyne and Substituted Azides Using Click Chemistry
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A novel series of alloxan-derived 1,4-disubstituted 1,2,3-triazoles was synthesized in excellent yields under catalytic conditions using a click reaction strategy through 1,3-dipolar cycloaddition. Their structures have been ascertained on the basis of spectroanalytical and elemental analysis data. Synthesis of hybrid compounds with varying substitutions in the triazole ring was achieved by reaction between alloxan-derived terminal alkyne and a pertinent azide derivative in the presence of clay-Cu(II) as the catalyst in methanolic medium. Also, comparative evaluation of various catalytic systems [viz., CuI, CuSO4, CuI-zeolite, K10Ti, and clay-Cu(II)] was investigated. Of these catalytic systems, clay-Cu(II) was observed to be the best. The catalyst was recyclable for several runs without showing significant loss in its activity. The good selectivity, cost-efficiency, short reaction time, milder reaction conditions, and simple workup procedure are the added salient features of this synthetic protocol.
- Dubey, Nitin,Sharma, Pratibha,Kumar, Ashok
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p. 2608 - 2626
(2015/11/28)
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- O-(triazolyl)methyl carbamates as a novel and potent class of Fatty Acid Amide Hydrolase (FAAH) inhibitors
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Inhibition of fatty acid amide hydrolase (FAAH) activity is under investigation as a valuable strategy for the treatment of several disorders, including pain and drug addiction. A number of potent FAAH inhibitors belonging to different chemical classes have been disclosed to date; O-aryl carbamates are one of the most representative families. In the search for novel FAAH inhibitors, a series of O-(1,2,3-triazol-4-yl)methyl carbamate derivatives were designed and synthesized exploiting a coppercatalyzed [3+2] cycloaddition reaction between azides and alkynes (click chemistry). Exploration of the structure-activity relationships within this new class of compounds identified potent inhibitors of both rat and human FAAH with IC50 values in the single-digit nanomolar range. In addition, these derivatives showed improved stability in rat plasma and kinetic solubility in buffer with respect to the lead compound. Based on the results of the study, the novel analogues identified can be considered to be promising starting point for the development of new FAAH inhibitors with improved drug-like properties.
- Colombano, Giampiero,Albani, Clara,Ottonello, Giuliana,Ribeiro, Alison,Scarpelli, Rita,Tarozzo, Glauco,Daglian, Jennifer,Jung, Kwang-Mook,Piomelli, Daniele,Bandiera, Tiziano
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supporting information
p. 380 - 395
(2015/02/05)
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- NOVEL TRIAZOLO[4,5-D]PYRIMIDINE DERIVATIVES
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The invention relates to a compound of formula (I) wherein R1 to R4 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.
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Page/Page column 25
(2015/03/28)
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- Phase-Vanishing Method with Acetylene Evolution and Its Utilization in Several Organic Syntheses
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A novel quadraphasic phase-vanishing system in which acetylene is evolved from calcium carbide and directly applied in situ to the Sonogashira coupling reaction was developed. This method, which provides a safe, convenient, and one-pot means to utilize gaseous reagents without special equipment, was also applied to a Cu-catalyzed azide-alkyne cycloaddition (CuAAC) reaction and a three-component aldehyde-alkyne-amine (A3) coupling reaction with excellent results. (Figure Presented).
- Matake, Ryosuke,Niwa, Yuki,Matsubara, Hiroshi
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supporting information
p. 2354 - 2357
(2015/06/02)
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- A dicationic, podand-like, ionic liquid water system accelerated copper-catalyzed azide-alkyne click reaction
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In this work, an effective, task specific, dicationic, podand-like ionic liquid was synthesized and applied to improve the capability features of click reaction. Moreover, to broaden the scope and decreasing the serious limitations of preparation methods of organic azides, a simple green procedure for the preparation of alkyl azides, the fundamental starting materials in click reactions, from alcohols under solvent-free conditions and microwave irradiation has been reported, for the first time.
- Javaherian, Mohammad,Kazemi, Foad,Ghaemi, Masoumeh
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p. 1643 - 1647
(2015/01/09)
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- One-pot green synthesis of azides from alcohols using bronsted acidic ionic liquid [HMIM][BF4] as solvent and catalyst
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Bronsted acidic ionic liquid, [HMIM][BF4], has been used as a non-volatile, eco-friendly solvent, and catalytic medium for the one-pot green synthesis of azides from corresponding alcohols. The [HMIM][BF 4] showed high reactivity than [BMIM][BF4] and [BMIM][PF6], affording azides in up to 97% yield, which could be easily separated from the reaction mixture. The ease of recyclability of [HMIM][BF4] makes the reaction economically and potentially viable for practical applications. Azides are versatile substrates in organic synthesis and serve as convenient intermediate in the synthesis of pharmaceutical heterocycles and natural products. By using dual functional [HMIM][BF 4] as solvent and catalyst, efficient synthesis of azides from their corresponding alcohols have been undertaken under eco-friendly conditions. This study may pave the way for practical application of [HMIM][BF4] in cholesterylamine synthesis.
- Garg, Bhaskar,Ling, Yong-Chien
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p. 737 - 742
(2014/07/22)
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- GPR17-MODULATING COMPOUNDS, DIAGNOSTIC AND THERAPEUTIC USES THEREOF
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Disclosed are compounds able to modulate the activity of the GPR17 receptor in a highly specific way, which are useful in the treatment and diagnosis of diseases or dysfunctions involving the activation of said receptor. In particular, the compounds according to the invention can be used for neuroprotective and/or reparatory purposes, in cerebral, cardiac and renal ischaemia, in cerebral trauma, in chronic neurodegenerative diseases such as amyotrophic lateral sclerosis (ALS), and in demyelinating diseases such as multiple sclerosis.
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Paragraph 0066-0067
(2014/06/11)
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- Synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters from arylmethyl azides via a domino process
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A convenient synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters via a domino process is described. The synthesis employs arylmethyl azides as the precursor which undergoes an acid-promoted rearrangement to give an N-aryl iminium ion. Following the addition with ethyl 3-ethoxyacrylate, intramolecular electrophilic aromatic substitution, elimination and subsequent oxidation, the quinoline products were obtained in moderate to excellent yields.
- Tummatorn, Jumreang,Thongsornkleeb, Charnsak,Ruchirawat, Somsak,Gettongsong, Tanita
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p. 1463 - 1467
(2013/05/08)
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