Synthesis of acetonylmalonaldehyde and its interaction with aminoazoles

Vartanyan, M. M.; Елисеев, О. Л.; Skov, Kh. R.; Караханов, Р. А.

doi:10.1007/bf02496225

Cited by 5 publications

(2 citation statements)

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“…The structural assignments of 1 − 6 and 7 − 16 were made on the basis of 2D NMR experiment analyses (NOESY and HMBC) for all synthesized compounds 1 − 16 and confirmed for compounds 9 and 12 based on the X-ray data (Figures S1 and S2 of Supporting Information). The data obtained are in a good agreement with the published NMR spectra and quantum chemical calculations for known analogues. ,, …”

Section: Discussionsupporting

confidence: 87%

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(3-Phenylsulfonylcycloalkano[e and d]pyrazolo[1,5-a]pyrimidin-2-yl)amines: Potent and Selective Antagonists of the Serotonin 5-HT₆ Receptor

Ivachtchenko

Dmitriev²,

Golovina³

et al. 2010

J. Med. Chem.

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5-HT(6) receptors are exclusively localized in the CNS and have high affinity with many psychotropic agents. Though the role of this receptor in many CNS diseases is widely anticipated, lack of definite progress in the development of 5-HT(6) receptor-oriented drugs indicates a need for further discoveries of novel chemotypes with high potency and high selectivity to the receptor. Here we present preparations and biological evaluation of a series of (3-phenylsulfonylcycloalkano[e and d]pyrazolo[1,5-a]pyrimidin-2-yl)amines. Phenylsulfonylcyclopentapyrazolopyrimidine 7 was found to be a highly selective 5-HT(6) receptor antagonist with high affinity (low picomolar range) and potency. 7 and a few of its analogues were further tested for biological effect on 5-HT(2B) receptors and hERG potassium channels, potential liability targets. Such liability appears to be minimal, based on the in vitro data.

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Section: Discussionsupporting

confidence: 87%

“…The data obtained are in a good agreement with the published NMR spectra and quantum chemical calculations for known analogues. 34,36,37…”

Section: Discussionmentioning

confidence: 99%

(3-Phenylsulfonylcycloalkano[e and d]pyrazolo[1,5-a]pyrimidin-2-yl)amines: Potent and Selective Antagonists of the Serotonin 5-HT₆ Receptor

Ivachtchenko

Dmitriev²,

Golovina³

et al. 2010

J. Med. Chem.

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ChemInform Abstract: Synthesis of Acetonylmalonaldehyde and Its Interaction with Aminoazoles.

Vartanyan¹,

Елисеев²,

Skov³

et al. 1997

ChemInform

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1997ketones ketones (acyclic compounds) P 0200 -086Synthesis of Acetonylmalonaldehyde and Its Interaction with Aminoazoles.-The title malonaldehyde (II), easily prepared for the first time by hydrolysis of the tetrahydrofuran (I), undergoes cyclocondensation with 2-aminoazoles to form azolopyrimidines (cf. (IV) and (VI)) in excellent yields. -(VARTANYAN, M. M.; ELISEEV, O. L.; SKOV, H. R.; KARAKHANOV, R. A.; Izv.

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Synthesis of cycloalkane-annelated 3-phenylsulfonyl-pyrazolo[1,5-a]pyrimidines and their evaluation as 5-HT6 receptor antagonists

Ivachtchenko

Dmitriev

Golovina

et al. 2010

Bioorganic & Medicinal Chemistry Letters

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Synthesis of acetonylmalonaldehyde and its interaction with aminoazoles

Cited by 5 publications

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(3-Phenylsulfonylcycloalkano[e and d]pyrazolo[1,5-a]pyrimidin-2-yl)amines: Potent and Selective Antagonists of the Serotonin 5-HT₆ Receptor

(3-Phenylsulfonylcycloalkano[e and d]pyrazolo[1,5-a]pyrimidin-2-yl)amines: Potent and Selective Antagonists of the Serotonin 5-HT₆ Receptor

ChemInform Abstract: Synthesis of Acetonylmalonaldehyde and Its Interaction with Aminoazoles.

Synthesis of cycloalkane-annelated 3-phenylsulfonyl-pyrazolo[1,5-a]pyrimidines and their evaluation as 5-HT6 receptor antagonists

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Synthesis of acetonylmalonaldehyde and its interaction with aminoazoles

Cited by 5 publications

References 0 publications

(3-Phenylsulfonylcycloalkano[e and d]pyrazolo[1,5-a]pyrimidin-2-yl)amines: Potent and Selective Antagonists of the Serotonin 5-HT6 Receptor

(3-Phenylsulfonylcycloalkano[e and d]pyrazolo[1,5-a]pyrimidin-2-yl)amines: Potent and Selective Antagonists of the Serotonin 5-HT6 Receptor

ChemInform Abstract: Synthesis of Acetonylmalonaldehyde and Its Interaction with Aminoazoles.

Synthesis of cycloalkane-annelated 3-phenylsulfonyl-pyrazolo[1,5-a]pyrimidines and their evaluation as 5-HT6 receptor antagonists

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Product

Resources

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(3-Phenylsulfonylcycloalkano[e and d]pyrazolo[1,5-a]pyrimidin-2-yl)amines: Potent and Selective Antagonists of the Serotonin 5-HT₆ Receptor

(3-Phenylsulfonylcycloalkano[e and d]pyrazolo[1,5-a]pyrimidin-2-yl)amines: Potent and Selective Antagonists of the Serotonin 5-HT₆ Receptor