Microwave synthesis of new 3-(3-aminopropyl)-5-arylidene- 2-thioxo-1,3-thiazolidine-4-ones as potential Ser/Thr protein kinase inhibitors

Ambeu, Christelle N’ta; Dago, Camille Déliko; Coulibaly, Wacothon Karime; Békro, Yves-Alain; Mamyrbékova-Békro, Janat Akhanovna; Foll-Josselin, Béatrice; Defontaine, Audrey; Delehouzé, Claire; Bach, Stéphane; Ruchaud, Sandrine; Guével, Rémy Le; Corlu, Anne; Jéhan, Philippe; Lambert, Fabian; Yondre, Nicolas Le; Bazureau, Jean Pierre

doi:10.1007/s00044-016-1719-3

Cited by 11 publications

(5 citation statements)

References 24 publications

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“…(Z)‐3‐(6‐Aminohexyl)‐5‐(1‐(4‐fluorobenzyl)‐2‐oxoindolin‐3‐ylidene)‐2‐thioxothiazolidin‐4‐one hydrochloride (33) : Prepared in 2 steps from 15 , using similar methodology as described by Ambeu [64] . Step 1: Boc‐33 [tert‐butyl (Z)‐(6‐(5‐(1‐(4‐fluorobenzyl)‐2‐oxoindolin‐3‐ylidene)‐4‐oxo‐2‐thioxothiazolidin‐3‐yl)hexyl)carbamate)] was prepared from 1‐(4‐fluorobenzyl)indoline‐2,3‐dione 16 (169 mg, 1 equiv, 0.66 mmol) and tert‐butyl (6‐(4‐oxo‐2‐thioxothiazolidin‐3‐yl)hexyl)carbamate 15 (220 mg, 1 equiv, 0.66 mmol) according to the procedure for 17 , except 1 M HCl was not added to the solid product prior to filtration from the reaction mixture.…”

Section: Methodsmentioning

confidence: 99%

Evaluation of Rhodanine Indolinones as AANAT Inhibitors

Hagemeister,

Hamilton,

Wandrey

et al. 2023

ChemMedChem

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Circadian rhythm (CR) dysregulation negatively impacts health and contributes to mental disorders. The role of melatonin, a hormone intricately linked to CR, is still a subject of active study. The enzyme arylalkylamine N‐acetyltransferase (AANAT) is responsible for melatonin synthesis, and it is a potential target for disorders that involve abnormally high melatonin levels, such as seasonal affective disorder (SAD). Current AANAT inhibitors suffer from poor cell permeability, selectivity, and/or potency. To address the latter, we have employed an X‐ray crystal‐based model to guide the modification of a previously described AANAT inhibitor, containing a rhodanine‐indolinone core. We made various structural modifications to the core structure, including testing the importance of a carboxylic acid group thought to bind in the CoA site, and we evaluated these changes using MD simulations in conjunction with enzymatic assay data. Additionally, we tested three AANAT inhibitors in a zebrafish locomotion model to determine their effects in vivo. Key discoveries were that potency could be modestly improved by replacing a 5‐carbon alkyl chain with rings and that the central rhodanine ring could be replaced by other heterocycles and maintain potency.

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Section: Methodsmentioning

confidence: 99%

Evaluation of Rhodanine Indolinones as AANAT Inhibitors

Hagemeister,

Hamilton,

Wandrey

et al. 2023

ChemMedChem

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“…Ambeu and co-workers 71 synthesized 3-substituted rhodanine derivatives as human recombinant proto-oncogene Pim-1 kinase ( Hs Pim1). HT 1 ( Figure 26 ) obtained micromolar concentration ranges against a few representatives of cancer cell lines (IC 50 = 14–18 μM), with HCT116 being the most sensitive to HT 1 (IC 50 = 14 μM).…”

Section: Pim Kinase Inhibitorsmentioning

confidence: 99%

Structure–Activity Relationship Study and Design Strategies of Hydantoin, Thiazolidinedione, and Rhodanine-Based Kinase Inhibitors: A Two-Decade Review

Naufal,

Hermawati,

Syah

et al. 2024

ACS Omega

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Cancer is one of the most prominent causes of the rapidly growing mortality numbers worldwide. Cancer originates from normal cells that have acquired the capability to alter their molecular, biochemical, and cellular traits. The alteration of cell signaling enzymes, such as kinases, can initiate and amplify cancer progression. As a curative method, the targeted therapy utilized small molecules' capability to inhibit kinase's cellular function. This review provides a brief history (1999−2023) of Small Molecule Kinase Inhibitors (SMKIs) discovery with their molecular perspective. Furthermore, this current review also addresses the application and the development of hydantoin, thiazolidinedione, and rhodanine-based derivatives as kinase inhibitors toward several subclasses (EGFR, PI3K, VEGFR, Pim, c-Met, CDK, IGFR, and ERK) accompanied by their structure−activity relationship study and their molecular interactions. The present work summarizes and compiles all the important structural information essential for developing hydantoin, thiazolidinedione, and rhodanine-based kinase inhibitors to improve their potency in the future.

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“…Routes A and B involve the use of mono-protected diamines 7(a, b); we chose the N-Boc protecting group because it is effectively removed in acid conditions. Tert-butyl {2-[4-(3aminopropyl)pyperazin-1-yl]propyl}carbamate 7a and tert-butyl (3-aminopropyl)carbamate 7b were synthesized according to the literature [15,16]. Treatment of diamines 6a and 6b with di-tertbutyldicarbonate (Boc) 2 O in 1,4-dioxane at room temperature for 24 hours produced mainly mono-N-Boc protected diamines 7a (56% yield) and 7b (80% yield).…”

Section: Synthesis Of Building Blocks a And Bmentioning

confidence: 99%

“…Compound 7b was prepared in 80% yield according to a previous procedure developed in our laboratory [16] as a colorless oil then, it was stocked at 4 °C as a solution (2 g/mL) in dry ether. (UV: $ max.…”

Section: Tert-butyl (3-aminopropyl)carbamate (7b)mentioning

confidence: 99%

A practical multi-step synthesis of ethyl N-functionalized $$\varvec{\upbeta }$$ β -amino benzimidazole acrylate derivatives as promising cytotoxic agents

et al. 2018

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A series of 16 new ethyl [Formula: see text]-amino benzimidazole acrylate derivatives 12(a-p) with a (2E)-s-cis/trans conformation and bearing two points of diversity was designed and synthesized by using a multi-step strategy (reductive amination, deprotection in acidic media and transamination) in moderate to good yields from ethyl 3-dimethylamino-2-(1H-benzimidazol-2-yl)acrylate (5) and monosubstituted N-Boc diamines (7a,7b) as starting building blocks. Products 12 were evaluated for their in vitro cytotoxic potential against six selected human cell lines (Huh7-D12, Caco2, MDA-MB231, HCT116, PC3 and NCI-H727). Compounds 12a, 12e and 12l exhibited selective and micromolar antitumor activities against Huh7-D12 and Caco2 cell lines.

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Microwave synthesis of new 3-(3-aminopropyl)-5-arylidene- 2-thioxo-1,3-thiazolidine-4-ones as potential Ser/Thr protein kinase inhibitors

Cited by 11 publications

References 24 publications

Evaluation of Rhodanine Indolinones as AANAT Inhibitors

Evaluation of Rhodanine Indolinones as AANAT Inhibitors

Structure–Activity Relationship Study and Design Strategies of Hydantoin, Thiazolidinedione, and Rhodanine-Based Kinase Inhibitors: A Two-Decade Review

A practical multi-step synthesis of ethyl N-functionalized $$\varvec{\upbeta }$$ β -amino benzimidazole acrylate derivatives as promising cytotoxic agents

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