Indeno[1,2-b]indole derivatives as a novel class of potent human protein kinase CK2 inhibitors

Hundsdörfer, Claas; Hemmerling, Hans-Jörg; Götz, Claudia; Totzke, Frank; Bednarski, Patrick J.; Borgne, Marc Le; Jose, Joachim

doi:10.1016/j.bmc.2012.02.017

Cited by 78 publications

(54 citation statements)

References 37 publications

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“…As a previous study on design of indeno [1,2-b]indole derivatives as CK2 inhibitors [43], predictive ADME parameters were used to determine their biological profile. Then for an evaluation of the cell permeability of pyrroloquinoxalines 1aeh and ken, fragmentbased partition coefficients (Clog P) and topological polar surface areas (TPSA) were calculated by the molinspiration web services [44].…”

Section: Lipophilicity and Cell Permeabilitymentioning

confidence: 99%

Synthesis and biological evaluation of novel substituted pyrrolo[1,2-a]quinoxaline derivatives as inhibitors of the human protein kinase CK2

Guillon¹,

Borgne²,

Rimbault³

et al. 2013

European Journal of Medicinal Chemistry

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a b s t r a c tHerein we describe the synthesis and properties of substituted phenylaminopyrrolo[1,2-a]quinoxalinecarboxylic acid derivatives as a novel class of potent inhibitors of the human protein kinase CK2. A set of 15 compounds was designed and synthesized using convenient and straightforward synthesis protocols. The compounds were tested for inhibition of human protein kinase CK2, which is a potential drug target for many diseases including inflammatory disorders and cancer. New inhibitors with IC 50 in the microand sub-micromolar range were identified. The most promising compound, the 4-[(3-chlorophenyl) amino]pyrrolo[1,2-a]quinoxaline-3-carboxylic acid 1c inhibited human CK2 with an IC 50 of 49 nM. Our findings indicate that pyrrolo[1,2-a]quinoxalines are a promising starting scaffold for further development and optimization of human protein kinase CK2 inhibitors.

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Section: Lipophilicity and Cell Permeabilitymentioning

confidence: 99%

Synthesis and biological evaluation of novel substituted pyrrolo[1,2-a]quinoxaline derivatives as inhibitors of the human protein kinase CK2

Guillon¹,

Borgne²,

Rimbault³

et al. 2013

European Journal of Medicinal Chemistry

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“…In addition, many of these fused heterocyclesh ave promising biological activities. [14] Now,a sacontinuation of our previous research in the design and construction of new heterocyclicc ompounds, [15] we report here an efficient and concises ynthesis of acenaphtho [1,2-b]indoles with different substitution patternsf rom commercially available enaminones, acenaphthoquinone, and alcohols by aza-enea ddition cyclization or three-component domino reactions (Scheme1). Although severalm ethods for the construction of acenaphtho [1,2-b]indoles have been reported, [16] for example, solid-phase reaction and l-proline-catalyzed three-component reaction of acenaphthoquinone, enaminones and barbituric acid, the development of methodsf or the synthesis of such products with the advantages of molecular diversity,m ild conditions, and sustainable chemistry was still necessary.…”

Section: Introductionmentioning

confidence: 86%

Selective Synthesis of Acenaphtho[1,2‐b]indole Derivatives via Tandem Regioselective Aza‐Ene Addition/N‐Cyclization/S_N1 Type Reaction

et al. 2015

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Ac oncise and efficient synthesis of acenaphtho [1,2-b]indoles with different substitution patternsf rom a[ 3+ +2] condensation of enaminones with acenaphthoquinone has been developed. During the first pathway,p roducts 3 were synthesized in the presence of Et 3 N, while as econd reactioni nt he presence of p-toluenesulfonic acid leads to compounds 5 via intramolecular cyclization and highly regioselectiveS N 1-typer eactionw ith alcoholsu nder solvent-free conditions. Both procedures give excellent yields and are highly eco-benign, are convenient one-pot operations, are highly regioselectivity,a nd use environmentally friendly solvent systems or operate under solvent-free conditions. This method offers an alternative to regioselective construction of biologically meaningful polycyclic indoles.

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“…[176][177] Thereafter, human protein kinase CK2 inhibition activity of the produced indeno [1,2-b]indole derivatives was evaluated and showed satisfactory results. [178][179] Li and co-workers discovered novel multicomponent reactions involving N-heteroannulations of enaminones 75, ninhydrin, and acid anhydride or aromatic amines to selectively produce multifunctionalized indeno [1,2-b]indoles with different substituted patterns 78 and 79 as a racemic mixture (Scheme 23). 180 The synthesis of tetrahydroindeno [2',1':4,5]pyrrolo [2,3-d]pyrimidinetrione derivatives 81, based on the addition reaction of ninhydrin and 6-aminouracils 80, was developed by Bazgir and coworkers (Scheme 24).…”

Section: -10mentioning

confidence: 99%

Ninhydrin in synthesis of heterocyclic compounds

Ziarani¹,

Lashgari²,

Azimian³

et al. 2015

Arkivoc

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Ninhydrin has been utilized in many heterocyclic preparations and considered as an important building block in organic synthesis. There is a wide range of reactions that include ninhydrin in the synthesis of heterocyclic compounds. This review highlights the advances in the use of ninhydrin as starting material in the synthesis of various organic compounds and drugs in a fully comprehensive way, from its first isolation in 1910 to the end of 2013. There is also a diversity of multi-component reactions of ninhydrin and we highlight the recent reports in this review.

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Indeno[1,2-b]indole derivatives as a novel class of potent human protein kinase CK2 inhibitors

Cited by 78 publications

References 37 publications

Synthesis and biological evaluation of novel substituted pyrrolo[1,2-a]quinoxaline derivatives as inhibitors of the human protein kinase CK2

Synthesis and biological evaluation of novel substituted pyrrolo[1,2-a]quinoxaline derivatives as inhibitors of the human protein kinase CK2

Selective Synthesis of Acenaphtho[1,2‐b]indole Derivatives via Tandem Regioselective Aza‐Ene Addition/N‐Cyclization/S_N1 Type Reaction

Ninhydrin in synthesis of heterocyclic compounds

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Indeno[1,2-b]indole derivatives as a novel class of potent human protein kinase CK2 inhibitors

Cited by 78 publications

References 37 publications

Synthesis and biological evaluation of novel substituted pyrrolo[1,2-a]quinoxaline derivatives as inhibitors of the human protein kinase CK2

Synthesis and biological evaluation of novel substituted pyrrolo[1,2-a]quinoxaline derivatives as inhibitors of the human protein kinase CK2

Selective Synthesis of Acenaphtho[1,2‐b]indole Derivatives via Tandem Regioselective Aza‐Ene Addition/N‐Cyclization/SN1 Type Reaction

Ninhydrin in synthesis of heterocyclic compounds

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Selective Synthesis of Acenaphtho[1,2‐b]indole Derivatives via Tandem Regioselective Aza‐Ene Addition/N‐Cyclization/S_N1 Type Reaction