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
  • [21] Toxicity of Food-Grade TiO2 to Commensal Intestinal and Transient Food-Borne Bacteria: New Insights Using Nano-SIMS and Synchrotron UV Fluorescence Imaging
    Radziwill-Bienkowska, Joanna M.
    Talbot, Pauline
    Kamphuis, Jasper B. J.
    Robert, Veronique
    Cartier, Christel
    Fourquaux, Isabelle
    Lentzen, Esther
    Audinot, Jean-Nicolas
    Jamme, Frederic
    Refregiers, Matthieu
    Bardowski, Jacek K.
    Langella, Philippe
    Kowalczyk, Magdalena
    Houdeau, Eric
    Thomas, Muriel
    Mercier-Bonin, Muriel
    FRONTIERS IN MICROBIOLOGY, 2018, 9
  • [22] A NEW APPROACH TO AMINOAROMATIC THIOLS - SYNTHESIS OF 6-AMINO-2-NAPHTHALENETHIOL
    ASLAM, M
    DAVENPORT, KG
    SYNTHETIC COMMUNICATIONS, 1987, 17 (15) : 1761 - 1768
  • [23] Global gene expression analysis of rat colon cancers induced by a food-borne carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine
    Fujiwara, K
    Ochiai, M
    Ohta, T
    Ohki, M
    Aburatani, H
    Nagao, M
    Sugimura, T
    Nakagama, H
    CARCINOGENESIS, 2004, 25 (08) : 1495 - 1505
  • [24] FORMATION AND REMOVAL OF DNA-ADDUCTS IN THE LIVER OF RATS CHRONICALLY FED THE FOOD-BORNE CARCINOGEN, 2-AMINO-3,8-DIMETHYLIMIDAZO[4,5-F]QUINOXALINE
    HIROSE, M
    WAKABAYASHI, K
    OCHIAI, M
    KUSHIDA, H
    SATO, H
    SUGIMURA, T
    NAGAO, M
    JAPANESE JOURNAL OF CANCER RESEARCH, 1995, 86 (06): : 516 - 522
  • [25] The food-borne carcinogenic 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) disrupts circadian rhythms and ameliorated by pterostilbene (PSB) in Caenorhabditis elegans
    Chang, Chun-Han
    Yen, Pei-Ling
    Pan, Min-Hsiung
    Liao, Vivian Hsiu-Chuan
    ARCHIVES OF TOXICOLOGY, 2024, 98 (12) : 4131 - 4141
  • [26] Chemoprotection against the formation of colon DNA adducts from the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in the rat
    Huber, WW
    McDaniel, LP
    Kaderlik, KR
    Teitel, CH
    Lang, NP
    Kadlubar, FF
    MUTATION RESEARCH-FUNDAMENTAL AND MOLECULAR MECHANISMS OF MUTAGENESIS, 1997, 376 (1-2) : 115 - 122
  • [27] Mlh1-dependent suppression of specific mutations induced in vivo by the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP)
    Smith-Roe, SL
    Hegan, DC
    Glazer, PM
    Buermeyer, AB
    MUTATION RESEARCH-FUNDAMENTAL AND MOLECULAR MECHANISMS OF MUTAGENESIS, 2006, 594 (1-2) : 101 - 112
  • [28] THE EFFECT OF DOSE AND CYTOCHROME-P450 INDUCTION ON THE METABOLISM AND DISPOSITION OF THE FOOD-BORNE CARCINOGEN 2-AMINO-3,8-DIMETHYLIMIDAZO[4,5-F]QUINOXALINE (MEIQX) IN THE RAT
    TURESKY, RJ
    MARKOVIC, J
    BRACCOHAMMER, I
    FAY, LB
    CARCINOGENESIS, 1991, 12 (10) : 1847 - 1855
  • [29] Mapping Serum Albumin Adducts of the Food-Borne Carcinogen 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by Data-Dependent Tandem Mass Spectrometry
    Peng, Lijuan
    Dasari, Surendra
    Tabb, David L.
    Turesky, Robert J.
    CHEMICAL RESEARCH IN TOXICOLOGY, 2012, 25 (10) : 2179 - 2193
  • [30] Current issues in mutagenesis and carcinogenesis, No 82 - Cancer chemoprevention from the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazol[4,5-b]pyridine: reconsideration of the evidence
    Paolini, M
    Biagi, GL
    Cantelli-Forti, G
    MUTATION RESEARCH-FUNDAMENTAL AND MOLECULAR MECHANISMS OF MUTAGENESIS, 1997, 381 (02) : 279 - 282
12345