- Synthesis, characterization, and biological evaluation of new derivatives targeting MbtI as antitubercular agents
-
Tuberculosis (TB) causes millions of deaths every year, ranking as one of the most dangerous infectious diseases worldwide. Because several pathogenic strains of Mycobacterium tuberculosis (Mtb) have developed resistance against most of the established anti-TB drugs, new therapeutic options are urgently needed. An attractive target for the development of new antitubercular agents is the salicylate synthase MbtI, an essential enzyme for the mycobacterial siderophore biochemical machinery, absent in human cells. A set of analogues of I and II, two of the most potent MbtI inhibitors identified to date, was synthesized, characterized, and tested to elucidate the structural requirements for achieving an efficient MbtI inhibition and a potent antitubercular activity with this class of compounds. The structure-activity relationships (SAR) here discussed evidenced the importance of the furan as part of the pharmacophore and led to the preparation of six new compounds (IV-IX), which gave us the opportunity to examine a hitherto unexplored position of the phenyl ring. Among them emerged 5-(3-cyano-5-(trifluoromethyl)phenyl)furan-2-carboxylic acid (IV), endowed with comparable inhibitory properties to the previous leads, but a better antitubercular activity, which is a key issue in MbtI inhibitor research. Therefore, compound IV offers promising prospects for future studies on the development of novel agents against mycobacterial infections.
- Mori, Matteo,Stelitano, Giovanni,Chiarelli, Laurent R.,Cazzaniga, Giulia,Gelain, Arianna,Barlocco, Daniela,Pini, Elena,Meneghetti, Fiorella,Villa, Stefania
-
-
- One-pot, three-component synthesis of polyfunctionalized benzo[h]pyrazolo[3,4-b][1,6]naphthyridine and benzo[g]pyrazolo[3,4-b]quinoline derivatives in the presence of silver nanoparticles (AgNPs)
-
An efficient and straightforward protocol for one-pot, three-component reaction of aryl glyoxal monohydrates 1a-h, 5-amino-1-aryl-3-methylpyrazoles 2a,b and 4-hydroxyquinoline-2(1H)-one (3) or 2-hydroxy-1,4-naphthoquinone (4) using silver nanoparticles (AgNPs) as a high performance nanocatalyst in H2O/EtOH at 60°C afforded the corresponding polyfunctionalized benzo[h]pyrazolo[3,4-b][1,6]naphthyridines 5a-h and benzo[g]pyrazolo[3,4-b]quinolines 6a-i, respectively. Excellent catalytic activity, high yields, employing green media and green nanocatalyst, cost-effective and simple procedure are some notable advantages of using AgNPs as a noble metal nanocatalyst in this synthetic strategy. The structures of fused heterocycles were confirmed by their Fourier transform infrared, proton nuclear magnetic resonance (1H-NMR), and 13C-NMR spectral data and microanalysis.
- Khalafy, Jabbar,Majidi Arlan, Fatemeh,Poursattar Marjani, Ahmad,Sarchami, Vahid
-
p. 3961 - 3969
(2020/09/01)
-
- Series of Functionalized 5-(2-Arylimidazo[1,2-a]pyridin-3-yl)pyrimidine-2,4(1 H,3 H)-diones: A Water-Mediated Three-Component Catalyst-Free Protocol Revisited
-
A water-mediated and catalyst-free practical method for the synthesis of a new series of pharmaceutically interesting functionalized 5-(2-arylimidazo[1,2-a]pyridin-3-yl)pyrimidine-2,4(1H,3H)-diones has been accomplished based on a one-pot multicomponent reaction between arylglyoxal monohydrates, 2-aminopyridines/2-aminopyrimidine, and barbituric/N,N-dimethylbarbituric acids under reflux conditions. The salient features of this protocol are avoidance of any additive/catalyst and toxic organic solvents, use of water as reaction medium, clean reaction profiles, operational simplicity, ease of product isolation/purification without the aid of tedious column chromatography, good to excellent yields, and high atom-economy and low E-factor.
- Brahmachari, Goutam,Nayek, Nayana,Karmakar, Indrajit,Nurjamal, Khondekar,Chandra, Swapan K.,Bhowmick, Anindita
-
p. 8405 - 8414
(2020/07/16)
-
- Synthesis of 4-Hydroxy-3-(2-arylimidazo[1,2-a]pyridin-3-yl)quinolin-2(1H)-ones in the Presence of DABCO as an Efficient Organocatalyst
-
The one-pot, three-component, synthesis of a new series of 4-hydroxy-3-(2-arylimidazo[1,2-a]pyridin-3-yl)quinolin-2(1H)-ones in the presence of DABCO as a catalyst has been achieved using aryl glyoxal monohydrates, quinoline-2,4(1H,3H)-dione, and 2-aminopyridine in H2O/EtOH under reflux conditions. The cheapness of organocatalyst, simple workup, operational simplicity, regioselectivity, and high yields are some advantages of this protocol.
- Khalafy, Jabbar,Etivand, Nasser,Poursattar Marjani, Ahmad,Khalillou, Neda
-
p. 1857 - 1865
(2019/05/21)
-
- Synthesis of Ethyl 2-Amino-4-benzoyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylates by a One-pot, Three-Component Reaction in the Presence of TPAB
-
In this research, in order to synthesize a series of ethyl 2-amino-4-benzoyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylates, a green and an efficient method is proposed through one-pot three-component reaction of substituted arylglyoxals, ethyl cyanoacetate, and 4-hydroxyquinolin-2(1H)-one in the presence of terapropylammonium bromide as a catalyst in good yields. All synthesized new substances were characterized by FTIR, 1H-NMR, and 13C-NMR spectral data and elemental analysis.
- Poursattar Marjani, Ahmad,Khalafy, Jabbar,Farajollahi, Ayda
-
p. 268 - 274
(2018/11/30)
-
- A Facile and Effective Procedure for Synthesis of Polyfunctionalized Bis (imidazolyl) Pyrrole/Imidazolyl Indole from Pyrrole/Indole with Arylglyoxals and N-aryl amidines
-
Heterocyclic systems containing bis (imidazolyl) pyrrole or imidazolyl indole moieties were synthesized by heterocyclization of pyrrole or indole with arylglyoxal monohydrates and N-aryl amidines in ethanol catalyzed by FeCl3 at room temperature. The paper reports a facile, efficient, and environmentally friendly protocol for the synthesis of new products. Products were isolated by simple filtration, and their structures were established from their spectroscopic data.
- Masoudi, Mozhgan,Shahbazi-Manshadi, Mohammad Reza,Anary-Abbasinejad, Mohammad
-
p. 2772 - 2778
(2019/11/03)
-
- A new synthesis of pyrrolo[3,2-d]pyrimidine derivatives by a one-pot, three-component reaction in the presence of L-proline as an organocatalyst
-
A one-pot, three-component reaction of 4-hydroxycoumarin, arylglyoxals, and 6-aminouracil or 1,3-dimethyl-6-aminouracil in the presence of L-proline as an organocatalyst in acetic acid under reflux conditions provided a series of new pyrrolo[3,2-d]pyrimidine derivatives in good yields.
- Javahershenas, Ramin,Khalafy, Jabbar
-
-
- Synthesis of new indolylpyrrole derivatives via a four-component domino reaction between arylglyoxals, acetylacetone, indole and aliphatic amines in aqueous media
-
A novel synthesis of indolylpyrrole derivatives is described by a four-component domino reaction between arylglyoxals, acetylacetone, indole and aliphatic amines in water as solvent at 60 °C without using any catalyst or promoter. The FT-IR, 1H NMR, 13C NMR spectral and elemental analysis confirm the structures of the products.
- Mousavizadeh, Fereshteh,Talebizadeh, Mahdiyeh,Anary-Abbasinejad, Mohammad
-
supporting information
p. 2970 - 2974
(2018/06/30)
-
- Regioselective N-1 and C-2 diacylation of 3-substituted indoles with arylglyoxal hydrates for the synthesis of indolyl diketones
-
A highly regioselective N-1 and C-2 diacylation of 3-substituted indoles with arylglyoxal hydrates to afford N-1 and C-2 indolyl diketones in moderate to good yields is described. Notably, the control of regioselectivity is achieved by small changes in the Cu catalyst, additive and solvent. Importantly, the intermediates for N-1 and C-2 diacylation were detected and two plausible pathways were also proposed.
- Pan, Dalong,Chu, Jinpeng,Gao, Xianrui,Wang, Cuiping,Meng, Qingtao,Chi, Haijun,Dong, Yan,Duan, Chunying,Zhang, Zhiqiang
-
supporting information
p. 6998 - 7003
(2018/10/17)
-
- An efficient synthesis of imidazo[2,1-b][1,3,4]thiadiazol-7-ium hydroxides by a one-pot, three-component reaction in water
-
An improved synthesis of 2-ethyl-5-(2-hydroxy-4-oxoquinolin-3(4H)-ylidene)-6-aryl-5,6-dihydroimidazo[2,1-b][1,3,4]thiadiazol-7-ium hydroxide derivatives 4a-k via the reaction of aryl glyoxal monohydrates 1a-k, quinoline-2,4-diol 2 and 2-amino-[1,3,4]thiadiazole (3) in the presence of Et3N/sulfamic acid in H2O is described. This green protocol is characterized by the use of the readily available catalyst and reactants, short reaction times, operational simplicity and high yields of products. The structures of all compounds were characterized by 1H NMR, 13C NMR and Fourier-transform infrared (FT-IR) spectral data and microanalyses.
- Khalafy, Jabbar,Etivand, Nasser,Khalillou, Neda
-
p. 297 - 302
(2018/12/04)
-
- The catalyst-free syntheses of pyrazolo[3,4-b]quinolin-5-one and pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5,7-dione derivatives by one-pot, three-component reactions
-
Herein we report the syntheses of pyrazolo[3,4-b]quinolin-5-one and pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5,7-dione derivatives by cyclocondensation of 1,3-diketones, 3-methyl-1-phenyl-1H-pyrazole-5-amine and arylglyoxals, under catalyst-free conditions in H2O/EtOH at reflux in 65–98% and 73–96% yields respectively. This protocol provides mild reaction conditions, good to high yields, non-catalytic, simple procedures and easy isolation of products to structurally diverse tricyclic pyrazolo[3,4-b]quinolin-5-one and pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5,7-dione derivatives, which may have biological and pharmacological activities.
- Ezzati, Mahnaz,Khalafy, Jabbar,Marjani, Ahmad Poursattar,Prager, Rolf H.
-
p. 6587 - 6596
(2017/10/23)
-
- A facile and effective procedure for synthesis of polyfunctionalized pyrrolines from simultaneously stirring of carbon disulfide, aniline, arylglyoxals and β-enaminocarbonyls
-
An efficient one-pot synthesis of 2H-pyrroline derivatives by a four-component reaction between carbon disulfide, aniline, arylglyoxals and β-enaminocarbonyls in acetonitrile at room temperature under mild reaction conditions is reported. The addition rea
- Masoudi, Mozhgan,Anary-Abbasinejad, Mohammad,Maleki, Alireza
-
p. 2299 - 2304
(2017/10/30)
-
- A Green Synthesis of 7-amino-5-(4-aroyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile Derivatives by a One-pot Three-component Reaction
-
The synthesis of polyfunctionalized 7-amino-5-(4-aroyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile derivatives by a green approach was achieved via one-pot three-component reaction of arylglyoxals, malononitrile, and 1,3-dimethyl-6-aminouracil in the presence of urea as organocatalyst in EtOH:H2O (1:1) at 60°C. This protocol provides a mild and fast procedure to structurally diverse bicyclic pyridopyrimidines in good to excellent yields.
- Javahershenas, Ramin,Khalafy, Jabbar
-
p. 3163 - 3168
(2017/10/06)
-
- Synthesis and X-ray Characterization of Alkali Metal 2-Acyl-1,1,3,3-tetracyanopropenides
-
A novel route for synthesis of 2-acyl-1,1,3,3-tetracyanopropenides (ATCN) salts in high yields and excellent purities starting from readily available methyl ketones, malononitrile, bromine, and alkali metal acetates is reported. The starting aryl(heteroaryl) methyl ketones were oxidized to the corresponding α-ketoaldehydes by new a DMSO-NaBr-H2SO4 oxidation system in yields up to 90% within a short reaction time of 8-10 min. The subsequent stages of ATCN preparation are realized in aqueous media without use of any toxic solvents, in accordance with principle 5 of "green chemistry". Lithium, sodium, potassium, rubidium, and cesium 2-benzoyl-1,1,3,3-tetracyanopropenides were characterized by X-ray diffraction analysis. These salts show a good potential for synthesis of five- and six-membered heterocycles and may serve as potentially useful ligands in coordination and supramolecular chemistry.
- Karpov, Sergey V.,Grigor'Ev, Arthur A.,Kayukov, Yakov S.,Karpova, Irina V.,Nasakin, Oleg E.,Tafeenko, Victor A.
-
p. 6402 - 6408
(2016/08/16)
-
- Regiospecific one-pot, combinatorial synthesis of new substituted pyrimido[4,5-c]pyridazines as potential monoamine oxidase inhibitors
-
New 3-aryl-6-methylpyrimido[4,5-c]pyridazine-5,7(6H ,8H)-diones and 3-aryl-6-ethyl-7-thioxo-7,8-dihydropyrimido[4,5- c]pyridazin-5(6H)-ones were efficiently synthesized via a regiospecific one-pot reaction of N -methylbarbituric acid and N -ethyl-2-thiobarbituric acid with various arylglyoxal monohydrates in the presence of hydrazine dihydrochloride in ethanol at 50°C. The target compounds were obtained in high yields and were regioisomerically pure after recrystallization. These new heterocycles may act as potential MAOB inhibitors.
- Rimaz, Mehdi,Pourhossein, Paria,Khalili, Behzad
-
p. 244 - 254
(2015/05/27)
-
- Two efficient one-pot approaches for regioselective synthesis of new 3-arylpyridazino[4,3-c]quinolin-5(6H)-ones
-
Two efficient regioselective approaches for the one-pot synthesis of 3-arylpyridazino[4,3-c]quinolin-5(6H)-one derivatives are reported, by the three-component reaction of arylglyoxal monohydrates, quinoline-2,4-diol, and hydrazinium dihydrochloride or hydrazine hydrate in ethanol and pyridine. In ethanol, the reactions were catalyzed by 1,4-diazobicyclo[2,2,2]octane. The features of both procedures are high regioselectivity, mild reaction conditions, good to high yields, and operational simplicity.
- Rimaz, Mehdi
-
p. 1529 - 1534
(2015/10/20)
-
- Nucleophilic addition of (difluoromethyl)trimethylsilane to selected α-imino ketones and aryl diketones
-
Abstract Chemoselective addition of (difluoromethyl)trimethylsilane (CHF2SiMe3) to the carbonyl bond of aryl glyoxal derived α-imino ketones, and selected diaryl 1,2-diketones were studied in the presence of initiators, such as potas
- Obijalska, Emilia,Utecht, Greta,Kowalski, Marcin K.,Mlostoń, Grzegorz,Rachwalski, Micha?
-
p. 4701 - 4703
(2015/07/28)
-
- Molybdate sulfuric acid-catalyzed one-pot synthesis of substituted coumarins under solvent-free conditions
-
An efficient method for the synthesis of new aryloylamido coumarins via a one-pot, three-component reaction of an aryl glyoxal, benzamide, and a 4-hydroxycoumarin in the presence of molybdate sulfuric acid under solvent-free conditions is reported. This h
- Khodabakhshi, Saeed,Karami, Bahador,Eskandari, Khalil
-
p. 7263 - 7272
(2015/09/29)
-
- Chemoselective trifluoromethylation of the C=N group of α-iminoketones derived from arylglyoxals
-
Chemoselective addition of (trifluoromethyl)trimethylsilane to the CN group of N-(tert-butyl)-α-iminoketones in the presence of a fluoride ion as a catalyst was achieved under acidic conditions. Subsequent diastereoselective reductions of the obtained α-a
- Obijalska, Emilia,Kowalski, Marcin K.,Mlostoń, Grzegorz,Linden, Anthony,Heimgartner, Heinz
-
p. 151 - 157
(2015/03/05)
-
- Metal-free dual sp3 C-H functionalization: I2- promoted domino oxidative cyclization to construct 2,5-disubstituted oxazoles
-
An I2-promoted sp3 C-H functionalization has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available methyl ketones and benzylamines without any metal and peroxide catalyst. This domino oxidative cyclization process involves the cleavage of C-H bond and the formation of C-N, C-O bonds.
- Gao, Qing-He,Fei, Zhuan,Zhu, Yan-Ping,Lian, Mi,Jia, Feng-Cheng,Liu, Mei-Cai,She, Neng-Fang,Wu, An-Xin
-
-
- Regiospecific synthesis of novel furo[4,5- c ]coumarins in a one-pot reaction
-
A new and expedient assembly of an interesting class of amido-substituted furo[4,5-c]coumarins has been successfully achieved through a one-pot sequential coupling and cyclization strategy starting from 4-hydroxycoumarin, aryl glyoxals and benz-amide. All
- Karami, Bahador,Khodabakhshi, Saeed,Eskandari, Khalil
-
p. 998 - 1000
(2013/06/27)
-
- Synthesis and characterization of a 4-nitrophenyl functionalized NHC ligand and its palladium(II) complex
-
The synthesis and characterization of a novel pyridine coordinated dichloridopalladium(II) NHC complex is described. This compound possesses a saturated NHC ligand that is substituted with a para-nitrophenyl function in the 4-position of the NHC backbone.
- Rajabi, Fatemeh,Trampert, Jens,Sun, Yu,Busch, Mark,Br?se, Stefan,Thiel, Werner R.
-
p. 101 - 107
(2013/10/01)
-
- Willgerodt-Kindler reaction of arylglyoxals with amines and sulfur in aqueous media: A simple and efficient synthesis of -ketothioamides
-
A simple and efficient method for the synthesis of -ketothioamides via the Willgerodt-Kindler reaction is developed. Reactions were carried out between arylglyoxal hydrates, amines and elemental sulfur in water at 80°C to afford corresponding -ketothioamides in good to high yields in a short reaction time.
- Eftekhari-Sis, Bagher,Vahdati-Khajeh, Saleh,Amini, S. Motahhareh,Zirak, Maryam,Saraei, Mahnaz
-
p. 464 - 473
(2013/10/21)
-
- A highly efficient and enantioselective intramolecular cannizzaro reaction under TOX/Cu(II) catalysis
-
An asymmetric intramolecular Cannizzaro reaction of aryl and alkyl glyoxals with alcohols has been realized with an unprecedented high level of enantioselectivity, on the basis of a newly developed congested TOX ligand and a gradual liberation protocol of active glyoxals from glyoxal monohydrates. Preliminary results suggested a mechanism of enantioselective addition of alcohols to glyoxals contributing most to the stereoselectivity, other than by the dynamic kinetic resolution of hemiacetal intermediates.
- Wang, Pan,Tao, Wen-Jie,Sun, Xiu-Li,Liao, Saihu,Tang, Yong
-
supporting information
p. 16849 - 16852
(2013/12/04)
-
- Microwave-assisted selenium dioxide oxidation of aryl methyl ketones to aryl glyoxals
-
We report an improved procedure for the synthesis of phenyl glyoxal and a series of para-substituted aryl glyoxals by microwave-assisted selenium dioxide oxidation. The reaction time has been reduced from several hours to three minutes for activated aryl methyl ketone substrates and 18 min for deactivated substrates, with all reactions affording quantitative conversion into the corresponding aryl glyoxals.
- Young, Ryan M.,Davies-Coleman, Michael T.
-
experimental part
p. 4036 - 4038
(2011/08/09)
-
- Catalytic oxidations of enolizable ketones using 2-alkylidene-4- oxothiazolidine vinyl bromide
-
Direct oxidation of enolizable ketones to α-hydroxy derivatives, vicinal dicarbonyls or tricarbonyl compounds has been achieved by a catalytic amount of 2-alkylidene-4-oxothiazolidine vinyl bromide in DMSO as a solvent. The yields range from moderate to good.
- Baranac-Stojanovi?, Marija,Markovi?, Rade,Stojanovi?, Milovan
-
experimental part
p. 8000 - 8008
(2011/11/06)
-
- Asymmetric synthesis of β-amino alcohols by the transfer hydrogenation of α-keto imines
-
The asymmetric transfer hydrogenation of representative aryl and benzofuranyl 2-tert-butylaminoethanones with formic acid-triethylamine, catalyzed by RhCl[(R,R)-TsDPEN](C5Me5), produced the corresponding β-tert-butylamino alcohols in 97-99% ee. A short asymmetric synthesis of (R)-bufuralol, a potent β-adrenergic receptor antagonist, is described. This approach to β-amino alcohols from ketones circumvents the halogenation-reduction-amination sequence.
- Tafelska-Kaczmarek, Agnieszka,Prewysz-Kwinto, Andrzej,Skowerski, Krzysztof,Pietrasiak, Katarzyna,Kozakiewicz, Anna,Zaidlewicz, Marek
-
scheme or table
p. 2244 - 2248
(2010/11/03)
-
- Reactions of α-imino ketones derived from arylglyoxals with (trifluoromethyl)trimethylsilane; A new route to β-amino-α- trifluoromethyl alcohols
-
The reactions of α-imino ketones, derived from arylglyoxals, with (trifluoromethyl)trimethylsilane (CF3SiMe3) in DME solution, in the presence of catalytic amount of CsF, at room temperature, yield O-silylated β-imino alcohols in the
- Mloston, Grzegorz,Obijalska, Emilia,Tafelska-Kaczmarek, Agnieszka,Zaidlewicz, Marek
-
scheme or table
p. 1289 - 1296
(2011/02/22)
-