173531-53-8Relevant articles and documents
Highly Efficient [3?+?2] Cycloaddition: Click Synthesis of Novel 1H-indol-3-yl-benzo[d]imidazole Bis-triazoles
Bakkolla, Mahesh Goud,Taduri, Ashok Kumar,Bhoomireddy, Rama Devi
, p. 2651 - 2658 (2019)
A series of novel 1-((1H-1,2,3-triazol-4-yl)methyl)-2-(1-((1H-1,2,3-triazol-4-yl)methyl)-5-substituted-1H-indol-3-yl)-6-substituted-1H-benzo[d]imidazoles 5a–i have been prepared using click chemistry as an ideal strategy where [3?+?2] cycloaddition of azides with terminal alkynes has been developed as the target compounds. In route-II, 5-substituted-1H-indole-3-carbaldehydes 1a–c react with 5-substituted orthophenylenediamine 8 to give desired products, that is, 6-substituted-2-(5-substituted-1H-indol-3-yl)-1H-benzo[d]imidazole 6a–i. Here, 6a–i react with 2?equiv of propargylbromide 7 to give novel 6-substituted 2-(5-substituted-1-(prop-2-yn-1-yl)-1H-indol-3-yl)-1-(prop-2-yn-1-yl)-1H-benzo[d]imidazole 4a–i. 4a–i were reacted with 2?equiv of NaN3 in t-butanol/water (1:2) and add catalytic amount of CuSO4.5H2O. Stir the reaction mixture at room temperature to get the target products 5a–i. Here, obtained products contain four rings, that is, one indole, two triazoles, and one benzimidazole. The main advantages of this method are short reaction times, easy workup, higher yields (88–92%), and no by-products formation.
Synthesis, Biological Evaluation, and Molecular Docking Studies of Novel 1,2,3-Triazole Tagged 5-[(1H-Indol-3-yl)methylene]pyrimidine-2,4,6(1H,3H,5H)trione Derivatives
Kumar, Ashok,Sathish Kumar,Sreenivas,Subbaiah
, p. 587 - 595 (2018)
Novel 5-{(1-[(1-phenyl-1H-1,2,3-triazol-4-yl)methyl]-1H-indol-3-yl)methylene}pyrimidine-2,4,6-(1H,3H,5H)trione derivatives (5a–5k) were synthesized by the click reaction. All compounds 5a–5k were characterized by 1H and 13C NMR, IR a
Synthesis of non-toxic anticancer active forskolin-indole-triazole conjugates along with their in silico succinate dehydrogenase inhibition studies
Ponnam, Devendar,Arigari, Niranjana Kumar,Kalvagunta Venkata Naga, Satya Srinivas,Jonnala, Kotesh Kumar,Singh, Shilpi,Meena, Abha,Misra, Pallavi,Luqman, Suaib
, p. 2090 - 2101 (2021)
Biologically important three different pharmacophores, forskolin, indole and 1,2,3-triazoles are coupled to obtain a hybrid molecule. Here, we described the synthesis of novel series of forskolin-indole-triazole conjugates 5a-5l by using the Cu(I) catalyzed 1,3-dipolar cycloaddition reaction. Furthermore, the biological significance of the synthesized molecules was assessed by in silico and in vitro modes. All the synthesized compounds were evaluated for in vitro anticancer activity against PC-3, MCF-7, MDA-MB-231, COLO-205, HeLa, WRL-68, RAJI, CHANG and RAW-264.7 cell lines. Compound 5g was found to be the most potent in all the tested cell lines (IC50 range 9.6–21.66 μg/ml, except COLO-205), 5a, 5b and 5k were observed to exert its effect only against WRL-68 (IC50 range 27.69–48.18 μg/ml), when compared to parent 3 (IC50 > 100 μg/ml, tested concentrations 10–50 μg/ml) and standard Doxorubicin (IC50 range 0.42–3.16 μg/ml). The most potent compound 5g (MEF50 0.57) was found non-toxic to human erythrocytes as compared to control (MEF50 0.60) at tested concentration (50 μg/ml). In silico-based succinate dehydrogenase inhibition showed that the synthesized compounds were having potent binding affinity compared to forskolin. Predictive ADMET and toxicity risk assessment analysis revealed that most of the compounds were complying with the standard limit of Lipinski's rule of five for oral bioavailability.
MCR-click synthesis, molecular docking and cytotoxicity evaluation of a new series of indole-triazole-coumarin hybrid peptidomimetics
Pathoor, Rajeena,Bahulayan
, p. 6810 - 6816 (2018)
The design and synthesis of a new series of indole-triazole-coumarin hybrids as potential CDK2 inhibitors is described. The new hybrid molecules were synthesized via copper(i) catalyzed [3+2] azide-alkyne cycloaddition and showed excellent binding affinity towards CDK2 kinase when subjected to virtual screening based on molecular docking. The molecular docking results were experimentally validated by cytotoxicity evaluation against human breast cancer cell line MCF-7 and western blot analysis. The IC50 value (17.5 μM) and binding affinity (-11.2 kcal mol-1) obtained for 6a against MCF-7 cells are promising for the development of potential anticancer drugs based on these new molecules.
Bis-triazole with indole pendant Organosilicon framework: Probe for recognition of Pb2+ ions
Singh, Gurjaspreet,Satija, Pinky,Singh, Akshpreet,Pawan,Mohit,Kaur, Jashan Deep,Devi, Anita,Saini, Anamika,Singh, Jandeep
, (2021)
Trace lead (II) ions detection platform by adjoining an indole group, bis-triazole molecules and a silatranyl motif, has been proposed in this article. The receptor has been prepared by employing click chemistry methodology and the hybrid network was successfully identified by elemental analysis, IR and NMR (1H, 13C) spectroscopy. Absorption spectra analysis marked that the sensor exhibit an exclusively fastidious response to Pb2+ ions with a measured detection limit of 0.032μM at 1:1 stiochiometry. Further, computational studies have been carried out to get an insight into their structure and properties.
Click linker: Efficient and high-yielding synthesis of a new family of SPOS resins by 1,3-dipolar cycloaddition
Loeber, Stefan,Rodriguez-Loaiza, Pilar,Gmeiner, Peter
, p. 1753 - 1755 (2003)
(Matrix presented) Highly efficient methodology for the construction of functionalized resins was presented involving 1,3-dipolar cycloaddition as the key reaction step. On the basis of this concept, the first series of click backbone amide linkers were s
Conventional and microwave-assisted synthesis of new indole-tethered benzimidazole-based 1,2,3-triazoles and evaluation of their antimycobacterial, antioxidant and antimicrobial activities
Ashok, Dongamanti,Gundu, Srinivas,Aamate, Vikas Kumar,Devulapally, Mohan Gandhi
, p. 1 - 10 (2018)
A new series of triheterocycles containing indole–benzimidazole-based 1,2,3-triazole hybrids have been synthesized in good yields via a microwave-assisted click reaction. All the compounds were characterized by IR, (Formula presented.) NMR, (Formula presented.) NMR and mass spectroscopy and were evaluated for their in vitro antitubercular activity against the Mycobacterium tuberculosis H37Rv strain. Compounds 4b, 4h and 4i displayed highly potent antitubercular activity with MIC 3.125–6.25 (Formula presented.). The antioxidant potential was evaluated using 2,2-diphenyl-1-picryl hydrazine and (Formula presented.) radical scavenging activity, and compounds 4e,4f and 4g showed excellent radical scavenging activity with (Formula presented.) values in the range of 08.50–10.05 (Formula presented.). Furthermore, the compounds were evaluated for antimicrobial activity against numerous bacterial and fungal strains, and compounds 4b, 4c and 4h were found to be the most promising potential antimicrobial molecules with MIC 3.125–6.25 (Formula presented.).
Design and synthesis of indole triazole pendant siloxy framework as a chemo sensor for sensing of Cu2+ and Ni2+: A comparison between traditional and microwave method
Singh, Gurjaspreet,Kalra, Pooja,Arora, Aanchal,Sanchita,Sharma, Geetika,Singh, Akshpreet,Verma, Vikas
, p. 186 - 193 (2018)
A triazole tethered chemo sensor molecules with the capability of sensing cations have been synthesized by coupling two sensor based alkynyl indole schiff base unit to azide. The hybrid networks were able to donate electron via azomethine linkage, traizole ring and indole motif to bind copper and nickel effectively. Such indole based hybrids would have potential applications in biological systems. Indole traizoles (In-Tz) were synthesized under microwave irradiation with auto generated pressure (at 60 °C) and characterized by 1H NMR, 13C NMR, Mass and FTIR spectroscopy, thin-layer chromatography (TLC) and elemental analyses. The fabricated sensor exhibited higher sensitivity, large-dynamic concentration ranges and long term stability towards In-Tz conjugated copper and nickel complex for selective Cu2+and Ni2+sensor. The calibration plot is linear (r2: 0.9895, r2: 0.9808) over the large Cu2+ ions and Ni2+concentration ranges (1.0 μM). This novel effort has initiated a well-organize way of efficient cationic sensor improvement with triazole for heavy metallic pollutants in environmental and health-care fields in large scales.
Simultaneous ultrasound- and microwave-assisted one-pot ‘click’ synthesis of 3-formyl-indole clubbed 1,2,3-triazole derivatives and their biological evaluation
Mokariya, Jaydeep A.,Kalola, Anirudhdha G.,Prasad, Pratibha,Patel, Manish P.
, (2021/04/19)
An environment friendly, high yielding, promising one-pot protocol for the click reaction of N-propargyl-3-formylindole 2(a–b), chloroacetic acid/ester 3(a–b) and sodium azide, leading to the formation of 3-formyl-indole clubbed 1,4-disubstituted-1,2,3-triazole derivatives 4(a–b), 5(a–b) and 6(a–f) aided by CuI catalyst accomplished under acceleration of simultaneous ultrasound and microwave irradiation in a very short reaction time has been described. Further, acid derivative 4(a–b) is subjected to acid–amine coupling reaction with secondary amine (p–t) in the presence of HATU to afford 6(p–t) and 7(p–t). The perspective of this protocol is to get rid of the hectic preparation and handling of organic azide which are generated in situ. Consequently, this protocol blossoms the click process by making it environment benign, user-friendly, safe and clean technique. All the synthesized compounds have been preliminarily screen for their in vitro antimicrobial activity against a panel of pathogenic strains. The majority of compounds possess noticeably inhibitory action against E. Coli, S. Typhi, P. Aeruginosa, C. tetani, S. aureus and B. subtillis. Among all compounds, 6p and 7q exhibit excellent inhibitory action against E.Coli and P. Aeruginosa strain, respectively, as compared to standard drug. One compound 5b shows remarkable potency against fungal strain. Molecular docking study was carried out to understand binding of compound with protein. In silico ADME prediction was carried out to check physicochemical properties of synthesized compound. Graphical abstract: [Figure not available: see fulltext.].
Polar Solvent–Mediated Synthesis of Terminal Alkyne Derivatives of Thiazoles and Evaluation of Their Antidiabetic Activity
Jivani, A. J.,Kapadiya, K. M.,Khunt, R. C.
, p. 801 - 808 (2021/06/12)
Abstract: Two new pharmacologically active series of N-alkyne-substituted indole–thiazoles and C-alkyne-substituted benzylidene–thiazoles were synthesized by a two-step procedure involving initial reactions of thiosemicarbazide with, respectively, [1-(pro
