- Synthesis, antimicrobial activities and binding mode analysis of some novel N-substituted imidazoles and nitroimidazoles
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Novel N-((2-(aryl)-imidazol-1-yl) methyl)-anilines 2a-n and 1-(3'-arylamino-2'- hydroxypropyl)-2-methyl-4-nitroimidazoles 4a-g have been synthesized. The compounds have been characterized on the basis of elemental analysis and spectral data. All the compounds were evaluated for their antibacterial activities. Among the synthesized compounds, compounds 2m, 2n and compounds 4c, 4e exhibited highest inhibitory activity against all the bacterial strains, comparable to the standard drug ciprofloxacin. Binding mode analysis of the highest active compounds was carried out in the active site of GlcN-6-P synthase (2VF5).
- Ganguly, Swastika,Mishra, Surbhi,Gupta, Ankita,Sankrityayan, Ira,Dev, Abhimanyu
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p. 373 - 380
(2019/01/21)
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- Multi-wall carbon nanotube supported manganese(III) porphyrin: An efficient and reusable catalyst for oxidation of 2-imidazolines with sodium periodate
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The oxidation of 2-substituted imidazolines with sodium periodate catalyzed by tetrakis(p-aminophenyl)-porphyrinatomanganese(III) chloride, [Mn(TNH 2PP)Cl], supported on functionalized multi-wall carbon nanotubes is reported. A wide variety of 2-imidazolines were efficiently converted to their corresponding imidazoles by this catalytic system. When the same reaction was subjected to ultrasonic irradiation, the reaction times were reduced significantly and the product yields were increased. This catalyst could be reused several times without significant loss of activity. The effects of reaction parameters such catalyst amount, choice of solvent, and the effects of ultrasonic irradiation on the catalytic activity have been investigated.
- Kargar, Hadi,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Rezaei, Simindokht
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- Synthesis, antimicrobial and antimycobacterial evaluation of [2-(substituted phenyl)-imidazol-1-yl]-pyridin-3-yl-methanones
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A series of [2-(substituted phenyl)-imidazol-1-yl]-pyridin-3-yl-methanones (111) were synthesized and screened for their antimicrobial and antimycobacterial activities. Further, a series of [2-(substituted phenyl)-benzimidazol-1-yl]-pyridin-3-yl-methanones (1220) reported in our earlier study was also screened for their antimycobacterial activity. The antimycobacterial activity results indicated that [2-(4-Nitro-phenyl)-imidazol- 1-yl]-pyridin-3-yl-methanone (8, minimum inhibitory concentration [MIC]=3.13 g) was equipotent as standard drug ciprofloxacin and [2-(4-Nitro-phenyl)- benzimidazol-1-yl]-pyridin-3-yl-methanone (16, MIC=1.56 g) was equipotent as standard drug ethambutol. The results of antimicrobial screening demonstrated that 2-[1-(Pyridine-3-carbonyl)-1H-imidazol-2-yl]-benzoic acid (compound 11, MIC=0.002 g) was two times more effective than standard drug ciprofloxacin (MIC=0.004 g) against tested bacterial strains and [2-(2,5-Dimethyl-phenyl)- imidazol-1-yl]-pyridin-3-yl-methanone (compound 3, MIC=0.005 g) was equipotent to the reference compound, fluconazole against tested fungal strains.
- Narasimhan, Balasubramanian,Sharma, Deepika,Kumar, Pradeep,Yogeeswari, Perumal,Sriram, Dharmarajan
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experimental part
p. 720 - 727
(2012/04/04)
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- Rapid and efficient biomimetic oxidation of 2-imidazolines to their corresponding imidazoles with NaIO4 catalyzed by Mn(salophen)Cl
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Rapid and efficient oxidation of 2-substituted imidazolines with sodium periodate is reported. The Mn(III)-salophen/NaIO4 catalytic system efficiently converted 2-imidazolines to their corresponding imidazoles at room temperature in 2: 1, CH3CN/H2O mixture.
- Kargar, Hadi
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experimental part
p. 863 - 866
(2011/06/25)
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- Dehydrogenation of 2-imidazolines with sodium periodate catalyzed by manganese(III) tetraphenylporphyrin
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In the present work, dehydrogenation of 2-substituted imidazolines with sodium periodate in the presence of tetraphenylporphyrinatomanganese(III) chloride, [Mn(TPP)Cl], is reported. A wide variety of 2-imidazolines efficiently converted to their corresponding imidazoles by [Mn(TPP)Cl]/NaIO4 catalytic system at room temperature in 1:2, CH3CN/H2O mixture. The effect of reaction parameters such as kind of solvent and catalyst amount was also investigated.
- Kargar, Hadi,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Nameni, Iman
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experimental part
p. 2146 - 2148
(2011/04/24)
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- Oxidation of 2-imidazolines to 2-imidazoles with sodium periodate catalyzed by polystyrene-bound manganese(III) porphyrin
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In the present work, the dehydrogenation of 2-substituted imidazolines with sodium periodate in the presence of tetraphenylporphyrinatomanganese(III) chloride supported on polystyrene-bound imidazole, [Mn(TPP)Cl@PSI] is reported. A wide variety of 2-imidazolines were efficiently converted to their corresponding imidazoles by the [Mn(TPP)Cl@PSI]/NaIO4 catalytic system in a 1:2 CH3CN/H2O mixture under agitation with magnetic stirring. Ultrasonic irradiation enhanced the catalytic activity of this catalyst in the oxidation of 2-imidazolines and this led to shorter reaction times and higher product yields. This catalyst could be reused several times without significant loss of its catalytic activity.
- Kargar, Hadi,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Naghipour, Mahmood
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experimental part
p. 1463 - 1468
(2011/06/27)
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- Direct Oxidative Conversion of Benzoyl Chlorides to 2-Imidazoles Using Heteropolyacids
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The reaction of benzoyl chlorides with ethylenediamine in the presence of catalytic amounts of Keggin-type heteropolyacids led to oxidative conversion of benzoyl chlorides to the corresponding 2-imidazoles in good yields.
- Sadjadi, Samaheh,Heravi, Majid M.,Poormohammad, Nargess,Oskooie, Hossein A.,Beheshtiha, Yahya. Sh.,Bamoharram, Fatemeh F.
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experimental part
p. 3119 - 3125
(2009/12/01)
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- Synthesis, antimicrobial and antiviral evaluation of substituted imidazole derivatives
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In the present study, we have synthesized 2-(substituted phenyl)-1H-imidazole (1-12) and (substituted phenyl)-[2-(substituted phenyl)-imidazol-1-yl]-methanone (13-26) analogues and screened them for their antimicrobial activity against Gram positive, Gram negative and fungal species. The results of antibacterial study indicated that compounds 15, 17 and 24 showed appreciable antibacterial activity and compound 26 emerged as the most potential antifungal agent. The results of SAR studies indicated that the presence of electron withdrawing groups is necessary for the antimicrobial activity of the synthesized compounds. The results of the present study indicated that compounds 15, 17 and 24 might be of interest for the identification of new antimicrobial molecules as their antibacterial activity is equivalent to the standard drug norfloxacin. Further, the antiviral screening of (substituted phenyl)-[2-(substituted phenyl)-imidazol-1-yl]-methanones (13-26) against a panel of viral strains indicated that compounds 16 and 19 can be selected as lead compounds for the development of novel antiviral agents.
- Sharma, Deepika,Narasimhan, Balasubramanian,Kumar, Pradeep,Judge, Vikramjeet,Narang, Rakesh,De Clercq, Erik,Balzarini, Jan
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experimental part
p. 2347 - 2353
(2009/12/03)
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- An efficient synthesis of 2-arylimidazoles by oxidation of 2-arylimidazolines using activated carbon-O2 system and its application to palladium-catalyzed Mizoroki-Heck reaction
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Oxidative conversion of 2-substituted imidazoline (dihydroimidazole) to the corresponding imidazole was achieved by an activated carbon-O2 system. Also, the 2-arylimidazolines and 2-arylimidazoles have been found to work as simple ligands in the palladium-catalyzed Mizoroki-Heck reaction.
- Haneda, Satoshi,Okui, Ayaka,Ueba, Chigusa,Hayashi, Masahiko
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p. 2414 - 2417
(2007/10/03)
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- Mild, efficient, and chemoselective dehydrogenation of 2-imidazolines, bis-imidazolines, and N-substituted-2-imidazolines with potassium permanganate supported on montmorillonite K-10
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Different types of 2-imidazolines, bis-imidazolines, and N-substituted-2-imidazolines are efficiently oxidized to their corresponding imidazoles with potassium permanganate (KMnO4) supported on montmorillonite K-10 under very mild conditions. The procedure is very simple and no strict conditions were required. Selective dehydrogenation of 2-alkyl-2-imidazolines in the presence of 2-aryl-2-imidazolines is a noteworthy advantage of this method and can be considered as a useful practical achievement in these reactions.
- Mohammadpoor-Baltork, Iraj,Abdollahi-Alibeik, Mohammad
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p. 110 - 114
(2007/10/03)
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- Novel and chemoselective dehydrogenation of 2-substituted imidazolines with potassium permanganate supported on silica gel
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Various types of 2-imidazolines are efficiently oxidized to the corresponding imidazoles using potassium permanganate supported on silica gel under mild conditions at room temperature. 2-Alkylimidazolines are selectively converted to their corresponding imidazoles in the presence of 2-arylimidazolines. Chemoselective oxidation of 2-imidazolines in the presence of other oxidizable functional groups such as sulfide, ether, aldehyde, acetal, and THP ether was also achieved by this reagent system.
- Mohammadpoor-Baltork, Iraj,Zolfigol, Mohammad Ali,Abdollahi-Alibeik, Mohammad
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p. 8687 - 8690
(2007/10/03)
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- Novel, mild and chemoselective dehydrogenation of 2-imidazolines with trichloroisocyanuric acid
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A rapid, mild and high-yielding method for dehydrogenation of a variety of structurally diverse 2-imidazolines to imidazoles jusing trichloroisocyanuric acid (TCCA) in the presence of DBU is reported. Chemoselective oxidation of 2-imidazolines can be achieved in the presence of sulfide and alcohol. The mild conditions of this procedure and the absence of any transition metal make this reaction suitable for safe laboratory use.
- Mohammadpoor-Baltork, Iraj,Zolfigol, Mohammad Ali,Abdollahi-Alibeik, Mohammad
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p. 2803 - 2805
(2007/10/03)
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- Alumina supported potassium permanganate: An efficient reagent for chemoselective dehydrogenation of 2-imidazolines under mild conditions
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An efficient method for the oxidation of 2-imidazolines to their corresponding imidazoles using KMnO4/Al2O3 under very mild reaction conditions is reported. Selective oxidation of 2-alkylimidazolines was also performed in the presence of 2-arylimidazolines and other functional groups such as sulfide, ether, aldehyde, acetal and THP ether. Potassium permanganate supported on alumina was found to be an efficient reagent system for dehydrogenation of 2-imidazolines to imidazoles under mild conditions at room temperature. Selective oxidation of 2-alkylimidazolines in the presence of 2-arylimidazolines was achieved using this reagent system. 2-Imidazolines were also selectively converted to their corresponding imidazoles in the presence of other oxidizable functional groups such as sulfide, ether, aldehyde, acetal and THP ether. The oxidation procedure described here is easy to carry out and does not require strict reaction conditions.
- Abdollahi-Alibeik, Mohammad,Mohammadpoor-Baltork, Iraj,Zolfigol, Mohammad Ali
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p. 6079 - 6082
(2007/10/03)
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- New one-step synthesis of 2-aryl-1H-imidazoles: Dehydrogenation of 2-aryl-δ2-imidazolines with dimethylsulfoxide
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A new one-step method for the preparation of 2-aryl-1Himidazoles 3, based on the DMSO dehydrogenation of 2-aryl-Δ2-imidazolines, is described. A comparative study between DMSO and 10% Pd/C, the best known catalyst employed in this transformation, has also been developed. Both protocols were carried out at 120 °C for 48 hours.
- Anastassiadou,Baziard-Mouysset,Payard
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p. 1814 - 1816
(2007/10/03)
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- 2,5-DIAZACYCLOPENTADIENYLIDENE: A STANDARD CARBENE OR A HIGHLY REACTIVE DIRADICAL?
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2,5-Diazacyclopentadienylidene (2H-imidazolidene), generated either by photolysis or thermolysis from 2-diazo-2H-imidazole, reacts with benzene derivatives to give mainly a mixture of o-, m-, p-substitued 2-phenylimidazoles.The carbene shows a strong diradical character, in sharp contrast with the well-known behavior of cyclopentadienylidene.
- Bru, Nuria,Vilarrasa, Jaume
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p. 1489 - 1492
(2007/10/02)
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