- Deep compositional understanding of TBA: AlCl3 ionic liquid for its applications
-
Chloroaluminate ionic liquids (ILs) have been immensely used as homogeneous catalyst in Friedel-Crafts reaction. We have recently synthesized chloroaluminate ILs by reacting aluminium chloride with a hydrophobic neutral ligand i.e. tributylamine (TBA:AlCl3). The current study elaborates on the investigations of the composition of the ionic liquids at various stages of their formation. The ionic liquids were synthesized using various mole ratios of tributyl amine and aluminium chloride in range of 1:1 to 1:2.3, in presence of an aromatic solvent in a one pot reaction. Various characterization techniques like Mass spectrometry, 27Al Nuclear Magnetic Resonance, 31P Nuclear Magnetic Resonance and Fourier Transform Infrared spectroscopy were used to elucidate the formation of various moieties of the TBA:AlCl3 Ionic Liquid. This study also elaborates on the investigations of the cationic and anionic moieties and their structure-property relationship for various applications. Various Friedel-Crafts reaction of industrial importance were performed using the ionic liquid having (Al2Cl7)?moiety to assess its performance and compared with conventional processes. The synthesized products were characterised by sophisticated analytical techniques like 1H NMR, 13C NMR, FTIR, GC–MS, GC-FID, to name a few. This class of ionic liquids also have importance in various electrochemical applications like aluminium deposition and aluminium batteries.
- Bhakthavatsalam, Vishnupriya,Chandra, Sudeshna,Choudhury, Rudra Prosad,Lande, Sharad V.,Pradhan, Jeevan,Sakhalkar, Mangesh
-
-
- Palladium-Catalyzed Decarboxylative ortho-C(sp2)?H Aroylation of N-Sulfoximine Benzamides at Room Temperature
-
A palladium-catalyzed method for the decarboxylative ortho C?H acylation of N-sulfoximine benzamides is developed at room temperature. The catalytic method enables easy access to various functionalized 2-aroylaromatic carboxylic acid derivatives in good isolated yields. Based on our mechanistic studies, a Pd(II)/Pd(IV) catalytic cycle that involves aroyl radical intermediate is proposed for the reaction.
- Das, Prasenjit,Biswas, Promita,Guin, Joyram
-
p. 920 - 925
(2020/03/04)
-
- Dibenzo[b,e]aza-6,11-diketotriazole compound as well as preparation method and application thereof
-
The invention provides a dibenzo[b,e]aza-6,11-diketotriazole compound and a preparation method thereof, belongs to the technical field of medicines, and specifically relates to a 5-((1-(R-phenyl)-1H-1,2,3-triazol-4-yl)methyl)-5H-dibenzo[b,e]aze-6,11-diketone anti-tumor compound as well as a preparation method and application thereof. The compound prepared by the invention has a function of inhibiting tumor activity and has excellent application prospect in the field of design, research and development of anti-tumor drugs; in addition, the preparation method is simple and easy to industrialize.
- -
-
Paragraph 0060-0063
(2019/09/05)
-
- 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
-
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
-
p. 2007 - 2022
(2019/01/10)
-
- Metal-Free Arylation-Lactonization Sequence of γ-Alkenoic Acids Using Anilines as Aryl Radical Precursors
-
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.
-
supporting information
p. 7735 - 7744
(2019/12/24)
-
- Ruthenium-Catalyzed Enantioselective Hydrogenation/Lactonization of 2-Acylarylcarboxylates: Direct Access to Chiral 3-Substituted Phthalides
-
Highly enantioselective tandem hydrogenation/lactonization of various 2-acylarylcarboxylates including 2-aroylarylcarboxylates were realized by using [RuCl(benzene)(S)-SunPhos]Cl as the catalyst under mild reaction conditions. Excellent enantioselectivities (up to 99.6 % ee) and activities (S/C=1000) were obtained. This convenient and practical method enables a direct access to a series of highly optically pure 3-substituted phthalides that are very important molecules as valuable pharmacological compounds and diversified synthons for medicinal chemistry. Moreover, a gram-scale reaction was performed to further demonstrate the practicality of this approach.
- Lu, Bin,Zhao, Mengmeng,Ding, Guangni,Xie, Xiaomin,Jiang, Lili,Ratovelomanana-Vidal, Virginie,Zhang, Zhaoguo
-
p. 3989 - 3996
(2017/09/13)
-
- COMPOUNDS FOR TREATING PARASITIC INFECTIONS
-
Compounds and compositions comprising them are provided. The compounds and compositions are useful for inhibiting transport of heme across membranes in parasitic heme auxotrophic organisms, thereby limiting their growth or killing the parasites.
- -
-
Paragraph 0040
(2016/11/21)
-
- Synthesis and Biological Evaluation of New Phthalazinone Derivatives as Anti-Inflammatory and Anti-Proliferative Agents
-
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
-
p. 150 - 159
(2016/02/09)
-
- Preparation method of synthetic anthraquinone
-
The invention discloses a preparation method of synthetic anthraquinone; the preparation method of synthetic anthraquinone comprises the following steps: step 1, polymerization: mixing phthalic anhydride, benzene and aluminum trichloride, and carrying out a reaction for 0.5-2 hr at the temperature of 50-70 DEG C; step 2, acidizing hydrolysis: adding sulfuric acid and water into the reactant obtained in the step 1, heating to reflux, and distilling to remove free benzene completely; and adding an organic solvent and water for diluting, precipitating o-benzoylbenzoic acid, filtering and washing with water; step 3, ring closing: taking the filter cake obtained in the step 2, carrying out dewatering treatment, adding concentrated sulfuric acid or fuming sulfuric acid, heating up to 130-135 DEG C, carrying out a heat preservation reaction for 0.5-2 hr, and dewatering to close ring; and step 4, carrying out purification treatment of the reactant obtained in the step 3, to obtain the synthetic anthraquinone pure product, wherein the organic solvent is selected from isopropyl alcohol or ethyl acetate, and has the effect of reducing the content difference of dry products of o-benzoylbenzoic acid.
- -
-
Paragraph 0018
(2017/04/29)
-
- Synthetic method for benzisoxazocine hydrochloride pharmaceutical intermediate--o-benzoylbenzoic acid
-
The invention provides a synthetic method for a benzisoxazocine hydrochloride pharmaceutical intermediate--o-benzoylbenzoic acid. The synthetic method comprises the following steps: adding 0.88 mol of 2-carboxyl-benzyl alcohol and 700 to 800 ml of phenol into a reaction vessel provided with a stirrer, a thermometer and a reflux condenser, controlling a stirring speed in a range of 130 to 170 rpm, adding 1.9 mol of cuprous chloride in batches, after the completion of addition, increasing a solution temperature to 80 to 85 DEG C, controlling reaction time in a range of 5 to 6 h, reducing a solution temperature to 35 to 40 DEG C, pouring reaction liquid into 1.3 L of a phosphoric acid solution, reducing a solution temperature to 5 to 7 DEG C, controlling a stirring speed in a range of 190 to 230 rpm so as to precipitate a white solid, then carrying out filtering, carrying out washing with a potassium bromide solution, dissolving an obtained filtered substance in a sodium sulfite solution, carrying out decolorizing with a molecular sieve, adding an oxalic acid solution until the pH value of the solution is 3 to 4 so as to precipitate a solid, reducing a solution temperature to 5 to 7 DEG C, carrying out filtering, carrying out washing with a salt solution, and carrying out drying under a temperature of 75 to 80 DEG C so as to obtain o-benzoylbenzoic acid.
- -
-
Paragraph 0014; 0015
(2016/11/17)
-
- Copper-mediated/catalyzed oxyalkylation of alkenes with alkylnitriles
-
A copper-promoted oxyalkylation of alkenes with alkylnitriles has been developed. The protocol provides rapid access to phthalides (γ-lactones) or isochromanones (d-lactones) via the formation of a C(sp3)-C(sp3) and a C(sp3)-O bond with the generation of up to two quaternary carbon atoms. Mechanistic studies suggest that this reaction is initiated by the formation of the C(sp3)-C(sp3) bond rather than the C(sp3)-O bond. Catalytic conditions were subsequently developed using carboxylic acid as an internal nucleophile.
- Bunescu, Ala,Wang, Qian,Zhu, Jieping
-
supporting information
p. 14633 - 14636
(2015/01/09)
-
- Ultrasound-promoted Friedel-Crafts acylation of arenes and cyclic anhydrides catalyzed by ionic liquid of [bmim]Br/AlCl3
-
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
-
p. 1825 - 1829
(2015/01/09)
-
- Synthesis and blood glucose lowering activity of some novel benzenesulfonylthiourea derivatives substituted with 4-aryl-1-oxophthalazin- 2(1H)yl-ones
-
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
-
p. 362 - 366
(2014/06/09)
-
- Silver-catalyzed decarboxylative acylation of arylglyoxylic acids with arylboronic acids
-
The silver-catalyzed coupling of arylboronic acids with arylglyoxylic acids was found to be an extremely efficient route for the synthesis of unsymmetrical diaryl ketones. It can be conducted on a gram scale under mild and open-flask conditions with good functional group compatibility, avoiding the addition of expensive and/or toxic metals. This journal is
- Cheng, Kai,Zhao, Baoli,Qi, Chenze
-
p. 48698 - 48702
(2014/12/10)
-
- Synthesis of biaryl imino/keto carboxylic acids via aryl amide directed C-H activation reaction
-
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
-
p. 9464 - 9466
(2013/10/01)
-
- Design, characterization, computational studies, and pharmacological evaluation of substituted-N′-[(1E) substituted-phenylmethylidene] benzohydrazide analogs
-
A series of substituted-N′-[(1E)-substituted-phenylmethylidene] benzohydrazide analogs were synthesized and authenticated by TLC, UV-Visible, FTIR, and NMR spectroscopic techniques. The physicochemical similarity of the new analogs with standard drugs was assessed by calculating from a set of ten physicochemical properties using software programs. The information so obtained can be related to prediction of biological activity for important targets. All the target compounds 4a-n were evaluated for their antioxidant, anti-inflammatory, and antimicrobial activity using different in vitro models. The test compounds demonstrated good similarity values with respect to the standard drugs. The compounds 4c, 4d, and 4e have emerged as important lead compounds showing potential anti-inflammatory; and 4b, 4f, and 4c having antioxidant profile. While studying MIC against bacterial strains 4c, 4f, 4i, 4k, and 4m were most active among all the target compounds. All compounds were found to have very good antifungal activity. The compounds having nitro substitution at the arylidene moiety i.e., 4c and 4f showed the most potent antifungal as well as antibacterial activities. While studying total antioxidant activity, all target compounds were found to have good antioxidant activity.
- Bala, Suman,Uppal, Goldie,Kamboj, Sunil,Saini, Vipin,Prasad
-
p. 2755 - 2767
(2013/07/26)
-
- Synthesis and biological evaluation of 4-arylphthalazones bearing benzenesulfonamide as anti-inflammatory and anti-cancer agents
-
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
-
p. 491 - 498
(2013/07/26)
-
- Design, synthesis and evaluation of N-(substituted benzothiazol-2-yl)amides as anticonvulsant and neuroprotective
-
A series of N-(substituted benzothiazol-2-yl)amide derivatives 2a-h and 4a-h were synthesized by the EDC coupling reactions of substituted-benzothiazol- 2-amine with 4-oxo-4-phenylbutanoic acid/2-benzoyl benzoic acid and evaluated for their anticonvulsant and neuroprotective effect. N-(6-methoxybenzothiazol-2- yl)-4-oxo-4-phenylbutanamide (2f) emerged as the most effective anticonvulsant with median doses of 40.96 mg/kg (MES ED50), 85.16 mg/kg (scPTZ ED50) and 347.6 mg/kg (TD50). Furthermore, compound 2f displayed promising neuroprotective effect by lowering the levels of MDA and LDH; therefore, it represents a potential lead in search for safer and effective anticonvulsants having neuroprotective effects.
- Hassan, Mohd. Zaheen,Khan, Suroor A.,Amir, Mohd.
-
p. 206 - 213
(2013/02/23)
-
- Kinetics of proton transfer between ortho substituted benzoic acids and the carbinol base of crystal violet in toluene. Ortho effect on the reactivity of benzoic acids in apolar aprotic solvents
-
Apolar aprotic solvents are particularly advantageous for investigating the intrinsic ortho effect free from complications of specific solvent effects. A kinetic study for toluene-phase proton transfers between ortho F, Cl, Br, I, OMe, OEt, OPh, OAc, Me, NO2, COMe, COPh, OH, NH2, and H benzoic acids and crystal violet carbinol base has shown the forward rate constant (log k+1) is the most appropriate reactivity parameter in toluene. log k+1 (toluene) as compared to other reported reactivity parameters in benzene, toluene, or chlorobenzene has been found more sensitive to the ortho substituent effect. The regression results of the correlation of log k+1 (toluene) of the acids (except OH and NH2 substituted ones) according to seven ortho effect models are all very significant, and the best result is given by Fujita-Nishiokas model. The overall analysis reveals that a substituents ortho effect pattern is a 58:24:18 ratio of its ordinary electrical, proximity electrical, and steric effects and that the proximity electrical effect is the major component to account for the peculiarity of the substituents ortho effect. The results further favor the transmission of this effect mainly through the molecular cavity. The effect may, however, be outweighed by the steric component for bulky enough substituents, e.g., Me. The enhanced strength exhibited by salicylic acid in toluene has been quantitatively described using Pytela-Lisas δHB i parameter. The abnormally high log k+1 observed for anthranilic acid in toluene has been ascribed to a very extensive homoconjugation in its acid-acid anion complex induced by the acids three hydrogen bond donors.
- Sen Gupta, Susanta K.,Mishra, Sangeeta
-
experimental part
p. 4616 - 4623
(2011/06/26)
-
- A rapid and efficient access to diaryldibenzo[b,f][1,5]diazocines
-
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
-
supporting information; experimental part
p. 709 - 711
(2011/04/24)
-
- An efficient one-pot synthesis of pyridazinones and phthalazinones using HY-zeolite
-
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
-
experimental part
p. 864 - 867
(2011/09/16)
-
- Synthesis, crystal structure, and characterization of dimeric tetraorganodistannoxane and two tricyclohexyltin carboxylates
-
Three diorganotin(IV) series and triorganotin(IV) complexes, [(C 6H11)2Sn]4(L1)2O 2(OH)2 (1), (C6H11) 3Sn(HL2) (2), and (C6H11) 3SnL3 (3) (where HL1 is 2-(4-isopropyl benzoyl) benzoic acid, H 2L2 is phthalic acid and HL3 is 2-benzoyl benzoic acid), were synthesized and their crystal structures were determined. There are four crystallographically unique Sn centers in the structure of 1, which consists of a Sn4O2(OH)2 ladder unit, and the ladder consists of four tins held together by two 3-oxygens and two 2-oxygens. The supermolecular motif of 1 is a 2-D structure linked by O-H O hydrogen bonds. The asymmetric unit of 2 contains two crystallographically independent monomers. The supramolecular architecture of 2 is a 2-D layer structure linked by face-to-face - interactions between phenyl rings of adjacent L2 anions. The structure of 3 contains one tricyclohexyltin cation and one L3 anion. The Sn O interactions lead the whole structure to a supramolecular chain. Elemental analysis, infrared, and 1H NMR of 1-3 were investigated and discussed.
- Sakho, Adama Moussa,Du, Dafeng,Li, Wenjie,Liu, Shuangshuang,Zhu, Dongsheng,Xu, Lin
-
experimental part
p. 2317 - 2327
(2010/12/19)
-
- Muscarinic Receptor Antagonists
-
Provided are muscarinic receptor antagonists, which can be useful in treating various diseases of the respiratory, urinary or gastrointestinal system mediated through muscarinic receptors. Also provided are processes for preparing compounds described herein, pharmaceutical compositions comprising compounds described herein, and methods for treating diseases mediated through muscarinic receptors.
- -
-
Page/Page column 17
(2009/01/23)
-
- First general, direct, and regioselective synthesis of substituted methoxybenzoic acids by ortho metalation
-
(Chemical Equation Presented) New general methodology of value in aromatic chemistry based on ortho-metalation sites in o-, m-, and p-anisic acids (1-3) (Scheme 1) is described. The metalation can be selectively directed to either of the ortho positions by varying the base, metalation temperature, and exposure times. Metalation of o-anisic acid (1) with s-BuLi/TMEDA in THF at -78°C occurs exclusively in the position adjacente to the carboxylate. On the other hand, a reversal of regioselectivity is observed with n-BuLi/t-BuOK. With LTMP at 0°C, the two directors of m-anisic acid (2) function in concert to direct introduction of the metal between them while n-BuLi/t-BuOK removes preferentially the proton located ortho to the methoxy and para to the carboxylate (H-4). s-BuLi/TMEDA reacts with p-anisic acid (3) exclusively in the vicinity of the carboxylate. According to these methodologies, routes to very simple methoxybenzoic acids with a variety of functionalities that are not easily accessible by other means have been developed (Table 1).
- Nguyen, Thi-Huu,Chau, Nguyet Trang Thanh,Castanet, Anne-Sophie,Nguyen, Kim Phi Phung,Mortier, Jacques
-
p. 3419 - 3429
(2008/02/03)
-
- Lithographic printing method
-
A lithographic printing plate precursor comprising a support and an image-recording layer containing at least one infrared absorbing agent of a cyanine dye in which a HOMO energy level of each of substituents present on both terminal nitrogen atoms is -10.0 eV or higher. An infrared absorbing agent of a cyanide dye represented by formula (V) shown below: wherein Z 1 and Z 2 each independently represents an aromatic ring which may have a substituent or a hetero aromatic ring which may have a substituent; R 10 and R 20 each independently represents a phenyl group, a naphtyl group, an anthracenyl group, a carbazolyl group or a phenothiazinyl group each of which may have a substituent; A - represents an anion which exists in case of being necessary for neutralizing a charge and is selected from a halogen ion, a perchlorate ion, a tetrafluoroborate ion, a hexafluorophosphate ion and a sulfonate ion; and n represents 1 or 2.
- -
-
-
- Synthesis of chiral 5-aryltetrahydrofuran-2-ones via yeast bioreduction of γ-keto acids and their esters
-
Enantioselective reduction of γ-keto acids and related γ-keto esters with Saccharomyces cerevisiae (baker's yeast) leads to the formation of the corresponding chiral 5-aryltetrahydrofuran-2-ones in satisfactory chemical and optical yields. Pleiades Publishing, Inc., 2006.
- Mahmoodi,Yousefi-Malekroudi
-
p. 365 - 368
(2007/10/03)
-
- Nonsteroidal anti-inflammatory drugs and their analogues as inhibitors of aldo-keto reductase AKR1C3: New lead compounds for the development of anticancer agents
-
Nonsteroidal anti-inflammatory drugs (NSAIDs) like indomethacin, flufenamic acid, and related compounds have been recently identified as potent inhibitors of AKR1C3. We report that some other NSAIDs (diclofenac and naproxen) also inhibit AKR1C3, with the IC50 values in the low micromolar range. In order to obtain more information about the structure-activity relationship and to identify new leads, a series of compounds designed on the basis of NSAIDs were synthesized and screened on AKR1C3. The most active compounds were 2-[(2,2-diphenylacetyl)amino]benzoic acid 4 (IC50 = 11 μM) and 3-phenoxybenzoic acid 10 (IC50 = 0.68 μM). These compounds represent promising starting points for the development of new anticancer agents.
- Gobec, Stanislav,Brozic, Petra,Rizner, Tea Lanisnik
-
p. 5170 - 5175
(2007/10/03)
-
- Isoindole derivatives
-
This invention relates to compounds represented by the general formula [I] ? wherein, R represents an azido group, etc., R1and R2are the same or different and represent hydrogen atoms, etc., R3and R4are the same or different and represent hydrogen atoms, etc., X1represents an oxygen atom, etc., X2represents an oxygen atom, etc., Y represents an oxygen atom, etc., and Z represents a condensed aryl group, etc., or a pharmaceutically acceptable salt thereof, preparation processes thereof, and an agent for treating diabetes, a prophylactic agent for chronic complications of diabetes or a drug against obesity, containing, as an effective ingredient, the compound or the pharmaceutically acceptable salt thereof.
- -
-
-
- An alternative route to syntheses of aryl keto acids in a chloroaluminate ionic liquid
-
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.
-
p. 650 - 651
(2007/10/03)
-
- Direct Synthesis of γ-Substituted Phthalides Via ortho-Aryl Benzoic Acid Mediated Benzyl Radical Cyclization
-
Direct synthesis of γ-substituted phthalids from related ortho-aryl benzoic acids with 48-85% yield are covered. The direct oxidation in the presence of peroxydisulphate-copper (II) chloride in aqueous medium was applied. The reaction is highly regioselective and leads exclusively to γ-butyrolactone, through very stable benzylic radical intermediate.
- Mahmoodi,Salehpour
-
p. 875 - 878
(2007/10/03)
-
- Direct synthesis of γ-substituted phthalides by cyclization of benzyl radicals generated from o-(arylmethyl)benzoic acids
-
Direct oxidation of o-(arylmethyl)benzoic acids with sodium peroxysulfate-copper(II) chloride in water yields γ-substituted phthalides. The reaction is highly regioselective, and the corresponding γ-butyro-lactones are the only products formed through intermediate stable arylmethyl radicals.
- Mahmoodi,Salehpour
-
p. 1760 - 1763
(2007/10/03)
-
- Friedel-crafts alkylation and acylation in the absence of solvent
-
A short and efficient synthetic route, for alkylation and acylation of aromatic compounds in the absence of solvent is developed. According to the reaction system and conditions used, different alkyl-, and acyl arenes are obtained in moderate to good yields. The structures are assigned by 1H and 13C NMR spectroscopy.
- Ghiaci,Asghari
-
p. 2213 - 2220
(2007/10/03)
-
- Chemistry and stereochemistry of benzyl-benzyl interactions in MH+ ions of dibenzyl esters upon chemical ionization and collision-induced dissociation conditions
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Isobutane chemical ionization mass spectra of dibenzyl esters of a wide variety of aliphatic, olefinic, alicyclic and aromatic dicarboxylic acids exhibit abundant m/z 181 C14H13+ ions, indicating a highly general rearrangement process involving the formation of a new bond between the two benzyl groups. An extensive collision-induced dissociation and deuterium labeling study suggested that these ions are an almost equimolar mixture of isomeric α-o-tolylbenzyl, α-p-tolylbenzyl and p-benzylbenzyl cation structures, and this composition is identical for all the diesters examined. This structural assignment of the C14H13 ions suggests a mechanistic pathway for their generation, based on the formation of the new bond between the benzyl methylene group of the protonated benzoxycarbonyl and the phenyl ring of the other ester moiety via π- (and/or ion-neutral) and α-complexes. Stereoisomeric diesters show an unusual steric effect: trans-isomers give rise to much more abundant C14H13+ ions than the cis counterparts. This behavior is explained by stabilized proton-bridged structures of the MH+ ions of the cis-isomers.
- Edelson-Averbukh,Mandelbaum
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p. 515 - 524
(2007/10/03)
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- Self-sensitized photolysis of N-(1-naphthoyl)-N-phenyl-O-(benzoyl-substituted benzoyl)hydroxylamines
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The mechanism of intramolecular triplet-triplet (T-T) energy transfer and subsequent reaction in N,O-diacylhydroxylamines was investigated using the model compounds N-( 1 -naphthoyl)-N-phenyl-O-(benzoyl-substituted benzoyl)hydroxylamines (NPB) with self-sensitization abilities. An examination of the UV absorption and phosphorescence behavior as well as of energy-minimized conformations of these relatively flexible model compounds established that T-T energy transfer from the benzophenone chromophore to the naphthoyl chromophore occurs in a nearly unit efficiency exhibiting only phosphorescence derived from the latter chromophore in both methanol-ethanol (1 : 1 v/v) and 2-chlorobutane at 77 K and is more likely to proceed by a "through-space" mechanism than by a "through-bond" mechanism. The self-sensitized photolysis of NPB with 366 nm light in methanol at room temperature was found to give the fragmentation products, N-phenyl-1-naphthalenecarboxamide (PNA), benzophenone (BP), and benzoyl-substituted benzoic acids (BBA), whereas no BBA was detected in the photolysis in 1,2-dichloroethane and acetonitrile. The finding that the reaction of NPB is efficiently quenched by trans-stilbene according to the Stern-Volmer equation in both methanol and 1,2-dichloroethane indicates that all the products come from the first excited triplet state of the naphthoyl chromophore. On the other hand, the enhanced hydrogen bonding ability of the medium resulted in an increase in the quantum yield for the formation of BBA (ΦBBA) accompanied by a decrease in ΦBA holding the magnitude of ΦBBA+ΦBA nearly constant. But neither ΦPNA nor the quantum yield for the disappearance of NPB was subject to such a hydrogen-bonding effect. This intriguing result was explained in terms of a mechanism in which the N-O bond cleavage in triplet NPB gives a vibrationally excited triplet radical pair whose relaxation is very slow compared to decarboxylation of the caged benzoyl-substituted benzoyloxyl radical in 1,2-dichloroethane. Solvation of this vibrationally hot radical pair through hydrogen bonding substantially promotes its relaxation eventually affording BBA.
- Nagakubo, Hiroshi,Kubota, Gou,Kubo, Kanji,Kaneko, Tsuyoshi,Sakurai, Tadamitsu,Inoue, Hiroyasu
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p. 2603 - 2611
(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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- Synthesis and Properties of Peroxy Ester Having a Benzophenone Chromophore
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Diperoxy esters having a benzophenone chromophore have been successfully synthesized from the reaction of 3-chloro-3-phenylphthalide (1) with 2,5-dihydroperoxy-3-hexyne (4a) or 2,5-dihydroperoxy-2,5-dimethylhexane (4b).The corresponding diperoxy esters had a UV absorption above 300 nm.The free radicals produced during the photolysis of those compounds initiated the radical polymerization of methyl methacrylate at room temperature under UV light.
- Kumura, Hiromi,Nakamura, Tomoyuki,Higuchi, Yoshiki,Suyama, Shuji
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p. 3538 - 3543
(2007/10/02)
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- Synthesis and Reactions of 2,3-Dihydro-oxazoloisoindol-5(9bH)-ones
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The synthesis and reactions with nucleophiles of 2,3-dihydro-oxazoloisoindol-5(9bH)-ones are described.
- Wharton, Clifford J.,Wrigglesworth, Roger
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p. 809 - 814
(2007/10/02)
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- Photoenolisation. XI. Photooxydation des o-methylbenzophenones
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Photoenols 2 of 2- (1a), 2,4- (1b), 2,5- (1c), 2,6- (1d), 2,2'- (1e) and 2,3'-dimethylbenzophenones (1f) were trapped by (3)O2.When a 350 nm wavelength Hg lamp (Rayonet RPR 100) was used (benzene solution) with ketones 1a-c, the corresponding 2-formyl- 4 and 2-carboxybenzophenones 8 were formed as well as 3-phenyl-phtalides 10.Compounds 4 arose from dehydration of the intermediate endoperoxydes 3.Throught photoenolisation, 2-formylbenzophenones 4 gave the intermediate ketene-enols 5 which either isomerised to phtalides 10 or added oxygen to form the corresponding endoperoxydes 6; the latter isomerised to peracids 7, which, by reaction with aldehydes 4, yielded the carboxylic acids 8.When the aerated irradiations were performed simultaneously with 350 nm light and with light above 380 nm (Hanovia 679 A-36, benzene solution), ketones 1a-f yielded the same compounds 4, 8 and 10 but also anthraquinones 13.The latter arose from reversible cyclisation of photoenols 2 E giving dihydroanthranols 11 which were trapped by oxygen, yielding the anthrones 12 which were subsequently photooxidized to anthraquinones 13.With 2,6-dimethylbenzophenone (1d), the corresponding photoenols 2 were trapped for the first time.Compounds 8d, and 13d were absent, but instead 1-carboxyanthraquinone 15 was obtained.The latter can arise from 1-methylanthraquinone 13d trough photoenolisation-oxidation process alredy reported for this compound.With 2,2'-dimethylbenzophenone 1e, 3,3'-spirobiphtalide 14 was obtained instead 2-methyl-2'-carboxybenzophenone 8e; the latter, through a photoenolisation-oxidation process analogous to that described in the second paragraph, yielded 2,2'-dicarboxybenzophenone which underwent dehydration to compound 14.Under the same conditions (Hanovia) but in acetic acid solution, anthraquinones 13 were not formed with ketones 1a-f, due to rapid reketonisation of photoenols 2 E in this medium; however, compounds 4, 8, 10 and 14 were produced.Products 8, 10, 13, 14 and 15 were isolated and characterised or identified.Yields were deduced from actual weights of the isolated compounds (carboxylic acids 8 and 15) and from GLC determinations (compounds 4, 10, 13 and 14).
- Pfau, Michel,Molnar, James,Heindel, Ned D.
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p. 164 - 169
(2007/10/02)
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- NEW ROUTES TO 5,8,8-TRIPHENYLBENZOHEPTAFULVENES FROM (3,4-BIS(DIPHENYLMETHYLENE)-2-OXOCYCLOBUTYLIDENE)TRIPHENYLPHOSPHORANE. ISOLATION OF EXCESSIVELY STABILIZED BETAINE.
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Thermal isomerization of HBr salt of the title phosphorane gave (2-hydroxy-5,8,8-triphenylbenzoheptafulvenyl)triphenylphophonium bromide, which upon dehydrobromination afforded excessively stabilized betaine.Thermal reaction of the title phosphorane with diphenylketene gave 5,8,8-triphenyl-benzoheptafulvene which is condensed with cyclopropane ring.
- Toda, Fumio,Tanaka, Koichi
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p. 4869 - 4872
(2007/10/02)
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