Antimykotische Wirkstoffe, 18. Mitt. Aromatisch substituierte 2‐(4‐Toluidino)pyrimidine

Keutzberger, Alfred; Gillessen, J.

doi:10.1002/ardp.19853180414

Cited by 17 publications

(3 citation statements)

References 10 publications

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“…Pyrimidines are an important class of compounds and have widespread applications from pharmaceuticals to materials (Brown, 1996), with activities such as Tie-2 kinase inhibitors (Matloobi and Kappe, 2007), HIV-1 inhibitor (Gadhachanda et al, 2007), antimalarial (Agarwal et al, 2005), adenosine A1 receptor antagonism (Chang et al, 2004), anticancer (Capdeville et al, 2002), analgesic (Zaki et al, 2006), cardiovascular (Atwal, 1987), and antiallergic (Ozeki et al, 1989) activities. A number of synthetic pharmacophores with antibacterial (Hegab et al, 2007), antifungal (Gholap et al, 2008), and antimycotic activities (Keutzberger and Gillessen, 1985) are based on the pyrimidyl motif. 2-pyrazoline derivatives have antimicrobial (Nauduri and Reddy, 1998;Grant et al, 1998;Turan-Zitouni et al, 2005a, 2005b, anti-inflammatory (Nasr and Said, 2003), and antihypertensive (Turan-Zitouni et al, 2000) activities.…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial activity of new 4,6-disubstituted pyrimidine, pyrazoline, and pyran derivatives

et al. 2010

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Section: Introductionmentioning

confidence: 99%

Antimicrobial activity of new 4,6-disubstituted pyrimidine, pyrazoline, and pyran derivatives

et al. 2010

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“…16 Pyrimidoquinolines are important compounds because of their biological properties such as antimalarial, 17 anticancer, 16 antimicrobial 18,19 and anti-inflammatory 20,21 activities. Furthermore, many synthetic pharmacophores possessing antibacterial, 22 antifungal 23 and antimycotic 24 activities are based on the pyrimidyl structures. The development of pyrimidine-based antitumour 25 and antiviral 26 drugs have inspired chemists all over the world to prepare a new series of pyrimidine-based compounds and to study their biological activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Studies of Some Quinolinylpyrimidine Derivatives

Munawar

Azad

Siddiqui

et al. 2008

J Chinese Chemical Soc

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The quinolinylpyrimidine derivatives were prepared by the condensation of quinolinyl chalcones with urea (or thiourea) under basic conditions by using both conventional and microwave heating. Their IR, 1H NMR, 13C NMR, mass spectra and CHN analyses confirmed the prepared compounds. The newly prepared quinolinylpyrimidine derivatives were screened for antimicrobial activities against the bacterial strains viz. S. aureus, Shigella, Salmonela, P. aeroginosa, B. Subtilus and E. coli and found considerably active against S. aureus, P. aeroginosa and E. coli.

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“…Pyrimidines represent an important class of heterocycles 1 and their structural framework is not only a key constituent of nucleic bases, alkaloids, and numerous pharmacophores with antibacterial, 2 antimicrobial, antifungal, 3 antimycotic, 4 antiviral, and antitumor activity, 5 but also functions as a central unit in grid-forming ligands for supramolecular scaffolds. 6,7 As a consequence, many pyrimidine syntheses are known, the most efficient of them applying cyclocondensations of 1,3-dicarbonyl compounds or their synthetic equivalents with amidines as a key step.…”

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Straightforward Novel One-Pot Enaminone and Pyrimidine Syntheses by Coupling-Addition-Cyclocondensation Sequences

Karpov¹,

Müller²

2003

Synthesis

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The coupling of acid chlorides 1 with terminal alkynes 2 using only one equivalent (!) of triethylamine under Sonogashira conditions followed by subsequent addition of primary or secondary amines 4 to the intermediate alkynones 3 represents a straightforward one-pot three component access to enaminones 5 under mild conditions and in excellent yields. Furthermore, 2,4-di-and 2,4,6-trisubstituted pyrimidines 7 can be synthesized in moderate to good yields according to a highly flexible coupling-addition-cyclocondensation sequence.Pyrimidines represent an important class of heterocycles 1 and their structural framework is not only a key constituent of nucleic bases, alkaloids, and numerous pharmacophores with antibacterial, 2 antimicrobial, antifungal, 3 antimycotic, 4 antiviral, and antitumor activity, 5 but also functions as a central unit in grid-forming ligands for supramolecular scaffolds. 6,7 As a consequence, many pyrimidine syntheses are known, the most efficient of them applying cyclocondensations of 1,3-dicarbonyl compounds or their synthetic equivalents with amidines as a key step. 8,9 Among these approaches the reaction of alkynones and amidinium salts 10,11 represents an intriguing entry to pyrimidines, in particular, since alkynones can readily be formed in catalytic way by a Sonogashira coupling of an acid chloride with a terminal alkyne. 12,13 As part of our program directed to design novel multi-component reactions based on in situ activation of alkynes by Sonogashira coupling, 13,14 we have now focused on coupling-amination sequences as an entry to heterocycle sequences. Here, we wish to report three-component syntheses of enaminones and 2,4-and 2,4,6-substituted pyrimidines with a flexible substitution pattern.The most elegant and atom-economic way of transforming acid chlorides into alkynones is the cross coupling of terminal alkynes under the conditions of the Sonogashira coupling. In turn, the resulting ynones are highly reactive Michael acceptors that readily react with all kinds of nucleophiles. Just recently, we discovered that adding only one equivalent of triethylamine as the hydrochloric acid scavenging base proves to be most favorable, in particular, for the successful coupling of (TMS)acetylene. 13Probing ynones generated under cross-coupling conditions for the feasibility in a consecutive aminovinylation, 15 the addition of primary and secondary amines should give rise to b-enaminones in a one-pot fashion. Besides their enormous synthetic potential as well-established three-carbon building blocks for cyclocondensations in heterocyclic chemistry, 16 enaminones 17 in their own right are highly pharmacologically active and reveal a pronounced anticonvulsant 18 and nonsteroidal antiinflammatory activity. 19 Therefore, in the sense of a consecutive three-component one-pot reaction, after reacting various acid chlorides 1 with terminal alkynes 2 under modified Sonogashira conditions for 1 hour at room temperature to furnish the expected alkynones 3, and subsequently adding methanolic solutio...

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Antimykotische Wirkstoffe, 18. Mitt. Aromatisch substituierte 2‐(4‐Toluidino)pyrimidine

Cited by 17 publications

References 10 publications

Antimicrobial activity of new 4,6-disubstituted pyrimidine, pyrazoline, and pyran derivatives

Antimicrobial activity of new 4,6-disubstituted pyrimidine, pyrazoline, and pyran derivatives

Synthesis and Antimicrobial Studies of Some Quinolinylpyrimidine Derivatives

Straightforward Novel One-Pot Enaminone and Pyrimidine Syntheses by Coupling-Addition-Cyclocondensation Sequences

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