Efficient synthesis of novel thieno[3,2-b]-, [2,3-c]- and [3,2-c]pyridones by Sonogashira coupling of bromothiophenes with terminal alkynes and subsequent intramolecular C–N bond-forming reaction

Iaroshenko, Viktor O.; Ali, Sajid; Babar, Tariq Mahmood; Abbasi, Muhammad Salman; Sosnovskikh, Vyacheslav Ya.; Villinger, Alexander; Tolmachev, Andrey A.; Langer, Peter

doi:10.1016/j.tet.2013.02.069

Cited by 15 publications

(28 citation statements)

References 47 publications

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“…Methyl 3‐(2‐Phenylethynyl)thiophene‐2‐carboxylate (4k): Yellow viscous oil23 (0.41 g, 84 %). NMR spectroscopic data were identical to those reported in the literature 23. MS (EI): m / z = 242 [M] + .…”

Section: Methodsmentioning

confidence: 99%

Copper‐ and Phosphane‐Free Sonogashira Coupling of Arenediazonium o‐Benzenedisulfonimides

Barbero¹,

Cadamuro²,

Dughera³

2013

Eur J Org Chem

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Arenediazonium o-benzenedisulfonimides can be used as efficient reagents in Sonogashira coupling reactions. In this work, reactions were carried out in DMSO under very mild conditions (without copper or phosphanes), and gave rise to arylated alkynes in good to excellent yields (25 examples, average yield 83 %). o-Benzenedisulfonimide could be reco- [a]598 vered from all the reactions in yields of Ͼ80 %, so it could be recycled for the preparation of other diazonium salts. Mechanistic insights revealed the fundamental roles of DMSO and the anion of o-benzenedisulfonimide in the formation of the catalyst, and also the importance of DMSO in the catalytic cycle.

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Section: Methodsmentioning

confidence: 99%

Copper‐ and Phosphane‐Free Sonogashira Coupling of Arenediazonium o‐Benzenedisulfonimides

Barbero¹,

Cadamuro²,

Dughera³

2013

Eur J Org Chem

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“…3) [28], 6 H -thieno [2,3- c ]pyridin-7-one ( 15 , Fig. 3) [29] and 5-phenyl-6 H -thieno[2,3- c ] pyridin-7-one ( 17 , Fig. 3) [30] were synthesized as reported in literature (Schemes S2–S5 of SI).…”

Section: Resultsmentioning

confidence: 99%

Scaffold hopping approach on the route to selective tankyrase inhibitors

Liscio¹,

Carotti²,

Asciutti³

et al. 2014

European Journal of Medicinal Chemistry

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A virtual screening procedure was applied to identify new tankyrase inhibitors. Through pharmacophore screening of a compounds collection from the SPECS database, the methoxy[l]benzothieno[2,3-c]quinolin-6(5H)-one scaffold was identified as nicotinamide mimetic able to inhibit tankyrase activity at low micromolar concentration. In order to improve potency and selectivity, tandem structure-based and scaffold hopping approaches were carried out over the new scaffold leading to the discovery of the 2-(phenyl)-3H-benzo[4,5]thieno[3,2-d]pyrimidin-4-one as powerful chemotype suitable for tankyrase inhibition. The best compound 2-(4-tert-butyl-phenyl)-3H-benzo[4,5]thieno[3,2-d]pyrimidin-4-one (23) displayed nanomolar potencies (IC50s TNKS-1 = 21 nM and TNKS-2= 29 nM) and high selectivity when profiled against several other PARPs. Furthermore, a striking Wnt signaling, as well as cell growth inhibition, was observed assaying 23 in DLD-1 cancer cells.

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“…1 (14), 287 (19), 279 (100), 266 (75), 245 (18), 233 (62), 204 (10), 191 (12), 177 (29), 131 (21), 57 (10), 43 (11), 41 (12). Mp 180 °C.…”

Section: -Nitro-4-oxo-2-phenyl-1-(3-phenylpropyl)quinoline (7bd)unclassified

“…The central core of each subunit consists of an extended β-sheet flanked by α-helices. 29 Most of this work relies on transition metal catalysed cyclizations of alkynes with amines. 4 TNAP hydrolyzes extracellular inorganic pyrophosphate (PPi), a potent mineralization inhibitor, to enable the physiological deposition of hydroxyapatite in bones and teeth.…”

Section: Introductionmentioning

confidence: 99%

Diversity oriented synthesis of 6-nitro- and 6-aminoquinolones and their activity as alkaline phosphatase inhibitors

et al. 2015

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During the optimization of the conditions of the cyclization, we were able to isolate sideproducts 9 and 10 (Scheme 2). The quantity of these compounds strongly depends on the conditions (see legend of Table 2). The formation of products 9 can be explained by reaction of 6 with two molecules of the amine, i.e. conjugate addition to the ynone and nucleophilic substitution at the arene. Products 10 are formed by conjugate addition of the amine to the alkynone moiety. Under the standard conditions applied for the synthesis of quinolones 7, sideproducts 9 and 10 were formed only in very small quantities (1-2%). However, 9a-d could be isolated and spectroscopically characterized when the reaction was carried out at lower temperature. Reduction of the reaction time during the synthesis of nitroquinolone derivatives allowed us to isolate intermediates 10a and 10b. In general, the yields of unwanted side-products 9 and 10 increased when potassium fluoride was employed instead of standard K 2 CO 3 and K 3 PO 4 . Scheme 2. Side-products 9 and 10. Yields of isolated compounds obtained in reaction conditions specified in footnotes g, h, and i of Table 2.

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Efficient synthesis of novel thieno[3,2-b]-, [2,3-c]- and [3,2-c]pyridones by Sonogashira coupling of bromothiophenes with terminal alkynes and subsequent intramolecular C–N bond-forming reaction

Cited by 15 publications

References 47 publications

Copper‐ and Phosphane‐Free Sonogashira Coupling of Arenediazonium o‐Benzenedisulfonimides

Copper‐ and Phosphane‐Free Sonogashira Coupling of Arenediazonium o‐Benzenedisulfonimides

Scaffold hopping approach on the route to selective tankyrase inhibitors

Diversity oriented synthesis of 6-nitro- and 6-aminoquinolones and their activity as alkaline phosphatase inhibitors

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