An efficient synthesis of pyrido-imidazodiazepinediones

Arama, Dominique P.; Lisowski, Vincent; Scarlata, Eliana; Fulcrand, Pierre; Maillard, Ludovic T.; Martinez, Jean; Masurier, Nicolas

doi:10.1016/j.tetlet.2012.12.087

Cited by 10 publications

(15 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recently, we reported a new series of heterocyclic compounds, based on the pyrido-imidazodiazepinone scaffold as competitive and reversible inhibitors of KLK7. [139][140][141] Among the synthesized derivatives, compound 13 (Fig. 18) showed the most potent inhibitory activity (K i = 27 M).…”

Section: Noncovalent Inhibitorsmentioning

confidence: 99%

Inhibitors of kallikrein‐related peptidases: An overview

Masurier

Arama

Amri

et al. 2017

Medicinal Research Reviews

Self Cite

View full text Add to dashboard Cite

Kallikrein-related peptidases (KLKs) are a family of 15 secreted serine proteases that are involved in various physiological processes. Their activities are subtly regulated by various endogenous inhibitors, ranging from metallic ions to macromolecular entities such as proteins. Furthermore, dysregulation of KLK activity has been linked to several pathologies, including cancer and skin and inflammatory diseases, explaining the numerous efforts to develop KLK-specific pharmacological inhibitors as potential therapeutic agents. In this review, we focus on the huge repertoire of KLKs inhibitors reported to date with a special emphasis on the diversity of their molecular mechanisms of inhibition.

show abstract

Section: Noncovalent Inhibitorsmentioning

confidence: 99%

Inhibitors of kallikrein‐related peptidases: An overview

Masurier

Arama

Amri

et al. 2017

Medicinal Research Reviews

Self Cite

View full text Add to dashboard Cite

show abstract

“…Pyrido-imidazodiazepinones 4-20 were synthesised starting from 2-amino-imidazo[1,2-a]pyridine 1, by selective C-3 acylation of the imidazo[1,2-a]pyridine nucleus (Scheme 1), using 9 different N-Boc amino-acids (Boc-Ala-OH, Boc-Nle-OH, Boc-Leu-OH, Boc-Asp(Bn)-OH, Boc-Pra-OH, S or R Boc-Lys(Cbz)-OH, Boc-6-azido-Nle-OH or Boc-Pro-OH), according to our previously reported methodology 10,11,13,14 . C-3 acylated compounds 2a-i were isolated in 36-97% yield after chromatography on alumina gel.…”

Section: Chemistrymentioning

confidence: 99%

“…Concerning the compounds modified in position 4 (compounds 13-22), the response towards the two tested melanoma cell lines appeared also different ( Table 1, entries [11][12][13][14][15][16][17][18][19][20]. Compounds 13, 16, 17 and 19 were more active on A375 cell line than on MDA-MB-435 (inverse of the JMV5038 profile).…”

Section: In Vitro Antiproliferative Activities On the Nci-60 Cancer Cmentioning

confidence: 99%

Imidazopyridine-fused [1,3]diazepinones: modulations of positions 2 to 4 and their impacts on the anti-melanoma activity

Baccon-Sollier

Malki

Maye

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

Self Cite

View full text Add to dashboard Cite

A series of 19 novel pyrido-imidazodiazepinones, with modulations of positions 2, 3 and 4 of the diazepine ring were synthesised and screened for their in vitro cytotoxic activities against two melanoma cell lines (A375 and MDA-MB-435) and for their potential toxicity against NIH-3T3 non-cancerous cells. Selected compounds were also evaluated on the NCI-60 cell line panel. The SAR study revealed that the molecular volume and the cLogP of compounds modified at position 2 were significantly correlated with the activity of these compounds on melanoma cell lines. Moreover, introduction of a heterocyclic group at position 2 or an azido-alkyl chain at position 4 led to compounds displaying a significantly different activity profile on the NCI-60 cell line panel, compared to phenyl-substituted compounds at position 2 of the diazepinone. This study provides us crucial information for the development of new derivatives active against melanoma.

show abstract

“…[3][4][5][6] Since the discovery of benzodiazepines as central nervous system depressants, many synthetic derivatives that display a wide range of therapeutic applications in antithrombotic, [7] antibiotic, [8] and antitumor [9,10] areas, have been extensively developed. [19,20] We also investigated the thiophene isoster (namely thieno- [1,4]diazepine) scaffold. [17,18] Recently, we focused our efforts on the development of a new azaheterocycle-fused [1,3]diazepine scaffold and successfully reported on the synthesis of the first series of imidazopyridine-fused [1,3]diazepinones.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Thieno[3,2‐e][1,4]diazepin‐2‐ones: Application of an Uncatalysed Pictet–Spengler Reaction

et al. 2015

Self Cite

View full text Add to dashboard Cite

A series of 5‐substituted thieno[3,2‐e][1,4]diazepin‐2‐ones was synthesized in four steps from methyl 3‐aminothiophene‐2‐carboxylate. After the coupling of 3‐aminothiophene with α‐amino acids, the key final step that involves an uncatalysed Pictet–Spengler reaction allowed the cyclization of the seven‐membered diazepinone ring. The reaction was first optimized and then exemplified in three different series (phenylalanine, alanine and proline) that led to 24 target diazepinones, which includes 19 optically pure diastereomers.

show abstract

An efficient synthesis of pyrido-imidazodiazepinediones

Cited by 10 publications

References 32 publications

Inhibitors of kallikrein‐related peptidases: An overview

Inhibitors of kallikrein‐related peptidases: An overview

Imidazopyridine-fused [1,3]diazepinones: modulations of positions 2 to 4 and their impacts on the anti-melanoma activity

Synthesis of Thieno[3,2‐e][1,4]diazepin‐2‐ones: Application of an Uncatalysed Pictet–Spengler Reaction

Contact Info

Product

Resources

About