- Regioselective synthesis, antibacterial, and antioxidant activities of ester-linked 1,4-disubstituted 1,2,3-triazoles
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Abstract: Synthesis of ester-linked 1,4-disubstituted 1,2,3-triazoles was carried out in water through cycloaddition between benzoic acid prop-2-yn-1-yl esters and aromatic azides using cellulose-supported cuprous iodide nanoparticles. Structures of all t
- Kaushik,Sangwan, Jyoti
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p. 807 - 819
(2020/05/18)
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- Design, synthesis and biological evaluation of novel inhibitors against cyanobacterial pyruvate dehydrogenase multienzyme complex E1
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Cyanobacterial pyruvate dehydrogenase multienzyme complex E1 (PDHc E1)is a potential target enzyme for finding inhibitors to control harmful cyanobacterial blooms. In this study, a series of novel triazole thiamin diphosphate (ThDP)analogs were designed a
- Feng, Jiangtao,He, Haifeng,Zhou, Yuan,Guo, Xiaoliang,Liu, Honglin,Cai, Meng,Wang, Fang,Feng, Lingling,He, Hongwu
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p. 2413 - 2420
(2019/01/30)
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- Rhodium-catalysed synthesis of fused pyrimidine derivatives employing N-sulfonyl-1,2,3-triazoles as a 1-aza-[4C] synthon
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A new synthetic application of N-sulfonyl-1,2,3-triazoles acting as a 1-aza-[4C] synthon via the 1,2-shift reaction of an α-imine rhodium carbene was developed for the synthesis of fused pyrimidine derivatives. The high reactivity of the strained three-me
- Xu, Ze-Feng,An, Yuehui,Chen, Yidian,Duan, Shengguo
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supporting information
p. 1849 - 1853
(2019/06/20)
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- 7-Chloroquinolinotriazoles: Synthesis by the azide-alkyne cycloaddition click chemistry, antimalarial activity, cytotoxicity and SAR studies
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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
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p. 295 - 309
(2014/02/14)
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- Combining oxidative N-heterocyclic carbene catalysis with click chemistry: A facile one-pot approach to 1,2,3-triazole derivatives
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A combination of the oxidative N-heterocyclic carbene catalysis and click chemistry has been explored for the direct, one-pot synthesis of 1,2,3-triazole derivatives from aromatic aldehydes. This procedure was found to be very efficient and a variety of 1
- Ramanjaneyulu,Reddy, Virsinha,Arde, Panjab,Mahesh, Sriram,Anand, R. Vijaya
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p. 1489 - 1496
(2013/07/26)
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- TBAF-promoted elimination of vicinal dibromides having an adjacent O-functional group: Syntheses of 2-bromoalk-1-enes and alkynes
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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
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experimental part
p. 2377 - 2382
(2011/09/16)
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- TBAF-promoted dehydrobrominations of vicinal dibromides having an adjacent O-functional group
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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
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experimental part
p. 2717 - 2720
(2010/12/25)
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- Synthesis of para-substituted 1,4,5,6,7,7-hexachlorobicyclo-[2.2.1]hepta-2, 5-dien-2-ylmethyl benzoates
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[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
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experimental part
p. 322 - 325
(2010/09/07)
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- Synthesis of 1,4,5,6-tetrachloro-7,7-dimethoxybicyclo[2.2.1]hepta-2,5- dienylmethyl esters of p-substituted benzoic acids
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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
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experimental part
p. 691 - 694
(2010/08/21)
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- Protic acid immobilized on solid support as an extremely efficient recyclable catalyst system for a direct and atom economical esterification of carboxylic acids with alcohols
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(Chemical Equation Presented) A convenient and clean procedure of esterification is reported by direct condensation of equimolar amounts of carboxylic acids with alcohols catalyzed by an easy to prepare catalyst system of perchloric acid immobilized on silica gel (HClO4-SiO2). The direct condensation of aryl, heteroaryl, styryl, aryl alkyl, alkyl, cycloalkyl, and long-chain aliphatic carboxylic acids with primary/secondary alkyl/cycloalkyl, allyl, propargyl, and long-chain aliphatic alcohols has been achieved to afford the corresponding esters in excellent yields. Chiral alcohol and N-t-Boc protected chiral amino acid also resulted in ester formation with the representative carboxylic acid or alcohol without competitive N-t-Boc deprotection and detrimental effect on the optical purity of the product demonstrating the mildness and chemoselectivity of the procedure. The esters of long-chain (>C10) acids and alcohols are obtained in high yields. The catalyst is recovered and recycled without significant loss of activity. The industrial application of the esterification process is demonstrated by the synthesis of prodrugs of ibuprofen and a few commercial flavoring agents. Other protic acids such as H2SO4, HBr, TfOH, HBF4, and TFA that were adsorbed on silica gel were less effective compared to HClO4-SiO2 following the order HClO4-SiO 2 ? H2SO4-SiO2 > HBr-SiO 2 > TfOH-SiO2 ? HBF4-SiO2 ≈ TFA-SiO2. When HClO4 was immobilized on other solid supports the catalytic efficiency followed the order HClO4-SiO 2 > HClO4-K10 > HClO4-Al 2O3 (neutral) > HClO4-Al2O 3 (acidic) > HClO4-Al2O3 (basic).
- Chakraborti, Asit K.,Singh, Bavneet,Chankeshwara, Sunay V.,Patel, Alpesh R.
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supporting information; experimental part
p. 5967 - 5974
(2009/12/24)
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