- Design and synthesis of novel benzenesulfonamide containing 1,2,3-triazoles as potent human carbonic anhydrase isoforms I, II, IV and IX inhibitors
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In a quest to discover new biologically active compounds, a series of twenty novel heterocyclic derivatives substituted at position 5 with -H (7a-7j) or -CF3 (8a-8j), bearing benzenesulfonamide at N-1 position and various aroyl groups at position 4 of the 1,2,3-triazole ring was synthesized and screened for their carbonic anhydrase (CA, EC 4.2.1.1) inhibition potential against four human (h) isoforms hCA I, II, IV and IX. All the compounds (7a-7j and 8a-8j) were synthesized via [3+2] cycloaddition reaction from 4-azidobenzenesulfonamide. Interestingly, compounds 7a-7j were prepared in one pot manner via enaminone intermediate using novel methodology. All the newly synthesized compounds (7a-7j & 8a-8j) were found to be excellent inhibitors of edema related isoform hCA I with their inhibition constant (Ki) ranging from 30.1 to 86.8 nM as compared to standard drug acetazolamide (AAZ) with Ki = 250 nM. Further it was found that most of tested compounds were weaker inhibitors of isoform, hCA II although compounds 7b, 7d-7e, 8a, 8d-8f, 8i (mostly with electron withdrawing substituents) have shown better inhibition potential (Ki i = 52.4 nM) than AAZ (Ki = 74 nM) while against tumor associated hCA IX, all the compounds have shown moderate inhibition potential. Present study have added one more step in exploring the 1,2,3-triazlole moiety in the medicinal field.
- Kumar, Rajiv,Vats, Lalit,Bua, Silvia,Supuran, Claudiu T.,Sharma, Pawan K.
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p. 545 - 551
(2018/06/18)
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- Lanthanide complex inside-outside double functionalized zeolite A hybrid materials for luminescence sensing
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In this paper, the so-called inside-outside double functionalization path is used to assemble the hybrid materials based on the zeolite A (ZA) host. Lanthanide complexes (Ln = Eu, Nd, Yb) with beta-diketones (1-(2-naphthoyl)-3,3,3-trifluoroacetonate (NTA), 1,3-diphenylpropane-1,3-dione (DBM)) are introduced into ZA through ion exchange/vapour diffusion (inside) and covalent grafting (outside), respectively. These hybrids exhibit different luminescence in visible (for Eu3+) and near infrared (for Nd3+, Yb3+) regions by means of the selective excitation of different lanthanide luminescent centres. Furthermore, a luminescent thin film is prepared based on the [DBM-Yb-ZA]-NTASi-Eu hybrid system. Besides, its luminescence sensing is investigated and it is found that [DBM-Yb-ZA]-NTASi-Eu has a selective fluorescence quenching effect for metal ions, especially Fe3+ shows the highest selectivity. These results can be expected to have potential application in practical fields of optical devices or sensors.
- Sun, Na-Na,Yan, Bing
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supporting information
p. 6924 - 6930
(2016/08/09)
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- 1,5-Diketones Synthesis via Three-Component Cascade Reaction
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A mild and efficient cascade synthesis of 1,5-diketones from readily available N,N-dicyclohexylmethylamine, 1,3-dicarbonyl compounds, and trifluoromethyl β-diketones has been developed. This cascade reaction occurs via an oxidation/Mannich reaction/Cope elimination/Michael addition/retro-Claisen reaction sequence, and provides multiple C-C bond formations in one pot. In addition, exquisite chemoselectivity is achieved in the reaction between 1,3-dicarbonyl compounds and trifluoromethyl β-diketones.
- Xing, Li-Juan,Lu, Tao,Fu, Wei-Li,Lou, Mei-Mei,Chen, Bo,Wang, Zhi-Shen,Jin, Yang,Li, Dan,Wang, Bin
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supporting information
p. 3076 - 3080
(2015/11/03)
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- Development of novel antibacterial agents against methicillin-resistant Staphylococcus aureus
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Methicillin-resistant Staphylococcus aureus (MRSA) poses a serious threat to public health because of its resistance to multiple antibiotics most commonly used to treat infection. In this study, we report the unique ability of the cyclooxygenase-2 (COX-2) inhibitor celecoxib to kill Staphylococcus aureus and MRSA with modest potency. We hypothesize that the anti-Staphylococcus activity of celecoxib could be pharmacologically exploited to develop novel anti-MRSA agents with a distinct mechanism. Examination of an in-house, celecoxib-based focused compound library in conjunction with structural modifications led to the identification of compound 46 as the lead agent with high antibacterial potency against a panel of Staphylococcus pathogens and different strains of MRSA. Moreover, this killing effect is bacteria-specific, as human cancer cells are resistant to 46. In addition, a single intraperitoneal administration of compound 46 at 30 mg/kg improved the survival of MRSA-infected C57BL/6 mice. In light of its high potency in eradicating MRSA in vitro and its in vivo activity, compound 46 and its analogues warrant continued preclinical development as a potential therapeutic intervention against MRSA.
- Chiu, Hao-Chieh,Lee, Su-Lin,Kapuriya, Naval,Wang, Dasheng,Chen, Yi-Ru,Yu, Sung-Liang,Kulp, Samuel K.,Teng, Lee-Jene,Chen, Ching-Shih
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experimental part
p. 4653 - 4660
(2012/08/29)
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- Comparative study of the regioselectivity and reaction media for the synthesis of 1-tert-butyl-3(5)-trifluoromethyl-1H-pyrazoles
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A study is presented for the synthesis of a series of 1-tert-butyl-3(5)- (trifluoromethyl)-1H-pyrazoles from the reaction of 4-alkoxy-1,1,1-trifluoro-3- alken-2-ones [CF3C(O)CH=C(R1)(OR), where R = Et and R 1 = H or R = Me and R1 = Me, Ph, 4-Me-C6H 4, 4-MeO-C6H4, 4-F-C6H4, 4-Cl-C6H4, 4-Br-C6H4, 4-I-C 6H4, fur-2-yl, thien-2-yl, or naphth-2-yl] with tert-butylhydrazine hydrochloride. When [BMIM][BF4] (1-butyl-3-methylimidazolium tetrafluoroborate) and pyridine were used as the reaction media, we obtained a mixture of 1-tert-butyl-3(5)- trifluoromethylpyrazoles. The formation of 5-trifluoromethyl-1-tert-butyl-1H- pyrazoles with high regioselectivity occurred when the reaction was carried out with NaOH in EtOH. The formation of 1-tert-butyl-3-trifluoromethyl-1H-pyrazoles occurred, after hydrolysis of the 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones in H2O and H2SO4, followed by cyclization in [BMIM][BF4] and pyridine.
- Martins, Marcos A. P.,Marzari, Mara R. B.,Frizzo, Clarissa P.,Zanatta, Marcileia,Buriol, Lilian,Andrade, Valquiria P.,Zanatta, Nilo,Bonacorso, Helio G.
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p. 7112 - 7119
(2013/02/21)
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- Synthesis and anti-microbial activity of some new fluorinated 1H-pyrazoles
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Several new trifluoromethyl-1H-pyrazoles were prepared by reaction of hydrazine monohydrate with 1,3-diketones. Their structures were confirmed by elemental analysis, IR, 1H NMR and EI-MS spectroscopy. The anti-microbial activities of the newly synthesized compounds were examined by disc diffusion method against Escherichia coli, Staphylococcus aureus, Pyricularia oryzae and Rhizoctnia solani. All the trifluoromethyl-1H-pyrazoles exhibited a certain degree of anti-bacterial and anti-fungal activities.
- Wang, Dun-Jia,Fan, Ling,Zheng, Chun-Yang,Fang, Zheng-Dong
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experimental part
p. 584 - 586
(2010/06/13)
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- Keto-enol and enol-enol tautomerism in trifluoromethyl-β-diketones
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The keto-enol (K?E) and enol-enol (E?E) equilibria of a variety of trifluoromethyl-β-diketones were investigated using 1H, 13C, 19F NMR spectroscopy, infrared spectroscopy and ultraviolet-visible spectrophotometry in nonpolar solvents. In general, NMR, IR and UV spectral evidence indicates that trifluoromethyl-β-diketones exist as mixtures of two chelated cis-enol forms in nonpolar media. Infrared spectroscopy and ultraviolet spectrophotometry show the E?E equilibrium lies in the direction of the enol form which maximizes conjugation in most cases. Exceptions are noted and discussed.
- Sloop, Joseph C.,Bumgardner, Carl L.,Washington, Gary,Loehle, W. David,Sankar, Sabapathy S.,Lewis, Adam B.
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p. 780 - 786
(2008/03/27)
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- Synthesis, characterization and crystal structures of two 2-naphthyl substituted pyrazoles
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The synthesis, characterization and X-ray crystal structures of two 2-naphthyl-substituted pyrazoles - 3-(2-naphthyl) pyrazole (1) and 5-(2-naphthyl)-3-trifluoromethyl-pyrazole (3) - are reported. In addition, the isolation and structural characterization of 5-hydroxy-3-(2-naphthyl)-5-trifluoromethyl-4,5-dihydropyrazole (2), an intermediate of the synthesis of 3, is included. Two simple methods of dehydration of 2 are also presented.
- Yang, Guang,Raptis, Raphael G.
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p. 659 - 664
(2007/10/03)
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- Synthesis of fluorinated heterocycles
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Selected 1,3-diketones having a trifluoromethyl group and/or a fluorine in the 2-position were condensed with aromatic hydrazines, hydroxylamine, urea, thiourea, guanidine, and substituted anilines producing pyrazoles, isoxazoles, pyrimidines, and quinolines, respectively, in yields ranging from 27 to 87%.
- Sloop, Joseph C.,Bumgardner, Carl L.,Loehle, W. David
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p. 135 - 147
(2007/10/03)
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- Pr(III), Nd(III) and Sm(III) Complexes of Some Fluoro β-Diketones
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Anhydrous chelates of Pr(III), Nd(III) and Sm(III) with fluoro β-diketones (trifluoro-2,4-hexanedione, trifluoro-5-methyl-2,4-hexanedione, trifluoro-6-methyl-2,4-heptanedione, trifluoro-7-methyl-2,4-octanedione and trifluoronaphthyl-1,3-butanedione) have been isolated by azeotropic removal of water from the corresponding hydrated derivatives.Infrared spectra in the region 600-200 cm-1 indicate the presence of at least three M-O bands which shift to higher frequencies on increasing the ring size of the chelate.Absorption spectra of these chelates in benzene indicate some covalent character in the metal-ligand bond.Nephelauxetic ratio (β), percentage covalency parameter (δ) and bonding parameters (b1/2) of these chelates have been calculated from the absorption spectral data.The molar conductances of the complexes in benzene indicate a very low degree of dissociation suggesting that the anhydrous chelates are essentially inner sphere complexes.
- Misra, Sudhindra N.
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p. 187 - 189
(2007/10/02)
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