The 4-azidobenzyloxycarbonyl function; application as a novel protecting group and potential prodrug modification for amines

Griffin, Roger J.; Evers, E.; Davison, Richard; Gibson, Ashleigh E.; Layton, Deborah; Irwin, W. J.

doi:10.1039/p19960001205

Cited by 36 publications

(42 citation statements)

References 21 publications

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“…Phenylazide was prepared following also reported methods [59], by reaction of aniline with NaNO 2 and NaN 3 in H 2 O at 0°C for 5 h. The IR spectrum of 1 shows a strong absorption at 1314 cm À1 , due to the P@N stretch [60][61][62], and the 31 P{ 1 H} NMR spectrum shows a single peak at 5.89 ppm. These results are similar to those observed in related species such as Ph 3 P@NPh [32].…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and structure of orthopalladated complexes derived from prochiral iminophosphoranes and phosphorus ylides

Camaño

Aragüés

Bielsa

et al. 2008

Journal of Organometallic Chemistry

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Section: Resultsmentioning

confidence: 99%

“…To a solution of N 3 Ph [59] (1.36 g, 11.9 mmol) in dry CH 2 Cl 2 (20 ml) under Ar atmosphere, a solution of PPh 2 Me (2.21 g, 11.9 mmol) in dry CH 2 Cl 2 (20 ml) was added dropwise during 20 min. The evolution of N 2 is evident even from the first steps of the addition.…”

Section: Synthesis Of Ph 2 Mep@nph (1)mentioning

confidence: 99%

Synthesis and structure of orthopalladated complexes derived from prochiral iminophosphoranes and phosphorus ylides

Camaño

Aragüés

Bielsa

et al. 2008

Journal of Organometallic Chemistry

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“…[22] Furthermore, alternative azide-based protecting groups that can be removed by mild reducing agents [23] have been described and could be applied to mask fluorophores. Consequently, the outlined strategy to cage fluorophores by modifying existing exocyclic substituents with phosphine-sensitive protecting groups is highly versatile in contrast to the reduction of aromatic azides, which is limited to specific cases only.…”

Section: Discussionmentioning

confidence: 99%

7‐Azidomethoxy‐Coumarins as Profluorophores for Templated Nucleic Acid Detection

Franzini

Kool

2008

ChemBioChem

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Templated nucleic acid detection is an emerging bioanalytical method that makes use of the target DNA or RNA strand to initiate a fluorogenic reaction. The Staudinger reduction holds particular promise for templated sensing of nucleic acids because the involved functional groups are highly chemoselective. Here, the azidomethoxy group, which can be removed under Staudinger conditions, is used to cage 7-hydroxycoumarin fluorophores. The reduction by phosphines and the subsequent loss of the azidomethoxy substituent induce a significant bathochromic shift of the major absorbance band in the near UV region. When excited at the appropriate wavelength, this change in the absorbance spectrum translates into a substantial fluorescence turn-on signal. The described profluorophores are readily conjugated to amino-modified DNAs and are rapidly uncaged by a triphenylphosphine-DNA probe under the control of a DNA template. In addition, turnover of the probes on the target strand is demonstrated, yielding substantial signal amplification.

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“…Azidobenzyl carbamates 35 have been proposed as triggers in fragmentation prodrugs similar to nitrobenzyl carbamates [76].…”

Section: Other Redox Centersmentioning

confidence: 99%

Anticancer Prodrugs for Application in Monotherapy Targeting Hypoxia, Tumor-Associated Enzymes, and Receptors

Groot¹,

Damen²,

Scheeren

2001

CMC

114

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In order to improve current chemotherapeutic treatment and diminish severe side effects, several prodrug strategies have evolved to achieve site-specific delivery of cytotoxic anticancer agents. This review concentrates on recent developments of antitumor prodrug monotherapy with prodrugs that are designed for direct recognition of tumor-associated factors, such as hypoxia, tumor-associated enzymes and receptors. Firstly, oxygen deficiency in the core of solid tumors leads to enhanced activity of reducing enzymes, like for example nitroreductases, which can be used for site- specific conversion of prodrug to drug. Secondly, some enzymes are present in elevated levels in tumor tissue: beta-glucuronidase leaks from necrotic areas within tumors, while tumor cells for invasive and metastatic activities need several tumor-associated proteases, like plasmin. These enzymes form an attractive target for designing selective prodrugs. Finally, tumor-selective expression of receptors can be exploited for the delivery of antitumor agents. Low molecular weight binding motifs for these receptors can be coupled to cytotoxic drugs in order to obtain tumor-homing conjugates. At present, receptor-binding motifs for a number of receptors that are required for angiogenesis are used for prodrug monotherapy. There exists an increasing body of literature, which describes the complex interplay not only between tumor-associated enzymes, but also between these enzymes and tumor-associated receptors in the process of tumor invasion and metastasis, indicating the feasibility of targeting cytotoxic drugs to these key players in tumor growth. This paper reviews the development and evaluation of anticancer prodrugs, and their application in the various prodrug monotherapy approaches.

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The 4-azidobenzyloxycarbonyl function; application as a novel protecting group and potential prodrug modification for amines

Cited by 36 publications

References 21 publications

Synthesis and structure of orthopalladated complexes derived from prochiral iminophosphoranes and phosphorus ylides

Synthesis and structure of orthopalladated complexes derived from prochiral iminophosphoranes and phosphorus ylides

7‐Azidomethoxy‐Coumarins as Profluorophores for Templated Nucleic Acid Detection

Anticancer Prodrugs for Application in Monotherapy Targeting Hypoxia, Tumor-Associated Enzymes, and Receptors

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