- Synthesis and biological evaluation of novel 3-O-tethered triazoles of diosgenin as potent antiproliferative agents
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Diosgenin, a promising anticancer steroidal sapogenin, was isolated from Dioscorea deltoidea. Keeping its stereochemistry rich architecture intact, a scheme for the synthesis of novel diosgenin analogues was designed using Cu (I)-catalysed alkyne-azide cy
- Masood-ur-Rahman,Mohammad, Younis,Fazili, Khalid Majid,Bhat, Khursheed Ahmad,Ara, Tabassum
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- Ultrasonic-Assisted Synthesis of Pyrazolo[3,4-d]pyrimidin-4-ol Tethered with 1,2,3-Triazoles and Their Anticancer Activity
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Abstract: In the presents work synthesis and characterization of new heterocyclic derivatives containing pyrazolo[3,4-d]pyrimidine linkage with 1,4-disubstituted-1,2,3-triazoles via methylene-oxy group. The selected synthesized compounds were tested for their in-vitro anticancer activity against various cancer cell lines. Synthesis of compounds was done under ultrasonic-assisted Huisgen 1,3-dipolar cycloaddition reaction with good yields. Some of the newly synthesized compounds demonstrated good to moderate anticancer activity, most of compounds shows activity against renal cancer cell lines.
- Bhatt, Tejal D.,Gojiya, Dinesh G.,Hadiyal, Sanjay D.,Joshi, Dr. Hitendra S.,Kapupara, Vimal H.,Prakash, L. Kalavadiya
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- Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential
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Here we report the design, synthesis and lead optimization of hydroxychavicol (1) a high yielding metabolite ubiquitously present in the Piper betel leaves with the significant cytotoxic activity. This is the first report to describe the synthetic strateg
- Kumar, Sunil,Pathania, Anoop S.,Satti, Naresh K.,Dutt, Parbhu,Sharma, Neha,Mallik, Fayaz A.,Ali, Asif
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- Synthesis of new triazole fused imidazo[2,1-b]thiazole hybrids with emphasis on Staphylococcus aureus virulence factors
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A series of new triazole fused imidazo[2,1-b]thiazole hybrids (9a–u) were designed, synthesized and evaluated as antimicrobial agents. Compounds 9c, 9d, 9e, 9j and 9l showed promising broad spectrum antimicrobial activity. Further, compound 9c exhibited s
- Shareef, Mohd Adil,Sirisha, Kanugala,Sayeed, Ibrahim Bin,Khan, Irfan,Ganapathi, Thipparapu,Akbar, Syed,Ganesh Kumar,Kamal, Ahmed,Nagendra Babu, Bathini
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- Antileishmanial activity and structure-activity relationship of triazolic compounds derived from the neolignans grandisin, veraguensin, and machilin G
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Sixteen 1,4-diaryl-1,2,3-triazole compounds 4-19 derived from the tetrahydrofuran neolignans veraguensin 1, grandisin 2, and machilin G 3 were tested against Leishmania (Leishmania) amazonensis intracellular amastigotes. Triazole compounds 4-19 were synthetized via Click Chemistry strategy by 1,3-dipolar cycloaddition between terminal acetylenes and aryl azides containing methoxy and methylenedioxy groups as substituents. Our results suggest that most derivatives were active against intracellular amastigotes, with IC50 values ranging from 4.4 to 32.7 μM. The index of molecular hydrophobicity (ClogP) ranged from 2.8 to 3.4, reflecting a lipophilicity/hydrosolubility rate suitable for transport across membranes, which may have resulted in the potent antileishmanial activity observed. Regarding structure-activity relationship (SAR), compounds 14 and 19, containing a trimethoxy group, were the most active (IC50 values of 5.6 and 4.4 μM, respectively), with low cytotoxicity on mammalian cells (SI = 14.1 and 10.6). These compounds induced nitric oxide production by the host macrophage cells, which could be suggested as the mechanism involved in the intracellular killing of parasites. These results would be useful for the planning of new derivatives with higher antileishmanial activities.
- Costa, Eduarda C.,Cassamale, Tatiana B.,Carvalho, Diego B.,Bosquiroli, Lauriane S. S.,Ojeda, Mariáh,Ximenes, Thalita V.,Matos, Maria F. C.,Kadri, M?nica C. T.,Baroni, Adriano C. M.,Arruda, Carla C. P.
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Read Online
- 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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- Synthesis of New Thieno[2,3-d]pyrimidines Containing a 1,2,3-Triazole Ring and Their Therapeutic Response in NCI-60 Cell Line Panel
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Abstract: A series of new tetrahydro[1]benzothieno[2,3-d]pyrimidines containing a 1,2,3-triazole fragment linkedthrough an oxymethylene spacer have been synthesized by click reaction of4-(prop-2-yn-1-yloxy)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidines with various aryl and alkyl azides inthe presence of copper sulfate and sodium ascorbate as a catalyst. Thestructures of the synthesized compounds were characterized by variousspectroscopic techniques (1H and13C NMR, FT-IR, and mass spectrometry), and theirin vitro anticancer activity against NCI-60 human tumor cell lines wasevaluated. Among the compounds tested, N-(pyridine-3-yl)-acetamide derivative exhibited significantactivity against several cancer cell lines, including SF-539 (CNS cancer),HCT-116 (colon cancer), OVCAR-8 (ovarian cancer), PC-3 (prostate cancer), andCCRF-CEM (leukemia).
- Baluja, S. H.,Bhensdadia, K. A.,Lalavani, N. H.
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p. 1668 - 1677
(2021/12/13)
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- Regioselective synthesis of 4-fluoro-1,5-disubstituted-1,2,3-triazoles from synthetic surrogates of α-fluoroalkynes
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α-Fluoroalkynes are elusive molecules due to their instability and inaccessibility. Here, we show that α-fluoronitroalkenes can serve as synthetic surrogates of α-fluoroalkynes in [3+2] cycloaddition reactions with organic azides facilitated by a catalytic amount of trifluoroacetic acid (TFA). This work provides the first regioselective method to access 4-fluoro-1,5-disubstituted-1,2,3-triazoles.
- Jana, Sampad,Adhikari, Sweta,Cox, Michael R.,Roy, Sudeshna
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supporting information
p. 1871 - 1874
(2020/02/20)
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- Synthesis and Antitrypanosomal Activity of 1,4-Disubstituted Triazole Compounds Based on a 2-Nitroimidazole Scaffold: a Structure-Activity Relationship Study
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Chagas disease affects 6–8 million people worldwide, remaining a public health concern. Toxicity, several adverse effects and inefficiency in the chronic stage of the disease are the major challenges regarding the available treatment protocols. This work involved the synthesis of twenty-two 1,4-disubstituted-1,2,3-triazole analogues of benznidazole (BZN), by using a click chemistry strategy. Analogues were obtained in moderate to good yields (40-97 %). Antitrypanosomal activity was evaluated against the amastigote forms of Trypanosoma cruzi. Compound 8 a (4-(2-nitro-1H-imidazol-1-yl)methyl)-1-phenyl-1H-1,2,3-triazole) without substituents on phenyl ring showed similar biological activity to BZN (IC50=3.0 μM, SI>65.3), with an IC50=3.1 μM and SI>64.5. Compound 8 o (3,4-di-OCH3?Ph) with IC50 = 0.65 μM was five-fold more active than BZN, and showed an excellent selectivity index (SI>307.7). Compound 8 v (3-NO2, 4-CH3?Ph) with IC50=1.2 μM and relevant SI>166.7, also exhibited higher activity than BZN. SAR analysis exhibited a pattern regarding antitrypanosomal activity relative to BZN, in compounds with electron-withdrawing groups (Hammett σ+) at position 3, and electron-donating groups (Hammett σ-) at position 4, as observed in 8 o and 8 v. Further research might explore in vivo antitrypanosomal activity of promising analogues 8 a, 8 o, and 8 v. Overall, this study indicates that approaches such as the bioisosteric replacement of amide group by 1,2,3-triazole ring, the use of click chemistry as a synthesis strategy, and design tools like Craig-plot and Topliss tree are promising alternatives to drug discovery.
- Assun??o, Elvis L. F.,Carvalho, Diego B.,das Neves, Amarith R.,Kawasoko Shiguemotto, Cristiane Y.,Portapilla, Gisele B.,de Albuquerque, Sergio,Baroni, Adriano C. M.
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p. 2019 - 2028
(2020/09/21)
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- Iron and Ruthenium Glycoporphyrins: Active Catalysts for the Synthesis of Cyclopropanes and Aziridines
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In view of the relevance of cyclopropanes and aziridines as synthetic building blocks as well as active parts in biological and pharmaceutical compounds, the development of sustainable synthetic procedures for obtaining these products continues to be a si
- Damiano, Caterina,Gadolini, Sebastiano,Intrieri, Daniela,Lay, Luigi,Colombo, Cinzia,Gallo, Emma
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supporting information
p. 4412 - 4420
(2019/11/03)
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- Synthesis, and evaluation of in vitro and in vivo anticancer activity of 14-substituted oridonin analogs: A novel and potent cell cycle arrest and apoptosis inducer through the p53-MDM2 pathway
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A series of novel oridonin derivatives bearing various substituents on the 14-OH position were designed and synthesised. Their antitumour activity was evaluated in vitro against three human cancer cell lines (HCT116, BEL7402, and MCF7). Most tested derivatives showed improved anti-proliferative activity compared to the lead compound oridonin and the positive control drug 5-fluorouracil (5-Fu). Among them, compound C7 (IC50 = 0.16 μM) exhibited the most potent anti-proliferative activity against HCT116 cells; it was about 43- and 155-fold more efficacious than that of oridonin (IC50 = 6.84 μM) and 5-Fu (IC50 = 24.80 μM) in HCT116 cancer cells. Interestingly, the IC50 value of compound C7 in L02 normal cells was 23.6-fold higher than that in HCT116 cells; it exhibited better selective anti-proliferative activity and specificity than oridonin and 5-Fu. Furthermore, compound C7 possibly induced cell cycle arrest and apoptosis by regulating the p53-MDM2 signalling pathway. Notably, C7 displayed more significant suppression of tumour growth than oridonin in colon tumour xenograft models where the tumour growth inhibition rate was 85.82%. Therefore, compound C7 could be a potential lead compound for the development of a novel antitumour agent.
- Shen, Qing-Kun,Deng, Hao,Wang, Shi-Ben,Tian, Yu-Shun,Quan, Zhen-Shan
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- Aryl Azides as Forgotten Electrophiles in the Van Leusen Reaction: A Multicomponent Transformation Affording 4-Tosyl-1-arylimidazoles
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Considering aryl azides as electrophilic partners for the TosMIC mediated Van Leusen reaction, a novel multicomponent synthesis of 4-tosyl-1-arylimidazoles is reported. In this transformation, two molecules of TosMIC participate in the reaction mechanism
- Necardo, Cristiana,Alfano, Antonella Ilenia,Del Grosso, Erika,Pelliccia, Sveva,Galli, Ubaldina,Novellino, Ettore,Meneghetti, Fiorella,Giustiniano, Mariateresa,Tron, Gian Cesare
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p. 16299 - 16307
(2019/12/27)
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- Design, synthesis and anticancer biological evaluation of novel 1,4-diaryl-1,2,3-triazole retinoid analogues of tamibarotene (AM80)
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We report herein the design and synthesis via click chemistry of twelve novel triazole retinoid analogues of tamibarotene (AM80) and the evaluation of their anticancer activities against six cancer cell lines: HL60, K562, 786, HT29, MCF7 and PC3. Among the synthesized compounds, two were more potent than tamibarotene against solid tumor cells, and one of them had similar potency to tamibarotene against HL60 cells. The bioisosteric exchange between the amide group and the 1,2,3-triazole core in the retinoid agent tamibarotene (AM80) reported in this work is a valid strategy for the generation of useful compounds against cancer.
- Aleixo, Mariana A. A.,Garcia, Taís M.,Carvalho, Diego B.,Viana, Luiz H.,Amaral, Marcos S.,Kassab, Najla M.,Cunha, Marilin C.,Pereira, Indiara C.,Guerrero, Palimécio G,Perdomo, Renata T.,Matos, Maria F. C.,Baroni, Adriano C. M.
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p. 109 - 124
(2017/12/08)
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- In vitro antiplasmodial efficacy of synthetic coumarin-triazole analogs
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Twenty two diverse coumarin-triazole derivatives were synthesized by alkylation of 7-hydroxy-4-methyl-coumarin followed by click chemistry at 7-position. These compounds were evaluated for their in vitro antiplasmodial activity against chloroquine sensitive strain of Plasmodium falciparum (3D7). Compound 9 (7-[1-(2, 4-dimethoxy-phenyl)-1H- [1–3] triazol-4-ylmethoxy]-4-methyl-chromen-2-one) was found most active with IC50 value 0.763 ± 0.0124 μg/mL. Further, the structure of compound 20 was characterized by single crystal X-ray diffraction. In view of impressive results, we considered it worthwhile to validate the results of in vitro antiplasmodial activity by assessing whether these compounds are capable of hampering the catalytic activity of DNA gyrase, thus preventing its supercoiling function.
- Yadav, Neesha,Agarwal, Drishti,Kumar, Satyanand,Dixit,Gupta, Rinkoo D.,Awasthi, Satish K.
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p. 735 - 745
(2018/02/06)
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- Design and synthesis of novel dehydroepiandrosterone analogues as potent antiproliferative agents
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The aim of the present study was to determine the cytotoxic effects of a series of novel dehydroepiandrosterone derivatives containing triazole at the C16 position on human cancer cells. The cancer cells used in the present study were A549, Hel
- Huang, Xing,Shen, Qing-Kun,Zhang, Hong-Jian,Li, Jia-Li,Tian, Yu-Shun,Quan, Zhe-Shan
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- QUINOLIN-2-ONE DERIVATIVES
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Compounds of the formula (I) in which X1, X2, X3, X4, R1, R2, R3, Q and Y have the meanings indicated in Claim 1, are inhibitors of c-Kit kinase, and can be employed for the treatment of cancer.
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Page/Page column 56; 59
(2017/08/07)
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- Novel 1-(3,4,5-trialkoxyphenyl)-1H-1,2,3-triazole derivatives, method for manufacturing the same and composition comprising the same
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In the present invention, disclosed are: a novel compound of 1-(3,4,5-trialkoxyphenyl)-1H-1,2,3-triazole derivative, which has osteoblast differentiation capacity and is represented by chemical formula 1; isomers of the compound, pharmaceutically acceptab
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Paragraph 0095-0097
(2017/11/23)
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- Synthesis of Gallic-Acid-1-Phenyl-1H-[1,2,3]Triazol-4-yl Methyl Esters as Effective Antioxidants
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Using a click chemistry approach, a series of gallic-acid-1-phenyl-1H-[1,2,3]triazol-4-ylmethyl esters was synthesized to develop more effective antioxidants. The results of DPPH screening indicate that few of the synthesized analogs display better antioxidant effect compared to the standards. Among all, compounds, 9 and 20 displayed highest DPPH radical scavenging effect with IC50 values as low as 6.4±0.2 and 7.9±0.4 μM respectively, compared to the standard ascorbic acid (IC50=12±0.8 μM) and gallic acid (IC50=9.0±0.6 μM). Compound 10 also displayed a potent antioxidant effect with IC50 of 10.80±0.4 μM. This study provides an important aspect with regard to the use of these gallic-acid based synthetic antioxidants in food industry as dietary supplements.
- Lone, Shabir H.,Rehman, Shakeel U,Bhat, Khursheed A.
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p. 111 - 118
(2017/02/15)
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- Synthesis of α-santonin derived acetyl santonous acid triazole derivatives and their bioevaluation for T and B-cell proliferation
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A new series of α-santonin derived acetyl santonous acid 1,2,3-triazole derivatives were synthesised using Huisgen 1,3-dipolar cyclo-addition reaction (click chemistry approach) and evaluated for their in vitro inhibition activity on concanavalin A (ConA) induced T cell proliferation and lipopolysaccharide (LPS) induced B cell proliferation. Among the synthesised series, compounds 2-10 and 19 exhibited significant inhibition against ConA and LPS stimulated T-cell and B-cell proliferation in a dose dependent manner. More significantly compounds 4, 9-10 and 19 exhibited potent inhibition activity with remarkably lower cytotoxicity on the mitogen-induced T cell and B cell proliferation at 1 μM concentration. The compound 6 displayed potent immunosuppressive effects with ~89% against LPS induced B-cell and ~83% against ConA stimulated T-cell proliferation at 100 μM concentration without cytotoxicity. Compound 10 was more selective against B cell proliferation and exhibited 81% and 69% suppression at 100 and 1 μM concentration respectively. The present study led to the identification of several santonin analogs with reduced cytotoxicity and strong inhibition activity against the cell proliferation induced by the mitogens.
- Dangroo, Nisar A.,Singh, Jasvinder,Dar, Alamgir A.,Gupta, Nidhi,Chinthakindi, Praveen K.,Kaul, Anpurna,Khuroo, Mohmmed A.,Sangwan, Payare L.
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p. 160 - 169
(2016/05/24)
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- Synthesis and Antitrypanosomastid Activity of 1,4-Diaryl-1,2,3-triazole Analogues of Neolignans Veraguensin, Grandisin and Machilin G
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Sixteen 1,4-diaryl-1,2,3-triazole compounds derived from the natural products veraguensin, grandisin and machilin G were synthesized, with yields of 78-92percent. Biological activity tests against Leishmania amazonensis promastigotes showed that three of these compounds were the most active, with maximum inhibitory concentration (IC50 ) values of 1.1, 3.71 and 7.23 μM. One compound was highly active against Leishmania infantum, with an IC50 value of 5.2 μM, and one derivative showed an IC50 value of 28.6 μM against Trypanosoma cruzi trypomastigotes. Regarding structureactivity relationship (SAR), hybrid 1,2,3-triazolic compounds containing a methylenedioxy group, showed the best antileishmanial and antitrypanosomal activities.
- Cassamale, Tatiana B.,Costa, Eduarda C.,Carvalho, Diego B.,Cassemiro, Nadla S.,Tomazela, Carolina C.,Marques, Maria C. S.,Ojeda, Mariáh,Matos, Maria F. C.,Albuquerque, Sérgio,Arruda, Carla C. P.,Baroni, Adriano C. M.
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p. 1217 - 1228
(2016/08/25)
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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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- A mode of action study of cationic anthraquinone analogs: a new class of highly potent anticancer agents
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Previously, we reported the synthesis and structure-activity relationship (SAR) study of a series of novel 4,9-dioxo-4,9-dihydro-1H-naphtho[2,3-d][1,2,3]triazol-3-ium salts, which had very potent anti-proliferative activities (low μM to nM GI50
- Shrestha, Jaya P.,Subedi, Yagya Prasad,Chen, Liaohai,Chang, Cheng-Wei Tom
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p. 2012 - 2022
(2015/11/23)
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- Regioselective conversion of arenes to N-aryl-1,2,3-triazoles Using C-H Borylation
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A one-pot protocol for the synthesis of N-aryl 1,2,3-triazoles from arenes by an iridium-catalyzed C-H borylation/copper catalyzed azidation/click sequence is described. 1mol % of Cu(OTf)2 was found to efficiently catalyze both the azidation and the click reaction. The applicability of this method is demonstrated by the late-stage chemoselective installation of 1,2,3-triazole moiety into unactivated molecules of pharmaceutical importance.
- Srinivasan, Rajavel,Coyne, Anthony G.,Abell, Chris
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p. 11680 - 11684
(2014/10/15)
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- Synthesis and anticancer structure activity relationship investigation of cationic anthraquinone analogs
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We have synthesized a series of novel 4,9-dioxo-4,9-dihydro-1H-naphtho[2,3- d][1,2,3]triazol-3-ium salts, which can be viewed as analogs of cationic anthraquinones. Unlike the similar analogs that we have reported previously, these compounds show relative
- Shrestha, Jaya P.,Fosso, Marina Y.,Bearss, Jeremiah,Chang, Cheng-Wei Tom
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- Magnetically recoverable CuFe2O4 nanoparticles: Catalyzed synthesis of aryl azides and 1,4-diaryl-1,2,3-triazoles from boronic acids in water
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Magnetically recoverable and reusable CuFe2O4 nanoparticles are shown to be highly efficient catalysts for the one-pot synthesis of biologically important 1,4-diaryl-1,2,3-triazoles starting from boronic acids, sodium azide, and acetylenes. The use of aqueous reaction medium at room temperature, the low cost and facile recovery of the catalyst by application of an external magnetic field, and consistently high catalytic efficiency for at least three consecutive cycles renders the protocol operationally attractive. Magnetic and catalytically competent CuFe 2O4 nanoparticles proved to be highly efficient in the three-component synthesis of 1,4-diaryl-1,2,3-triazoles, a class of compounds that has been recognized for its anticancer activity. Copyright
- Kumar, A. Suresh,Reddy, M. Amarnath,Knorn,Reiser,Sreedhar
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p. 4674 - 4680
(2013/07/26)
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- Synthesis of 3-O-propargylated betulinic acid and its 1,2,3-triazoles as potential apoptotic agents
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Cytotoxic agents from nature are presently the mainstay of anticancer chemotherapy, and the need to reinforce the arsenal of anticancer agents is highly desired. Chemical transformation studies carried out on betulinic acid, through concise 1,2,3-triazole
- Majeed, Rabiya,Sangwan, Payare L.,Chinthakindi, Praveen K.,Khan, Imran,Dangroo, Nisar A.,Thota, Niranjan,Hamid, Abid,Sharma, Parduman R.,Saxena, Ajit K.,Koul, Surrinder
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p. 782 - 792
(2013/07/25)
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- Design, synthesis and antimicrobial activity of novel benzothiazole analogs
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In an attempt to design and synthesize a new class of antimicrobials, dialkyne substituted 2-aminobenzothiazole was reacted with various substituted aryl azides to generate a small library of 20 compounds (3a-t) by click chemistry. Structures of the newly synthesized compounds were established on the basis of spectral data. These compounds were screened for their antibacterial activity against Gram+ bacteria (Staphylococcus aureus and Enterococcus faecalis), Gram- bacteria (Salmonella typhi, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Shigella boydii) and antifungal activity against Candida tropicalis, Candida albicans, Candida krusei, Cryptococcus neoformans) as well as molds (Aspergillus niger, Aspergillus fumigatus). The compound 3e showed maximum potency against all Gram+/gram- bacterial strains with MIC value 3.12 μg/ml, which is two fold more active as compared to standard drug ciprofloxacin (MIC 6.25 μg/ml). However, all compounds were found ineffective against S. boydii (clinical isolate). Further, only one compound 3n was found to be the most active against all fungal strains with MIC value in the range of 1.56 μg/ml-12.5 μg/ml while the remaining compounds showed moderate to weak antifungal activity.
- Singh, Manavendra K.,Tilak, Ragini,Nath, Gopal,Awasthi, Satish K.,Agarwal, Alka
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p. 635 - 644
(2013/07/27)
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- Zinc mediated azide-alkyne ligation to 1,5- and 1,4,5-substituted 1,2,3-triazoles
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A mild method for regioselective formation of 1,5-substituted 1,2,3-triazoles is described. The zinc-mediated reaction works at room temperature and is successful across a wide range of azido/alkynyl substrates. Additionally, the triazole 4-position can be further functionalized through the intermediate aryl-zinc to accommodate a diverse three-component coupling strategy.
- Smith, Christopher D.,Greaney, Michael F.
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supporting information
p. 4826 - 4829
(2013/10/08)
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- Increased endothelial cell selectivity of triazole-bridged dihalogenated A-ring analogues of combretastatin A-1
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The antiproliferative activity on ovarian cancer (SK-OV-3) cells of a series of triazole-bridged combretastatin analogues (37, 38, 40-43) containing dihalogenation of the A-ring is reported, and compared with their trimethoxy analogues (5, 15, 39). It was found that dihalogenation with either bromine or iodine was a tolerated modification when compared to the parent compound combretastatin (CA-4, 1) and had less effect than B-ring modification on potency. These compounds exhibited G2/M arrest, and maintained antitubulin activity. Further assays on human umbilical vein endothelial cells (HUVECs) demonstrated the potential antivascular effects of these triazoles. Of particular note was a 3,5-diiodo-4-methoxyaryl triazole (43) which had promising 7-fold selectivity for HUVECs over ovarian cancer cells.
- Beale, Thomas M.,Bond, Peter J.,Brenton, James D.,Charnock-Jones, D. Stephen,Ley, Steven V.,Myers, Rebecca M.
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experimental part
p. 1749 - 1759
(2012/04/10)
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- Metal-free 1,5-regioselective azide-alkyne [3+2]-cycloaddition
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[3+2]-cycloaddition reactions of aromatic azides and silylated alkynes in aqueous media yield 1,5-disubstituted-4-(trimethyl-silyl)-1H-1,2,3-triazoles. The formation of the 1,5-isomer is highly favored in this metal-free cycloaddition, which could be proven by 1D selective NOESY and X-ray investigations. Additionally, DFT calculations corroborate the outstanding favoritism regarding the 1,5-isomer. The described method provides a simple alternative protocol to metal-catalyzed "click chemistry" procedures, widening the scope for regioselective heavy-metal-free synthetic applications.
- Kloss, Florian,Koehn, Uwe,Jahn, Burkhard O.,Hager, Martin D.,Goerls, Helmar,Schubert, Ulrich S.
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supporting information; experimental part
p. 2816 - 2824
(2012/06/01)
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- Targeting bacterial biofilms: Design of a terpenoid-like library as non-toxic anti-biofilm compounds
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A new class of anti-biofilm compounds possessing 1,4-disubstituted-(1H)-1, 2,3-triazolic cores was designed. Their efficient synthesis was performed by means of click chemistry through 1,3-dipolar cycloadditions. Two compounds were found to act as specific anti-biofilm agents against a gram negative species.
- Sall, Cheikh,Dombrowsky, Linda,Bottzeck, Olivier,Praud-Tabaris, Annie,Blache, Yves
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experimental part
p. 1493 - 1497
(2011/04/23)
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- 1,2,3-Triazole analogs of combretastatin A-4 as potential microtubule-binding agents
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A series of cis-restricted 1,4- and 1,5-disubstituted 1,2,3-triazole analogs of combretastatin A-4 (1) have been prepared. Cytotoxicity and tubulin inhibition studies showed that 2-methoxy-5-((5-(3,4,5-trimethoxyphenyl)-1H-1,2, 3-triazol-1-yl)methyl)aniline (5e) and 2-methoxy-5-(1-(3,4,5-trimethoxybenzyl)- 1H-1,2,3-triazol-5-yl)aniline (6e) were two of the most active compounds. Molecular modeling studies revealed that the N-2 and N-3 atoms in the triazole rings in 5e and 6e did not form hydrogen bonds with the amino acids in the anticipated pharmacophore.
- Odlo, Kristin,Fournier-Dit-Chabert, Jérémie,Ducki, Sylvie,Gani, Osman A.B.S.M.,Sylte, Ingebrigt,Hansen, Trond Vidar
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experimental part
p. 6874 - 6885
(2010/10/19)
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- In situ "click" assembly of small molecule matrix metalloprotease inhibitors containing zinc-chelating groups
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(Chemical Equation Presented) A panel of small molecule-based MMP inhibitors containing rhodanine warheads was assembled using "one-pot" click chemistry. Upon biological screening, moderate inhibitors were identified which specifically targets MMP-7 and MMP-13 over other MMPs.
- Hu, Mingyu,Li, Junqi,Yao, Shao Q.
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supporting information; experimental part
p. 5529 - 5531
(2009/06/17)
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- COMPOUNDS FOR THE TREATMENT OF ANGIOGENESIS
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The invention relates to isoxazole, isothiazole, and triazole compounds that are useful for treating or inhibiting angiogenesis.
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Page/Page column 302
(2008/06/13)
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- 1,5-Disubstituted 1,2,3-triazoles as cis-restricted analogues of combretastatin A-4: Synthesis, molecular modeling and evaluation as cytotoxic agents and inhibitors of tubulin
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A series of cis-restricted 1,5-disubstituted 1,2,3-triazole analogues of combretastatin A-4 (1) have been prepared. The triazole 12f, 2-methoxy-5-(1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazol-5-yl)aniline, displayed potent cytotoxic activity against severa
- Odlo, Kristin,Hentzen, Jean,dit Chabert, Jeremie Fournier,Ducki, Sylvie,Gani, Osman A.B.S.M.,Sylte, Ingebrigt,Skrede, Martina,Florenes, Vivi Ann,Hansen, Trond Vidar
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p. 4829 - 4838
(2008/12/22)
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- 1, 2, 3 -TRIAZOLES INHIBITORS OF TUBULIN POLYMERIZATION FOR THE TREATMENT OF POLIFERATIVE DISORDERS
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The invention relates to compounds of structural formula (I): formula (I) or a pharmaceutically acceptable salt, solvate, clathrate, and prodrug thereof, wherein Ra, Rb, and R2 are defined herein. These compounds inhibit t
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Page/Page column 195
(2008/06/13)
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- Chemoselective hydrogenation method catalyzed by Pd/C using diphenylsulfide as a reasonable catalyst poison
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While Pd/C is one of the most useful catalysts for hydrogenation, the high catalyst activity of Pd/C causes difficulty in its application to chemoselective hydrogenation between different types of reducible functionalities. In order to achieve chemoselective hydrogenation using Pd/C, we investigated catalyst poison as a controller of the catalyst activity. We found that the addition of Ph2S (diphenylsulfide) to the Pd/C-catalyzed hydrogenation reaction mixture led to reasonable deactivation of Pd/C. By the use of the Pd/C-Ph2S catalytic system, olefins, acetylenes, and azides can be selectively reduced in the coexistence of aromatic carbonyls, aromatic halides, cyano groups, benzyl esters, and N-Cbz (benzyloxycarbonyl) protecting groups. The present method is promising as a general and practical chemoselective hydrogenation process in synthetic organic chemistry.
- Mori, Akinori,Mizusaki, Tomoteru,Miyakawa, Yumi,Ohashi, Eri,Haga, Tomoko,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao
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p. 11925 - 11932
(2007/10/03)
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- Rapid synthesis of triazole-modified resveratrol analogues via click chemistry
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Resveratrol is a phytoalexin able to display an array of biological activities. We decided to replace the double bond with a triazole ring using the archetypical click reaction: the Huisgen [3 + 2] cycloaddition. Seventy-two triazole derivatives were synt
- Pagliai, Francesca,Pirali, Tracey,Del Grosso, Erika,Di Brisco, Riccardo,Tron, Gian Cesare,Sorba, Giovanni,Genazzani, Armando A.
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p. 467 - 470
(2007/10/03)
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- Hypervalent iodine-induced nucleophilic substitution of para-substituted phenol ethers. Generation of cation radicals as reactive intermediates
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A novel hypervalent iodine induced nucleophilic substitution of para-substituted phenol ethers in the presence of a variety of nucleophiles is described. UV and ESR spectroscopic studies indicate that this reaction proceeds via cation radicals, [ArH?+], as reactive intermediates generated by single-electron transfer (SET) from a charge-transfer (CT) complex of phenol ethers with phenyliodine(III) bis(trifluoroacetate) (PIFA). This is the first case that involves a radical intermediate on hypervalent iodine oxidations of aromatic compounds.
- Kita, Yasuyuki,Tohma, Hirofumi,Hatanaka, Kenji,Takada, Takeshi,Fujita, Shigekazu,Mitoh, Shizue,Sakurai, Hiromu,Oka, Shigenori
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p. 3684 - 3691
(2007/10/02)
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