142321-23-1Relevant articles and documents
The preparation of 1,5-dioxygenated-pent-2-ynes
Katritzky,Bao,Fang,Qi,Prakash
, p. 253 - 256 (1999)
1,5-Dioxygenated-pent-2-ynes were prepared via the reductive lithiations of 4-alkoxybut-2-ynylbenzotriazoles and subsequent condensations with ketones and aldehydes.
New coumarin-benzotriazole based hybrid molecules as inhibitors of acetylcholinesterase and amyloid aggregation
Arora, Saroj,Attri, Shivani,Bhagat, Kavita,Kaur Gulati, Harmandeep,Kaur, Prabhjot,Kumar, Nitish,Mohinder Singh Bedi, Preet,Sharma, Sahil,Singh, Atamjit,Singh, Harbinder,Vir Singh, Jatinder
, (2020)
A novel series of triazole tethered coumarin-benzotriazole hybrids based on donepezil skeleton has been designed and synthesized as multifunctional agents for the treatment of Alzheimer's disease (AD). Among the synthesized compounds 13b showed most potent acetylcholinesterase (AChE) inhibition (IC50 = 0.059 μΜ) with mixed type inhibition scenario. Structure-activity relationship revealed that three-carbon alkyl chain connecting coumarin and triazole is well tolerable for inhibitory potential. Hybrids obtained from 4-hydroxycoumarin and 1-benzotriazole were most potent AChE inhibitors. The inhibitory potential of all compounds against butyrylcholinesterase was also evaluated but all showed negligible activity suggesting that the hybrid molecules are selective AChE inhibitors. 13b (most potent AChE inhibitor) also showed copper-induced Aβ1-42 aggregation inhibition (34.26% at 50 μΜ) and chelating properties for metal ions (Cu2+, Fe2+, and Zn2+) involved in AD pathogenesis along with DNA protective potential against degenerative actions of [rad]OH radicals. Molecular modelling studies confirm the potential of 13b in blocking both PAS and CAS of AChE. In addition, interactions of 13b with Aβ1-42 monomer are also streamlined. Therefore, hybrid 13b can act as an effective hit lead molecule for further development of selective AChE inhibitors as multifunctional anti-Alzheimer's agents.
Synthesis and antimicrobial evaluation of 1,4-disubstituted 1,2,3-triazoles containing benzofused N-heteroaromatic moieties
Kaushik,Kumar, Krishan,Lal, Kashmiri,Narasimhan, Balasubramanian,Kumar, Ashwani
, p. 817 - 828 (2016)
Synthesis of a small library of 1,4-disubstituted 1,2,3-triazoles containing benzofused N-heteroaromatic moieties was carried out through click reaction of various benzofused N-heteroaromatic alkynes with aromatic azides. All the synthesized compounds were characterized by spectroscopic techniques like IR, 1H NMR, 13C NMR, mass spectrometry and evaluated in vitro for antimicrobial activity against two Gram-positive bacteria (Bacillus subtilis, Staphylococcus aureus), one Gram-negative bacteria (Escherichia coli) and two fungi (Candida albicans, Aspergillus Niger). Most of the synthesized 1,4-disubstituted 1,2,3-triazoles were found to possess significant antibacterial and antifungal activity against tested microbial species. Moreover, docking simulation of the compound 1-[(1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methyl]-1H-benzo[d]imidazole was also carried out against E. coli topoisomerase II DNA gyrase B enzyme to study the binding modes and mechanism of action.
Anti-migration of Nitrogen-rich N-Heterocyclic Ferrocenes and Their Combustion Catalytic Properties in the Thermal Decomposition of Energetic Oxidizers
Shi, Xiaoling,Yang, Lufei,Jiang, Liping,Bi, Fuqiang,Zhang, Guofang
, (2021/12/14)
To retard high migration tendency of alkylferrocene-based burning rate catalysts and ameliorate their combustion catalytic activity, twenty new nitrogen-rich N-heterocyclic ferrocenyl compounds 1–20 were synthesized by click reaction and characterized by NMR, UV-Vis, FT-IR, ESI-MS, etc. Six compounds were structurally confirmed by single crystal X-ray diffraction additionally. TG studies showed that the new ferrocenyl compounds are highly thermal stable. Cyclic voltammetry results implied that some new ferrocenyl compounds exhibit reversible electrochemical behavior, which are favorable for their combustion catalytic performance in the composite solid propellants. The anti-migration tests confirmed that the new ferrocenyl compounds exhibit neglectable migration trends after four-week aging on comparison with ferrocene and catocene. The catalytic combustion tests of AP, RDX and HMX over the compounds 1–20 indicated that these N-heterocyclic ferrocenes are all highly active for improving thermal degradation of AP and RDX and more active than the aniline-derived counterparts prepared by click reaction.
Design, click conventional and microwave syntheses, DNA binding, docking and anticancer studies of benzotriazole-1,2,3-triazole molecular hybrids with different pharmacophores
Alharbi, Khalid,Ali, Imran,Aljuhani, Ateyatallah,Alraqa, Shaya Yahya,Aouad, Mohamed Reda,Rezki, Nadjet
, (2020/09/11)
Despite the availability of some drugs, there is an urgent need for effective anti-cancer medication. It is due to various side effects and non-functionality of the present drugs; especially at the late stage of cancer. Therefore, three series (4a-e, 6a-e and 8a-j; 21 compounds) of benzotriazole-1,2,3-triazole hybrids (carrying different pharmacophores) have been designed and synthesized (by both conventional and microwave syntheses) through the Cu(I)-catalyzed click 1,3-dipolar cycloaddition reaction of the propargylated benzotriazole with the appropriate aliphatic, aromatic and phenyl/benzyl acetamide azides. The syntheses times were from 6 to 12 h and 4 to 8 min in conventional and microwave syntheses. The yields were 80 to 86percent and 89 to 95percent in conventional and microwave syntheses; confirming microwave synthesis as an economic and eco-friendly method. These compounds were characterized by proper spectroscopic methods. The anticancer activities with A549 and H1299 lung cancer cell lines were in the range of 70.0 to 90.0percent for 4a-e series, 78.0 to 90.0percent for 6a-e series and 81.0 to 90.0percent for 8a-j series. The reported compounds showed good DNA binding constants in the range of 1.3 × 103 to 11.90 × 105 M?1. The docking results suggested strong DNA bindings of the reported compounds in the minor grooves of DNA; through hydrogen bonding and hydrophobic interactions. The quite good anticancer activities and high DNA binding constants have indicated that the reported molecules may be future anticancer agents.
Copper-Catalyzed Hydroamination of N-Allenylazoles: Access to Amino-Substituted N-Vinylazoles
Perego, Luca Alessandro,Blieck, Rémi,Michel, Julie,Ciofini, Ilaria,Grimaud, Laurence,Taillefer, Marc,Monnier, Florian
supporting information, p. 4388 - 4392 (2017/10/23)
Building on mechanistic studies, the innate capability of azoles to act as a directing group has been exploited to design an efficient and simple procedure for the hydroamination of N-allenylazoles with secondary amines. The reaction proceeds under mild conditions by copper(I) catalysis yielding the corresponding original linear E allylic amines with total regio- and stereoselectivity. Density Functional Theory (DFT) calculations offer a mechanistic explanation of the significantly higher reactivity of N-allenyl-(1,2)-azoles compared to their 1,3-analogues as a result of the reaction-enhancing coordination of the pyridine-like nitrogen to the copper center. (Figure presented.).
Synthesis, characterization, and antimicrobial potential of some 1,4-disubstituted 1,2,3-bistriazoles
Kaushik,Kumar, Krishan,Singh, Dharmendra,Singh,Jindal, Deepak Kumar,Luxmi, Raj
supporting information, p. 1977 - 1985 (2015/08/18)
A convenient synthesis of some new 1,4-disubstituted 1,2,3-bistriazoles (3a-3f, 4a-4f, 6a-6b, 7a-7b) is reported via copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of various terminal alkynes with 1,4-bis(azidomethyl)benzene and 1,6-diazidohexane.
Mitsunobu reaction of 1,2,3-NH-triazoles: A regio- and stereoselective approach to functionalized triazole derivatives
Yan, Wuming,Liao, Tao,Tuguldur, Odbadrakh,Zhong, Cheng,Petersen, Jeffrey L.,Shi, Xiaodong
supporting information; experimental part, p. 2720 - 2724 (2012/06/01)
The Mitsunobu reaction was used in the preparation of chiral triazole derivatives. The reactions gave good to excellent yields with large substrate scope. Complete stereochemistry inversion was obtained, making this strategy one practical approach for the
Iron-catalyzed C-O bond activation for the synthesis of propargyl-1,2,3-triazoles and 1,1-bis-triazoles
Yan, Wuming,Wang, Qiaoyi,Chen, Yunfeng,Petersen, Jeffrey L.,Shi, Xiaodong
scheme or table, p. 3308 - 3311 (2010/10/19)
(Equation Presented). The FeCl3-catalyzed triazole propargylation was developed. This transformation was suitable for a large scope of substituted propargyl alcohols, giving the corresponding propargyl triazoles in excellent yields (up to 96%). Further derivatization produced the 1,1-bis-triazoles in excellent yields and regioselectivity, which could be applied as potential transition metal ligands or new reagents.
Synthesis of polynuclear nonfused azoles
Verkhozina,Kizhnyaev,Vereshchagin,Rokhin,Smirnov
, p. 1792 - 1796 (2007/10/03)
Polynuclear blocks consisting of nonfused heterocycles of the azole series, connected through methylene bridges, were synthesized by successive addition of azole units via cycloaddition of organic azides to the triple bond of N-(2-propynyl)azoles, as well
