Structure–activity relationships of 2-arylamido-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxamide derivatives as cannabinoid receptor agonists and their analgesic action

Thur, Yithachu; Bhalerao, Amit; Munshi, Zaki; Pansare, Nisha; Mann, Klaus; Hanauer, Guido; Kley, Hans-Peter; Nappe, Sandra; Weiss-Haljiti, Cornelia; Ostermann, Claude; Zitt, Christof; Schaefer, Michaela; Mondal, Dibyendu; Siddiki, Afsar Ali; Armugam, Velavan; Gudaghe, Vinod; Gupta, Mahendra Kumar; Rayudu, P V; Dautzenberg, Frank M.; Sarma, Koushik Das

doi:10.1016/j.bmcl.2012.10.087

Cited by 7 publications

(2 citation statements)

References 17 publications

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“…The pyridine derivatives have been known for their uses in potassium channel opener , antibacterial , anticancer , and human A3 adenosine receptor applications. Similarly, pyran derivatives are well known for their activities such as cannabinoid receptor agonists , antibacterial , and antitubercular activities. The pyridine and pyran motifs are prepared by MCR of aryl aldehyde, malononitrile, and indane 1,3‐dione.…”

Section: Introductionmentioning

confidence: 99%

Sequence Selective Michael Addition for Synthesis of Indeno-Pyridine and Indeno-Pyran Derivatives in One-Pot Reaction Using CuO Nanoparticles in Water

Valekar

Patil

Gore

et al. 2014

J. Heterocyclic Chem.

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The alternate synthesis of indeno-pyridine and indeno-pyran derivatives have been described by an unprecedented, green, one-pot reaction of aromatic aldehydes, malononitrile, and indane 1,3-dione. The formation of either indeno-pyridine or indeno-pyran derivatives based on a precise change in the Michael addition of indane 1,3-dione or malononitrile on Knoevenagel product during the progress of reaction has been investigated. The reaction completed up to 30 min of time using CuO nanoparticles in water at an ambient temperature renders the protocol novel and environment friendly. All the synthesized compounds have been confirmed on the basis of their spectroscopic data. The CuO nanoparticles have been prepared by coprecipitation method and characterized by SEM, PXRD spectroscopy, and UV spectroscopy.

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Section: Introductionmentioning

confidence: 99%

Sequence Selective Michael Addition for Synthesis of Indeno-Pyridine and Indeno-Pyran Derivatives in One-Pot Reaction Using CuO Nanoparticles in Water

Valekar

Patil

Gore

et al. 2014

J. Heterocyclic Chem.

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“…4) 4H-Pyran and its derivatives are an important class of heterocyclic compounds possessing broad biological activities, such as anti-inflammatory, 5) analgesic, 6) antioxidant, 7) antitubercular, 8) antidepressant, 9) sedative, 10) antiamoebic 11) and oral analgesic. 12) From the aforementioned reports, it seemed that the development of an efficient, rapid, and clean synthetic route towards focused libraries of such compounds is of great importance to both medicinal and synthetic chemists. The combination of multicomponent reactions (MCR 2 ), [13][14][15] which combines different types of MCRs in one pot process inheriting the high selectivity, efficiency, and atom economy of MCR, has gained more and more attention, since Dömling and Ugi reported the first MCR 2 of a modified four-component reaction (4CR) and the Ugi 4CR.…”

mentioning

confidence: 99%

Multicomponent Reactions of Acetoacetanilide Derivatives with Aromatic Aldehydes and Cyanomethylene Reagents to Produce 4<i>H</i>-Pyran and 1,4-Dihydropyridine Derivatives with Antitumor Activities

Azzam

Mohareb

2015

Chem. Pharm. Bull.

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The multi-component reaction of either acetoacetanilide derivative 1a or b with any of the aldehyde derivatives 2a-d and malononitrile 3 in the presence of triethylamine as a catalyst gave the 4H-pyran derivatives 4a-g, respectively. Carrying the same reaction but using a catalytic amount of ammonium acetate gave the 1,4-dihydropyridine derivatives 5a-f, respectively. The use of ethyl cyanoacetate instead of malononitrile in the presence of a catalytic amount of triethylamine gave the 4H-pyran derivatives 7a-d, respectively. Compound 4e was used to synthesize 1,4-dihydropyridine 9a-c and arylhydraone 11a-e derivatives were synthesized from 4a and e. The anti-tumor evaluations of the newly synthesized products were tested against six human cancer and normal cell lines. The results showed that compounds 4a, b, f, 5d, f, 9 and 11a-d had optimal cytotoxic effect against cancer cell lines with IC 50 <550 nM. The toxicity of the most active compounds was further measured against shrimp larvae.Key words 4H-pyran; 1,4-dihydropyridine; cyanomethylene; cytotoxicity Multicomponent reactions (MCRs) are one-pot reactions employing more than two starting materials, e.g. 3, 4, ... , 7, where most of the atoms of the starting materials are incorporated in the final product.1) Several descriptive tags are regularly attached to MCRs they are atom economic, e.g. the majority if not all of the atoms of the starting materials are incorporated in the product; they are efficient, e.g. they efficiently yield the product since the product is formed in onestep instead of multiple sequential steps; they are convergent, e.g. several starting materials combine in one reaction to form the product; they exhibit a very high bond-forming-index (BFI), e.g. several non-hydrogen atom bonds are formed in one synthetic transformation.2,3) Therefore MCRs are often a useful alternative to sequential multistep synthesis.In view of the increasing interest in the preparation of a large variety of heterocyclic compound libraries, the development of new synthetically valuable MCRs with several diversity points remains a challenge for both academic and industrial institutions.4) 4H-Pyran and its derivatives are an important class of heterocyclic compounds possessing broad biological activities, such as anti-inflammatory, 5) analgesic, 6) antioxidant,antiamoebic 11) and oral analgesic. 12) From the aforementioned reports, it seemed that the development of an efficient, rapid, and clean synthetic route towards focused libraries of such compounds is of great importance to both medicinal and synthetic chemists. The combination of multicomponent reactions (MCR 2 ), [13][14][15] which combines different types of MCRs in one pot process inheriting the high selectivity, efficiency, and atom economy of MCR, has gained more and more attention, since Dömling and Ugi reported the first MCR 2 of a modified four-component reaction (4CR) and the Ugi 4CR.16) However, most of the reported MCR 2 cases are limited in isonitrile based multicomponent reactions. [17][18][19][20]...

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Discovery of highly potent analgesic activity of isopulegol-derived (2R,4aR,7R,8aR)-4,7-dimethyl-2-(thiophen-2-yl)octahydro-2H-chromen-4-ol

et al. 2016

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Structure–activity relationships of 2-arylamido-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxamide derivatives as cannabinoid receptor agonists and their analgesic action

Cited by 7 publications

References 17 publications

Sequence Selective Michael Addition for Synthesis of Indeno-Pyridine and Indeno-Pyran Derivatives in One-Pot Reaction Using CuO Nanoparticles in Water

Sequence Selective Michael Addition for Synthesis of Indeno-Pyridine and Indeno-Pyran Derivatives in One-Pot Reaction Using CuO Nanoparticles in Water

Multicomponent Reactions of Acetoacetanilide Derivatives with Aromatic Aldehydes and Cyanomethylene Reagents to Produce 4<i>H</i>-Pyran and 1,4-Dihydropyridine Derivatives with Antitumor Activities

Discovery of highly potent analgesic activity of isopulegol-derived (2R,4aR,7R,8aR)-4,7-dimethyl-2-(thiophen-2-yl)octahydro-2H-chromen-4-ol

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