Synthesis of a staurosporine analogue possessing a 7-azaindole unit instead of an indole moiety

Samir Messaoudi; Fabrice Anizon; Bruno Pfeiffer; Roy Golsteyn; Michelle Prudhomme

doi:10.1016/j.tetlet.2004.04.102

Synthesis of a staurosporine analogue possessing a 7-azaindole unit instead of an indole moiety

Samir Messaoudi
, Fabrice Anizon
, Bruno Pfeiffer
, Roy Golsteyn
, Michelle Prudhomme

Clermont-Auvergne University
Institut de Recherches Servier, Croissy-sur-Seine

Research output: Contribution to journal › Article › peer-review

Abstract

The synthesis of a new staurosporine analogue possessing a 7-azaindole unit instead of an indole moiety is described. This synthesis could be achieved by coupling a sugar moiety previously tosylated in 2′ position to the azaindolocarbazole aglycone. Nucleophilic substitution on the carbon bearing the tosyl group yielded to the key cyclization leading to a compound in which the carbohydrate part is linked to both indole and azaindole nitrogens.

Original language	English
Pages (from-to)	4643-4647
Number of pages	5
Journal	Tetrahedron Letters
Volume	45
Issue number	24
DOIs	https://doi.org/10.1016/j.tetlet.2004.04.102
Publication status	Published - 7 Jun 2004
Externally published	Yes

Keywords

7-Azaindole
Antitumor compounds
Enzyme inhibitors
Rebeccamycin
Staurosporine

Access to Document

10.1016/j.tetlet.2004.04.102

Cite this

@article{b313b7b91b734a919d1a57d5904136bb,

title = "Synthesis of a staurosporine analogue possessing a 7-azaindole unit instead of an indole moiety",

abstract = "The synthesis of a new staurosporine analogue possessing a 7-azaindole unit instead of an indole moiety is described. This synthesis could be achieved by coupling a sugar moiety previously tosylated in 2′ position to the azaindolocarbazole aglycone. Nucleophilic substitution on the carbon bearing the tosyl group yielded to the key cyclization leading to a compound in which the carbohydrate part is linked to both indole and azaindole nitrogens.",

keywords = "7-Azaindole, Antitumor compounds, Enzyme inhibitors, Rebeccamycin, Staurosporine",

author = "Samir Messaoudi and Fabrice Anizon and Bruno Pfeiffer and Roy Golsteyn and Michelle Prudhomme",

year = "2004",

month = jun,

day = "7",

doi = "10.1016/j.tetlet.2004.04.102",

language = "English",

volume = "45",

pages = "4643--4647",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "24",

}

TY - JOUR

T1 - Synthesis of a staurosporine analogue possessing a 7-azaindole unit instead of an indole moiety

AU - Messaoudi, Samir

AU - Anizon, Fabrice

AU - Pfeiffer, Bruno

AU - Golsteyn, Roy

AU - Prudhomme, Michelle

PY - 2004/6/7

Y1 - 2004/6/7

N2 - The synthesis of a new staurosporine analogue possessing a 7-azaindole unit instead of an indole moiety is described. This synthesis could be achieved by coupling a sugar moiety previously tosylated in 2′ position to the azaindolocarbazole aglycone. Nucleophilic substitution on the carbon bearing the tosyl group yielded to the key cyclization leading to a compound in which the carbohydrate part is linked to both indole and azaindole nitrogens.

AB - The synthesis of a new staurosporine analogue possessing a 7-azaindole unit instead of an indole moiety is described. This synthesis could be achieved by coupling a sugar moiety previously tosylated in 2′ position to the azaindolocarbazole aglycone. Nucleophilic substitution on the carbon bearing the tosyl group yielded to the key cyclization leading to a compound in which the carbohydrate part is linked to both indole and azaindole nitrogens.

KW - 7-Azaindole

KW - Antitumor compounds

KW - Enzyme inhibitors

KW - Rebeccamycin

KW - Staurosporine

U2 - 10.1016/j.tetlet.2004.04.102

DO - 10.1016/j.tetlet.2004.04.102

M3 - Article

AN - SCOPUS:2442687670

SN - 0040-4039

VL - 45

SP - 4643

EP - 4647

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 24

ER -

Synthesis of a staurosporine analogue possessing a 7-azaindole unit instead of an indole moiety

Abstract

Keywords

Access to Document

Fingerprint

Cite this