Bioorganic & Medicinal Chemistry Letters, Aug 1, 2017
This is a PDF file of an unedited manuscript that has been accepted for publication. As a service... more This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. Supplementary Material Materials and methods, synthesis, compound characterization, and 1 Hand 13 C-NMR spectra.
A Facile Synthesis of 3-Glycosyl-5-substituted-2-isoxazoles.-1,3-Dipolar cycloaddition between 2-... more A Facile Synthesis of 3-Glycosyl-5-substituted-2-isoxazoles.-1,3-Dipolar cycloaddition between 2-deoxy-D-aldose oximes and alkynes as dipolarophile provides new glycosyl-substituted isoxazoles [cf. (III)].
and 13 C spectroscopic data for 5H-[1,3]thiazolo[2,3-b]quinazolin-5-one and 12H-[1,3]benzothiazol... more and 13 C spectroscopic data for 5H-[1,3]thiazolo[2,3-b]quinazolin-5-one and 12H-[1,3]benzothiazolo[2,3-b]quinazolin-12one derivatives were fully assigned by combination of one-and two-dimensional experiments (DEPT, HMBC and HMQC). Both heterocyclic systems show similar spectroscopic properties with some remarkable differences.
Neste trabalho são apresentados os procedimentos para a síntese de diferentes compostos heterocíc... more Neste trabalho são apresentados os procedimentos para a síntese de diferentes compostos heterocíclicos a partir do 2,3-O-isopropilideno-D-gliceraldeído: ciclização intramolecular, cicloadição 1,3-dipolar e reação de acoplamento bimolecular. Os produtos sintetizados foram caracterizados por espectroscopia de 1 H RMN e 13 C RMN e análise elementar. Os novos heterocíclicos e seus derivados (12 compostos) foram testados como inhibidores da enzima acetilcolinesterase. We report herein the convenient procedures for the syntheses of different heterocyclic compounds from 2,3-O-isopropylidene-D-glyceraldehyde using intramolecular cyclization, 1,3-dipolar cycloaddition or bimolecular coupling reactions. The products were characterized by 1 H and 13 C NMR spectroscopy and elemental analysis. The new heterocycles and their derivatives were evaluated as inhibitors of acetylcholinesterase enzyme.
We present here the study of selective synthesis of 1,3-thiazolidin-4-ones via microwave-assisted... more We present here the study of selective synthesis of 1,3-thiazolidin-4-ones via microwave-assisted multi-component reaction under solvent-free conditions. Although, theoretically two different products are possible (benzothiazepinones 4 and thiazolidinones 5), the reaction gave only two diasteroisomers of 1,3-thiazolidin-4-ones (48-97%) in the threecomponent reaction between 2,3 : 4,5-di-O-isopropiliden-β-D-arabino-hexos-2-ulo-2,6piranosa 1, different heteroaromatics anilines 3 and mercaptoacetic acid 2 as can be seen in the scheme of Figure 1. The synthesized compounds were characterized by IR, 1 H-, 13 C, DEPT and HSQC-RMN. The stereochemistry of both the diasteroisomers was elucidated with the help of NOE experiments.
Fused pyrimidine derivatives R 0515 Mild Method for Ullmann Reaction of 2-Chlorobenzoic Acids and... more Fused pyrimidine derivatives R 0515 Mild Method for Ullmann Reaction of 2-Chlorobenzoic Acids and Aminothiazoles or Aminobenzothiazoles under Ultrasonic Irradiation.-Derivatives of [1,3]thiazolo[2,3-b]quinazolin-5-one (III) and [1,3]benzothiazolo[2,3-b]quinazolin-12-one (V) are synthesized in one-pot procedures using the copper-catalyzed Ullmann condensation. Under ultrasonic irradiation, the yields are enhanced and the reaction times are reduced.
A Synthetic Pathway to Obtain Heterocyclic Derivatives Containing Isoxazole and Tetrazole Rings J... more A Synthetic Pathway to Obtain Heterocyclic Derivatives Containing Isoxazole and Tetrazole Rings Joined by a Carbohydrate Tether.-With a view to their potential biological activity title compounds (IV) are prepared. The new compounds involved in this synthesis are physically and spectroscopically characterized.-(MARTINEZ ESPERON, MARIA F.;
Tailor-Made and Functionalized Biopolymer Systems, 2021
Abstract In medicine, the applications of biopolymers are of great interest because of their easy... more Abstract In medicine, the applications of biopolymers are of great interest because of their easy accessibility, low cost, and high functionality. In this context, collagen, albumin, alginate, gelatin, cyclodextrins (CDs), chitosan (CS), dextran, starch, agarose, cellulose, hyaluronic acid, etc. are the most attractive for their several biomedical uses. The incorporation of thiol groups into these biopolymers leads to the production of thiomers, which show an improved possibility to interact with the glycoproteins on the mucosal surfaces. These mucoadhesive properties of thiomers eventually make them ideal substrates for drug delivery and biomedical applications. In this chapter, recent advances in the synthesis of thiolated biopolymers based on CS, starch, gelatin, β-CD, hyaluronic acid, whey protein, pullulan, and alginate are reported.
According to the strategy to search alternative products which can replace (partially) the use of... more According to the strategy to search alternative products which can replace (partially) the use of expensive polymers in polymer-flood projects, this work helps to find the optimum combination between polymer and xanthan-gum to develop a mixture that generates viscosity in good economical and rheological conditions. The aim of this work is the characterization of the mixture of a biopolymer (xanthan gum) and a synthetic polyacrylamide in specific proportions and reservoir conditions. Both polymers are suitable for polymer flooding, but they have weaknesses on their own: the polyacrylamide is very susceptible to saline environments and mechanical degradation, while biopolymers as xanthan gum exceed these reservoir conditions but are highly degraded by some bacteria. A polymer blend of mother solutions was prepared by mechanical mixing. It is proved that a blend improves the desirable properties of mobility control if the polymers show miscibility. Several techniques were used to evide...
ABSTRACTThree new bisglycidyl monomers; 1,4‐bis((2‐hydroxy‐3‐methacryloxypropoxy) methyl)benzene ... more ABSTRACTThree new bisglycidyl monomers; 1,4‐bis((2‐hydroxy‐3‐methacryloxypropoxy) methyl)benzene (MB‐Phe‐OH), 1,4‐bis(2‐hydroxy‐3‐methacryloxypropoxy)2‐cis‐butene (MB‐Cis‐OH), and 1,7‐bis(2‐hydroxy‐3‐methacryloxypropoxy)heptane (MB‐1,7‐OH); were synthesized and used as Bis‐GMA/TEGDMA (bisphenolglycidyl methacrylate/triethylene glycol dimethacrylate) composite resin additives. Flexural properties and double bond conversion of the dental resins composed of silanizated inorganic filler and organic matrices containing new monomers were evaluated. The composite resins formulated, using the monomers MB‐Cis‐OH and MB‐1,7‐OH, have mechanical properties and double bond conversion comparable with those of Bis‐GMA/TEGDMA composite resin used as control. The composite containing the new monomer MB‐Phe‐OH has better flexural properties (flexural strength 65.01 MPa and flexural modulus 5675.91 MPa) than the control composite resin (flexural strength 52.85 MPa and flexural modulus 4879.72 MPa); th...
and 13 C spectroscopic data for 5H-[1,3]thiazolo[2,3-b]quinazolin-5-one and 12H-[1,3]benzothiazol... more and 13 C spectroscopic data for 5H-[1,3]thiazolo[2,3-b]quinazolin-5-one and 12H-[1,3]benzothiazolo[2,3-b]quinazolin-12one derivatives were fully assigned by combination of one-and two-dimensional experiments (DEPT, HMBC and HMQC). Both heterocyclic systems show similar spectroscopic properties with some remarkable differences.
An atom-economic strategy is proposed to valorise the byproducts from an invasive bamboo with imp... more An atom-economic strategy is proposed to valorise the byproducts from an invasive bamboo with improved thermal stability for potential use in composites.
Bioorganic & Medicinal Chemistry Letters, Aug 1, 2017
This is a PDF file of an unedited manuscript that has been accepted for publication. As a service... more This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. Supplementary Material Materials and methods, synthesis, compound characterization, and 1 Hand 13 C-NMR spectra.
A Facile Synthesis of 3-Glycosyl-5-substituted-2-isoxazoles.-1,3-Dipolar cycloaddition between 2-... more A Facile Synthesis of 3-Glycosyl-5-substituted-2-isoxazoles.-1,3-Dipolar cycloaddition between 2-deoxy-D-aldose oximes and alkynes as dipolarophile provides new glycosyl-substituted isoxazoles [cf. (III)].
and 13 C spectroscopic data for 5H-[1,3]thiazolo[2,3-b]quinazolin-5-one and 12H-[1,3]benzothiazol... more and 13 C spectroscopic data for 5H-[1,3]thiazolo[2,3-b]quinazolin-5-one and 12H-[1,3]benzothiazolo[2,3-b]quinazolin-12one derivatives were fully assigned by combination of one-and two-dimensional experiments (DEPT, HMBC and HMQC). Both heterocyclic systems show similar spectroscopic properties with some remarkable differences.
Neste trabalho são apresentados os procedimentos para a síntese de diferentes compostos heterocíc... more Neste trabalho são apresentados os procedimentos para a síntese de diferentes compostos heterocíclicos a partir do 2,3-O-isopropilideno-D-gliceraldeído: ciclização intramolecular, cicloadição 1,3-dipolar e reação de acoplamento bimolecular. Os produtos sintetizados foram caracterizados por espectroscopia de 1 H RMN e 13 C RMN e análise elementar. Os novos heterocíclicos e seus derivados (12 compostos) foram testados como inhibidores da enzima acetilcolinesterase. We report herein the convenient procedures for the syntheses of different heterocyclic compounds from 2,3-O-isopropylidene-D-glyceraldehyde using intramolecular cyclization, 1,3-dipolar cycloaddition or bimolecular coupling reactions. The products were characterized by 1 H and 13 C NMR spectroscopy and elemental analysis. The new heterocycles and their derivatives were evaluated as inhibitors of acetylcholinesterase enzyme.
We present here the study of selective synthesis of 1,3-thiazolidin-4-ones via microwave-assisted... more We present here the study of selective synthesis of 1,3-thiazolidin-4-ones via microwave-assisted multi-component reaction under solvent-free conditions. Although, theoretically two different products are possible (benzothiazepinones 4 and thiazolidinones 5), the reaction gave only two diasteroisomers of 1,3-thiazolidin-4-ones (48-97%) in the threecomponent reaction between 2,3 : 4,5-di-O-isopropiliden-β-D-arabino-hexos-2-ulo-2,6piranosa 1, different heteroaromatics anilines 3 and mercaptoacetic acid 2 as can be seen in the scheme of Figure 1. The synthesized compounds were characterized by IR, 1 H-, 13 C, DEPT and HSQC-RMN. The stereochemistry of both the diasteroisomers was elucidated with the help of NOE experiments.
Fused pyrimidine derivatives R 0515 Mild Method for Ullmann Reaction of 2-Chlorobenzoic Acids and... more Fused pyrimidine derivatives R 0515 Mild Method for Ullmann Reaction of 2-Chlorobenzoic Acids and Aminothiazoles or Aminobenzothiazoles under Ultrasonic Irradiation.-Derivatives of [1,3]thiazolo[2,3-b]quinazolin-5-one (III) and [1,3]benzothiazolo[2,3-b]quinazolin-12-one (V) are synthesized in one-pot procedures using the copper-catalyzed Ullmann condensation. Under ultrasonic irradiation, the yields are enhanced and the reaction times are reduced.
A Synthetic Pathway to Obtain Heterocyclic Derivatives Containing Isoxazole and Tetrazole Rings J... more A Synthetic Pathway to Obtain Heterocyclic Derivatives Containing Isoxazole and Tetrazole Rings Joined by a Carbohydrate Tether.-With a view to their potential biological activity title compounds (IV) are prepared. The new compounds involved in this synthesis are physically and spectroscopically characterized.-(MARTINEZ ESPERON, MARIA F.;
Tailor-Made and Functionalized Biopolymer Systems, 2021
Abstract In medicine, the applications of biopolymers are of great interest because of their easy... more Abstract In medicine, the applications of biopolymers are of great interest because of their easy accessibility, low cost, and high functionality. In this context, collagen, albumin, alginate, gelatin, cyclodextrins (CDs), chitosan (CS), dextran, starch, agarose, cellulose, hyaluronic acid, etc. are the most attractive for their several biomedical uses. The incorporation of thiol groups into these biopolymers leads to the production of thiomers, which show an improved possibility to interact with the glycoproteins on the mucosal surfaces. These mucoadhesive properties of thiomers eventually make them ideal substrates for drug delivery and biomedical applications. In this chapter, recent advances in the synthesis of thiolated biopolymers based on CS, starch, gelatin, β-CD, hyaluronic acid, whey protein, pullulan, and alginate are reported.
According to the strategy to search alternative products which can replace (partially) the use of... more According to the strategy to search alternative products which can replace (partially) the use of expensive polymers in polymer-flood projects, this work helps to find the optimum combination between polymer and xanthan-gum to develop a mixture that generates viscosity in good economical and rheological conditions. The aim of this work is the characterization of the mixture of a biopolymer (xanthan gum) and a synthetic polyacrylamide in specific proportions and reservoir conditions. Both polymers are suitable for polymer flooding, but they have weaknesses on their own: the polyacrylamide is very susceptible to saline environments and mechanical degradation, while biopolymers as xanthan gum exceed these reservoir conditions but are highly degraded by some bacteria. A polymer blend of mother solutions was prepared by mechanical mixing. It is proved that a blend improves the desirable properties of mobility control if the polymers show miscibility. Several techniques were used to evide...
ABSTRACTThree new bisglycidyl monomers; 1,4‐bis((2‐hydroxy‐3‐methacryloxypropoxy) methyl)benzene ... more ABSTRACTThree new bisglycidyl monomers; 1,4‐bis((2‐hydroxy‐3‐methacryloxypropoxy) methyl)benzene (MB‐Phe‐OH), 1,4‐bis(2‐hydroxy‐3‐methacryloxypropoxy)2‐cis‐butene (MB‐Cis‐OH), and 1,7‐bis(2‐hydroxy‐3‐methacryloxypropoxy)heptane (MB‐1,7‐OH); were synthesized and used as Bis‐GMA/TEGDMA (bisphenolglycidyl methacrylate/triethylene glycol dimethacrylate) composite resin additives. Flexural properties and double bond conversion of the dental resins composed of silanizated inorganic filler and organic matrices containing new monomers were evaluated. The composite resins formulated, using the monomers MB‐Cis‐OH and MB‐1,7‐OH, have mechanical properties and double bond conversion comparable with those of Bis‐GMA/TEGDMA composite resin used as control. The composite containing the new monomer MB‐Phe‐OH has better flexural properties (flexural strength 65.01 MPa and flexural modulus 5675.91 MPa) than the control composite resin (flexural strength 52.85 MPa and flexural modulus 4879.72 MPa); th...
and 13 C spectroscopic data for 5H-[1,3]thiazolo[2,3-b]quinazolin-5-one and 12H-[1,3]benzothiazol... more and 13 C spectroscopic data for 5H-[1,3]thiazolo[2,3-b]quinazolin-5-one and 12H-[1,3]benzothiazolo[2,3-b]quinazolin-12one derivatives were fully assigned by combination of one-and two-dimensional experiments (DEPT, HMBC and HMQC). Both heterocyclic systems show similar spectroscopic properties with some remarkable differences.
An atom-economic strategy is proposed to valorise the byproducts from an invasive bamboo with imp... more An atom-economic strategy is proposed to valorise the byproducts from an invasive bamboo with improved thermal stability for potential use in composites.
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