Gastric antisecretory agents. 2. Antisecretory activity of 9-[(aminoalkyl)thio]-9H-xanthenes and 5-[(aminoalkyl)thio]-5H-[1]benzopyrano[2,3-b]pyridines

Bristol, James A.; Gold, Elijah H.; Gross, Irwin; Lovey, Raymond G.; Long, James F.

doi:10.1021/jm00140a020

Cited by 34 publications

(21 citation statements)

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“…We then synthesized 3,5-bis((E)-4-bromobenzylidene)-1-methylpiperidin-4-one 7h from the reaction of 5 and p-bromobenzaldehyde following literature procedure [44]. Subsequently, the reaction of 7h and cyclohexane-1,3-dione 8a affording chromeno [3,2-c] [1][2][3][4][5]. We then tried this reaction in acidic conditions and observed that in the presence of p-tolunesulfonic acid the reaction afforded 9h in a moderate yield of 45 % (Scheme 4, entry 7).…”

Section: Resultsmentioning

confidence: 99%

“…Found: C,81.23;H,6.40;N,3.75 %. -2methyl-3,4,6,7,8,10-hexahydro-1H-chromeno [3,2c] 5,27.6,36.9,44.6,54.4,55.0,119.9,126.3,127.3,127.8,128.5,128.6,129.4,129.6,130.0,130.4,133.5,134.1,133.5,134.1,134.7,139.9,166.4,196.9. Anal.…”

Section: General Experimentalmentioning

confidence: 99%

“…Found: C,81.26;H,6.54;N,3.00 %. 2-methyl-3,4,6,7,8,10-hexahydro-1H-chromeno[3,2c] 5,36.8,44.6,54.3,54.9,65.9,112.9,115.6,120.1,126.8,127.5,128.2,128.5,128.9,129.1,129. 2,131.9,132.2,133.1,133.4,136.9,140.0,143.3,166.4,196.8.…”

Section: General Experimentalmentioning

confidence: 99%

“…Amlexanox 1 is an antiallergic and antiulcer agent, whereas compounds 2, 3 and 4 inhibit mitogen-activated protein kinase-activated kinase 2, histamine-stimulated gastric acid secretion in animals and selective D4 receptor antagonist, respectively [2][3][4][5] (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

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A facile tandem Michael addition/O-cyclization/elimination route to novel chromeno[3,2-c]pyridines

2015

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Section: Resultsmentioning

confidence: 99%

Section: General Experimentalmentioning

confidence: 99%

Section: General Experimentalmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A facile tandem Michael addition/O-cyclization/elimination route to novel chromeno[3,2-c]pyridines

2015

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“…Examples of structurally relevant biologically active compounds are benzopyranopyridines B, found to inhibit mitogen-activated protein kinase-activated protein kinase 2 and attenuate the production of pro-inflammatory TNFα, 12 and C, reported to inhibit histamine-stimulated gastric acid secretion in animals. 13 We previously disclosed a one-step three-component synthesis of 3,5-dicyanopyridines D starting from various aldehydes, thiols and malononitrile (Fig. 2).…”

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Convenient One‐Step Synthesis of a Medicinally Relevant Benzopyranopyridine System.

et al. 2007

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Benzopyrano [2,3-b]pyridine is an important privileged medicinal scaffold. A three-component reaction of salicylaldehydes, thiols and 2 equiv of malononitrile that leads to the formation of a series of compounds incorporating 2,4-diamino-3-cyano-5-sulfanylbenzopyrano[2,3-b]pyridine framework is described. A proposed mechanism with the supporting experimental data is presented. KeywordsMulticomponent reaction; Privileged medicinal scaffold; Drug-like heterocycle The rapid assembly of molecular diversity utilizing multi-component reactions has received a great deal of attention, most notably for the construction of heterocyclic `drug-like' libraries. 1 These methodologies are of particularly great utility when they lead to the formation of `privileged medicinal scaffolds,' defined as molecular frameworks serving as the basis for the generation of ligands for functionally and structurally discreet biological receptors. 2 Such chemistry greatly facilitates the development of pharmaceutical agents for diverse applications.Benzopyrano [2,3-b]pyridine scaffold is of a significant medicinal relevance. The examples of approved therapeutic agents incorporating this molecular framework include amlexanox and pranoprofen (Fig. 1).In addition, many of these compounds possess anti-pro-liferative, 3 cancer chemopreventive, 4 anti-bacterial (including anti-tubercular), 5 anti-myopic, 6 anti-histaminic, 7 hypotensive, 8 anti-rheumatic 9 and anti-asthmatic activities. 10 processes allowing the synthesis of previously inaccessible analogues for biological evaluation. In this letter, we describe a multi-component strategy for the rapid preparation of library A (Fig. 1). Examples of structurally relevant biologically active compounds are benzopyranopyridines B, found to inhibit mitogen-activated protein kinase-activated protein kinase 2 and attenuate the production of pro-inflammatory TNFα, 12 and C, reported to inhibit histamine-stimulated gastric acid secretion in animals. 13 We previously disclosed a one-step three-component synthesis of 3,5-dicyanopyridines D starting from various aldehydes, thiols and malononitrile (Fig. 2). 14 In an attempt to extend the method for the preparation of pyridines E we employed salicylic aldehydes and obtained a library of compounds whose elemental analysis data and the NMR spectra were inconsistent with the expected structures. The X-ray analysis showed these compounds to have a benzopyrano[2,3-b]pyridine framework A (Fig. 3). 15 The reaction works well for all salicylaldehyde and thiol combinations tested. The products precipitate from refluxing ethanolic solutions and are isolated by simple filtration. The yields of recrystallized benzopyranopyridines are given in Table 1. 16,17 Our proposed mechanistic interpretation of the divergence in reaction paths for o,ounsubstituted aldehydes, leading to formation of pyridines D, and salicylic aldehydes, resulting in benzopyranopyridines A, is shown in Figure 4.Base-catalyzed Michael addition of thiols to Knoevenagel adducts F, produced fr...

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Aza‐, Di‐ und Triazaxanthone aus Azachromonen

Eiden

Rademacher

1985

Archiv der Pharmazie

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Eiden und RademacherArch. Phann. The E isomer recrystallized form methano1:m.p. 2W203" (110 mg). 'H-NMR: 6 (ppm): 1.42 (s, 6H), 2.03(~,3H),4.82(d,J =5.4Hz,2H),5.61(s,lH),6.78(t,J=5.4Hz,lH),6.868.37(7H,aromatic protons). C2,H,05 (376.Die aus den pyridylsubstituierten 1,3-Dicarbonyl-Verbindungen 5s und Sb herstellbaren Acylmethylthio-azachromone 7s und 7b setzten sich mit Aminen, Hydrazin und Amidinen bzw. CH-aciden Verbindungen zu den Azaxanthonen 88, Eb, 9s und 9b, 11s und l l b bzw. U und 14 um. 0365-6233/85/1010-092 S U2.50/0 0 VCH Vcrlagsgesellschaft mbH. D-6940 Weinhcim, 1985

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Gastric antisecretory agents. 2. Antisecretory activity of 9-[(aminoalkyl)thio]-9H-xanthenes and 5-[(aminoalkyl)thio]-5H-[1]benzopyrano[2,3-b]pyridines

Cited by 34 publications

References 5 publications

A facile tandem Michael addition/O-cyclization/elimination route to novel chromeno[3,2-c]pyridines

A facile tandem Michael addition/O-cyclization/elimination route to novel chromeno[3,2-c]pyridines

Convenient One‐Step Synthesis of a Medicinally Relevant Benzopyranopyridine System.

Aza‐, Di‐ und Triazaxanthone aus Azachromonen

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