- Synthesis, antimicrobial activity, and QSAR studies of amide-ester linked 1,4-disubstituted 1,2,3-triazoles
-
Abstract: Synthesis of some amide-ester linked 1,4-disubstituted 1,2,3-triazoles was carried out by employing copper(I)-catalyzed 1,3-dipolar cycloaddition of 2-azido-N-substituted acetamides and benzoic acid prop-2-ynyl esters. All the synthesized 28 1,4-disubstituted 1,2,3-triazoles are new. The synthesized triazoles were characterized by IR, 1H NMR, 13C NMR, HRMS and evaluated for their antimicrobial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Candida albicans, and Aspergillus niger. Compounds displaying potent antimicrobial activity against each of these microorganisms were found. Quantitative structure activity relationship studies for the synthesized compounds were also carried out to check the effect of various substituents in parent compound on antimicrobial activity. Graphical abstract: [Figure not available: see fulltext.]
- Kaushik,Kumar, Krishan,Narasimhan, Balasubramanian,Singh, Dharmendra,Kumar, Pradeep,Pahwa, Ashima
-
-
Read Online
- Iron-catalyzed one-pot oxidative esterification of aldehydes
-
A highly efficient, mild, and simple protocol for Fe(ClO4) 3·xH2O-catalyzed oxidative esterification of aldehydes was developed. Several aromatic and aliphatic aldehydes reacted with simple primary and secondary alcohols, used as the solvent, smoothly in the presence of an iron salt catalyst (10 mol-%) and hydroperoxide (4 equiv.) as an oxidant to generate the corresponding esters in good to excellent yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
- Wu, Xiao-Feng,Darcel, Christophe
-
-
Read Online
- Synthesis, characterization, and antimicrobial potential of some 1,4-disubstituted 1,2,3-bistriazoles
-
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.
- Kaushik,Kumar, Krishan,Singh, Dharmendra,Singh,Jindal, Deepak Kumar,Luxmi, Raj
-
-
Read Online
- New ursolic acid derivatives bearing 1,2,3-triazole moieties: design, synthesis and anti-inflammatory activity in vitro and in vivo
-
Abstract: In order to discover novel anti-inflammatory agents, three series of compounds obtained by appending 1,2,3-triazole moieties on ursolic acid were designed and synthesized. All compounds have been screened for their anti-inflammatory activity by using an ear edema model. The potent anti-inflammatory compound was subjected to in vitro cyclooxygenase COX-1/COX-2 inhibition assays. In general, the derivatives were found to be potent anti-inflammatory activity. Especially, the compound 11b exhibited the strongest activity of all of the compounds prepared, with 82.81% inhibition after intraperitoneal administration, which was better than celecoxib as a positive control. Molecular docking results unclose the rationale for the interaction of the compound 11b with COX-2 enzyme. Further studies revealed that compound 11b exhibited effective COX-2 inhibitory activity, with half-maximal inhibitor concentration (IC50) value of 1.16?μM and selectivity index (SI = 64.66) value close to that of celecoxib (IC50 = 0.93?μM, SI = 65.47). Taken together, these results could suggest a promising chemotype for development of new COX-2-targeting anti-inflammatory agent. Graphic abstract: [Figure not available: see fulltext.]
- Bai, Xue-Qian,Cao, Li-Ting,Li, Chun-Shi,Sun, Si-Mei,Zhang, Tian-Yi,Zhao, Dong-Hai
-
-
- Synthesis of Cyclopenta[b]indoles via a Formal [3+2] Cyclization of N-Sulfonyl-1,2,3-triazoles and Indoles
-
Annulation of benzoxy-tethered N-sulfonyl-1,2,3-triazoles and indoles has been developed in this paper, providing an efficient and convenient access to valuable cyclopenta[b]indoles in moderate to good yields. α,β-Unsaturated imine, which generated in situ from denitrogenation and 1,2-OBz migration of triazole, provided three carbons for the formal [3+2] cyclization reaction for the first time. (Figure presented.).
- Duan, Shengguo,Zhang, Wan,Hu, Yuntong,Xu, Ze-Feng,Li, Chuan-Ying
-
supporting information
p. 3570 - 3575
(2020/08/05)
-
- Synthesis and Antimicrobial Evaluation of (1-(2-(Benzyloxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl Benzoate Analogues
-
A convenient one pot synthesis of 20 (1-(2-(benzyloxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl benzoate analogues (5a–5t) with ester functionality was carried out via Cu(I) catalyzed click reaction between prop-2-yn-1-yl benzoates and benzyl 2-azidoacetates. The structure of synthesized triazoles were explicated by various spectral techniques like FT-IR, 1H NMR, 13C NMR, and high-resolution mass spectrometry and evaluated for in vitro antimicrobial potential against Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Enterobacter aerogenes, Candida albicans, and Aspergillus niger. Most of synthesized triazole derivatives exhibited average to excellent activity against tested microbial strains.
- Kaushik,Pahwa, Ashima,Kumar, Devinder,Kumar, Ashwani,Singh, Dharmendra,Kumar, Krishan,Luxmi, Raj
-
p. 1720 - 1728
(2018/07/25)
-
- Tris(2,4,6-trifluorophenyl)borane: An Efficient Hydroboration Catalyst
-
The metal-free catalyst tris(2,4,6-trifluorophenyl)borane has demonstrated its extensive applications in the 1,2-hydroboration of numerous unsaturated reagents, namely alkynes, aldehydes and imines, consisting of a wide array of electron-withdrawing and donating functionalities. A range of over 50 borylated products are reported, with many reactions proceeding with low catalyst loading under ambient conditions. These pinacol boronate esters, in the case of aldehydes and imines, can be readily hydrolyzed to leave the respective alcohol and amine, whereas alkynyl substrates result in vinyl boranes. This is of great synthetic use to the organic chemist.
- Lawson, James R.,Wilkins, Lewis C.,Melen, Rebecca L.
-
supporting information
p. 10997 - 11000
(2017/08/22)
-
- Click synthesis of some mono/bis 1,2,3-triazoles with ester linkage and their microbicidal activity
-
Synthesis of some new 1,4-disubstituted 1,2,3-triazoles with ester functionality is reported employing Cu(I) catalyzed Huisgen [3+2] cycloaddition reaction of prop-2-yn-1-yl benzoates with 1,4-phenylenebis(methylene) bis(2-azidoacetate) and benzyl 2-azidoacetates. The synthesized compounds were well characterized through FTIR, 1H NMR, 13C NMR and HRMS. Further, the synthesized triazole derivatives were accessed for in vitro antimicrobial activity against one Gram-positive bacterial strain Staphylococcus aureus, three Gram-negative bacterial strains Escherichia coli, Klebsiella pneumoniae, Enterobacter aerogenes and two fungi Candida albicans and Aspergillus niger. Few of the synthesized disubstituted 1,2,3-triazoles displayed moderate to good inhibitory activity against tested microbial strains.
- Kaushik,Pahwa, Ashima
-
p. 2171 - 2176
(2017/10/06)
-
- Synthesis of Ketones and Esters from Heteroatom-Functionalized Alkenes by Cobalt-Mediated Hydrogen Atom Transfer
-
Cobalt bis(acetylacetonate) is shown to mediate hydrogen atom transfer to a broad range of functionalized alkenes; in situ oxidation of the resulting alkylradical intermediates, followed by hydrolysis, provides expedient access to ketones and esters. By modification of the alcohol solvent, different alkyl ester products may be obtained. The method is compatible with a number of functional groups including alkenyl halides, sulfides, triflates, and phosphonates and provides a mild and practical alternative to the Tamao-Fleming oxidation of vinylsilanes and the Arndt-Eistert homologation.
- Ma, Xiaoshen,Herzon, Seth B.
-
p. 8673 - 8695
(2016/10/17)
-
- The Propargyl Rearrangement to Functionalised Allyl-Boron and Borocation Compounds
-
A diverse range of Lewis acidic alkyl, vinyl and aryl boranes and borenium compounds that are capable of new carbon–carbon bond formation through selective migratory group transfer have been synthesised. Utilising a series of heteroleptic boranes [PhB(Cs
- Wilkins, Lewis C.,Lawson, James R.,Wieneke, Philipp,Rominger, Frank,Hashmi, A. Stephen K.,Hansmann, Max M.,Melen, Rebecca L.
-
supporting information
p. 14618 - 14624
(2016/10/03)
-
- A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts
-
4-Dimethylaminopyridine (DMAP) is shown to undergo Pd/PtBu3 catalyzed coupling with aryl halides and carbon monoxide to form electrophilic aroyl-DMAP salts. The reaction is easily scalable to prepare multigram quantities with low catalyst loadings, while the precipitation of these salts as they form leads to products with low impurities. These reagents rapidly react with a variety of nucleophiles, including those that contain potentially incompatible functional groups under standard carbonylative conditions.
- Quesnel, Jeffrey S.,Fabrikant, Alexander,Arndtsen, Bruce A.
-
p. 295 - 300
(2015/12/30)
-
- Novel One-Pot Synthetic Method for Propargyl Alcohol Derivatives from Allyl Alcohol Derivatives
-
An efficient one-pot procedure for the synthesis of propargyl alcohol derivatives from allyl alcohol derivatives has been developed. The key to this transformation from a C-C double bond to a C-C triple bond is that hydrogen bromide elimination from 1,2-dibromoalkanes that contain a neighboring oxygen functional group is promoted by the inductive electron-withdrawing effect of the oxygen functional group. In the one-pot reaction, tetrabutylammonium hydroxide was the best base, and the addition of molecular sieves 13X also promoted the reaction.
- Kutsumura, Noriki,Inagaki, Mai,Kiriseko, Akito,Saito, Takao
-
p. 1844 - 1850
(2015/06/30)
-
- Metal-free, room-temperature, radical alkoxycarbonylation of aryldiazonium salts through visible-light photoredox catalysis
-
The first radical alkoxycarboxylation of aryldiazonium salts using CO gas through visible-light-induced photoredox catalysis (16 W blue LEDs) has been developed. This reaction is entirely metal-free, is carried out at room temperature with a low loading of an organic dye as a photocatalyst (0.5 mol%), and provides a wide range of arylcarboxylic acid esters in high yields. Importantly, this photocatalytic system can be successfully extended to other carboxylation reactions.
- Guo, Wei,Lu, Liang-Qiu,Wang, Yue,Wang, Ya-Ni,Chen, Jia-Rong,Xiao, Wen-Jing
-
supporting information
p. 2265 - 2269
(2015/02/19)
-
- 7-Chloroquinolinotriazoles: Synthesis by the azide-alkyne cycloaddition click chemistry, antimalarial activity, cytotoxicity and SAR studies
-
Twenty-seven 7-chloroquinolinotriazole derivatives with different substituents in the triazole moiety were synthesized via copper-catalyzed cycloaddition (CuAAC) click chemistry between 4-azido-7-chloroquinoline and several alkynes. All the synthetic compounds were evaluated for their in vitro activity against Plasmodium falciparum (W2) and cytotoxicity to Hep G2A16 cells. All the products disclosed low cytotoxicity (CC50 > 100 μM) and five of them have shown moderate antimalarial activity (IC50 from 9.6 to 40.9 μM). As chloroquine analogs it was expected that these compounds might inhibit the heme polymerization and SAR studies were performed aiming to explain their antimalarial profile. New structural variations can be designed on the basis of the results obtained.
- Pereira, Guilherme R.,Brand?o, Geraldo Célio,Arantes, Lucas M.,De Oliveira Jr., Háliton A.,De Paula, Renata Cristina,Do Nascimento, Maria Fernanda A.,Dos Santos, Fábio M.,Da Rocha, Ramon K.,Lopes, Júlio César D.,De Oliveira, Alaíde Braga
-
p. 295 - 309
(2014/02/14)
-
- Synthesis and evaluation of novel oleanolic acid derivatives as potential antidiabetic agents
-
Antidiabetic agents simultaneously inhibiting hepatic glucose production and stimulating hepatic glucose consumption could apply a better control over hyperglycemia. A series of oleanolic acid derivatives with bulky substituents at C-3 position were designed and synthesized in order to search for this kind of agents. All of the compounds were evaluated biologically in vitro using glycogen phosphorylase and HepG2 cells. The results indicated that several derivatives exhibited moderate-to-good inhibitory activities against glycogen phosphorylase. Compound 8g showed the best inhibition with an IC50 value of 5.4 μm. Moreover, most of the derivatives were found to increase the glucose consumption in HepG2 cells in a dose-dependent manner. The possible binding mode of compound 8g with glycogen phosphorylase was also explored by docking study. 8g was found to have hydrogen bonding interactions with Arg193, Arg310, and Arg60 of the allosteric site.
- Zhang, Liying,Jia, Xiaojian,Dong, Jizhe,Chen, Dongyin,Liu, Jun,Zhang, Luyong,Wen, Xiaoan
-
p. 297 - 305
(2014/03/21)
-
- Cooperative N-Heterocyclic Carbene (NHC) and Ruthenium Redox Catalysis: Oxidative Esterification of Aldehydes with Air as the Terminal Oxidant
-
The paper describes a cooperative NHC (N-heterocyclic carbene) and ruthenium-based redox catalysis for the mild aerobic oxidative esterification of various aromatic and heteroaromatic aldehydes. The ruthenium(II) complex Ru(bpz)3(PF6)2 (bpz=2,2′-bipyrazine) as catalyst is shown to be compatible with free NHCs. The NHC is used in these cascade reactions for the umpolung of the aldehyde to form the corresponding Breslow intermediate which in turn gets oxidized to an acylazolium ion by the ruthenium redox catalyst. Air is used as a terminal oxidant for oxidation (regeneration) of the ruthenium catalyst. In addition, we will show that in the absence of the ruthenium redox catalyst and alcohol, NHC-catalyzed aerobic oxidation of aldehydes delivers the corresponding acids in good to excellent yields. Mechanistic studies and DFT calculations supporting our suggested mechanisms are provided. Copyright
- Zhao, Junfeng,Mueck-Lichtenfeld, Christian,Studer, Armido
-
supporting information
p. 1098 - 1106
(2013/05/21)
-
- Oxidative cross-esterification of dithiolanes with alcohols through a cross-dehydrogenative coupling (CDC)/deprotection sequence
-
An unprecedented oxidative cross-esterification in an equimolar mixture of dithiolanes, alcohols and water through a CDC/deprotection sequence has been developed. The reaction itself features simple experimental procedures under very mild conditions and offers a new strategic protocol for the direct and efficient synthesis of structurally diverse esters.
- Fu, Liang,Yao, Chang-Jiang,Chang, Ning-Jie,Chen, Jia-Rong,Lu, Liang-Qiu,Xiao, Wen-Jing
-
supporting information; experimental part
p. 506 - 508
(2012/01/15)
-
- TBAF-promoted elimination of vicinal dibromides having an adjacent O-functional group: Syntheses of 2-bromoalk-1-enes and alkynes
-
Syntheses of 2-bromoalk-1-enes and alkynes were achieved in good yields by dehydrobromination of vicinal dibromides with tetrabutylammonium fluoride. Neighboring O-functional-group participation is important in determining elimination reactivity. Georg Thieme Verlag Stuttgart New York.
- Kutsumura, Noriki,Kubokawa, Keisuke,Saito, Takao
-
experimental part
p. 2377 - 2382
(2011/09/16)
-
- TBAF-promoted dehydrobrominations of vicinal dibromides having an adjacent O-functional group
-
Regioselective HBr elimination of vicinal dibromides having an adjacent oxygen functional group to give the corresponding 2-bromoalk-1-enes was controlled using 1.1 equivalents of TBAF. Two-step elimination to give the corresponding alkynes was controlled using 5.0 equivalents of TBAF. High yield and high selectivity require the presence of an oxygen functional group at the neighboring position of the elimination site.
- Kutsumura, Noriki,Kubokawa, Keisuke,Saito, Takao
-
experimental part
p. 2717 - 2720
(2010/12/25)
-
- Synthesis of para-substituted 1,4,5,6,7,7-hexachlorobicyclo-[2.2.1]hepta-2, 5-dien-2-ylmethyl benzoates
-
[4 + 2]-Cycloaddition of hexachlorocyclopentadiene to para-substituted prop-2-yn-1-yl benzoates gave the corresponding 1,4,5,6,7,7-hexachlorobicyclo[2. 2.1]hepta-2,5-dien-2-ylmethyl benzoates. The structure of the adducts was confirmed by independent synthesis, esterification of para-substituted benzoic acids with 1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hepta-2,5-dien-2-ylmethanol.
- Mamedbeili,Kyazimova,Gasanov,Efendieva,Rzabekova
-
experimental part
p. 322 - 325
(2010/09/07)
-
- Synthesis of 1,4,5,6-tetrachloro-7,7-dimethoxybicyclo[2.2.1]hepta-2,5- dienylmethyl esters of p-substituted benzoic acids
-
The possibility of preparing 1,4,5,6-tetrachloro-7,7-dimethoxybicyclo[2.2. 1]hepta-2,5-dienyl-methyl esters of p-substituted benzoic acids by [4+2]cycloaddition of tetrachlorodimethoxycyclo-pentadine to propargyl esters of the corresponding acids was exam
- Mamedbeili,Kyazimova,Zeinalov,Gasanov,Nagiev
-
experimental part
p. 691 - 694
(2010/08/21)
-
- 5H-3-oxa-Octafluoropentanesulfonyl fluoride: a novel and efficient condensing agent for esterification, amidation and anhydridization
-
The use of 5H-3-oxa-octafluoropentanesulfonyl fluoride (HCF2CF2OCF2CF2SO2F) as a novel and efficient condensing reagent for esterification of carboxylic acids with alcohols and amidation of carboxylic acids with amines in the presence of 1,3-diazabicyclo[5.4.0]-undec-7-ene (DBU) is reported. HCF2CF2OCF2CF2SO2F cannot serve as a condensing agent for anhydridization of carboxylic acids, however, HCF2CF2OCF2CF2SO2F/(CH3)3SiCN system can mediate anhydridization of some aromatic carboxylic acids.
- Yan, Zhaohua,Tian, Weisheng,Zeng, Fanrong,Dai, Yanfeng
-
experimental part
p. 2727 - 2729
(2009/09/06)
-
- A hierarchy of aryloxide deprotection by boron tribromide
-
Aryl propargyl ethers and esters are cleaved selectively in the presence of aryl methyl ethers and esters by boron tribromide in dichloromethane. Under the same conditions, allyl ethers undergo very rapid Claisen rearrangement, and benzyl ethers are also cleaved more rapidly than propargyl. A mechanism involving intramolecular delivery of bromide to the propargyl terminus is proposed.
- Punna, Sreenivas,Meunier, Stephane,Finn
-
p. 2777 - 2779
(2007/10/03)
-