- Synthesis and evaluation of trypanocidal activity of chromane-type compounds and acetophenones
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American trypanosomiasis (Chagas disease) caused by the Trypanosoma cruzi parasite, is a severe health problem in different regions of Latin America and is currently reported to be spreading to Europe, North America, Japan, and Australia, due to the migration of populations from South and Central America. At present, there is no vaccine available and chemotherapeutic options are reduced to nifurtimox and benznidazole. Therefore, the discovery of new molecules is urgently needed to initiate the drug development process. Some acetophenones and chalcones, as well as chromane-type substances, such as chromones and flavones, are natural products that have been studied as trypanocides, but the relationships between structure and activity are not yet fully understood. In this work, 26 compounds were synthesized to determine the effect of hydroxyl and isoprenyl substituents on trypanocide activity. One of the compounds showed interesting activity against a resistant strain of T. cruzi, with a half effective concentration of 18.3 μM ± 1.1 and an index of selectivity > 10.9.
- Escobar, Gustavo,González, Luis A.,Qui?ones, Wiston,Robledo, Sara,Upegui, Yulieth
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- Practical and efficient synthesis of hydroxyaryl ketones catalyzed by HF@SiO2 under solvent-free condition
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A wide variety of hydroxyaryl ketones bearing different motifs was successfully synthesized with good yields and excellent selectivities in the presence of HF@SiO2 as an environmental friendly acid under solvent-free condition. Mild and green reaction conditions and excellent yields (50-91%) make this method an attractive method for the efficient synthesis of hydroxyaryl ketones. Fries rearrangement of phenyl benzoate in the presence of HF@SiO2 led to p-hydroxybenzophenone, while phenyl acetate in the same conditions produced o-hydroxyacetophenone as a single isomer.
- Paghandeh, Hossein,Saeidian, Hamid,Ghaffarzadeh, Mohammad
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p. 809 - 814
(2018/09/26)
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- Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation
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Polyprenylated acylphloroglucinols (PPAPs) are structurally complex natural products with promising biological activities. Herein, we present a biosynthesis-inspired, diversity-oriented synthesis approach for rapid construction of PPAP analogs via double decarboxylative allylation (DcA) of acylphloroglucinol scaffolds to access allyl-desoxyhumulones followed by dearomative conjunctive allylic alkylation (DCAA).
- Grenning, Alexander J.,Boyce, Jonathan H.,Porco, John A.
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supporting information
p. 11799 - 11804
(2014/10/16)
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- Catalytic application of fluorous silica gel in Fries rearrangement
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Commercially available fluorous silica gel (Fluoro Flash) with no further post-modification was successfully investigated and applied merely as a catalyst in Fries rearrangement of various aryl esters under solvent free conditions in 4 h and optimized temperatures. In addition to good yields and recyclability of the catalyst, toxicity of reaction medium, by-products, and wastes were minimized. Also, low catalyst loading was another advantage of this methodology.
- Ghaffarzadeh, Mohammad,Ahmadi, Maryam
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- NaOAc-mediated selective deprotection of aromatic acetates and Its application in the synthesis of natural products
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We have developed an efficient method to deacetylate the aromatic acetates using NaOAc in excellent yields and demonstrated the application of the procedure in the synthesis of natural products.
- Narender,Reddy, K. Papi,Madhur
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experimental part
p. 1949 - 1956
(2009/10/17)
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- Design and synthesis of novel benzofurans as a new class of antifungal agents targeting fungal N-myristoyltransferase. Part 1
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Potent and selective Candida albicans N-myristoyltransferase (CaNmt) inhibitors have been identified through optimization of a lead compound 1 discovered by random screening. The inhibitor design is based on the crystal structure of the CaNmt complex with compound (S)-3 and structure-activity relationships (SARs) have been clarified. Modification of the C-4 side chain of 1 has led to the discovery of a potent and selective CaNmt inhibitor 11 (RO-09-4609), which exhibits antifungal activity against C. albicans in vitro.
- Masubuchi, Miyako,Kawasaki, Ken-ichi,Ebiike, Hirosato,Ikeda, Yoshihiko,Tsujii, Shinji,Sogabe, Satoshi,Fujii, Toshihiko,Sakata, Kiyoaki,Shiratori, Yasuhiko,Aoki, Yuko,Ohtsuka, Tatsuo,Shimma, Nobuo
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p. 1833 - 1837
(2007/10/03)
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- The cyanide catalyzed isomerization of enol esters derived from cyclic 1,3-diketones
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Cross-over experiments unveil that the mechanism of the title reaction consists in cleavage of enol esters by cyanide with transient formation of acyl cyanides. These react as 'soft' C-acylating agents with the enolates freed in the initial step. Use is made of the acyl cyanide derived from pyrrole-2-carboxylic acid to set up the triketide type skeleton 12 of the antibiotic pyoluteorin 16. The aromatization of 12 with mercuric acetate gave the pyrrolo[a]indolone 18.
- Montes, Imber Flores,Burger, Ulrich
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p. 1007 - 1010
(2007/10/03)
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- Method for dyeing keratinous fibres using a monohydroxyindole or dihydroxyindole and a non-oxidizing aromatic carbonyl derivative and dyeing agent
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The present invention relates to a method for dyeing keratinous fibers, characterized in that the following are applied to the fibers: a) a composition (A) containing, in a medium appropriate for dyeing, at least one monohydroxyindole or dihydroxyindole, this application being preceded or followed by the application of b) a composition (B) containing, in a medium appropriate for dyeing, at least one aromatic carbonyl derivative chosen from hydroxyacetophenones, hydroxybenzophenones, 2-hydroxy-1,4-benzoquinones, hydroxy-1,4-naphthoquinones,amino-1,4-naphthoquinones,hydroxy-9,10-anthraquinones and amino-9,10-anthraquinones. It also relates to the dyeing agents for carrying it out.
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- Method of preparing 2-acylresorcinols
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A method of preparing a 2-acylresorcinol which comprises dehydrogenating a 2-acyl-1,3-cyclohexanedione of the general formula wherein R1 represents an alkyl, aralkyl or aryl group, and RZrepresents hydrogen, or an alkyl, alkoxy or acylamino group, in the presence of a dehydrogenation catalyst (such as a Group VIII metal) or a dehydrogenation agent (such as sulphur or selenium) at an elevated temperature, to provide a 2-acylresorcinol of the general formula wherein R1 and R2 are as defined.
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- Cromolyn binding protein in highly purifed form, and methods for the isolation thereof
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Substantially pure cromolyn binding protein is prepared by means of affinity chromatography of cromolyn derivatives bound to insoluble matrices. Aminocromolyn is prepared by a six-step synthesis and amine derivatives thereof are prepared by conventional means. Obtaining a compound having an amine group instead of the OH group at the 2-carbon of the propane link of cromolyn permits many kinds of reactions without interfering with the portion of the cromolyn molecule with causes its pharmacological activity. The cromolyn derivatives can be conjugated to proteins such as BSA by means of glutaraldehyde cross-linking and such conjugates can be covalently bound to agarose beads. Cromolyn binding protein can be isolated by passing lysates of RBL-2H3 cells through chromatographic columns packed with such beads. The cromolyn binding protein can be further purified by means of lectin-agarose columns.
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- REARRANGEMENT OF 2-ACYL-2-CHLORO-1,3-CYCLOHEXANEDIONES INTO 2-ACYLRESORCINOLS AND 2-ACYL-4-CHLORO-1,3-CYCLOHEXANEDIONES
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2-Acetylresorcinol was prepared in 80-88percent yield from 2-acetyl-1,3-cyclohexanedione by 2-chlorination (excess of NCS in boiling carbon tetrachloride or one equivalent of molecular chlorine in the cold solvent) followed by aromatization in a heated dry solution of hydrogen chloride in dimethylformamide.The scope of the method was extended to the preparation of 2-propionyl- and 2-isobutyrylresorcinol (resp. 79percent and 66percent yield).Application of the method on 2-acryl-5,5-dimethyl-1,3-cyclohexanediones (acyl=acetyl, propionyl, n-butyryl, i-butyryl) affrded the corresponding 2-acyl-4-chlorodimedone derivatives in 40-77percent yields.
- De Buyck, L.,Seynaeve, D.,De Kimpe, N.,Verhe, R.,Schamp, N.
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p. 363 - 370
(2007/10/02)
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