A new application of diphenylphosphorylazide (DPPA) reagent: convenient transformations of quinolin-4-one, pyridin-4-one and quinazolin-4-one derivatives into the 4-azido and 4-amino counterparts

Aizikovich, A. Ya.; Кузнецов, В. В.; Gorohovsky, Sofia; Levy, Amalia; Meir, Simha; Byk, Gérardo; Gellerman, Garry

doi:10.1016/j.tetlet.2004.04.032

Cited by 19 publications

(10 citation statements)

References 6 publications

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“…The synthesis of the cyclic peptides was done by a previously described procedure [43–48]. Briefly, 2-chlorotrityl chloride resin (1.12 mmol/gr) was placed in a reactor and suspended in DCM under nitrogen atmosphere.…”

Section: Methodsmentioning

confidence: 99%

Toward the development of a novel non-RGD cyclic peptide drug conjugate for treatment of human metastatic melanoma

et al. 2016

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The newly discovered short (9 amino acid) non-RGD S-S bridged cyclic peptide ALOS-4 (H-cycl(Cys-Ser-Ser-Ala-Gly-Ser-Leu-Phe-Cys)-OH), which binds to integrin αvβ3 is investigated as peptide carrier for targeted drug delivery against human metastatic melanoma. ALOS4 binds specifically the αvβ3 overexpressing human metastatic melanoma WM-266-4 cell line both in vitro and in ex vivo assays. Coupling ALOS4 to the topoisomerase I inhibitor Camptothecin (ALOS4-CPT) increases the cytotoxicity of CPT against human metastatic melanoma cells while reduces dramatically the cytotoxicity against non-cancerous cells as measured by the levels of γH2A.X, active caspase 3 and cell viability. Moreover, conjugating ALOS4 to CPT even increases the chemo-stability of CPT under physiological pH. Bioinformatic analysis using Rosetta platform revealed potential docking sites of ALOS4 on the αvβ3 integrin which are distinct from the RGD binding sites. We propose to use this specific non-RGD cyclic peptide as the therapeutic carrier for conjugation of drugs in order to improve efficacy and reduce toxicity of currently available treatments of human malignant melanoma.

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Section: Methodsmentioning

confidence: 99%

Toward the development of a novel non-RGD cyclic peptide drug conjugate for treatment of human metastatic melanoma

et al. 2016

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“…The compound was rapidly advanced to the next step to avoid photochemical degradation. The compound has been prepared previously40 and is also commercially available. 1 H NMR (DMSO- d 6 , 500 MHz): δ 6.36 (s, 1H), 7.19 (t, J = 10 Hz, 1H), 7.57 (td, J = 7.73, 1.37 Hz, 1H), 7.68 (d, J = 15 Hz, 1H).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of aryl-heteroaryl ureas (AHUs) based on 4-aminoquinoline and their evaluation against the insulin-like growth factor receptor (IGF-1R)

Engen

O’Brien

Kelly

et al. 2010

Bioorganic & Medicinal Chemistry

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The insulin-like growth factor receptor (IGF-1R) is a receptor tyrosine kinase (RTK) involved in all stages of the development and propagation of breast and other cancers. The inhibition of IGF-1R by small molecules remains a promising strategy to treat cancer. Herein, we explore SAR around previously characterized lead compound (1), which is an aryl-heteroaryl urea (AHU) consisting of 4-aminoquinaldine and a substituted aromatic ring system. A library of novel AHU compounds was prepared based on derivatives of the 4-aminoquinoline heterocycle (including various 2-substituted derivatives, and naphthyridines). The compounds were screened for in vitro inhibitory activity against IGF-1R, and several compounds with improved activity (3-5 μM) were identified. Furthermore, a computational docking study was performed, which identifies a fairly consistent lowest energy mode of binding for the more-active set of inhibitors in this series, while the less-active inhibitors do not adopt a consistent mode of binding.

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“…6 Organic azides have assumed an important position at the interface between chemistry, biology, medicine, and materials science. 7 Diphenylphosphoryl azide has been used extensively as a peptide coupling reagent, 8 in the transformation of alcohols into amines, 9 in the transformation of the oxo-function of quinoline/pyridine/quinazolin-4-ones to form 4-azido-derivatives, 10 in the transformation of acids into acyl azide intermediates, 11,12 and in the synthesis of ruthenium complexes containing iminophosphorane ligands. 13 To our knowledge, the reactivity of DPPA toward 1,2-bis(diphenylphosphino)ethane has not been investigated.…”

Section: Introductionmentioning

confidence: 99%

A versatile synthesis of a new bisiminophosphorane

Micle¹,

Miklášova

Varga

et al. 2009

Tetrahedron Letters

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A new application of diphenylphosphorylazide (DPPA) reagent: convenient transformations of quinolin-4-one, pyridin-4-one and quinazolin-4-one derivatives into the 4-azido and 4-amino counterparts

Cited by 19 publications

References 6 publications

Toward the development of a novel non-RGD cyclic peptide drug conjugate for treatment of human metastatic melanoma

Toward the development of a novel non-RGD cyclic peptide drug conjugate for treatment of human metastatic melanoma

Synthesis of aryl-heteroaryl ureas (AHUs) based on 4-aminoquinoline and their evaluation against the insulin-like growth factor receptor (IGF-1R)

A versatile synthesis of a new bisiminophosphorane

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