- Synthesis and evaluation of intrinsic bioactivity of fluorescein and phenolphthalein derivatives
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Fluorescein and phenolphthalein derivatives have been synthesized and screened for their bioactivity via molecular docking, cytotoxicity and antioxidant studies. In molecular docking studies, the compounds 3d have exhibited better glide score and hydrogen bonding ability when docked with t-RNA Dimethylallyltransferase. Antioxidant capabilities were evaluated via DPPH and ABTS radical scavenging activity. In this screening, compound 3d exhibited better inhibition efficiency in the DPPH and ABTS methods. Cytotoxicity of the compounds was assessed by the cell sustainability assay against human cervical cancer cell line (HeLa). All the synthesized compounds exhibited cytotoxic effects against HeLa cells and compounds 3d displayed better activity (IC50) than the standard drug (doxorubicin).
- Bharathkumar, Kuruba,Durairaj, Arulappan,Mohanapriya, Raman,Obadiah, Asir,Ramanathan, Subramanian,Santhoshkumar, Palanichamy,Vasanthkumar, Samuel
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- NbCl5 Promoted the Efficient Synthesis of Phthalein Derivatives: Optical Characterization and Solvatochromic Effect
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Organic dyes derived from phthaleins have a large number of industrial applications and can be synthesized using a Lewis acid by Friedel–Crafts acylation, followed by an addition reaction to the carbonyl compound. This work aims to investigate the use of NbCl5 as a catalyst for the acylation reaction. The behavior of the phthalein derivatives in several solvents and when subjected to different pH conditions was studied. These compounds showed a color-changing effect depending on the pH and solvent, making them useful for applications as indicators. The phthaleins change their conformations depending on the condition of the medium. Photophysical studies of these compounds were carried out through their UV–Vis absorption spectra. Here, we show the umbrella-like conformation change of phthalein derivatives that depend on the solvent and the pH of the medium.
- Moreno, Vitor Fernandes,dos Santos, Giovanny Carvalho,da Costa, Gyordanna Mayara Gaspar,Gomes, Marcelo Henrique Ayala,Silva-Filho, Luiz Carlos da
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supporting information
p. 2811 - 2821
(2019/08/26)
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- CONTINUOUS METHODS OF MANUFACTURE OF 2-ARYL-3,3-BIS(4-HYDROXYARYL)PHTHALIMIDINES, AND POLYMERS DERIVED THEREFROM
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A continuous method for the manufacture of a 2-aryl-3,3-bis(hydroxyaryl)phthalimidine comprising continuously heating an anhydride with a phenol in the presence of a catalyst and a first co-catalyst, to form a first reaction mixture comprising a phenolphthalein compound; precipitating the phenolphthalein compound; combining a primary arylamine with an acid catalyst and a second co-catalyst to form a second reaction mixture; adding the phenolphthalein compound to the second reaction mixture; continuously heating the second reaction mixture to provide a third reaction mixture comprising a crude phthalimidine; and treating the crude phthalimidine to remove aminophenol and purify the phthalimidine is provided.
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Paragraph 0064
(2018/03/25)
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- Use of metal-accumulating plants for implementing chemical reactions
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The use of metal-accumulating plants for implementing chemical reactions.
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Page/Page column 41
(2015/10/28)
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- USE OF COMPOSITIONS OBTAINED BY CALCINING PARTICULAR METAL-ACCUMULATING PLANTS FOR IMPLEMENTING CATALYTICAL REACTIONS
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The use of metal-accumulating plants for implementing chemical reactions especially catalytical reactions.
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Paragraph 0717-0721
(2016/01/25)
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- New chemical markers based on phthaleins
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New chemical markers based on mixtures of individual phthaleins were developed. These markers are characterized by high level of secrecy in use, good transferability to contacting persons, enhanced retention on the objects marked, and reliable identification of phthaleins by expert investigation. The experimental studies of the markers obtained show that the synthesized mixture of three phthalein homologs contains the previously unknown phthalein with unsymmetrical phenolic substituents, o-cresolphenolphthalein [3-(3′-methyl-4′-hydroxyphenyl)-3-(4?-hydroxyphenyl)phthalide], which decreases the probability of the marker falsification. Quantum-chemical calculations of the reaction of the o-cresolphthalein synthesis show that the overall reaction is characterized by small positive changes in the enthalpy and Gibbs free energy, and the second and third steps occur with negative changes in the Gibbs energy. The optimum structure of the transition state was calculated.
- Nekhoroshev,Nekhoroshev,Poleshchuk,Yarkova,Nekhorosheva,Gasparyan
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p. 711 - 718
(2015/08/03)
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- Use of compositions obtained by calcing particular metal-accumulating plants for implementing catalytical reactions
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The invention relates to the use of compositions derived from metal-accumulating plants, wherein the metals are more particularly zinc, nickel and copper, for implementing chemical reactions especially catalytical reactions, a method for the preparation of specific Ni-containing composition, and said Ni-containing composition.
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Page/Page column
(2014/09/03)
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- Design and performance of supported Lewis acid catalysts derived from metal contaminated biomass for Friedel-Crafts alkylation and acylation
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The main goal of this work was to prove the interest of metal hyperaccumulator plants in supported Lewis acid catalysis. Friedel-Crafts alkylation and acylation reveal the great catalytic activity of different plant extracts. This approach is a green solution with chemical benefits including high yield, excellent regioselectivity, small amounts of catalyst, mild conditions and concrete perspectives towards the depletion of mineral resources. The results also constitute an incentive for the development of phytoextraction programs on metal-bearing soils.
- Losfeld, Guillaume,Escande, Vincent,Vidal De La Blache, Paul,L'Huillier, Laurent,Grison, Claude
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scheme or table
p. 111 - 116
(2012/09/08)
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- Identification of the catalytic residues of carboxylesterase from arthrobacter globiformis by diisopropyl fluorophosphate-labeling and site-directed mutagenesis
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The role of amino acid residues in the enzymatic activity of carboxylesterase from Arthrobacter globiformis was analyzed by diisopropyl fluorophosphate (DFP) labeling and site-directed mutagenesis. The electrospray ionization mass spectrometric (ESI-MS) analysis of the esterase, covalently labeled by DFP, showed stoichiometric incorporation of the inhibitor into the enzyme. The further comparison of endopeptidase-digested fragments between native and DFP-labeled esterase by fast atom bombardment mass spectrometric (FAB-MS) analysis as well as site-directed mutagenesis indicated that Ser59 in the consensus sequence Ser-X-X-Lys, which is conserved exclusively in penicillin-binding proteins and some esterases, served as a catalytic nucleophile. In addition, the results obtained from analysis of the mutants at position 62 suggested the importance of the basic amino acid side chain at this position, and suggested the significance of this residue acting directly as a general base rather than its involvement in the maintenance of the optimum hydrogenbonding network at the active site.
- Nishizawa, Masako,Yabusaki, Yoshiyasu,Kanaoka, Masaharu
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experimental part
p. 89 - 94
(2011/09/30)
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- Ferric hydrogensulphate as a recyclable catalyst for the synthesis of fluorescein derivatives
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Polycondensation reactions of phenols with phthalic anhydride were carried out in the presence of ferric hydrogensulphate under melt conditions. The reactions proceeded in short reaction times by using a catalytic amount of Fe(HSO4)3 and the corresponding fluorescein derivatives were obtained in high yields. The simplicity, scale-up, along with the use of an inexpensive, non-toxic, recyclable catalyst of an environmentally benign nature, are other remarkable features of the procedure. The absorption and emission properties of these fluorescein derivatives were studied.
- Eshghi, Hossein,Mirzaie, Narges
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experimental part
p. 504 - 509
(2012/07/13)
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- Physical-chemical parameters and validation of a colorimetric method for deoxycholic and ursodeoxycholic acids: Kit reagent and optical sensor
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The simple and low cost β-cyclodextrin (β-CD)-phenolphthalein (PHP) inclusion complex was used for both the study of physical-chemical parameters and validation of analytical procedures for deoxycholic acid (DCA) and ursodeoxycholic acid (UDCA) determinations in different formulations. The usefulness of this inclusion complex is proposed either in the form of kit reagent and as an original optical sensor for DCA and UDCA. The results showed that temperature had a negative effect on the equilibrium constant resulting in high negative values of enthalpy and positive values of entropy. The half-life values for DCA and UDCA measurements were 68.71 and 294.71 days, respectively. The method was validated showing limits of detection and quantification of 4.92 × 10-5 mol L-1 and 1.64 × 10-4 mol L-1 for DCA, 1.14 × 10-5 mol L-1 and 3.79 × 10-5 mol L-1 for UDCA, respectively. The developed optical sensor also showed response linearity, ease of implementation and potential application in fast screening tasks even out of the laboratory.
- Cadena, Pabyton G.,Araújo, Alberto N.,Montenegro, Maria C.B.S.M.,Pimentel, Maria C.B.,Filho, José L. Lima,Silva, Valdinete L.
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experimental part
p. 99 - 105
(2012/02/05)
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- METHOD FOR PRODUCING PHENOLPHTHALEIN COMPOUND USING IONIC LIQUID CATALYST COMPOSITION
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A method for producing a phenolphthalein compound is disclosed, comprising: reacting a phenolic compound of the formula: wherein Ra is a hydrogen or a C1-C12 hydrocarbyl group, with a phthalic anhydride compound of the formula: wherein Rb is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen, in the presence of an ionic liquid catalyst composition and a promoter to form a reaction mixture comprising a phenolphthalein compound of the formula: wherein each Ra is independently a hydrogen or a C1-C12 hydrocarbyl group, and Rb is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen; wherein the ionic liquid catalyst composition comprises a combination of an ionic liquid and a metal halide wherein the metal is selected from the group consisting of a Group IIB, IIIA, VIII, or IVA metal, and a combination thereof
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Page/Page column 6
(2010/04/25)
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- CATALYTIC METHOD FOR PRODUCING PHENOLPHTHALEIN COMPOUNDS
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A method of producing a phenolphthalein comprises reacting a phenolic compound of the formula: wherein R1 is a hydrogen or a C1-C12 hydrocarbyl group, with a phthalic anhydride compound of the formula: wherein R2 is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen, in the presence of a heterogeneous catalyst and a promoter to form a reaction mixture comprising a phenolphthalein compound of the formula: wherein each R1 is independently a hydrogen or a C1-C12 hydrocarbyl group, and R2 is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen; wherein the heterogeneous catalyst comprises a metal oxide composition in combination with a porous support, wherein the metal is molybdenum, tungsten, or a combination comprising at least one of the foregoing metals.
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Page/Page column 6-7
(2010/04/25)
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- METHOD FOR PRODUCING PHENOLPHTHALEIN USING A HETEROPOLYACID CATALYST
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A method for producing a phenolphthalein compound comprises: reacting a phenolic compound of the formula: wherein R1 is a hydrogen or a C1-C12 hydrocarbyl group, with a phthalic anhydride compound of the formula: wherein R2 is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen, in the presence of a heterogeneous catalyst and a promoter to form a reaction mixture comprising a phenolphthalein compound of the formula: wherein each R1 is independently a hydrogen or a C1-C12 hydrocarbyl group; and R2 is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen; wherein the heterogeneous catalyst comprises, on a porous support, a calcination product of a heteropolyacid composition.
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Page/Page column 7-8
(2010/04/25)
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- A facile synthesis of phthalein indicator dyes
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The use of methanesulfonic acid offers a novel and highly efficient method for the synthesis of phthalein indicator dyes in excellent yields on an industrial scale.
- Sabnis, Ram W.
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experimental part
p. 6261 - 6263
(2010/01/11)
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- METHODS FOR PRODUCING AND PURIFYING PHENOLPHTHALEIN
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A phthalic anhydride, a phenol, a catalyst, and a promoter are reacted to form a reaction mixture comprising phenolphthalein. The reaction mixture is treated with a first solvent system to form a slurry. The first solvent system comprises a first polar organic solvent. In some embodiments the first solvent system additionally comprises a non-polar organic solvent. Use of the solvent system to treat the reaction mixture simplifies subsequent purification.
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Page/Page column 3-5
(2008/12/07)
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- Phthalein derivatives as a new tool for selectivity in thymidylate synthase inhibition
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A new set of phthalein derivatives stemming from the lead compound, phenolphthalein, were designed to specifically complement structural features of a bacterial form of thymidylate synthase (Lactobacillus casei, LcTS) versus the human TS (hTS) enzyme. The new compounds were screened for their activity and their specificity against TS enzymes from different species, namely, L. casei (LcTS), Pneumocystis carinii (PcTS), Cryptococcus neoformans (CnTS), and human thymidylate synthase (hTS). Apparent inhibition constants (K(i)) for all the compounds against LcTS were determined, and inhibition factors (IF, ratio between the initial rates of the enzymatic reaction in the presence and absence of each inhibitor) against each of the four TS species were measured. A strong correlation was found between the two activity parameters, IF and K(i), and therefore the simpler IF was used as a screening factor in order to accelerate biological evaluation. Compounds 5b, 5c, 5ba, and 6bc showed substantial inhibition of LcTS while remaining largely inactive against hTS, illustrating for the first time remarkable species specificity among TSs. Due to sequence homology between the enzymes, several compounds also showed high activity and specificity for CnTS. In particular, 3-hydroxy-3-(3-chloro-4-hydroxyphenyl)-6-nitro-1H,3H-naphtho[1,8-c,d]pyran- 1-one (6bc) showed an IF 0.04 for CnTS (K(i) = 0.45 μM) while remaining inactive in the hTS assay at the maximum solubility concentration of the compound (200 μM). In cell culture assays most of the compounds were found to be noncytotoxic to human cell lines but were cytotoxic against several species of Grampositive bacteria. These results are consistent with the enzymatic assays. Intriguingly, several compounds also had selective activity against Cr. neoformans in cell culture assay. In general, the most active and selective compounds against the Gram-positive bacteria were those designed and found in the enzyme assay to be specific for LcTS versus hTS. The original lead compound was least selective against most of the cell lines tested. To our knowledge these compounds are the first TS inhibitors selective for bacterial TS with respect to hTS.
- Costi, Paola M.,Rinaldi, Marcella,Tondi, Donatella,Pecorari, Piergiorgio,Barlocco, Daniela,Ghelli, Stefano,Stroud, Robert M.,Santi, Daniel V.,Stout, Thomas J.,Musiu, Chiara,Marangiu, Elena M.,Pani, Alessandra,Congiu, Donatella,Loi, Giulia A.,La Colla, Paolo
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p. 2112 - 2124
(2007/10/03)
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- Dihydrobenzofuran- and chroman-carboxamide derivatives, processes for the preparation thereof and use thereof as neuroleptics
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The invention relates to new dihydrobenzofuran- and chroman-carboxamide derivatives of the general formula: STR1 in which R and R' are each hydrogen or methyl; n is 1 or 2; m is 1 or 2; Z is either STR2 wherein R1 and R2 are lower alkyl, or STR3 wherein R3 is alkyl, alkenyl, cycloalkyl-alkyl, cycloalkenyl-alkyl, X is H, NH2, methoxy, or methyl and Y is H, Cl, cycloalkylmethylsulfonyl, alkylsulfamoyl or alkylsulfonyl and to their pharmacologically acceptable acid addition salts and their optical isomers, to the processes for the preparation thereof and to the use thereof as medicaments, especially as neuroleptics.
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- Method for preparing aromatic bischloroformate compositions
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Bischloroformate oligomer compositions are prepared by passing phosgene into a heterogeneous aqueous-organic mixture containing at least one dihydroxyaromatic compound, with simultaneous introduction of a base at a rate to maintain a specific pH range and to produce a specific volume ratio of aqueous to organic phase. By this method, it is possible to employ a minimum amount of phosgene. The reaction may be conducted batchwise or continuously. The bischloroformate composition may be employed for the preparation of cyclic polycarbonate oligomers or linear polycarbonate, and linear polycarbonate formation may be integrated with bischloroformate composition formation in a batch or continuous process.
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- Bischoloroformate preparation method with phosgene removal and monochloroformate conversion
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Aqueous bischloroformates are prepared by the reaction of a dihydroxyaromatic compound (e.g., bisphenol A) with phosgene in a substantially inert organic liquid (e.g., methylene chloride) and in the presence of an aqueous alkali metal or alkaline earth metal base, at a pH below about 8. After all solid dihydroxyaromatic compound has been consumed, the pH is raised to a higher value in the range of about 7-12, preferably 9-11, and maintained in said range until a major proportion of the unreacted phosgene has been hydrolyzed. At the same time, any monochloroformate in the product may be converted to bischloroformate.
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- Cyclic monocarbonate bishaloformates
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Cyclic monocarbonate bischloroformates are prepared by the reaction of a carbonyl halide such as phosgene with a bridged substituted resorcinol or hydroquinone such as bis(2,4-dihydroxy-3-methylphenyl)methane or bis(2,5-dihydroxy-3,4,6-trimethylphenyl)methane in the presence of aqueous alkali metal hydroxide. The cyclic monocarbonate bischloroformates may be used for the preparation of linear or cyclic polycarbonates containing cyclic carbonate structural units, which may in turn be converted to crosslinked polycarbonates.
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- Polyetherimide bisphenol compositions
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Polyetherimide bisphenols and bischloroformates are prepared by the reaction of dianhydrides or certain bisimides with aminophenols or mixtures thereof with diamines. They are useful as intermediates for the preparation of cyclic heterocarbonates, which may in turn be converted to linear copolycarbonates. The bisphenols can also be converted to salts which react with cyclic polycarbonate oligomers to form block copolyetherimidecarbonates.
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- Triazolidine-3,5-dione/formaldehyde/amine condensates and compositions thereof
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A triazolidine-3,5-dione/formaldehyde/amine condensate is disclosed of the formula STR1 in which wherein the terms R1, R2 and R5 are defined hereinafter in the specification a process for the preparation of such condensate by reaction of a triazolidine-3,5-dione with formaldehyde and a suitable nitrogen compound and the use of the condensate as a flame-proofing agent for thermoplastics, especially polyamide and as an auxiliary for modifying polymeric substances.
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- Carboxymethylated derivatives of β-1,3-glucan
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It has been found that water-insoluble, thermogelable β-1,3-glucan produced by microorganisms, lower polymers obtainable upon partial hydrolysis of the glucan or, carboxymethylated derivatives of said glucan or of said lower polymers are useful for inhibiting growth of tumors in a warm-blooded animal. The inhibitory activity against various tumors of these polysaccharides is very strong and significant whenever administered to warm-blooded animals from the early to very late stage of tumor progression or even when administered prior to plantation of tumors. The carboxymethylated derivatives above-mentioned are novel water-soluble compounds which can be produced by carboxymethylation of said glucan and partial hydrolyzate thereof.
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- Hydroxyalkyl- and alkoxyalkyl-triazolidine-3,5-dione compounds and their processes for their preparation
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An hydroxyalkyl- and alkoxyalkyl-triazolidine-3,5-dione is disclosed of the formula STR1 wherein R1 represents an unsubstituted or substituted aliphatic radical, which is straight-chain or branched, with 1-20 C atoms, mono- or poly-cycloaliphatic radical with 5 to 21 C atoms, araliphatic radical with 7 to 17 C atoms or aromatic radical with 6 to 20 C atoms, each radical carrying m of the radicals shown in brackets, and it being possible for the aliphatic radicals to be interrupted by one or more oxygen atoms or tertiary nitrogen atoms and for the cycloaliphatic, araliphatic and aromatic radicals to be interrupted by one or more oxygen atoms, tertiary nitrogen atoms or methylene groups with 1 to 4 C atoms, R2 and R3 independently of one another denote hydrogen or a straight-chain or branched aliphatic radical with 1 to 10 C atoms, R4 represents hydrogen or an aliphatic radical, which is straight-chain or branched, with 1 to 20 C atoms, mono- or poly-cycloaliphatic radical with 5 to 10 C atoms or araliphatic radical with 7 to 17 C atoms and m denotes an integer from 1 to 5, and wherein, in the case where m=1, R1 can also represent the radical STR2 a process for the preparation of such compounds by reaction of a triazolidine-3,5-dione with an aliphatic aldehyde or ketone, optionally simultaneously with or followed by reaction of the resultant hydroxyalkyl triazolidine-3,5-diones with an alcohol.
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- Biocidal 3,5-dibromosalicylic acid salts
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Biocides which have fungicidal and bactericidal activity are metal salts of 3,5-dibromosalicylic acid of the following formula: SPC1 Wherein Me is a divalent metal such as copper.
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