- Synthesis, Docking, and Biological activities of novel Metacetamol embedded [1,2,3]-triazole derivatives
-
ERα controls the breast tissue development and progression of breast cancer. In our search for novel compounds to target Estrogen Receptor Alpha Ligand-Binding Domain, we identified “N-(3-((1H-1,2,3-triazol-4-yl)methoxy)phenyl)acetamide” derivatives as lead compounds. The Docking studies indicated good docking score for Metacetamol derivatives when docked into the 1XP6. A series of metacetamol derivatives have been synthesized, characterized and evaluated for cytotoxicity, anti bacterial and anti oxidant activities. Among the tested twelve hybrid compounds, “7a, 7g, 7h and 7i” derivatives showed promising cytotoxicity with IC50 value of 50 value of 30 μM, whereas Compounds “7a, 7b, 7c, 7d, 7g, 7j, 7k and 7l” showed moderate anti bacterial activity with the MIC value of 300 μM.
- Battu, Satyanarayana,Joolakanti, Hima Bindhu,Kamepalli, Ramanjaneyulu,Miryala, Jeevanreddy
-
-
- Carbocation Catalyzed Bromination of Alkyl Arenes, a Chemoselective sp3 vs. sp2 C?H functionalization.
-
The versatility of the trityl cation (TrBF4) as a highly efficient Lewis acid organocatalyst is demonstrated in a light induced benzylic brominaion of alkyl-arenes under mild conditions. The reaction was conducted at ambient temperature under common hood light (55 W fluorescent light) with catalyst loadings down to 2.0 mol% using N-bromosuccinimide (NBS) as the brominating agent. The protocol is applicable to an extensive number of substrates to give benzyl bromides in good to excellent yields. In contrast to most previously reported strategies, this protocol does not require any radical initiator or extensive heating. For electron-rich alkyl-arenes, the trityl ion catalyzed bromination could be easily switched between benzylic sp3 C?H functionalization and arene sp2 C?H functionalization by simply alternating the solvent. This chemoselective switch allows for high substrate control and easy preparation of benzyl bromides and bromoarenes, respectively. The chemoselective switch was also applied in a one-pot reaction of 1-methylnaphthalene for direct introduction of both sp3 C?Br and sp2 C?Br functionality. (Figure presented.).
- Ni, Shengjun,El Remaily, Mahmoud Abd El Aleem Ali Ali,Franzén, Johan
-
supporting information
p. 4197 - 4204
(2018/09/25)
-
- Synthesis of Phenanthridines through Palladium-Catalyzed Cascade Reaction of 2-Halo-N-Ms-arylamines with Benzyl Halides/Sulfonates
-
An efficient palladium-catalyzed nucleophilic substitution/C–H activation/aromatization cascade reaction between readily available 2-halo-N-Ms-arylamines (Ms = methanesulfonyl) and benzyl halides/sulfonates has been described. A wide variety of phenanthridines were synthesized in a one-pot fashion in moderate to high yields (37–86 %). Notably, this method provides a straightforward, facile approach for the synthesis of phenanthridines. The practicality was further substantiated by successfully carrying out a gram-scale preparation.
- Yang, Si-Yi,Han, Wen-Yong,Zhang, Ding-Lei,Zhou, Xiao-Jian,Bai, Mei,Cui, Bao-Dong,Wan, Nan-Wei,Yuan, Wei-Cheng,Chen, Yong-Zheng
-
p. 996 - 1003
(2017/02/15)
-
- Improved Halogenation of Methyl Aromatics and Methyl Heteroaromatics: Unexpected Reactivity of Tetrahalogeno-diphenylglycolurils
-
1,3,4,6-Tetrachloro (TCDGU) and 1,3,4,6-tetrabromo-3α,6α-diphenylglycolurils smooth halogen oxidizers have been exploited in a new direction as reagents for free radical substitution toward some N-halosuccinimide nonreactive bis-heterocycles. An unexpected selectivity and reactivity were observed with methyl benzenes, methyl heterocycles, and methyl-bis-heterocycles of interest. A chemometric study has been performed to optimize five independent factors of the chlorination reaction with TCDGU. The predictive model was established either for the halogenation conversion and the ratio of monochlorination.
- Moretti, Florian,Poisson, Guillaume,Marsura, Alain
-
p. 173 - 183
(2016/05/19)
-
- Palladium(0)-catalyzed cyclopropanation of benzyl bromides via C(sp 3)-H bond activation
-
A novel and highly efficient Pd(0)-catalyzed domino reaction to prepare cyclopropane derivatives has been established. The process involves a Heck-type coupling reaction and a C(sp3)-H bond activation. Preliminary DFT calculations suggest that a four-membered palladacycle intermediate is involved. This journal is the Partner Organisations 2014.
- Mao, Jiangang,Zhang, Shuo-Qing,Shi, Bing-Feng,Bao, Weiliang
-
supporting information
p. 3692 - 3694
(2014/04/03)
-
- Catalyst and solvent-free bromination of toluene derivatives by HBr-H 2O2 with visible-light photocatalysis using a continuous-flow micro reactor
-
The efficiency of the bromination of toluene derivatives has been improved significantly by utilising a combination of hydrogen peroxide (30%) and hydrogen bromide (40%) in a continuous-flow micro reactor. This catalyst and solvent-free reaction takes place by visible-light photocatalysis.
- Yu, Wu-Bin,Yu, Dong-Ping,Zheng, Ming-Ming,Shan, Shu-Ting,Li, Yu-Jin,Gao, Jian-Rong
-
experimental part
p. 258 - 260
(2012/09/22)
-
- High selectively oxidative bromination of toluene derivatives by the H 2O2-HBr system
-
An aqueous solution of hydrogen peroxide and hydrogen bromide illuminated by a 60 W incandescent light bulb serves as a source of bromine radicals. Various substituted toluenes (NO2, Cl, Br, H, CH3) were high selectively brominated at the benzyl position for monobromination in CH2Cl2 at ice water with catalyst free. This simple but effective bromination of toluene derivatives with an aqueous H2O 2-HBr system is characterized with the use of inexpensive reagents and a lower impact on the environment, which make it a good alternative to the existing bromination methods.
- Ju, Jie,Li, Yu Jin,Gao, Jian Rong,Jia, Jian Hong,Han, Liang,Sheng, Wei Jian,Jia, Yi Xia
-
experimental part
p. 382 - 384
(2012/01/05)
-
- Visible-light-promoted Wohl-Ziegler functionalization of organic molecules with N-bromosuccinimide under solvent-free reaction conditions
-
The visible-light-induced transformation of toluenes with N-bromosuccinimide (NBS) under solvent-free reaction conditions (SFRC) was studied. The reaction took place in spite of the very restricted molecular motion; toluenes could be regioselectively converted to benzyl bromides. Selective radical-chain reactions with NBS were carried out in liquid/liquid and in solid/solid systems; furthermore, reactions could be performed in the presence of air. The radical scavenger TEMPO (=2,2,6,6-tetramethylpiperidin-1- yloxy) completely suppressed the side-chain bromination of toluenes with NBS under SFRC. Electron-withdrawing groups decreased the reactivity of the toluenes, and the Hammett reaction constant ρ+ = -1.7 indicated involvement of polar radical intermediates with electrophilic character.
- Jereb, Marjan,Zupan, Marko,Stavber, Stojan
-
experimental part
p. 555 - 566
(2009/09/06)
-
- Poly(N,N′-dibromo-N-ethyl-benzene-1,3-disulfonamide), N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide and novel poly(N,N′-dibromo-N-phenylbenzene-1,3-disulfonamide) as powerful reagents for benzylic bromination
-
N,N,N′,N′-Tetrabromobenzene-1,3-disulfonamide [TBBDA], poly(N,N′-dibromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS], and novel poly(N,N′-dibromo-N-phenylbenzene-1,3-disulfonamide) [PBPS] can be used for bromination of benzylic positions in solvent.
- Ghorbani-Vaghei, Ramin,Chegini, Mohammad,Veisi, Hojat,Karimi-Tabar, Mehdi
-
scheme or table
p. 1861 - 1865
(2009/07/19)
-
- Contrasting chemoselectivities in the ultrasound and microwave assisted bromination reactions of substituted alkylaromatics with N-bromosuccinimide
-
Ultrasound and microwave assisted bromination reactions of various alkylaryls with N-bromosuccinimide, either neat or in water, shows diverse chemoselectivity. Thus, ring substitution occurs in water with ultrasound, whereas with microwaves both side-chain α-bromination and ring substitution occur. With neat reactants, side-chain α-bromination predominates for microwave assisted reactions. In the presence of water the chemoselectivity with microwave-promoted bromination is similar to that observed using classical methods.
- Heropoulos, Georgios A.,Cravotto, Giancarlo,Screttas, Constantinos G.,Steele, Barry R.
-
p. 3247 - 3250
(2008/02/02)
-
- Free radical bromination by the H2O2-HBr system on water
-
An aqueous solution of hydrogen peroxide and hydrogen bromide illuminated by a 40 W incandescent light bulb serves as a source of bromine radicals. Various substituted toluenes (H, Me, tBu, Br, COOEt, COPh, NO2) were brominated at the benzyl position. This haloperoxidase-like system for benzylic bromination does not require the presence of metal ions or an organic solvent for efficient conversion of methyl-arenes to benzyl bromides.
- Podgor?ek, Ajda,Stavber, Stojan,Zupan, Marko,Iskra, Jernej
-
p. 7245 - 7247
(2007/10/03)
-
- Side chain bromination of mono and dimethyl heteroaromatic and aromatic compounds by solid phase N-bromosuccinimide reaction without radical initiator under microwave
-
A series of side chain mono and dibromo derivatives of mono and dimethyl heteroaromatic and aromatic compounds (1-17) were synthesized by one step solid phase N-bromosuccinimide (NBS) reaction without radical initiator by microwave irradiation. The benzylic mono and dibromo products were exclusively preferred except in the case of 6-methylpyridine amides (8 and 9) where nuclear and also side chain bromination resulted. Naphthyridine systems resulted improved yields. By this method, we also report the synthesis of 2-pivaloylaminopterin-6- carbaldehyde.
- Goswami, Shyamaprosad,Dey, Swapan,Jana, Subrata,Adak, Avijit Kumar
-
p. 916 - 917
(2007/10/03)
-
- A practical synthesis of the F-ring of halichondrin B via ozonolytic desymmetrization of a C2-symmetric dihydroxycyclohexene
-
C2-symmetric dihydroxycyclohexene 1 was desymmetrized via a one-pot Criegee ozonolysis/acylation protocol to afford acetal-lactone 2. Installation of the allyl side chain on the convex face of the bicyclic system and subsequent reduction provided the desired tetrahydrofuran 4 with the correct relative and absolute stereochemistries. Simple functional group manipulations led to the desired F-ring module 3 of halichondrin B.
- Jiang, Lei,Martinelli, Joseph R.,Burke, Steven D.
-
p. 1150 - 1153
(2007/10/03)
-
- Synthesis and in vitro evaluation of substituted aryl- and hetarylmethyl phosphonate and phosphate - UMP derivatives as potential glucosyltransferase inhibitors
-
The enzyme β (1→4)-glucosyltransferase (BGT) catalyses the transfer of glucose from uridine diphospho-glucose (UDP-Glc) to 5-hydroxymethylcytosine (5-HMC) bases in double-stranded DNA. Potential inhibitors of BGT were developed by structure-based design and synthesized. The designed inhibitors 1-6 provide conformational mimicry of the transition state in glucosyltransfer reactions. The key synthetic steps involve a Michaelis-Arbuzov reaction followed by coupling with uridine-5′-morpholidophosphate as activated UMP derivative. The compounds were tested for in vitro inhibitory activity against BGT and the inhibition kinetics were examined. Three of the designed molecules were found to be potential inhibitors of BGT having IC50 values in the micromolar (μM) range. Useful structure-activity relationships were established which provide guidelines for the design of future generations of inhibitors of BGT.
- Bhattacharya, Asish K.,Stolz, Florian,Kurzeck, Juergen,Rger, Wolfgang,Schmidt, Richard R.
-
p. 973 - 982
(2007/10/03)
-
- Carbon tetrabromide - A new brominating agent for alkanes and arylalkanes
-
Quantitative catalytic bromination of alkanes, cycloalkanes, and arylalkanes with carbon tetrabromide as brominating agent was accomplished for the first time.
- Smirnov,Zelikman,Beletskaya,Golubeva,Tsvetkov,Levitskii,Kazankova
-
p. 962 - 966
(2007/10/03)
-
- Design and synthesis of aryl/hetarylmethyl phosphonate-UMP derivatives as potential glucosyltransferase inhibitors
-
A novel class of glucosyltransferase inhibitors has been designed and synthesised. The designed inhibitors 1-4 provide conformational mimicry of the transition-state in glucosyltransfer reactions. The key synthetic steps involve a Michaelis-Arbuzov reaction followed by coupling with uridine-5′-morpholidophosphate as activated UMP derivative.
- Bhattacharya, Asish K.,Stolz, Florian,Schmidt, Richard R.
-
p. 5393 - 5395
(2007/10/03)
-
- Scavenger assisted combinatorial process for preparing libraries of tertiary amine compounds
-
This invention relates to a novel solution phase process for the preparation of tertiary amine combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.
- -
-
-
- Selectivity in bromination of alkylbenzenes in the presence of montmorillonite clay
-
Bromination of alkylbenzenes using bromine in carbon tetrachloride yields ring brominated products in the presence of K10-montmorillonite. In contrast, bromination without clay results only in side-chain bromination.
- Venkatachalapathy, Chockalingam,Pitchumani, Kasi
-
p. 2581 - 2584
(2007/10/03)
-
- NUCLEOPHILIC SUBSTITUTION REACTION OF BENZYL BROMIDE WITH N,N-DIMETHYLANILINE: SIGNIFICANCE OF EQUILIBRIUM CROSS-INTERACTION CONSTANT
-
Kinetic studies on the reversible reactions of benzyl bromides with N,N-dimethylanilines were carried out for both the forward (kf) and reverse (kr) directions.The equilibrium constants, K were calculated using the ratio kf//kr and the equilibrium cross-interaction constant, ρeXY was determined.The ρeXY value was shown to represent a maximum intensity of interactions between substituents X and Y through covalent bonds within a molecule.The normalized values of ρX (ρnuc) and ρXY indicate that in the transition state the fractional development or loss of polar and resonance interactions in the benzyl system are imbalanced or non-perfectly synchronized.In the forward reaction the fractional loss of resonance interaction becomes enhanced, whereas in the reverse reaction the fractional development of resonance interaction lags behind the corresponding changes of polar interaction by ca 45percent.
- Lee, Ikchoon,Park, Yong Kyun,Huh, Chul,Lee, Hai Whang
-
p. 555 - 560
(2007/10/02)
-
- ORGANIC PHOSPHORUS COMPOUNDS 91. SYNTHESIS AND PROPERTIES OF 1-AMINO-2-ARYLETHYLPHOSPHONIC AND -PHOSPHINIC ACIDS AS WELL AS -PHOSPHINE OXIDES
-
The preparation, physical and spectroscopic properties of 1-amino-2-arylethylphosphonic, and -phosphinic acids as well as -phosphine oxides, the phosphorus analogues of phenylalanine are described, and the reactions of 1-amino-2-(4-fluorophenyl)ethylphosphonates with acetals, isocyanides, esters, acid anhydrides, activated aromatic nitro- and halogen compounds, and with N-protected alanine are reported.It is shown that several of the 1-amino-2-arylethylphosphonic acids are strong inhibitors of PAL and anthocyanin synthesis and also are quite active botryticides.Among the active compounds were 1-amino-2-(4-fluorophenyl)ethylphosphonic acid, 3f, and the methyl-substituted compounds 3k, 3l, and 3m.The fluoroderivative 3f was also effective as a seed-dressing agent in barley showing a 100percent protection against the fungus Fusarium nivale at 600 ppm.
- Maier, Ludwig
-
-
- Halogenation of benzyl- and (heteroaromatic methyl)cobaloximes: Direct competition between ring halogenation and cobalt-carbon bond cleavage
-
(4-Acetamidobenzyl)- and (4-(dimethylamino)benzyl)cobaloximes react rapidly with low concentrations of chlorine and bromine in acetic acid or chloroform at room temperature under nitrogen. Both ring-halogenated organometallic products and direct Co-C cleavage products are formed. However, (4-methoxybenzyl)cobaloxime forms 4-methoxy-2-halotoluene as the exclusive product. (3-Methylbenzyl)cobaloxime undergoes a substantial proportion of ring substitution by both Br2 and Cl2 in competition with the cleavage of the Co-C bond. (3-Methoxybenzyl)cobaloxime forms only the ring-substituted organometallic product. A remarkable difference in reactivity between 2- and 3-isomers of the (thienylmethyl)- and (furylmethyl)cobaloximes is observed; for example, Co-C cleavage is the primary process in furfuryl- and (2-thienylmethyl)cobaloximes whereas ring halogenation occurs much faster in the 3-isomer. The results are discussed in terms of a σ-π delocalization phenomenon by which the electronic effect of a substituent in the benzyl group is effectively transmitted to the Co-C bond reactivity. The substituent effect of the metallomethyl group -CH2Co(dmgH)2py is found to be more than that of the methoxy group. The mechanism of the Co-C cleavage is described.
- Gupta,Kumar, Manoj,Roy, Sujit
-
-
- Trimethylamine-Borane Bromide as Alternative Reagent for Reductive Bromation of Aromatic Carbonyl Compounds
-
The reaction of bromine with aromatic carbonyl compounds and trimethylamine-borane in chloroform leads to benzyl bromides.
- Corre, Maurice Le,Gheerbrant, Emmanual,Deit, Herve Le
-
p. 313 - 314
(2007/10/02)
-
- New Three- and Sixfold Bridged Phenylogous Cyclophanes
-
The syntheses of the threefold bridged cyclophanes 4, 5, of the sixfold bridged cyclophane 6, and of the triple-layered cyclophanes 7, 8 are reported.The yields have been optimized by variation of the reaction conditions and by use of the cesium effect.The enantiomer resolution of 7 and the X-ray structural analysis of 4 are discussed.
- Sendhoff, Norbert,Kissener, Wolfram,Voegtle, Fritz,Franken, Sybille,Puff, Heinrich
-
p. 2179 - 2186
(2007/10/02)
-
- Halogenolysis of Benzylcobaloximes
-
The reaction of substituted benzylcobaloximes p-RC6H4Co(dmgH)2-Py (R=OMe, NHCOCH3 and NMe2) and m-RC6H4CH2Co(dmgH)2Py (R=Me, OMe) with halogens (Cl2 and Br2) in chloroform under nitrogen forms ring substituted organic and organometallic products.
- Gupta, B. D.,Kumar, Manoj
-
p. 701 - 704
(2007/10/02)
-
- Kinetics and Mechanism of Bromination of Toluene and Substituted Toluenes by N-Bromo Acetamide (NBA)
-
Kinetics of bromination of toluene and substituted toluenes by N-Bromo Acetamide (NBA) in aqueous acetic acid perchloric acid medium has been reported.The reaction is first order in NBA, first order in substrate and fractional order in acid in case of toluene.In case of o-xylene, m-xylene and p-xylene the reaction is first order with respect to NBA, zero order in substrate and first order in acid.The effect of solvent composition has been investigated.Activation parameters have been computed.Suitable mechanism is postulated taking into consideration all the observed kinetic data.
- Pati, Subas C.,Pathy, H. P.,Dev, B. R.
-
p. 385 - 391
(2007/10/02)
-
- New Methods of Formation of Meta-Substituted Aromatic Compounds
-
The addition of organolithium reagents to the oxa tricyclic ketone 1 occurs stereospecifically to produce the corresponding tertiary carbinols 2a-d.When the alcohols 2a-d are treated with TiCl4, ring fragmentation and dehydration occur to produce good yields of 5,6-dihydrobenzaldehydes 3a-d.Oxidation of aldehydes 3a-d then leads to the corresponding meta-substituted benzaldehydes 4a-d.Alternatively, use of the Lewis acid Me2BBr did not stop at the dihydrobenzaldehyde stage.Tautomerization of the diene aldehydes 3a-d produced meta-substituted benzyl alcohols 7a-d or benzyl bromides 8a-d under prolonged reaction times.The addition of silica gel to the reactions accelerated the formation of the benzyl bromides.
- Adams, Julian,Belley, Michel
-
p. 3878 - 3881
(2007/10/02)
-
- SYNTHESIS OF INDENES FROM PHENYLPROPANONES USING ALUMINA CATALYST
-
1,3-Diphenylpropan-2-one undergoes dehydration over alumina at around 400 deg C to form 1,3-diphenylallene which cyclizes to 2-phenylindene.Since the parent ketone can be obtained under the reaction conditions from phenylacetic acid, the present reaction forms a one step syntheses of 2-phenylindene from phenylacetic acid. 3- and 4-methylphenylacetic acids also give the corresponding indenes. 1,3-Diphenylpropan-1-ones also give phenylindenes, presumably by a direct cyclodehydration reaction.
- Jayamani, M.,Pant, Nalin,Ananthan, S.,Narayanan, K.,Pillai, C. N.
-
p. 4325 - 4332
(2007/10/02)
-
- HOMOLYTIC DISPLACEMENT AT CARBON VI. SYNTHESIS OF TRICHLOROETHYLARENES FROM BENZYLCOBALOXIMES
-
Benzylbis(dimethylglyoximato)pyridinecobalt(III) reacts with bromotrichloromethane at from 50 to 90 deg C in chloroform to give good yields of trichloroethylbenzene, which are higher when imidazole is present in the reaction mixture.Methyl- and polymethyl-substituted benzylbis(dimethylglyximato)pyridinecobalt(III) complexes give higher yields of the corresponding trichloroethylarenes (85-90percent), whereas 4-chlorobenzylbis(dimethylglyoximato)pyridinecobalt(III) only gives the 4-nitro-trichloroethylarene when imidazole is present during the reaciton.Similar reactions were observed with benzylcobaloximes and trichloromethanesulphonyl chloride both thermally and under irradiation by tungsten lamps through all-pyrex apparatus.The reactions are interpreted as a direct attack of the trichloromethyl radical on the α-carbon of the benzyl ligand.
- Bougeard, Peter,Gupta, B. Dass,Johnson, Michael D.
-
p. 211 - 219
(2007/10/02)
-