Highly efficient synthesis of fused bicyclic 2,3-diaryl-pyrimidin-4(3H)-ones via Lewis acid assisted cyclization reaction

Yang, Kunyong; He, Xiaohui; Choi, Ha-soon; Wang, Zhicheng; Woodmansee, David H.; Liu, Hong

doi:10.1016/j.tetlet.2008.01.071

Cited by 11 publications

(2 citation statements)

References 18 publications

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“…25 Subsequent condensation with the imidoyl chloride generated from benzamide 6 afforded amidines that were directly ring closed using TiCl 4 (ref. 26) and microwave heating, to obtain 7 and 8.…”

Section: Resultsmentioning

confidence: 99%

Identification of pyrazolo-pyrimidinones as GHS-R1a antagonists and inverse agonists for the treatment of obesity

et al. 2013

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A pyrazolo-pyrimidinone based series of growth hormone secretagogue receptor type 1a (GHS-R1a) antagonists and inverse agonists were identified using a scaffold hop from known quinazolinone GHS-R1a modulators. Lipophilicity was reduced to decrease hERG activity while maintaining GHS-R1a affinity.SAR exploration of a piperidine substituent was used to identify small cyclic groups as a functional switch from partial agonists to neutral antagonists and inverse agonists. A tool compound was identified which had good overall properties and sufficient oral plasma and CNS exposure to demonstrate reduced food intake in mice through a mechanism involving GHS-R1a.

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Section: Resultsmentioning

confidence: 99%

Identification of pyrazolo-pyrimidinones as GHS-R1a antagonists and inverse agonists for the treatment of obesity

et al. 2013

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“…Yang et al [ 17 ] reported one‐pot synthesis of fused bicyclic 2,3‐diaryl‐pyrimidin‐4(3 H )‐ones 15 by heating amide 14 with pyrazole amino ester 11 in SOCl 2 at 80°C for 2 h. It was reported that Lewis acid and microwave irradiation could be employed to accelerate the reaction (Scheme 4).…”

Section: Synthetic Routes Of Pyrazolo[34‐d]pyrimidinesmentioning

confidence: 99%

Pyrazolo[3,4‐d]pyrimidine scaffold: A review on synthetic approaches and EGFR and VEGFR inhibitory activities

Kassab

2022

Archiv der Pharmazie

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The pyrazolo[3,4‐d]pyrimidine core has received a lot of interest from the medicinal chemistry community as a promising framework for drug design and discovery. It is an isostere of the adenine ring of adenosine triphosphate, which allows it to mimic kinase active site hinge region binding contacts. This scaffold has a wide pharmacological and biological value, one of which is as an anticancer agent. Many successful anticancer medicines have been designed and synthesized using pyrazolo[3,4‐d]pyrimidine as a key pharmacophore. The main synthetic routes of pyrazolo[3,4‐d]pyrimidines as well as their recent developments as promising anticancer agents acting as endothelial growth factor receptors and vascular endothelial growth factor receptor inhibitors, published in the time frame from 1999 to 2022, are summarized in this review to set the direction for the design and synthesis of novel pyrazolo[3,4‐d]pyrimidine derivatives for clinical deployment in cancer treatment.

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ChemInform Abstract: Highly Efficient Synthesis of Fused Bicyclic 2,3‐Diaryl‐pyrimidin‐4(3H)‐ones via Lewis Acid Assisted Cyclization Reaction.

Yang

Choi

et al. 2008

ChemInform

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Fused pyrimidine derivatives R 0515Highly Efficient Synthesis of Fused Bicyclic 2,3-Diaryl-pyrimidin-4(3H)-ones via Lewis Acid Assisted Cyclization Reaction. -Imidoyl chlorides, generated by treatment of starting amides with thionyl chloride, undergo cyclocondensation with various heteroaromatic amino esters. This key step is efficiently promoted by an excess of TiCl4 under microwave irradiation. -(YANG*, K.; HE, X.; CHOI, H.-S.; WANG, Z.; WOODMANSEE, D. H.; LIU, H.; Tetrahedron Lett. 49 (2008) 11, 1725-1728; Genomics Inst., Novartis Res. Found., San Diego, CA 92121, USA; Eng.) -S. Adam 26-162

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Highly efficient synthesis of fused bicyclic 2,3-diaryl-pyrimidin-4(3H)-ones via Lewis acid assisted cyclization reaction

Cited by 11 publications

References 18 publications

Identification of pyrazolo-pyrimidinones as GHS-R1a antagonists and inverse agonists for the treatment of obesity

Identification of pyrazolo-pyrimidinones as GHS-R1a antagonists and inverse agonists for the treatment of obesity

Pyrazolo[3,4‐d]pyrimidine scaffold: A review on synthetic approaches and EGFR and VEGFR inhibitory activities

ChemInform Abstract: Highly Efficient Synthesis of Fused Bicyclic 2,3‐Diaryl‐pyrimidin‐4(3H)‐ones via Lewis Acid Assisted Cyclization Reaction.

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