- A facile greener synthesis, antimicrobial evaluation and molecular modelling of new 4-aryl-2-(3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridin-2-yl)phthalazin-1(2H)-one derivatives
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Abstract: The synthesis of 4-aryl-2-(3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridin-2-yl)phthalazin-1(2H)-ones was performed by cyclization of 2-hydrazinyl-3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridine with 2-aroylbenzoic acids in ethanol containing a catalytic amount of concentrated sulfuric acid under solid state conditions. All these synthesized compounds (8a–h) were screened for their in vitro antibacterial activity against gram-positive bacteria such as (Staphylococcus aureus) and gram-negative bacteria (Escherichia coli) and also evaluated for their antifungal activity against Aspergillus Niger and Helmenthosphorium oryzae fungal strains. Some of the products demonstrate good antibacterial activity and moderate antifungal activity. In predominantly, 8b, 8d, 8g, and 8h compounds showed good to excellent antibacterial and antifungal activities. The antimicrobial activity of the compound 8 was further investigated with the help of in LibDock score docking study to predict the active sites. Graphical abstract: [Figure not available: see fulltext.].
- Sakram, Boda,Ravi, Dharavath,Raghupathi, Mutyala,Kumar, Boda Sathish,Anantha Lakshmi
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p. 2007 - 2022
(2019/01/10)
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- Metal-Free Arylation-Lactonization Sequence of γ-Alkenoic Acids Using Anilines as Aryl Radical Precursors
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The presence of salicylic acid (10 mol-%) and H2O (10 equiv.) significantly improves the arylation-lactonization sequence of γ-alkenoic acids with in situ formed diazonium salts (from bench stable anilines). The reaction is finished in less than 5 h without thermal or photochemical activation, giving access to a variety of γ,γ-disubstituted butyrolactones. The protocol is user-friendly and can be used at gram-scale or adapted to transform alkenols into phthalanes. Control experiments revealed that aryl radicals participate in the reaction and a plausible mechanism is proposed to include this and other mechanistic investigations, for the catalyzed and the background reaction.
- Felipe-Blanco, Diego,Gonzalez-Gomez, Jose C.
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supporting information
p. 7735 - 7744
(2019/12/24)
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- Synthesis and Biological Evaluation of New Phthalazinone Derivatives as Anti-Inflammatory and Anti-Proliferative Agents
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The chemistry of phthalazine derivatives has been of increasing interest since many of these compounds have found many chemotherapeutic applications. So this study aims to synthesize a library of phthalazine derivatives and to investigate their anti-inflammatory and anti-proliferative activities. Sixteen new phthalazinone derivatives (2a-p) were synthesized and tested for their in vitro antiproliferative and in vivo anti-inflammatory activities. All the synthesized compounds were identified and characterized by IR, 1H NMR, 13C NMR spectroscopy, and MS. Two compounds, 2b and 2i, showed significant anti-inflammatory activity comparable with that of the standard drug etoricoxib in the carrageenan-induced rat paw edema model at 3 and 5 h, respectively. Three compounds (2h, 2j, and 2g) showed moderate sensitivity toward the renal cancer cell line UO-31. A library of new phthalazone compounds (2a-p) was synthesized as dual inhibitors (COX-2/LOX-5) and evaluated for their anti-inflammatory, anticancer activities. Two compounds showed significant anti-inflammatory activity comparable with that of the standard drug etoricoxib, whereas three compounds showed moderate sensitivity toward the renal cancer cell line UO-31.
- Hameed, Alhamzah Dh.,Ovais, Syed,Yaseen, Raed,Rathore, Pooja,Samim, Mohammed,Singh, Surender,Sharma, Kalicharan,Akhtar, Mymona,Javed, Kalim
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p. 150 - 159
(2016/02/09)
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- Ultrasound-promoted Friedel-Crafts acylation of arenes and cyclic anhydrides catalyzed by ionic liquid of [bmim]Br/AlCl3
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A simple and efficient method of Friedel-Crafts acylation of arenes with succinic anhydride, phthalic anhydride and glutaric anhydride under the action of 1-butyl-3-ethylimidazolium ([bmim]Br/AlCl3 ([bmim]+) cation (ionic liquid) and ultrasound irradiation is presented. Thy purity of products was tested by GC-MS and their structures evaluated by IR and 1H NMR spectroscopy.
- Fekri, Leila Zare,Nikpassand, Mohammad
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p. 1825 - 1829
(2015/01/09)
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- Synthesis and blood glucose lowering activity of some novel benzenesulfonylthiourea derivatives substituted with 4-aryl-1-oxophthalazin- 2(1H)yl-ones
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Some new benzenesulfonylthiourea derivatives substituted with phthalazones (2a-q) were synthesized by refluxing the appropriate 4-aryl-1-oxophthalazin- 2(1H)yl benzenesulfonamides with isothiocyanate in dry acetone over anhydrous K2CO3. All the synthesized compounds were characterized on the basis of IR, 1H NMR, MS data and elemental analysis. These synthesized compounds (2a-q) at the dose of 20 mg/kg were tested for antihyperglycemic activity in the glucose-fed hyperglycemic normal rat model and among these compounds 2f and 2m showed modest antihyperglycemic activity.
- Yaseen, Shafiya,Bashir, Rafia,Ovais, Syed,Rathore, Pooja,Samim, Mohammed,Javed, Kalim
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p. 362 - 366
(2014/06/09)
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- Synthesis of biaryl imino/keto carboxylic acids via aryl amide directed C-H activation reaction
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A novel Pd-catalysed C-H activation reaction for the synthesis of biaryl imino/keto carboxylic acids is developed. This reaction underwent aryl amide directed C-H activation ortho-acylation followed by ring closing and ring opening processes to give a range of biaryl imino/keto carboxylic acids. Our methodology features the utilization of a cheap and green oxidant (TBHP) as well as readily available aldehydes.
- Zhang, Nana,Yu, Qingzhen,Chen, Ruixue,Huang, Jianhui,Xia, Yeqing,Zhao, Kang
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p. 9464 - 9466
(2013/10/01)
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- Palladium-catalyzed chemoselective decarboxylative ortho acylation of benzoic acids with α-oxocarboxylic acids
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Palladium-catalyzed chemoselective decarboxylative cross coupling of benzoic acids with α-oxocarboxylic acids was realized via an arene sp 2 C-H functionalization process. This work represents the first example of transition-metal-catalyzed cro
- Miao, Jinmin,Ge, Haibo
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supporting information
p. 2930 - 2933
(2013/07/26)
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- Synthesis and biological evaluation of 4-arylphthalazones bearing benzenesulfonamide as anti-inflammatory and anti-cancer agents
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Nine 4-arylphthalazones bearing benzenesulfonamide (2a-i) were synthesized by the condensation of the appropriate 2-aroylbenzoic acid (1a-i) and 4-hydrazinobenzenesulfonamide in ethanol. The structures of these compounds were elucidated by elemental analysis, IR, 1H NMR, 13C NMR, and MS spectroscopy. Two compounds, 2b and 2i, showed significant anti-inflammatory activity comparable to that of the standard drug celecoxib in the carrageenan-induced rat paw edema model. These compounds (2b and 2i) had selective inhibitory activity towards the COX-2 enzyme. Compound 2b had a better selectivity ratio (COX-1/COX-2) compared to that of celecoxib and can be used as a novel template for the design of selective COX-2 inhibitors. Compounds 2d and 2i were screened for their antiproliferative activity toward 60 human cancer cell lines by the National Cancer Institute (USA). The compounds 2d and 2i displayed mild activity toward the renal cancer cell line UO-31. Nine 4-arylphthalazones bearing benzenesulfonamide (2a-i) were synthesized by the condensation of the appropriate 2-aroylbenzoic acid (1a-i) and 4-hydrazinobenzenesulfonamide in ethanol. Compounds 2b and 2i showed anti-inflammatory activity comparable to that of celecoxib in the carrageenan-induced rat paw edema model. Compounds 2d and 2i were screened for their antiproliferative activity towards 60 human cancer cell lines, displaying mild activity toward the renal cancer cell line UO-31. Copyright
- Yaseen, Shafiya,Ovais, Syed,Bashir, Rafia,Rathore, Pooja,Samim, Mohammed,Singh, Surender,Nair, Vinod,Javed, Kalim
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p. 491 - 498
(2013/07/26)
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- 2-Hydroxy-1-oxo-1,2-dihydroisoquinoline-3-carboxylic Acid with Inbuilt β-NHydroxy-γ-keto-Acid pharmacophore as HCV NS5B polymerase inhibitors
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The inbuilt 2-N-hydroxy-1-oxo-3-carboxylic acid of isoquinolone was designed as pyrophosphate mimic for hepatitis C NS5B polymerase. Various 2-hydroxy-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid derivatives 11a-p were synthesized and evaluated as HCV NS5B polymerase inhibitors. Compound 11c exhibited moderate inhibitory potency based on the inorganic pyrophosphate generation (IC50 = 9.5 μM) and based on NTP incorporation by NS5B enzyme (IC50 = 5.9 μM). Compound 11c demonstrated antiviral activity (EC50 = 15.7 μM) and good selectivity in HCV genotype 1b replicon Ava.5 cells. Compound 11c reduced the interaction of NTP to NS5B polymerase. Docking model showed that 11c situated in similar orientation to the bound uridine triphosphate in the active site of NS5B polymerase. As a result, 2-hydroxy-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid was disclosed as a novel inbuilt β-Nhydroxy-γ-keto-acid pharmacophore for HCV NS5B polymerase inhibitors.
- Deore,Chen,Chen,Chang,Chuang,Chern,Wang,Chern
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body text
p. 613 - 624
(2012/07/28)
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- Conformational analysis of 2-anthryl-ethylene derivatives: Photochemical and computational investigation
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2-Anthrylethylene derivatives 1 E-5 E and 1 Z are synthesized to study the cis-trans photoisomerization. Interestingly, unlike 9-anthrylethylene derivatives, 2-anthrylethylene derivatives 1 E to 5 E do not exhibit E(trans) to Z (cis) photoisomerization upon direct and triplet sensitization. One-way Z (cis) to E (trans) photoisomerization of 1 Z is found to be very efficient under direct and triplet sensitization conditions, demonstrating the involvement of both singlet and triplet states. 1 E-5 E exhibits excitation wavelength dependent fluorescence indicating the existence of conformers (rotamers) at room temperature, which is confirmed by fluorescence lifetimes measurements of compounds 1 E and 2 E. Theoretical studies are carried out at DFT and ab initio methodology and the calculated relative energy difference of the conformers is very small; it ranges between 2.9 kJ·mol-1 to 6.3 kJ·mol-1 for both ground and excited states.
- Srinivas,Arun Kumar,Srinivas, Kolupula,Bhanuprakash,Jayathirtha Rao
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p. 851 - 865
(2013/05/08)
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- A rapid and efficient access to diaryldibenzo[b,f][1,5]diazocines
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2-Benzoylbenzoyl azides undergo facile cyclization under acidic conditions to give substituted dibenzo[b,f][1,5]-diazocines in good yields. This approach shortens the synthetic steps toward these compounds as compared with conventional methods. The mechanism of the diazocine synthesis is assumed to proceed by an unprecedented intermolecular [2 + 2] cyclization.
- Wang, Xiao,Li, Jianzhong,Zhao, Na,Wan, Xiaobo
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supporting information; experimental part
p. 709 - 711
(2011/04/24)
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- An efficient one-pot synthesis of pyridazinones and phthalazinones using HY-zeolite
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Figure represented. The first one-pot synthesis of pyridazinones and phthalazinones from arenes, cyclic anhydrides, and ArNHNH2 in the presence of efficient recyclable heterogeneous catalyst, HY-zeolite, in high yield and short reaction time is reported.
- Zare, Leila,Mahmoodi, Nosratollah,Yahyazadeh, Asieh,Mamaghani, Manouchehr,Tabatabaeian, Khalil
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experimental part
p. 864 - 867
(2011/09/16)
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- Synthesis, crystal structure and biological activities of four novel tetranuclear di-organotin(IV) carboxylates
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Four complexes: [Bu2(L1)SnOSn(L1)Bu2]2 (1), [Bu2(L2)SnOSn(L2)Bu2]2 (2), [Bu2(L3)SnOSn(L3)Bu2]2 (3), and [Bu2(L4)SnOSn(L4)Bu2]2 (4), (HL1 = 2-(4-methylbenzoyl)benzoic acid, HL2 = 2-(2,4-diethylbenzoyl)benzoic acid, HL3 = 2-(4-chlorobenzoyl)benzoic acid, HL4 = 2-(4-isopropylbenzoyl)benzoic acid) have been prepared and structurally characterized by means of elemental analysis and vibrational, 1H NMR and FT-IR spectroscopies. The crystal structures of all complexes have been determined by X-ray crystallography. Three distannoxane rings are present to the dimeric tetraorganodistannoxane of planar ladder arrangement. Each structure is centro-symmetric and features a central rhombus Sn2O2 unit with two additional tin atoms linked at the O atoms. Complex 1 exhibited good antibacterial and antitumor activities and have a potential to be used as drugs.
- Kang, Wanli,Wu, Xiaoyan,Huang, Jianbin
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experimental part
p. 2402 - 2408
(2009/09/30)
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- Poly(phthalazinone ether ketone) ionomers synthesized via N-C coupling reaction for fuel cell applications
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Sulfonated poly(phthalazinone ether ketone)s with different sulfonation degrees were directly polymerized via N-C coupling reaction. The resulting polymers with inherent viscosity ranging from 0.97 to 1.29 dL/g were characterized by 1H NMR and elemental analysis. Membranes were obtained by casting 5% solution in DMAc (N,N′-dimethylacetamide) of the polymers at 60°C. Because of their specially designed structure, the membranes of the polymer have excellent thermal and oxidative stability. TGA curves showed that the loss of sulfonic groups occurred at around 300°C. The membranes demonstrated excellent acidic stability; their forms could be maintained for at least 47 h when subjected to Fenton's reagent (30 ppm FeSO4 in 30% H2O2) at 25°C. For the polymer with a sulfonation degree of 2, the highest water uptake of 46% at 80°C and the best proton conductivity of 1.77 × 10-2 S/cm at 95°C 100% relative humidity were obtained, and a low Ea of 5.6 kJ/mol was calculated.
- Chen, Yu-Lin,Meng, Yue-Zhong,Li, Xiu-Hua,Hay, Allan S.
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p. 10007 - 10013
(2008/02/01)
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- An alternative route to syntheses of aryl keto acids in a chloroaluminate ionic liquid
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The Lewis acidic 1-butyl-3-methylimidazolium chloroaluminate ionic liquid [bmim]Cl.AlCl3, N=0.67, is employed as a catalyst as well as the solvent for the quick and efficient syntheses of aryl keto acids by Friedel-Crafts acylation and aroylation of aromatic hydrocarbons using cyclic acid anhydrides.
- Mohile, Swapnil S.,Potdar, Mahesh K.,Salunkhe, Manikrao M.
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p. 650 - 651
(2007/10/03)
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- The reaction of arylcoppermagnesium and other organometallic reagents with phthalic anhydride
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Arylcoppermagnesium reagents, prepared from 5ArMgX + 2.5CuI, (Ar = 4-CH3C6H4, 4-CH3OC6H4, 4-ClC6H4, 2-C4H3S) react with one equivalent of phthalic anhydride in ether or THF at -5 deg C for 2.5 h to give 2-aroylbenzoic acid in 83-98percent yields.The phenylcoppermagnesium reagent (Ar = C6H5) under similar conditions gives 2-benzoylbenzoic acid and 3,3-diphenylphthalide in 40-42percent and 42-45percent yield, respectively.The yield of the 2-benzoylbenzoic acid rises to 93percent in the presence of dimethyl sulphide.Under these conditions no phthalide is formed.Lithium diphenylcuprate reactswith phthalic anhydride in ether-hexane to give 92percent of 2-benzoylbenzoic acid and 7percent of 3,3-diphenylphthalide.The reaction of phenylcopper reagent, prepared from PhMgBr + CuI, under similar conditions is slow and gives 2-benzoylbenzoic acid in 15percent yield.The reaction of phenylmagnesium bromide in the presence or absence of catalytic amounts of copper(I) iodide gives unsatisfactory results.Use of two equivalents of phenyllithium with one equivalent of phthalic anhydride, on the other hand, affords 3,3-diphenylphthalide in 77percent yield.The mechanisms of these reactions are discussed.
- Rahman, Mohammed T.,Nahar, Syeda K.
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p. 201 - 208
(2007/10/02)
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