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Synthesis of novel 2-aminoimidazo[4,5-b]pyridines, including the thieno analogue of the cooked-food mutagen IFP
Södertörn University, School of Life Sciences. Karolinska Institute.
Södertörn University, School of Life Sciences. Karolinska Institute.
2006 (English)In: Journal of Heterocyclic Chemistry, ISSN 0022-152X, E-ISSN 1943-5193, Vol. 43, no 1, 101-109 p.Article in journal (Refereed) Published
Abstract [en]

Eight new compounds, including three new ring systems obtained via the Friedlander condensation of ortho-aminothiophenecarbaldehydes 11, 21 and 24 with creatinine (8), are reported. The condensation afforded 1, which is the thieno analogue of the cooked-food mutagen IFP (2-amino-1,6-dimethylfuro[2,3-e]imidazo[4,5-b]pyridine), and the benzothieno[2,3-e]- and benzothieno[3,2-e]imidazo[4,5-b]pyridines 2 and 3. Attempts to condense 11 with isocreatinine (12) were unsuccessful. Desulfurization of 3 gave the known cooked-food carcinogen PhIP. The 2-nitro (4) and 2-hydroxy (5) derivatives of 3 are reported. The related 2-amino-1-methyl-imidazo[4,5-b]benzothiophene (25) was synthesized by a different route. Fully assigned H-1 and C-13 nmr data of all new compounds are reported.

Place, publisher, year, edition, pages
2006. Vol. 43, no 1, 101-109 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:sh:diva-14317DOI: 10.1002/jhet.5570430116ISI: 000234531100016ScopusID: 2-s2.0-30844448805OAI: oai:DiVA.org:sh-14317DiVA: diva2:468087
Note

Som manuskript i avhandling. As manuscript in dissertation.

Available from: 2011-12-20 Created: 2011-12-20 Last updated: 2017-02-08Bibliographically approved
In thesis
1. Synthesis of sulfur and seleniumn heterocycles, including derivatives of imidazopyridine and benzimidazole
Open this publication in new window or tab >>Synthesis of sulfur and seleniumn heterocycles, including derivatives of imidazopyridine and benzimidazole
2005 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The chemistry developed in this thesis can be divided into two parts. The first part, which is the major part of the thesis, contains syntheses towards analogues to mutagenic heterocyclic amines found in e.g. meat fried at high temperatures. The second part concentrates on the palladium-(0)catalyzed cross-coupling reactions of 4- and 5-substituted 2,1,3-benzoselenadiazoles. The heterocyclic amines described can be divided into the linear and the angular compounds. Five linear imidazo[4,5-b]pyridines were synthesised via the Friedländer reaction: 2-amino-1 - methylbenzothieno[2,3-e]imidazo[4,5-b]pyridine, 2-amino-1-methy-benzothieno [3,2-e] imidazo[4,5-b] pyridine, 2-amino-1-methylthieno[2,3-elimidazo[4,5-b]-pyridine, 2-amino-1methylthieno[3,2-e]imidazo[4,5-b]pyridine and the sulfur analogue to the cooked-food mutagen IFP, 2-amino- 1,6-dimethylthieno[2,3-e]imidazo[4,5-b]pyridine. Attempts were made to form three thienoimidazo[4,5-b]pyridines via stepwise condensation. The first condensation between creatinine and 2-nitro-3-thiophene-carbaldehyde, 3-amino-2thiophenecarbaldehyde and 4-azido3-thiophenecarbaldehyde yielded thenylidenomethyleneimidazolinones, but only one of these gave the ring closed compound 2-amino-1-methylthieno[2,3-e]imidazo[4,5-b]pyridine by a second condensation. In addition, 2-amino- 1 methyl benzoth ieno[3,2-e] imidazo[4,5 -b] pyridine was transformed into the 2-nitro- and 2-hydroxy derivative. The last linear isomer 2-amino-1methylimidazo[4,5-b]benzothiophene, was synthesized by a different route. The series of angular compounds are considered analogues to the food-mutagen IQx. A series of six homologues of 7-amino-imidazo[4,5-e]-2,1,3-benzoselenadiazoles. Four ring systems were obtained by treating 4-methylamino-3-nitro-phenylenedianmine with a range of biselectrophiles, namely: 2-amino-1-methylbenzo-thiadiazole, -triazole, -diazepinone and 2amino1 -methylimidazobenzimidazole. Among the palladium-(0)-catalyzed cros s- couplings, the Suzuki, Stille, Fleck and Sonogashira reactions were used. These were applied to 4-, or 5-bromo-2,1,3-benzoselenadiazoles. In addition, the 4- and 5-trimethyltin-2,1,3-benzoselenadiazole were synthesized.

Place, publisher, year, edition, pages
Stockholm: Karolinska instiutet, 2005. 40 p.
National Category
Organic Chemistry
Identifiers
urn:nbn:se:sh:diva-32000 (URN)91-7140-597-6 (ISBN)
Public defence
2005-12-15, Hörsalen, plan 4, NOVUM, Hälsovägen 7-9, Huddinge, 10:00 (English)
Opponent
Supervisors
Available from: 2017-02-08 Created: 2017-02-08 Last updated: 2017-02-08Bibliographically approved

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