170244-01-6Relevant articles and documents
Synthesis and activity of phenyl derivatives containing 5,6-dimethyl-thieno [2,3-d] pyrimidin-4(1H)-one or 4H-pyrimido [5,4-b] indol-4-one heterocyclic system as potential non steroidal anti-inflammatory drugs
Santagati, Andrea,Granata, Giuseppe,Santagati, Maria,Cutuli, Vincenza,Mangano, Nunzio Guido,Caruso, Antonina
, p. 448 - 454 (2007/10/03)
The synthesis, the analgesic and anti-inflammatory activities of two series of phenyl derivatives containing 5,6-dimethyl-thieno[2,3-d]pyrimidin-4(1H)-one and 4H-pyrimido[5,4-b]indol-4-one system, respectively, are reported. Two of these derivatives, 6A and 9B, showed interesting activities. The results of the pharmacological assays are discussed.
[[(Arylpiperazinyl)alkyl]thio]thieno[2,3-d]pyrimidinone derivatives as high-affinity, selective 5-HT(1A) receptor ligands
Modica, Maria,Santagati, Maria,Russo, Filippo,Parotti, Luca,De Gioia, Luca,Selvaggini, Carlo,Salmona, Mario,Mennini, Tiziana
, p. 574 - 585 (2007/10/03)
A series of 2-[[(4-aryl-1-piperazinyl)alkyl]thio]thieno[2,3- d]pyrimidin-4(1H)-one and 3-substituted 2-[[(4-aryl-1- piperazinyl)alkyl]thio]thieno[2,3-d]pyrimidin-4(3H)-one derivatives was prepared and evaluated for in vitro 5-HT(1A) receptor affinity by radioligand binding assays; the selectivity for 5-HT(1A) receptors rather than α1- adrenoceptors was also examined (ratio of the IC50 α1 to IC50 5- HT(1A)). The binding tests gave indications about the best features of the [(arylpiperazinyl)alkyl]thio moiety and of the substituents on the thiophene and pyrimidinone rings for efficacious and selective 5-HT(1A) ligands. The most effective derivative for displacing [3H]-8-OH-DPAT from rat hippocampal membranes was the 3-amino-2-[[3-[4-(2-methoxyphenyl)-1- piperazinyl]propyl]thio]-5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-one (70) (IC50 = 0.3 nM) with selectivity of 24 for the 5-HT(1A) over the α1- adrenoceptor. Compound 73, where the 2-methoxyphenyl on the N4 piperazine ring was replaced with a pyrimidine group, showed the best selectivity, with a ratio of 74, while its affinity IC50 for 5-HT(1A) was 6.8 nM. These results, compared to those for compounds 40 (IC50 24 nM; selectivity 2) and 49 (IC50 226 nM; selectivity 5), N3 unsubstituted analogues of derivatives 70 and 73, show the importance of an amino group in position 3 of the thienopyrimidine system for the interaction with 5-HT(1A) receptor binding sites, although this fragment can affect the affinity and selectivity only if linked to the (arylpiperazinyl)alkyl moiety. The better selectivity of piperidine 74 (IC50 0.8; selectivity 45) compared to the analogous piperazine 70 is also noteworthy. Twenty of the 30 molecules used for determining the binding affinity to 5-HT(1A) and α1-adrenergic receptors were selected for QSAR analysis using a series of molecular descriptors and calculated with the TSAR software.
Synthesis and pharmacological properties of thieno[2',3':4,5]pyrimido [2,1-b][1,3,4]thiadiazine derivatives
Santagati,Modica,Santagati,Cutuli,Amore,Caruso
, p. 605 - 609 (2007/10/03)
A new series of 2-substituted-7,8-dimethyl-3H,9H-thieno[2',3':4,5]pyrimido[2,1b][1,3,4 ]thiadiazin-9-ones 5a-d and 6a,b was synthesized through the hydrazinium(1+) salt of 3-amino-2,3-dihydro-5,6-dimethyl-2-thioxo-thieno[2,3-d]pyrimidin-4(1H- one, 2. Thes
