Identification and structure–activity relationship of 8-hydroxy-quinoline-7-carboxylic acid derivatives as inhibitors of Pim-1 kinase

Sliman, Faten; Blairvacq, Mélina; Durieu, Emilie; Meijer, Laurent; Rodrigo, Jordi; Desmaële, Didier

doi:10.1016/j.bmcl.2010.03.061

Cited by 40 publications

(20 citation statements)

References 46 publications

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“…An intriguing application was reported by Tong et al [95], who took advantage of docking studies for the optimization of isoxazolo [3,4-b]quinoline-3,4(1H,9H)-diones as Pim1 inhibitors. Other interesting examples include the optimization of 3-aryl-6-amino-triazolo[4,3-b]pyridazines [83], thiazolidine-2,4-dione derivatives [96] and 8-hydroxyquinoline-7-carboxylic acid derivatives [97].…”

Section: Discussionmentioning

confidence: 99%

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Using Insights into Pim1 Structure to Design New Anticancer Drugs

Schenone

Tintori²,

Botta³

2010

CPD

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Human Pim1 (proviral integration site for Moloney murine leukemia virus) kinase is a 313-amino acid serine-threonine kinase that possesses several biological functions in cell survival, proliferation and differentiation, and its overexpression has been observed in a number of human cancers. Indeed, this kinase is a proto-oncogene that has been implicated in early transformation and tumor progression, especially in hematopoietic malignancies and prostate carcinoma where it is a marker of a poor prognosis. For these reasons, Pim1 is emerging as an important target in drug discovery, and many Pim1 inhibitors have been reported in the last three years. The challenge of this research is to obtain compounds that specifically inhibit only Pim1 and not Pim2 and Pim3, the other members of the Pim family, with the aim of providing selective inhibitors as potential therapeutic agents and also of studying the different roles of the three enzymes. In this review Pim1 functions and Pim1 role in human cancer are summarized, but the primary focus of the article is on the Pim1 three-dimensional structure that was deeply analyzed by a detailed inspection of the available crystallographic data and all complexes of small molecule inhibitors reported in the literature to this point. Finally, the use of molecular modeling techniques for the identification and optimization of Pim1 inhibitors is extensively discussed. This data collection, which to the best of our knowledge was not previously reviewed in such detail, could offer a useful tool for medicinal chemists working in the field of small molecule kinase inhibitors.

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Section: Discussionmentioning

confidence: 99%

“…Similarly, the binding mode of 8-hydroxy-quinoline-7-carboxylic acid derivatives was predicted by docking simulations within the ATP binding site of Pim1 [97] and the results were used to refine structure-activity relationship analysis.…”

Section: Fig (9) Structures Of Pim1 Inhibitors Discovered By Dockinmentioning

confidence: 99%

Using Insights into Pim1 Structure to Design New Anticancer Drugs

Schenone

Tintori²,

Botta³

2010

CPD

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“…The most potent NCI hit (25) illustrated IC 50 value of kinase inhibitors (i.e., Pim-1 kinase [65] and CSF-1R kinase [66]). In fact, other aminoquinolines were also reported to possess potent anti-CDK1 activities [67].…”

Section: In Silico Screening Of Databasesmentioning

confidence: 99%

Discovery of novel CDK1 inhibitors by combining pharmacophore modeling, QSAR analysis and in silico screening followed by in vitro bioassay

Al-Sha’er

Taha

2010

European Journal of Medicinal Chemistry

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“…The structure assignment of dipeptide derivatives 10-13(a-f) is based on (6). To a solution of acetic anhydride (450 mL) at 0 °C was slowly added (very exothermic) concentrated HCl (138 mL, 37%).…”

Section: Methodsmentioning

confidence: 99%

“…antimalarial, 2 antibacterial, 3,4 antitubuerculosis, 5 anticancer activity, 6,7 analgesic activity, 8 anti-inflammatory activity, 8 anti-rheumatic, 9 antitinephritic, 10 or in treating alzheimer's disease (AD).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino] alkanoates and methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonyl-amino)alkanamido] alkanoate

Fathala¹,

Pazdera²

2017

Arkivoc

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A series of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino] alkanoates 7a-f has been developed by the direct condensation of ethyl [4-hydroxy-2-oxo--1-phenyl-1,2-dihydro-3-quinoline] carboxylate 4 with amino acid ester hydrochloride in the presence of triethylamine. The quinoline amino acid esters 7a-f were the key intermediate for the preparation of a series of methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino)alkanamido] alkanoate 10-13(a-f) via azide coupling method with amino acid ester.

show abstract

Identification and structure–activity relationship of 8-hydroxy-quinoline-7-carboxylic acid derivatives as inhibitors of Pim-1 kinase

Cited by 40 publications

References 46 publications

Using Insights into Pim1 Structure to Design New Anticancer Drugs

Using Insights into Pim1 Structure to Design New Anticancer Drugs

Discovery of novel CDK1 inhibitors by combining pharmacophore modeling, QSAR analysis and in silico screening followed by in vitro bioassay

Synthesis of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino] alkanoates and methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonyl-amino)alkanamido] alkanoate

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