A rapid and versatile synthesis of novel pyrimido[5,4-b]carbazoles

Caruso, Anna; Lancelot, Jean‐Charles; El‐Kashef, Hussein; Sinicropi, Maria Stefania; Legay, Rémi; Lesnard, Aurélien; Rault, Syl­vain

doi:10.1016/j.tet.2009.10.025

Cited by 38 publications

(33 citation statements)

References 54 publications

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“…In this case, the hygroscopic compound 9 was isolated in quantitative yield as a solid after lyophilization of the reaction mixture. The methodology was then successfully employed to prepare a new series of tricyclic molecules, pyrazolo[4,3-f ]quinazoline derivatives (13)(14)(15)(16)(17)(18)(19)(20)(21), from variously N-substituted indazolo-guanidines. As indicated in Table 2, the reaction conditions are compatible with a wide variety of substituents.…”

Section: Chemistrymentioning

confidence: 99%

“…Most of them involve the pyrimidine ring closure and require orthosubstituted benzenes, such as anthranilic acids, as starting materials. We and others groups recently reported short and efficient pathways using simple aromatic or heteroaromatic amines as precursors for the synthesis of quinazoline [10][11][12] or quinazolin-4-one derivatives [13,14].…”

Section: Introductionmentioning

confidence: 99%

“…So far, quinazolin-4-one syntheses required the use of Lewis acid catalysts [13] or toxic reagents [14]. Considering the importance of this class of molecules, finding greener alternatives to these procedures appeared highly desirable.…”

Section: Introductionmentioning

confidence: 99%

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Catalyst-free synthesis of quinazolin-4-ones from (hetero)aryl-guanidines: application to the synthesis of pyrazolo[4,3-f]quinazolin-9-ones, a new family of DYRK1A inhibitors

et al. 2012

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A small library of heterocycle-fused quinazolin-4-ones was prepared and evaluated as kinase inhibitors. The key step of the two-step process involves the environmental friendly thermolysis of N-ethoxycarbonyl-N'-(hetero) arylguanidines at 130 °C in water. The cyclization is fully regioselective. The most active molecules, 7-(2-hydroxyethylamino)- and 7-(3-hydroxypropylamino)-pyrazolo[4,3-f]quinazolin-9-ones, inhibit DYRK1A and CLK1 at submicromolar concentrations, indicating the potential interest of this new heterocycle in drug design.

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Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Catalyst-free synthesis of quinazolin-4-ones from (hetero)aryl-guanidines: application to the synthesis of pyrazolo[4,3-f]quinazolin-9-ones, a new family of DYRK1A inhibitors

et al. 2012

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“…The chemistry and biology of carbazole have attracted an increasing interest over the last 50 years. The presence of a desirable electronic and charge transport properties, and also large pieconjugated system in carbazole make the introduction of various functional groups into the structurally rigid carbazolyl ring easy, resulting in the extensive potential application of carbazole in the field of medicinal chemistry [5]. Some carbazole derivatives are known to possess anticancer, antimicrobial, anti HIV, antihypertensive, antiparkinsonian, antipsychotic, anti-emetic and antidiabetic activities [6].…”

Section: ------------------------------------------------------------mentioning

confidence: 99%

Synthesis and <i>in vitro</i> antidiabetic activity of some alkyl carbazole compounds

Eseyin¹,

Edem²,

Johnson³

et al. 2018

Trop. J. Pharm Res

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“…Very recently, we also described a one-pot synthesis of pyrimidocarbazole starting from 3-aminocarbazoles. 24 We would now like to report a new simple and efficient one-pot synthesis of the hitherto unknown title compounds.…”

Section: Introductionmentioning

confidence: 99%

Triazine-fused β-carbolines: a facile three-step, one-pot synthesis of novel 2-alkyl(aryl)amino and 2-dialkylamino-7H-[1,3,5]triazino [1',2':1,6]pyrido[3,4-b]indol-4-ones

Primas¹,

El‐Kashef²,

Lancelot³

et al. 2010

Arkivoc

Self Cite

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Triazine-fused β-carbolines: a facile three-step, one-pot synthesis of novel 2-alkyl(aryl)amino and 2-dialkylamino- [3,4-b]indol-4-ones is presented. The construction of these compounds was achieved by one-pot synthesis involving condensation of 3-amino-β-carbolines with ethoxycarbonyl isothiocyanate followed by amination of the resulting thioureas and finally thermal ring closure of the resulting guanidines which allowed access to the unreported title heterocycles.Keywords: Triazinopyridoindoles, fused β-carbolines, triazino-β-carbolines, 2-aminotriazino-β-carbolines, cyclization IntroductionThe β-carboline skeleton is common in the structure of many natural and synthetic products associated with a broad spectrum of biological activities and pharmaceutical properties including sedative, anxiolytic, hypnotic, anticonvulsant, antitumor, antiviral, antiparasitic, and antimicrobial activities 1-7 as well as phosphodiesterase (PDE5) However, to the best of our knowledge, no reports have appeared concerning the synthesis of 1,3,5-triazino-β-carbolines. Thus it was deemed of interest to find a facile and efficient methodology to synthesize this hitherto unknown annulated β-carboline ring system. The presumed co-planarity and linearity of this fused polyheterocyclic system could in addition favour DNA intercalation and potentially provide anticancer compounds.Recently, Demeunynck et al. 21published a synthetic route to the 2-alkylaminoquinolino[2,3-f]quinazolin-1-one skeleton from 3-aminoacridine 1 (Scheme 1). The authors followed Manimala and Anslyn's methodology, 22 by condensing the aminoacridines with ethoxycarbonyl isothiocyanate followed by coupling with aliphatic amines and deprotection of the guanidine function. The authors noted that the ethoxycarbonyl group of the N-protected guanidino intermediates was ideally positioned to react by intramolecular Friedel-Crafts type substitution to form, in one step, the fused pyrimidinone ring of 3 (Scheme 1). The same paper 21 also described a two-step methodology for the synthesis of substituted 2-propylaminoquinazolin-4(3H)-ones 6 from simple aromatic or heteroaromatic amines 4 (Scheme 2). The preparation of the ethoxycarbonyl guanidines 5 was performed in one pot by careful control of the stoechiometry of the reagents successively added to the chosen aromatic amine dissolved in CH 2 Cl 2 . In most cases, the resulting protected guanidines 5 were easily isolated with excellent levels of purity by simple precipitation from water.

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A rapid and versatile synthesis of novel pyrimido[5,4-b]carbazoles

Cited by 38 publications

References 54 publications

Catalyst-free synthesis of quinazolin-4-ones from (hetero)aryl-guanidines: application to the synthesis of pyrazolo[4,3-f]quinazolin-9-ones, a new family of DYRK1A inhibitors

Catalyst-free synthesis of quinazolin-4-ones from (hetero)aryl-guanidines: application to the synthesis of pyrazolo[4,3-f]quinazolin-9-ones, a new family of DYRK1A inhibitors

Synthesis and <i>in vitro</i> antidiabetic activity of some alkyl carbazole compounds

Triazine-fused β-carbolines: a facile three-step, one-pot synthesis of novel 2-alkyl(aryl)amino and 2-dialkylamino-7H-[1,3,5]triazino [1',2':1,6]pyrido[3,4-b]indol-4-ones

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