The Experts below are selected from a list of 372 Experts worldwide ranked by ideXlab platform
Vittoria Colotta - One of the best experts on this subject based on the ideXlab platform.
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Novel human adenosine receptor antagonists based on the 7-amino-thiazolo[5,4-d]pyrimidine scaffold. Structural investigations at the 2-, 5- and 7-positions to enhance affinity and tune selectivity.
Bioorganic & medicinal chemistry letters, 2018Co-Authors: Flavia Varano, Daniela Catarzi, Matteo Falsini, Diego Dal Ben, Michela Buccioni, Gabriella Marucci, Rosaria Volpini, Vittoria ColottaAbstract:Abstract This paper describes the synthesis of novel 7-amino-thiazolo[5,4-d]pyrimidines bearing different substituents at positions 2, 5 and 7 of the Thiazolopyrimidine scaffold. The synthesized compounds 2–27 were evaluated in radioligand binding (A1, A2A and A3) and adenylyl cyclase activity (A2B and A2A) assays, in order to evaluate their affinity and potency at human adenosine receptor subtypes. The current study allowed us to support that affinity and selectivity of 7-amino-thiazolo[5,4-d]pyrimidine derivatives towards the adenosine receptor subtypes can be modulated by the nature of the groups attached at positions 2, 5 and 7 of the bicyclic scaffold. To rationalize the hypothetical binding mode of the newly synthesized compounds, we also performed docking calculations in human A2A, A1 and A3 structures.
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Identification of novel thiazolo[5,4-d]pyrimidine derivatives as human A1 and A2A adenosine receptor antagonists/inverse agonists.
Bioorganic & medicinal chemistry, 2018Co-Authors: Flavia Varano, Daniela Catarzi, Matteo Falsini, Fabrizio Vincenzi, Silvia Pasquini, Katia Varani, Vittoria ColottaAbstract:Abstract In this study a new set of thiazolo[5,4-d]pyrimidine derivatives was synthesized. These derivatives bear different substituents at positions 2 and 5 of the Thiazolopyrimidine core while maintaining a free amino group at position-7. The new compounds were tested for their affinity and potency at human (h) A1, A2A, A2B and A3 adenosine receptors expressed in CHO cells. The results reveal that the higher affinity of these new set of Thiazolopyrimidines is toward the hA1 and hA2A adenosine receptors subtypes and is tuned by the substitution pattern at both the 2 and 5 positions of the Thiazolopyrimidine nucleus. Functional studies evidenced that the compounds behaved as dual A1/A2A antagonists/inverse agonists. Compound 3, bearing a 5-((2-methoxyphenyl) methylamino) group and a phenyl moiety at position 2, displayed the highest affinity (hA1 Ki = 10.2 nM; hA2A Ki = 4.72 nM) and behaved as a potent A1/A2A antagonist/inverse agonist (hA1 IC50 = 13.4 nM; hA2A IC50 = 5.34 nM).
Noor Shahina Begum - One of the best experts on this subject based on the ideXlab platform.
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Synthesis and Crystal Structure of Thiazolopyrimidine Derivatives: Insights into Weak Interactions
Crystallography Reports, 2020Co-Authors: R. Shashi, N. L. Prasad, Noor Shahina BegumAbstract:Thiazolo[3,2-a]pyrimidines namely ethyl 2-acetyl-5-(2-fluorophenyl)-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate 3a , ethyl 2-acetyl-5-(3-fluorophenyl)-3,7-dimethyl-5 H -thiazolo[3,2-a]pyrimidine-6-carboxylate 3b , and ethyl 2-acetyl-5-(4-fluorophenyl)-3,7-dimethyl-5 H -thiazolo[3,2- a ]pyrimidine-6-carboxylate 3c were obtained by one pot synthesis using substituted 3,4 dihydropyrimidine2-thione ( 1a – 1c) and 3-chloro-2,4-pentanedione in ethanol and characterized by single-crystal X-ray diffraction. The variation in the position of fluorine atom on pyrimidine nucleus and insight into the self-assembly of compounds with varied types of non-covalent interactions has great influence on crystal packing.
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Synthesis of Some New Derivatives of Thiazolopyrimidines and Hydrolysis of Its Arylidene Derivative.
ChemInform, 2015Co-Authors: H. Nagarajaiah, Imtiyaz Ahmed M. Khazi, Noor Shahina BegumAbstract:The synthesis of a variety of new derivatives of Thiazolopyrimidine including tricyclic compound (XX) and some arylidene derivatives (III) is described.
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Synthesis of some new derivatives of Thiazolopyrimidines and hydrolysis of its arylidene derivative
Journal of Chemical Sciences, 2015Co-Authors: H. Nagarajaiah, Imtiyaz Ahmed M. Khazi, Noor Shahina BegumAbstract:A new ammonium acetate-assisted, convenient and efficient procedure for the synthesis of arylidene derivatives of Thiazolopyrimidine is described. The main advantages of this protocol is that it is economical, short reaction time, commonly available chemicals, and ease of isolation of products. In addition, a new series of thiazole-fused pyrimidines were synthesized and hydrolysis of one of its arylidene derivative studied. All the compounds were characterized by analytical and spectroscopic methods. Further, the structure of hydrolyzed product and two other compounds were confirmed by X-ray crystal structure analysis. The crystal structures are stabilized by intermolecular C-H. . .O, C-H. . .N, C-H. . .π and π. . .π weak interactions. The anti-microbial screening was done on the compounds in order to test their anti-bacterial and anti-fungal activities.
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Synthesis of some new derivatives of Thiazolopyrimidines and hydrolysis of its arylidene derivative
Journal of Chemical Sciences, 2015Co-Authors: H. Nagarajaiah, Imtiyaz Ahmed M. Khazi, Noor Shahina BegumAbstract:A new ammonium acetate-assisted, convenient and efficient procedure for the synthesis of arylidene derivatives of Thiazolopyrimidine is described. The main advantages of this protocol is that it is economical, short reaction time, commonly available chemicals, and ease of isolation of products. In addition, a new series of thiazole-fused pyrimidines were synthesized and hydrolysis of one of its arylidene derivative studied. All the compounds were characterized by analytical and spectroscopic methods. Further, the structure of hydrolyzed product and two other compounds were confirmed by X-ray crystal structure analysis. The crystal structures are stabilized by intermolecular C-H. . .O, C-H. . .N, C-H. . . π and π . . . π weak interactions. The anti-microbial screening was done on the compounds in order to test their anti-bacterial and anti-fungal activities. Graphical Abstract A new ammonium acetate–assisted, convenient and efficient procedure for the synthesis of arylidene derivative of Thiazolopyrimidine is described. In addition, a new series of thiazolefused pyrimidines were synthesized and hydrolysis of arylidene derivative was studied.
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Crystal structure of ethyl 2-cyano-3-[(1-ethoxyethylidene)amino]-5-(3-methoxyphenyl)-7-methyl-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate
International Union of Crystallography, 2015Co-Authors: M. S. Krishnamurthy, Noor Shahina BegumAbstract:In the title compound, C22H24N4O4S, the central pyrimidine ring adopts a sofa conformation with the ring-junction N atom displaced by 0.2358 (6) Å from the mean plane of the remaining ring atoms. The 3-methoxyphenyl ring, at the chiral C atom opposite the other N atom, is positioned axially and is inclined to the Thiazolopyrimidine ring with a dihedral angle of 83.88 (7)°. The thiazole ring is essentially planar (r.m.s. deviation = 0.0034 Å). In the crystal, pairs of weak C—H...O hydrogen bonds link molecules related by twofold rotation axes to form R22(8) rings, which in turn are linked by weak C—H...N interactions, forming ribbons along [-110]. In addition, π–π stacking interactions [centroid—centroid distance = 3.5744 (15) Å] connect the ribbons, forming slabs lying parallel to (001)
Flavia Varano - One of the best experts on this subject based on the ideXlab platform.
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Novel human adenosine receptor antagonists based on the 7-amino-thiazolo[5,4-d]pyrimidine scaffold. Structural investigations at the 2-, 5- and 7-positions to enhance affinity and tune selectivity.
Bioorganic & medicinal chemistry letters, 2018Co-Authors: Flavia Varano, Daniela Catarzi, Matteo Falsini, Diego Dal Ben, Michela Buccioni, Gabriella Marucci, Rosaria Volpini, Vittoria ColottaAbstract:Abstract This paper describes the synthesis of novel 7-amino-thiazolo[5,4-d]pyrimidines bearing different substituents at positions 2, 5 and 7 of the Thiazolopyrimidine scaffold. The synthesized compounds 2–27 were evaluated in radioligand binding (A1, A2A and A3) and adenylyl cyclase activity (A2B and A2A) assays, in order to evaluate their affinity and potency at human adenosine receptor subtypes. The current study allowed us to support that affinity and selectivity of 7-amino-thiazolo[5,4-d]pyrimidine derivatives towards the adenosine receptor subtypes can be modulated by the nature of the groups attached at positions 2, 5 and 7 of the bicyclic scaffold. To rationalize the hypothetical binding mode of the newly synthesized compounds, we also performed docking calculations in human A2A, A1 and A3 structures.
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Identification of novel thiazolo[5,4-d]pyrimidine derivatives as human A1 and A2A adenosine receptor antagonists/inverse agonists.
Bioorganic & medicinal chemistry, 2018Co-Authors: Flavia Varano, Daniela Catarzi, Matteo Falsini, Fabrizio Vincenzi, Silvia Pasquini, Katia Varani, Vittoria ColottaAbstract:Abstract In this study a new set of thiazolo[5,4-d]pyrimidine derivatives was synthesized. These derivatives bear different substituents at positions 2 and 5 of the Thiazolopyrimidine core while maintaining a free amino group at position-7. The new compounds were tested for their affinity and potency at human (h) A1, A2A, A2B and A3 adenosine receptors expressed in CHO cells. The results reveal that the higher affinity of these new set of Thiazolopyrimidines is toward the hA1 and hA2A adenosine receptors subtypes and is tuned by the substitution pattern at both the 2 and 5 positions of the Thiazolopyrimidine nucleus. Functional studies evidenced that the compounds behaved as dual A1/A2A antagonists/inverse agonists. Compound 3, bearing a 5-((2-methoxyphenyl) methylamino) group and a phenyl moiety at position 2, displayed the highest affinity (hA1 Ki = 10.2 nM; hA2A Ki = 4.72 nM) and behaved as a potent A1/A2A antagonist/inverse agonist (hA1 IC50 = 13.4 nM; hA2A IC50 = 5.34 nM).
Daniela Catarzi - One of the best experts on this subject based on the ideXlab platform.
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Novel human adenosine receptor antagonists based on the 7-amino-thiazolo[5,4-d]pyrimidine scaffold. Structural investigations at the 2-, 5- and 7-positions to enhance affinity and tune selectivity.
Bioorganic & medicinal chemistry letters, 2018Co-Authors: Flavia Varano, Daniela Catarzi, Matteo Falsini, Diego Dal Ben, Michela Buccioni, Gabriella Marucci, Rosaria Volpini, Vittoria ColottaAbstract:Abstract This paper describes the synthesis of novel 7-amino-thiazolo[5,4-d]pyrimidines bearing different substituents at positions 2, 5 and 7 of the Thiazolopyrimidine scaffold. The synthesized compounds 2–27 were evaluated in radioligand binding (A1, A2A and A3) and adenylyl cyclase activity (A2B and A2A) assays, in order to evaluate their affinity and potency at human adenosine receptor subtypes. The current study allowed us to support that affinity and selectivity of 7-amino-thiazolo[5,4-d]pyrimidine derivatives towards the adenosine receptor subtypes can be modulated by the nature of the groups attached at positions 2, 5 and 7 of the bicyclic scaffold. To rationalize the hypothetical binding mode of the newly synthesized compounds, we also performed docking calculations in human A2A, A1 and A3 structures.
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Identification of novel thiazolo[5,4-d]pyrimidine derivatives as human A1 and A2A adenosine receptor antagonists/inverse agonists.
Bioorganic & medicinal chemistry, 2018Co-Authors: Flavia Varano, Daniela Catarzi, Matteo Falsini, Fabrizio Vincenzi, Silvia Pasquini, Katia Varani, Vittoria ColottaAbstract:Abstract In this study a new set of thiazolo[5,4-d]pyrimidine derivatives was synthesized. These derivatives bear different substituents at positions 2 and 5 of the Thiazolopyrimidine core while maintaining a free amino group at position-7. The new compounds were tested for their affinity and potency at human (h) A1, A2A, A2B and A3 adenosine receptors expressed in CHO cells. The results reveal that the higher affinity of these new set of Thiazolopyrimidines is toward the hA1 and hA2A adenosine receptors subtypes and is tuned by the substitution pattern at both the 2 and 5 positions of the Thiazolopyrimidine nucleus. Functional studies evidenced that the compounds behaved as dual A1/A2A antagonists/inverse agonists. Compound 3, bearing a 5-((2-methoxyphenyl) methylamino) group and a phenyl moiety at position 2, displayed the highest affinity (hA1 Ki = 10.2 nM; hA2A Ki = 4.72 nM) and behaved as a potent A1/A2A antagonist/inverse agonist (hA1 IC50 = 13.4 nM; hA2A IC50 = 5.34 nM).
Matteo Falsini - One of the best experts on this subject based on the ideXlab platform.
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Novel human adenosine receptor antagonists based on the 7-amino-thiazolo[5,4-d]pyrimidine scaffold. Structural investigations at the 2-, 5- and 7-positions to enhance affinity and tune selectivity.
Bioorganic & medicinal chemistry letters, 2018Co-Authors: Flavia Varano, Daniela Catarzi, Matteo Falsini, Diego Dal Ben, Michela Buccioni, Gabriella Marucci, Rosaria Volpini, Vittoria ColottaAbstract:Abstract This paper describes the synthesis of novel 7-amino-thiazolo[5,4-d]pyrimidines bearing different substituents at positions 2, 5 and 7 of the Thiazolopyrimidine scaffold. The synthesized compounds 2–27 were evaluated in radioligand binding (A1, A2A and A3) and adenylyl cyclase activity (A2B and A2A) assays, in order to evaluate their affinity and potency at human adenosine receptor subtypes. The current study allowed us to support that affinity and selectivity of 7-amino-thiazolo[5,4-d]pyrimidine derivatives towards the adenosine receptor subtypes can be modulated by the nature of the groups attached at positions 2, 5 and 7 of the bicyclic scaffold. To rationalize the hypothetical binding mode of the newly synthesized compounds, we also performed docking calculations in human A2A, A1 and A3 structures.
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Identification of novel thiazolo[5,4-d]pyrimidine derivatives as human A1 and A2A adenosine receptor antagonists/inverse agonists.
Bioorganic & medicinal chemistry, 2018Co-Authors: Flavia Varano, Daniela Catarzi, Matteo Falsini, Fabrizio Vincenzi, Silvia Pasquini, Katia Varani, Vittoria ColottaAbstract:Abstract In this study a new set of thiazolo[5,4-d]pyrimidine derivatives was synthesized. These derivatives bear different substituents at positions 2 and 5 of the Thiazolopyrimidine core while maintaining a free amino group at position-7. The new compounds were tested for their affinity and potency at human (h) A1, A2A, A2B and A3 adenosine receptors expressed in CHO cells. The results reveal that the higher affinity of these new set of Thiazolopyrimidines is toward the hA1 and hA2A adenosine receptors subtypes and is tuned by the substitution pattern at both the 2 and 5 positions of the Thiazolopyrimidine nucleus. Functional studies evidenced that the compounds behaved as dual A1/A2A antagonists/inverse agonists. Compound 3, bearing a 5-((2-methoxyphenyl) methylamino) group and a phenyl moiety at position 2, displayed the highest affinity (hA1 Ki = 10.2 nM; hA2A Ki = 4.72 nM) and behaved as a potent A1/A2A antagonist/inverse agonist (hA1 IC50 = 13.4 nM; hA2A IC50 = 5.34 nM).