Oxazolopyrimidine and thiazolopyrimidine derivatives related to the xanthines

Design and Synthesis of Novel Thiazolo[5,4-d]pyrimidine Derivatives with High Affinity for Both the Adenosine A1 and A2A Receptors, and Efficacy in Animal Models of Depression

“…The bicyclic thiazolopyrimidine core suitably decorated at position-2 was first synthesized, then introduction of the diverse substituents at position-5 was performed. Briefly, by reacting 2-aminothiole 20 [ 36 ] with the suitable arylacetylchloride 21 – 24 [ 37 , 38 , 39 ] at high temperature, the corresponding thiazolo[5,4-d]pyrimidine-5,7-dihydroxy derivatives 25 – 28 were obtained ( Scheme 1 ). The latter were chlorinated by reaction with POCl 3 under microwave irradiation to the corresponding 5,7-dichloro bicyclic derivatives 29 – 32 , which in the presence of aqueous ammonia solution (33%) furnished the 7-amino-5-chloro substituted intermediates 33 – 36 .…”

“…To a suspension of the 5-amino-6-sulfanylpyrimidine-2,4-diol 20 [ 36 ] (8.7 mmol) in dry NMP, the suitable arylacetyl chloride 21 , 22 [ 37 ], 23 [ 38 ], and 24 [ 39 ] (10.5 mmol) was added. The resulting mixture was heated at 150 °C for 10–15 h, then was cooled to rt and diluted with cold water (100 mL), affording a precipitate, which was collected by filtration and purified by crystallization.…”

Design, Synthesis, and Pharmacological Characterization of 2-(2-Furanyl)thiazolo[5,4-d]pyrimidine-5,7-diamine Derivatives: New Highly Potent A2A Adenosine Receptor Inverse Agonists with Antinociceptive Activity

“…The synthetic pathway yielding the novel compounds 2−18 is outlined in Scheme 1, and it involves the synthesis of the 7-amino-5-chlorothiazolo [5,4-d]pyrimidine derivative 22 starting from the readily accessible compound 19. 37 Heating 19 with 2-furoyl chloride at 150 °C in NMP yielded the 2-(2-furanyl)thiazolo [5,4-d]pyrimidine-5,7-diolo 20, which was allowed to react with POCl 3 at reflux temperature to give the corresponding 5,7-dichloro substituted compound 21. The latter was treated at reflux with 33% aqueous ammonia solution, affording the desired 5-chloro-7-amino 22 as the only regioisomer as expected on the basis of the different reactivity of the two chlorine atoms in the thiazolopyrimidine ring system.…”

“…The synthetic pathway yielding the novel compounds 2 – 18 is outlined in Scheme , and it involves the synthesis of the 7-amino-5-chlorothiazolo­[5,4- d ]­pyrimidine derivative 22 starting from the readily accessible compound 19 . Heating 19 with 2-furoyl chloride at 150 °C in NMP yielded the 2-(2-furanyl)­thiazolo­[5,4- d ]­pyrimidine-5,7-diolo 20 , which was allowed to react with POCl 3 at reflux temperature to give the corresponding 5,7-dichloro substituted compound 21 .…”

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“…To innovations in biotechnology for sustainable development of agriculture belongs the elaboration of new PGRs on the basis of low molecular weight synthetic heterocyclic compounds (LMWHC), derivatives of pyridine, pyrimidine, pyrazole, triazine, and oxazole to intensify plant growth and development, and increase crop productivity. As is known LMWHC are widely used in the medicine as drugs for the treatment of bacterial, infectious, viral, fungal, inflammatory, neural, allergic, cancer, and autoimmune diseases [42][43][44][45][46][47][48][49][50][51][52][53][54][55], and in the agriculture as PGRs, herbicides, fungicides, insecticides, acaricides, and antibacterial agents [56][57][58][59][60][61][62][63][64][65][66][67][68][69][70][71]. Our numerous works devoted to study of plant growth regulatory activity of LMWHC, synthesized in the Institute of Bioorganic Chemistry and Petrochemistry of NAS of Ukraine, showed that different classes of LMWHC used at very low non-toxic for human health and environment concentrations 10 -8 M -10 -9 M revealed the broad spectrum of biological action on various crops [72][73][74][75] …”