- Design, synthesis and biological evaluation of novel benzimidazole amidines as potent multi-target inhibitors for the treatment of non-small cell lung cancer
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A series of novel amidino 2-substituted benzimidazoles linked to 1,4-disubstituted 1,2,3-triazoles were synthesized by implementation of microwave and ultrasound irradiation in click reaction and subsequent condensation of thus obtained 4-(1,2,3-triazol-1
- Bistrovi?, Andrea,Krstulovi?, Luka,Harej, Anja,Grb?i?, Petra,Sedi?, Mirela,Ko?trun, Sanja,Paveli?, Sandra Kraljevi?,Baji?, Miroslav,Rai?-Mali?, Silvana
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- [HDBU][HSO4]-catalyzed facile synthesis of new 1,2,3-triazole-tethered 2,3-dihydroquinazolin-4[1H]-one derivatives and their DPPH radical scavenging activity
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A simple and efficient protocol has been developed for the synthesis of new1,2,3-triazole-2,3-dihydroquinazolin-4[1H]-one (DHQ) conjugates(6a?j) via ultrasound-assisted, solvent-free ionic liquid [HDBU][HSO4]-catalyzed reaction in good to excellent yields. This non-conventional, ultrasound-assisted route has taken the reactions over the conventional reflux method to provide good to excellent yields of the corresponding products (6a?j) in a very short time. In addition, mild reaction conditions, tolerance to functionalized substrates, ease of product isolation, prevention of its over oxidation and reusability of catalyst [HDBU][HSO4] are some key striking features of the methodology. The newly synthesized derivatives (6a?j) were screened for antioxidant activity using 1,1-diphenyl-2-picryl hydrazyl (DPPH) assay and are found to be a potent scavenger. The compounds 6b, 6c, 6d, 6e and 6i showed significant antioxidant activity. Molecular docking studies showed significant binding affinity in the active site of myeloperoxidase (MPO) enzyme and hence scavenged by inhibition of MPO. In silico ADMET and pharmacokinetic studies of the conjugates are very promising; a cumulative body of evidence suggests their medicinal value as a potential orally active drug candidate. Graphical abstract: [Figure not available: see fulltext.]
- Akolkar, Satish V.,Khedkar, Vijay M.,Nagargoje, Amol A.,Pisal, Parshuram M.,Sangshetti, Jaiprakash N.,Shingate, Bapurao B.,Siddiqui, Madiha M.
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- Selective CDK4/6 inhibition of novel 1,2,3-triazole tethered acridinedione derivatives induces G1/S cell cycle transition arrest via Rb phosphorylation blockade in breast cancer models
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CDK4 & CDK6 are essential regulators of initial cell cycle phases and are always considered an exciting choice for anti-cancer therapy. In the present study, we presented the structure-based rational design & synthesis of a new class of 1,2,3-triazole tet
- Praveenkumar,Gurrapu, Nirmala,Kolluri, Prashanth Kumar,Shivaraj,Subhashini,Dokala, Appaji
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- Synthesis, antiproliferative and antitrypanosomal activities, and DNA binding of novel 6-amidino-2-arylbenzothiazoles
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A series of 6-amidinobenzothiazoles, linked via phenoxymethylene or directly to the 1,2,3-triazole ring with a p-substituted phenyl or benzyl moiety, were synthesised and evaluated in?vitro against four human tumour cell lines and the protozoan parasite T
- Racané, Livio,Rep, Valentina,Kraljevi? Paveli?, Sandra,Grb?i?, Petra,Zonji?, Iva,Radi? Stojkovi?, Marijana,Taylor, Martin C.,Kelly, John M.,Rai?-Mali?, Silvana
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p. 1952 - 1967
(2021/09/03)
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- [Et3NH][HSO4] catalyzed solvent-free synthesis of new 1,2,3-triazolidene-indolinone derivatives
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A series of new 1,2,3-triazolidene-indolinone derivatives (17a-j) were designed and synthesized via [Et3NH] [HSO4] catalyzed solvent-free approach. The synthesis strongly relied on Knoevenagel condensation of 1,4-disubstituted 1,2,3-
- Nagargoje, Amol A.,Pisal, Parshuram M.,Raza, Akram K.,Shingate, Bapurao B.,Siddiqui, Madiha M.
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- Alternative Route Triggering Multistep Spin Crossover with Hysteresis in an Iron(II) Family Mediated by Flexible Anion Ordering
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Multistep spin crossover (SCO) compounds have attracted much attention, since they can be great candidates for high-density multinary memory devices. The introduction of substituents, such as methyl (Me), chloro (Cl), bromo (Br), and methoxy (MeO) groups,
- Hagiwara, Hiroaki,Minoura, Ryo,Udagawa, Taro,Mibu, Ko,Okabayashi, Jun
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supporting information
p. 9866 - 9880
(2020/07/24)
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- Synthesis and bioevaluation of α,α’-bis(1H-1,2,3-triazol-5-ylmethylene) ketones
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Abstract: Curcumin is an active component of turmeric that has poor solubility, stability and bioavailability. The monocarbonyl curcumin analogues were modified from curcumin to achieve more stable and active compounds as compared to curcumin. Therefore,
- Deshmukh, Tejshri R.,Krishna, Vagolu S.,Sriram, Dharmarajan,Sangshetti, Jaiprakash N.,Shingate, Bapurao B.
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p. 809 - 820
(2019/09/06)
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- Synthesis, characterization and photodynamic activity against bladder cancer cells of novel triazole-porphyrin derivatives
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Novel triazole-porphyrin derivatives (TZ-PORs) were synthesized through the Heck reaction and then incorporated into polyvinylpyrrolidone (PVP) micelles. After verifying that this incorporation did not compromise the photophysical and chemical features of
- Gomes, Ana T.P.C.,Fernandes, Rosa,Ribeiro, Carlos F.,Tomé, Jo?o P.C.,Neves, Maria G.P.M.S.,da Silva, Fernando de C.,Ferreira, Vítor F.,Cavaleiro, José A.S.
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- An allenylidene Au(i) catalyst derived from triazole units and its initial application
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An allenylidene Au(i) catalyst based on triazolylidene moieties, featuring the high s-donating ability (comparable to that of other NHC ligands) and largely enhanced p-accepting ability of its ligand, was developed for the first time. As compared with the
- Chen, Bai-Ling,Zhang, Yuan,Lei, Ya-Ru,Wang, Hui-Ming,Chen, Zili
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supporting information
p. 5787 - 5790
(2020/06/03)
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- Synthesis and Anticancer Activity of (E)-5-[(1-Aryl-1H-1,2,3-triazol-4-yl)methylene]thiazolidine-2,4-diones
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Abstract: A novel series of 1,2,3-triazolylthiazolidinedione analogs have been synthesized by the condensation of the corresponding 1-aryl-1H-1,2,3-triazole-4-carbaldehydes with thiazolidine-2,4-dione in the presence of KOH. The title compounds were evaluated for their in vitro anticancer activity using MTT assay against four cancer cell lines: A549 (lung), HT-29 (colon), MCF-7 (breast), and A375 (melanoma). Most compounds displayed good anticancer activity, but hydroxy- and nitro-substituted derivatives showed higher activity than the others.
- Manikala, V. K.,Rao, V. M.
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p. 863 - 868
(2020/07/03)
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- Electrophotocatalytic SNAr Reactions of Unactivated Aryl Fluorides at Ambient Temperature and Without Base
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The electrophotocatalytic SNAr reaction of unactivated aryl fluorides at ambient temperature without strong base is demonstrated.
- Huang, He,Lambert, Tristan H.
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supporting information
p. 658 - 662
(2019/11/28)
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- Ultrasound assisted rapid synthesis, biological evaluation, and molecular docking study of new 1,2,3-triazolyl pyrano[2,3-c]pyrazoles as antifungal and antioxidant agent
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In search of new generation of triazole based antifungal agents, synthesis of series of new 1,2,3-triazolyl pyrano[2,3-c]pyrazoles under ultrasonic irradiation using NaHCO3 has been reported. The bioevaluation results indicate that, the compoun
- Khare, Smita P.,Deshmukh, Tejshri R.,Sangshetti, Jaiprakash N.,Khedkar, Vijay M.,Shingate, Bapurao B.
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p. 2521 - 2537
(2019/07/15)
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- New 1,2,3-triazole-linked tetrahydrobenzo[b]pyran derivatives: Facile synthesis, biological evaluation and molecular docking study
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Abstract: An efficient ultrasound-promoted one-pot three-component synthesis of a series of new 1,2,3-triazole-linked tetrahydrobenzo[b]pyran derivatives as antifungal and antioxidant agents using NaHCO3 has been described for the first time. T
- Khare, Smita P.,Deshmukh, Tejshri R.,Akolkar, Satish V.,Sangshetti, Jaiprakash N.,Khedkar, Vijay M.,Shingate, Bapurao B.
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p. 5159 - 5182
(2019/07/04)
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- Synthesis and Antimicrobial Activity of (E)-2-[(1-Substituted Phenyl-1H-1,2,3-triazol-4-yl)methylene]-2,3-dihydro-1H-inden-1-ones
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A series of novel (E)-2-[(1-phenyl-1H-1,2,3-triazol-4-yl)methylene]-2,3-dihydro-1H-inden-1-one derivatives has been synthesized by condensation of 1-phenyl-1H-1,2,3-triazole-4-carbaldehydes with 2,3-dihydro-1H-inden-1-one. The synthesized compounds are ch
- Swamy,Swapna,Sandeep,Venkateswar Rao
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p. 1884 - 1886
(2019/11/02)
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- Design, synthesis and biological evaluation of 1H-1,2,3-triazole-linked- 1H-dibenzo[b,h]xanthenes as inductors of ROS-mediated apoptosis in the breast cancer cell line MCF-7
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Background: Low molecular weight 1,2,3-triazoles and naphthoquinones are endowed with various types of biological activity, such as against cancer, HIV and bacteria. However, in some cases, the conjugation of these two nuclei considerably increases their biological activities. Objective: In this work, we decided to study the synthesis and screening of bis-naphthoquinones and xanthenes tethered to 1,2,3-triazoles against cancer cell lines, specifically the human breast cancer cell line MCF-7. Results: Starting from lawsone and aryl-1H-1,2,3-triazole-4-carbaldehydes (10a-h) several new 7- (1-aryl-1H-1,2,3-triazol-4-yl)-6H-dibenzo[b,h]xanthene-5,6,8,13(7H)-tetraones (12a-h) and 3,3'- ((1-aryl-1H-1,2,3-triazol-4-yl)methylene)bis(2-hydroxynaphthalene-1,4-diones) 11a-h were synthesized and evaluated for their cytotoxic activities using the human breast cancer cell line MCF-7 and the non-tumor cell line MCF10A as control. We performed test of cell viability, cell proliferation, intracellular ATP content and cell cytometry to determine reactive oxygen species (ROS) formation. Conclusions: Based on these results, we found that compound 12a promotes ROS production, interfering with energy metabolism, cell viability and proliferation, and thus promoting whole cell damage.
- Bortolot, Carolina S.,Forezi, Luana da S. M.,Marra, Roberta K. F.,Reis, Marcelo I. P.,e Sá, Bárbara V. F.,Filho, Ricardo I.,Ghasemishahrestani, Zeinab,Sola-Penna, Mauro,Zancan, Patricia,Ferreira, Vitor F.,da Silva, Fernando de C.
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p. 119 - 129
(2019/06/11)
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- Searching for new drugs for Chagas diseases: triazole analogs display high in vitro activity against Trypanosoma cruzi and low toxicity toward mammalian cells
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Chagas disease is one of the most relevant endemic diseases in Latin America caused by the flagellate protozoan Trypanosoma cruzi. Nifurtimox and benzonidazole are the drugs used in the treatment of this disease, but they commonly are toxic and present severe side effects. New effective molecules, without collateral effects, has promoted the investigation to develop new lead compounds with to advance for clinical trials. Previously, 3-nitro-1H-1,2,4-triazole-based amines and 1,2,3-triazoles demonstrated significant trypanocidal activity against T. cruzi. In this paper, we synthesized a new series of 92 examples of 1,2,3-triazoles. Six compounds exhibited antiparasitic activity, 14, 25, 27, 31 and 40, 43 and were effective against epimastigotes of two strains of T. cruzi (Y and Dm28-C) and 25, 27 and 31 exhibited trypanocidal activity similar to benzonidazole. Notably, the compound 25 compared to benzonidazole increase the toxicity against T. cruzi, with no apparent toxicity to the cell line of mice macrophages or primary mice peritoneal macrophages. As results, we calculated selectivity indexes up to 2000 to 25 and 31 in both T. cruzi strains. Derivative 14 caused a trypanostatic effect because it did not damage external epimastigote membrane. Triazoles 40 and 43 impaired parasites viability using a pathway not dependent on ROS production.
- Faria, Robson Xavier,Gonzaga, Daniel Tadeu Gomes,Pacheco, Paulo Anastácio Furtado,Souza, André Luis Almeida,Ferreira, Vitor Francisco,da Silva, Fernando de Carvalho
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- Triazole-diindolylmethane conjugates as new antitubercular agents: synthesis, bioevaluation, and molecular docking
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We describe the synthesis of novel triazole-incorporated diindolylmethanes (DIMs) using a molecular hybridization approach. The in vitro antitubercular activity of the DIMs against Mycobacterium tuberculosis H37Ra (ATCC 25177) was tested in the active and
- Danne, Ashruba B.,Choudhari, Amit S.,Chakraborty, Shakti,Sarkar, Dhiman,Khedkar, Vijay M.,Shingate, Bapurao B.
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supporting information
p. 1114 - 1130
(2018/08/01)
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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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- Synthesis and biological evaluation of novel triazole-biscoumarin conjugates as potential antitubercular and anti-oxidant agents
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Abstract: The synthesis of a new series of triazole-biscoumarin conjugates by using a molecular hybridization approach is described. The newly synthesized compounds 6a–k were evaluated for their in vitro antitubercular activity against active and dormant
- Danne, Ashruba B.,Choudhari, Amit S.,Sarkar, Dhiman,Sangshetti, Jaiprakash N.,Khedkar, Vijay M.,Shingate, Bapurao B.
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p. 6283 - 6310
(2018/06/07)
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- Design, synthesis, molecular-docking and antimycobacterial evaluation of some novel 1,2,3-triazolyl xanthenones
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As part of an ongoing effort to develop new antitubercular and antimicrobial agents, a series of substituted xanthenone derivatives (7a-p) were synthesized. Xanthenone derivatives (7a-p) were prepared via a one-pot three-component thermal cyclization reac
- Goud, Gudikadi Linga,Ramesh, Seela,Ashok, Dongamanti,Reddy, Vummenthala Prabhakar,Yogeeswari, Perumal,Sriram, Dharmarajan,Saikrishna, Balabadra,Manga, Vijjulatha
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p. 559 - 570
(2017/03/30)
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- Green synthesis and antibacterial evaluation of some new 1-aryl-3-(1-aryl-1H-[1,2,3]triazol-4-yl)-propenones
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A new series of 1-aryl-3-(1-aryl-1H-[1,2,3]triazol-4-yl)propenones (6a–6j) was synthesized by condensation of substituted acetophenones (5a–5c) with substituted 1-aryl-1H-[1,2,3]triazole-4-carbaldehydes (4a–4d) in the presence of potassium hydroxide under
- Linga Goud,Ramesh,Ashok,Prabhakar Reddy
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p. 1419 - 1423
(2016/08/10)
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- Synthesis and antifungal activity of 1,2,3-triazole phenylhydrazone derivatives
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A series of 1,2,3-triazole phenylhydrazone derivatives were designed and synthesized as antifungal agents. Their structures were determined based on 1H-NMR spectroscopy, MS, elemental analysis and X-ray single-crystal diffraction. The antifunga
- Dai, Zhi-Cheng,Chen, Yong-Fei,Zhang, Mao,Li, Sheng-Kun,Yang, Ting-Ting,Shen, Li,Wang, Jian-Xin,Qian, Shao-Song,Zhu, Hai-Liang,Ye, Yong-Hao
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p. 477 - 486
(2015/02/02)
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- 1-Phenyl-1H- and 2-phenyl-2H-1,2,3-triazol derivatives: Design, synthesis and inhibitory effect on alpha-glycosidases
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Due to aging and increasingly overweight in human population, the incidence of non-insulin dependent diabetes mellitus (NIDDM or Type 2 DM) is increasing considerably. Therefore, searching for new α-glycosidase inhibitors (GIs) capable of slowing down carbohydrate assimilation by humans is an important strategy towards control of NIDDM. In this report, we disclose the search for new easily accessible synthetic triazoles as anti-diabetic compounds. Two series of non-glycosid triazoles were synthesized (series A and B) and screened against baker's yeast α-glucosidase (MAL12) and porcine pancreatic α-amylase activity (PPA). Of the 60 compounds tested at 500 μM, were considered hits (≥60% inhibition) six triazoles against MAL12 and three against PPA, with the inhibition reaching up to 99.4% on MAL12 and 88.6% on PPA. The IC50 values were calculated for both enzymes and ranged from 54 to 482 μM for MAL12 and 145 to 282 μM for PPA. These results demonstrated the potential activity of simple and non-glycosidic triazoles as an important novel class of GIs for the development of drugs to treat Type 2 DM.
- Gonzaga, Daniel,Senger, Mario Roberto,Da Silva, Fernando De Carvalho,Ferreira, Vitor Francisco,Silva Jr., Floriano Paes
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p. 461 - 476
(2014/02/14)
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- Synthesis of novel 1,2,3-triazole substituted-N-alkyl/aryl nitrone derivatives, their anti-inflammatory and anticancer activity
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A series of novel 1,2,3-triazole substituted N-phenyl nitrone derivatives 5a-e were prepared in three steps starting from 1-substituted-1,2,3-triazole-4- carbaldehydes 2 via Schiff's base formation, reduction followed by oxidation. Similarly, 1,2,3-triazo
- Sambasiva Rao,Kurumurthy,Veeraswamy,Santhosh Kumar,Poornachandra,Ganesh Kumar,Vasamsetti, Sathish Babu,Kotamraju, Srigiridhar,Narsaiah
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supporting information
p. 184 - 191
(2014/05/20)
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- Synthesis of 1H-1,2,3-triazoles and study of their antifungal and cytotoxicity activities
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We report herein the results of antifungal activity of fifteen 1,2,3-triazoles against Candida albicans, Candida krusei, Candida parapsilosis, Candida kefyr, Candida tropicalis, Candida dubliniensis, Tricophyton rubrum, Microporum canis and Aspergillus ni
- Da Silva, Iara F.,Martins, Prisicila R.C.,Da Silva, Emanuelly G.,Ferreira, Sabrina B.,Ferreira, Vitor F.,Da Costa, Karen Regina C.,De Vasconcellos, Marne C.,Lima, Emerson S.,Da Silva, Fernando De C.
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p. 1085 - 1090
(2014/01/06)
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- Novel 1,2,3-triazole derivatives for use against mycobacterium tuberculosis H37Rv (ATCC 27294) strain
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The purpose of this study was to prepare various 4-substituted N-phenyl-1,2,3-triazole derivatives using click chemistry. The derivatives were screened in vitro for antimicrobial activity against Mycobacterium tuberculosis strain H37Rv (ATCC 27294) using
- Boechat, Nubia,Ferreira, Vitor F.,Ferreira, Sabrina B.,Ferreira, Maria De Lourdes G.,Da Silva, Fernando De C.,Bastos, Monica M.,Costa, Marilia Dos S.,Louren?o, Maria Cristina S.,Pinto, Angelo C.,Krettli, Antoniana U.,Aguiar, Anna Caroline,Teixeira, Brunno M.,Da Silva, Nathalia V.,Martins, Priscila R. C.,Bezerra, Flavio Augusto F. M.,Camilo, Ane Louise S.,Da Silva, Gerson P.,Costa, Carolina C. P.
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experimental part
p. 5988 - 5999
(2011/10/09)
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- AZOLE COMPOUNDS USED AS TUBERCULOSTATIC AND LEISHMANICIDE AGENTS
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This invention refers to new 1, 2, 3-triazole and imidazole compounds included in the families of compounds represented by general formula VIII (see formula VIII) where: X is an atom of "C" or "N"; where X is "N" the radicals do triazole ring are represen
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Page/Page column 26-27
(2008/06/13)
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- Synthesis, tuberculosis inhibitory activity, and SAR study of N-substituted-phenyl-1,2,3-triazole derivatives
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The aim of this work was to describe the synthesis, the in vitro anti-Mycobacterium tuberculosis profile, and the structure-activity relationship (SAR) study of new N-substituted-phenyl-1,2,3-triazole-4-carbaldehydes (3a-l). The reactions of aromatic amin
- Costa, Marilia S.,Boechat, Nubia,Rangel, Erica A.,da Silva, Fernando de C.,de Souza, Alessandra M.T.,Rodrigues, Carlos R.,Castro, Helena C.,Junior, Ivan N.,Lourenco, Maria Cristina S.,Wardell, Solange M.S.V.,Ferreira, Vitor F.
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p. 8644 - 8653
(2008/02/08)
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- Antiplatelet properties of novel N-substituted-phenyl-1,2,3-triazole-4-acylhydrazone derivatives
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This paper describes the design, synthesis and pharmacological evaluation of new N-acylhydrazone (NAH) compounds, belonging to the N-substituted-phenyl-1,2,3-triazole-4-acylhydrazone class (2a-p). Classical heteroaromatic ring bioisosterism strategies wer
- Cunha, Anna C.,Figueiredo, Juliana M.,Tributino, Jorge L. M.,Miranda, Ana L. P.,Castro, Helena C.,Zingali, Russolina B.,Fraga, Carlos A. M.,De Souza, Maria Cecilia B. V.,Ferreira, Vitor F.,Barreiro, Eliezer J.
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p. 2051 - 2059
(2007/10/03)
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- Molecular Rearrangements of 4-Iminomethyl-1,2,3-Triazoles. Replacement of 1-Aryl Substituents in 1H-1,2,3-Triazole-4-carbaldehydes
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The two structural isomers, 4 and 5, of 1-substituted-4-iminomethyl-1,2,3-triazoles are interconvertible when heated in dimethyl sulfoxide at 80 deg C.The equilibrium position depends on the electronic properties of the R-substituent, favoring 5 for R = alkyl, benzyl and anisyl, and 4 for p-chlorophenyl and p-nitrophenyl.An interesting application is the synthesis of 1-alkyl-1,2,3-triazole-4-carbaldehydes from 1-phenyl-1,2,3-triazole-4-carbaldehyde by Scheme I.The hydrazones 4i, j and the oxime 4k do not rearrange due to an unfavorable Z-configuration around the C=N bond, whereas the acyloximino derivative 4m is converted into the nitrile 11.The structures of the products have been fully characterized by 13C nmr spectroscopy and the mechanistic details of the rearrangement are discussed.
- L'abbe, Gerrit,Bruynseels, Maria,Delbeke, Pieter,Toppet, Suzanne
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p. 2021 - 2027
(2007/10/02)
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