2-amino-X-nitrobenzimidazoles as precursors of food-borne carcinogens: A new approach to IQ synthesis

被引：9
|
作者：
Bella, Maros [1 ]
Milata, Viktor [1 ]
Larina, Lyudmila I. [2 ]
机构：
[1] Slovak Univ Technol Bratislava, Dept Organ Chem, Inst Organ Chem Catalysis & Petrochem, Fac Chem & Food Technol, Bratislava 81237, Slovakia
[2] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, Irkutsk 664033, Russia
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2012年 / 49卷 / 02期
关键词：
C-13;
D O I：
10.1002/jhet.786
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cyclization of (non)-methylated nitro-o-phenylenediamines with cyanogen bromide provided nitro-substituted 2-aminobenzimidazoles in good up to excellent yields. Catalytic hydrogenation of 2-amino-1-methyl-5-nitrobenzimidazole yielded 2,5-diamino-1-methylbenzimidazole, which on treatment with 1,1,3,3-tetramethoxypropane in methanol and subsequently after removal of methanol in polyphosphoric acid afforded food-borne carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in 20% yield. J. Heterocyclic Chem.,(2011).
引用
收藏
页码：293 / 296
页数：4
相关论文
共 50 条
  • [31] Whole genome comparisons of serotype 4b and 1/2a strains of the food-borne pathogen Listeria monocytogenes reveal new insights into the core genome components of this species
    Nelson, KE
    Fouts, DE
    Mongodin, EF
    Ravel, J
    DeBoy, RT
    Kolonay, JF
    Rasko, DA
    Angiuoli, SV
    Gill, SR
    Paulsen, IT
    Peterson, J
    White, O
    Nelson, WC
    Nierman, W
    Beanan, MJ
    Brinkac, LM
    Daugherty, SC
    Dodson, RJ
    Durkin, AS
    Madupu, R
    Haft, DH
    Selengut, J
    Van Aken, S
    Khouri, H
    Fedorova, N
    Forberger, H
    Tran, B
    Kathariou, S
    Wonderling, LD
    Uhlich, GA
    Bayles, DO
    Luchansky, JB
    Fraser, CM
    NUCLEIC ACIDS RESEARCH, 2004, 32 (08) : 2386 - 2395
  • [32] SPECIES-DIFFERENCES IN THE BIOTRANSFORMATION OF THE FOOD-BORNE CARCINOGEN 2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE BY HEPATIC MICROSOMES AND CYTOSOLS FROM HUMANS, RATS, AND MICE
    LIN, DX
    LANG, NP
    KADLUBAR, FF
    DRUG METABOLISM AND DISPOSITION, 1995, 23 (04) : 518 - 524
  • [33] PHASE I AND PHASE II XENOBIOTIC REACTIONS AND METABOLISM OF THE FOOD-BORNE CARCINOGEN 2-AMINO-3,8-DIMETHYLIMIDAZO[4,5-F]QUINOXALINE IN AGGREGATING LIVER-CELL CULTURES
    SCHILTER, B
    TURESKY, RJ
    JUILLERAT, M
    HONEGGER, P
    GUIGOZ, Y
    BIOCHEMICAL PHARMACOLOGY, 1993, 45 (05) : 1087 - 1096
  • [34] Deconjugation of N-glucuronide conjugated metabolites with hydrazine hydrate -: Biomarkers for exposure to the food-borne carcinogen 2-amino-l-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)
    Frandsen, H.
    FOOD AND CHEMICAL TOXICOLOGY, 2007, 45 (05) : 863 - 870
  • [35] Induction of aberrant crypt foci in DNA mismatch repair-deficient mice by the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP)
    Smith-Roe, Stephanie L.
    Lohr, Christiane V.
    Bildfell, Robert J.
    Fischer, Kay A.
    Hegan, Denise Campisi
    Glazer, Peter M.
    Buermeyer, Andrew B.
    CANCER LETTERS, 2006, 244 (01) : 79 - 85
  • [36] Msh2 DNA mismatch repair gene deficiency and the food-borne mutagen 2-amino-1-methyl-6-phenolimidazo [4,5-b] pyridine (PhIP) synergistically affect mutagenesis in mouse colon
    Zhang, SL
    Lloyd, R
    Bowden, G
    Glickman, BW
    de Boer, JG
    ONCOGENE, 2001, 20 (42) : 6066 - 6072
  • [37] Induction of intestinal tumors and lymphomas in C57BL/6N mice by a food-borne carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine
    Ochiai, M
    Imai, H
    Sugimura, T
    Nagao, M
    Nakagama, H
    JAPANESE JOURNAL OF CANCER RESEARCH, 2002, 93 (05): : 478 - 483
  • [38] 1H nuclear magnetic resonance spectroscopy-based studies of the metabolism of food-borne carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline by human intestinal microbiota
    Humblot, C
    Combourieu, B
    Väisänen, ML
    Furet, JP
    Delort, AM
    Rabot, S
    APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2005, 71 (09) : 5116 - 5123
  • [39] Validation in rats of two biomarkers of exposure to the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP): PhIP-DNA adducts and urinary PhIP
    Friesen, MD
    Cummings, DA
    Garren, L
    Butler, R
    Bartsch, H
    Schut, HAJ
    CARCINOGENESIS, 1996, 17 (01) : 67 - 72
  • [40] Msh2 DNA mismatch repair gene deficiency and the food-borne mutagen 2-amino-1-methy1-6-phenolimidazo [4,5-b] pyridine (PhIP) synergistically affect mutagenesis in mouse colon
    Shulin Zhang
    Ruth Lloyd
    Greg Bowden
    Barry W Glickman
    Johan G de Boer
    Oncogene, 2001, 20 : 6066 - 6072
12345