Facile Synthesis of 1-Amino[1,3,5]triazino[1,2a]-benzimidazolo-2-one and Pyrimidino[1,2a]benzimidazolo-4-one Derivatives

REFERENCES

• Gavrilov , M. Y. ; Mardanova , L. G. ; Kolla , V. E. ; Konshin , M. E. Synthèses, anti-inflammatory and analgesic activities of 2-arylamino-5,6,7,8-tetrahydroquinoline-3-carbo-xamides . Pharm. Chem. J. 1989 , 22 ( 7 ), 554 – 556 .
   Google Scholar
• Abdel-Rahman , B. A. ; El-Gazzar , M. ; El-Enany , M. ; Mahmoud , N. M. Synthesis, analgesic, anti-inflammatory, and antimicrobial activity of some novel pyrimido[4,5-b]quinolin-4-ones . Bioorg. Med. Chem. 2008 , 16 ( 6 ), 3261 – 3273 .
   PubMedGoogle Scholar
• Bernier , J. L. ; Henichart , J. P. ; Warin , V. ; Baert , T. Synthesis and structure–activity relation ship of a pyrimido[4,5-d]pyrimidine derivative with antidepressant activity . J. Pharm. Sci. 1980 , 69 ( 11 ), 1343 – 1345 .
   PubMedGoogle Scholar
• Dinan , F. J. ; Bardos , T. J. Synthesis of some new S-alkylated derivatives of 5-mercapto-2′-deoxyuridine as potential antiviral agents . J. Med. Chem. 1980 , 23 ( 5 ), 569 – 572 .
   PubMedGoogle Scholar
• Settimo , F. D. ; Primofiore , G. ; Taliani , S. ; Marini , A. M. ; La Motta , C. ; Novellino , E. ; Greco , G. ; Lavecchia , A. ; Trincavelli , L. ; Martini , C. 3-Aryl[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-ones: A new class of selective A1 adenosine receptor antagonists . J. Med. Chem. 2001 , 44 ( 3 ), 316 – 327 .
   PubMedGoogle Scholar
• Said , M. ; Abouzid , K. ; Mouneer , A. ; Ahmedy , A. ; Osman , A. M. Synthesis and biological evaluation of new thiazolopyrimidines. Arch. Pharm. Res. 2004, 27(5), 471–477.
   PubMed Web of Science ®Google Scholar
• Shaaban , M. R. ; Saleh , T. S. ; Mayhoub , A. S. ; Mansour , A. ; Farag , A. M. Synthesis and analgesic/anti-inflammatory evaluation of fused heterocyclic ring systems incorporating phenylsulfonyl moiety . Bioorg. Med. Chem. 2008 , 16 , 6344 – 6352 .
   PubMed Web of Science ®Google Scholar
• Nawrocka , W. ; Sztuba , B. ; Kowalska , M. W. ; Liszkiewicz , H. ; Wietrzyk , J. ; Nasulewicz , A. ; Pelczynska , M. ; Opolski , A. Synthesis and antiproliferative activity in vitro of 2-aminobenzimidazole derivatives . Farmaco 2004 , 59 ( 2 ), 83 – 91 .
   PubMedGoogle Scholar
• Kumar , D. ; Jacob , M. R. ; Reynolds , M. B. ; Kerwin , S. M. Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to UK-1 . Bioorg. Med. Chem. 2002 , 10 , 3997 – 4004 .
   PubMed Web of Science ®Google Scholar
• Ojha , V. ; Singh , J. ; Bhakuni , D. S. ; Singh , S. ; Chatterjee , R. K. Synthesis of 5-substituted 2-carbalkoxyamino-1H-benximidazoles as possible microfilaricida agents . Indian J. Chem. 1991 , 30B , 324 – 326 .
   Google Scholar
• Wahe , H. ; Asobo , P. F. ; Cherkasov , R. A. ; Nkengfack , A. E. ; Folefoc , G. N. ; Fomum , Z. T. ; Doepp , D. Heterocycles of biological importance, part 6: The formation of novel biologically active pyrimido[1,2a]benzimidazoles from electron-deficient alkynes and 2-aminobenzimidazoles . Arkivoc 2003 , 14 , 170 .
   Google Scholar
• Dolzhenko , A. V. ; Chui , W. K. ; Dolzhenko , A. V. ; Chan , L. W. Synthesis and biological activity of fluorinated 2-amino-4-aryl-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazoles . J. Fluorine Chem. 2005 , 126 ( 5 ), 759 – 763 .
   Google Scholar
• Gulyas , G. ; Emri , T. ; Simon , A. ; Gyorgydeak , Z. In vitro antimicrobial activity of 3,4-dihydro-s-triazinobenzimidazole derivatives . Folia Microbiol. 2002 , 47 , 29 – 31 .
   PubMedGoogle Scholar
• Toyoda , T. ; Brobey , R. K. B. ; Sano , G. I. ; Horii , T. ; Tomioka , N. ; Itai , A. Lead discovery of inhibitors of the dihydrofolate reductase domain of Plasmodium falciparum dihydrofolate reductase–thymidylate synthase . Biochem. Biophys. Res. Commun. 1997 , 235 , 515 – 519 .
   PubMed Web of Science ®Google Scholar
• Ridley , R. G. Chemotherapeutic hope on the horizon for Plasmodium vivax malaria . Proc. Natl. Acad. Sci. U.S.A. 2002 , 99 ( 21 ), 13362 – 13364 .
   PubMedGoogle Scholar
• Berman , E. M. ; Werbel , L. M. The renewed potential for folate antagonists in contemporary cancer chemotherapy . J. Med. Chem. 1991 , 34 ( 2 ), 479 – 485 .
   PubMed Web of Science ®Google Scholar
• Dolzhenko , A. V. ; Chui , W.-K. Synthesis of 2-amino-s-triazino[1,2-a]benzimidazoles as potential antifolates from 2-guanidino- and 2-guanidino-5-methylbenzimidazoles . J. Heterocyclic Chem. 2006 , 43 ( 1 ), 95 – 100 .
   Google Scholar
• Hussein , M. B. G. ; Abdel-Alim , M. A. ; Hashem , A. A. M. Synthesis and antimicrobial activity of some new 1-alkyl-2-alkylthio-1,2,4-triazolobenzimidazole derivatives . Arch. Pharm. Res. 2006 , 29 ( 1 ), 26 – 33 .
   PubMedGoogle Scholar
• Abderrahim , R. ; Hajjem , B. ; Baccar , B. A convenient synthesis of [1,2-a]benzimidazo-1,3,5-triazin-4-thiones and [1,2-a]benzimidazo-1,3,5-triazin-4-ones . J. Soc. Chim. Tunisie 1994 , 3 , 423 – 426 .
   Google Scholar
• Raouafi , N. ; Abderrahim , R. ; Belhadj Amor , A. ; Boujlel , K. ; Ben Khoud , M. L. Reactivité des N-benzimidazoyl imidate en milieu basique: Synthèse de pyrimido[1,2a]benzimidazole . J. Soc. Alg. Chim. 2002 , 12 ( 2 ), 225 – 232 .
   Google Scholar
• Abderrahim , R. ; Hajjem , B. ; Zantour , H. ; Baccar , B. Reaction of N-2-(1-carbethoxy)-and N-2-(1-acyl)-benzimidazoimidates with Grignard reagents: Synthesis of 1,3,5-oxadiazino-(1,2-a)benzimidazoles . Synth. Commun. 1997 , 27 , 3039 – 3046 .
   Web of Science ®Google Scholar
• Abderrahim , R. ; Medini , H. ; Kossai , R. ; Boujlel , K. Reduction of N-2-substituted benzimidazoyl imidates . Synth. Commun . 2002 , 32 ( 2 ), 241 – 245 .
   Web of Science ®Google Scholar
• Abderrahim , R. ; Baccar , B. ; Ben Khoud , M. L. Synthèse de [1,2a]benzimidazolo-1,3,5,2-triazaphosphorine-2-oxydes . Phosphorus, Sulfur, Silicon Relat. Elem. 2002 , 177 , 1033 – 1040 .
   Web of Science ®Google Scholar