Synthesis of Novel Indeno[1,2-c]isoquinoline Derivatives

REFERENCES

• Coelho , F. ; Veronese , D. ; Lopes , E. C. S. ; Rossi , R. C. An approach to substituted dihydroisoquinolin-1(2H)-ones from Baylis–Hillman adducts . Tetrahedron Lett. 2003 , 44 , 5731 – 5735 .
   Google Scholar
• (a) Bentley , K. B. β-Phenylethylamines and the isoquinoline alkaloids . Nat. Prod. Rep. 2000 , 17 , 247 ; (b) Hoshino , O. The amaryllidaceae alkaloids; In The Alkaloids, G. A. Cordell (Ed.); AC Press: San Diego, 1998; vol. 51, pp. 323–424 .
   PubMed Web of Science ®Google Scholar
• Muller , G. 2,3,10-Trimethoxy-8-oxoberbine. French Patent M. 5415, 1967 ; Chem. Abstr. 1969 , 71 , 91735y .
   Google Scholar
• Shaabani , A. ; Soleimani , E. ; Khavasi , H. R. An unexpected, novel, three-component reaction between isoquinoline, an isocyanide and strong CH-acids in water . Tetrahedron Lett. 2007 , 48 , 4743 – 4747 .
   Web of Science ®Google Scholar
• (a) Pop , E. ; Wu , W. M. ; Shek , E. ; Bodor , N. Brain-specific chemical delivery systems for β-lactam antibiotics: Synthesis and properties of some dihydropyridine and dihydroiosquinoline derivatives of benzylpenicillin . J. Med. Chem. 1989 , 32 , 1774 – 1781 ; (b) Sheha , M. M. ; El-Koussi , N. A. ; Farag , H. H. Brain Delivery of HIV Protease Inhibitors . Archiv Pharm. 2003 , 336 , 47 – 52 ; (c) Mahmoud , S. ; Aboul-Fadl , T. ; Sheha , M. M. ; Farag , H. H. ; Mouhamed , A. M. I. 1, 2-Dihydroisoquinoline-N-acetic acid derivatives as new carriers for specific brain delivery I: Synthesis and estimation of oxidation kinetics using multivariate calibration method . Archiv Pharm. 2003 , 336 , 573 – 584 ; (d) Prokai , L. ; Prokai-Tatrai , K. ; Bodor , N. Targeting drugs to the brain by redox chemical delivery systems . Med. Res. Rev. 2000 , 20 , 367 – 416 .
   PubMed Web of Science ®Google Scholar
• Lukevics , E. ; Segal , I. ; Zablotskaya , A. ; Germane , S. Synthesis and neurotropic activity of novel quinoline derivatives. Molecules 1997, 2, 180–185.
   Web of Science ®Google Scholar
• (a) Maryanoff , B. E. ; McComsey , D. F. ; Gardocki , J. F. ; Shank , R. P. ; Costanzo , M. J. ; Nortey , S. O. ; Schneider , C. R. ; Setler , P. E. Pyrroloisoquinoline antidepressants, 2: In-depth exploration of structure-activity relationships . J. Med. Chem. 1987 , 30 , 1433 – 1454 ; (b) Sorgi , K. L. ; Maryanoff , C. A. ; McComsey , D. F. ; Graden , D. W. ; Maryanoff , B. E. Asymmetric induction in an enammonium–iminium rearrangement: Mechanistic insight via NMR, deuterium labeling, and reaction rate studies: Application to the stereoselective synthesis of pyrroloisoquinoline antidepressants . J. Am. Chem. Soc. 1990 , 112 , 3567 – 3579 .
   PubMed Web of Science ®Google Scholar
• (a) Tietze , L. F. ; Rackelmann , N. ; Müller , I. Enantioselective total syntheses of the ipecacuanha alkaloid emetine, the alangium alkaloid tubulosine, and a novel benzoquinolizidine alkaloid by using a domino process chemistry . Chem. Eur. J. 2004 , 10 , 2722 – 2731 ; (b) Knjlker , H. J. ; Agarwal , S. Total synthesis of the antitumor active pyrrolo[2,1-a]isoquinoline alkaloid (±)-crispine A . Tetrahedron Lett. 2005 , 46 , 1173 – 1175 ; (c) Scott , J. D. ; Williams , R. M. Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics . Chem. Rev. 2002 , 102 , 1669 – 1730 .
   PubMed Web of Science ®Google Scholar
• Harris , J. D. ; Pope , W. J. CXXII—Isoquinoline and the isoquinoline-reds . J. Chem. Soc. 1922 , 121 , 1029 .
   Google Scholar
• Katritsky , A. R. ; Rees , C. W. ; Scriven , E. F. (Eds.) . Comprehensive Heterocyclic Chemistry II: A Review of the Literature 1982–1995 ; Elsevier : Tarrytown , NY , 1996 , vol. 5 .
   Google Scholar
• (a) Jayaraman , M. ; Fox , B. M. ; Hollingshead , M. ; Koblhagen , G. ; Pommier , Y. ; Cushman , M. Synthesis of new dihydroindeno[1,2-c]isoquinoline and indenoisoquinolinium chloride topoisomerase I inhibitors having high in vivo anticancer activity in the hollow fiber animal model . J. Med. Chem. 2002 , 45 , 242 – 249 ; (b) Cushman , M. ; Jayaraman , M. ; Vroman , J. A. ; Fukunaga , A. K. ; Fox , B. M. ; Koblhagen , G. ; Strumberg , D. ; Pommier , Y. Synthesis of new indeno[1,2-c]isoquinolines: Cytotoxic non-camptothecin topoisomerase I inhibitors . J. Med. Chem. 2000 , 43 , 3688 – 3698 .
   PubMedGoogle Scholar
• (a) Reimann , E. ; Erdle , W. ; Weigl , C. ; Polborn , K. Protoberberine aus Reissert-Verbindungen, 6. Mitt.: Diastereoselektive Synthese und relative Konfiguration von 2-Benzoyl-1-cyano-1-(1-phenylalkyl)-1,2-dihydroisochinolinen . Monatsh. Chem. 1999 , 130 , 313 ; (b) Warrener , R. N. ; Liu , L. ; Russell , R. A. ; Tiekink , E. R. T. The Synthesis of 13-spiro-substituted protoberberines via the tandem addition–cyclisation reaction of 3-methoxyphthalide anions to 3,4-dihydroisoquinolines . Synlett 1998 , 4 , 387 ; (c) Warrener , R. N. ; Liu , L. ; Russell , R. A. A concise, regio- and stereoselective route to fluorinated protoberberines via tandem addition-cyclisation reactions of phthalide anions with 3,4-dihydroisoquinolines . Tetrahedron 1998 , 54 , 7485 – 7496 ; (d) Vicente , T. ; Dominguez , E. ; Villa , M. J. A facile access to benzocphenanthridines via 4-functionalized 3-arylisoquinolines . Heterocycles 1998 , 48 , 243 – 248 .
   Google Scholar
• Kaldor , I. ; Feldman , P. L. ; Mook , R. A. ; Ray , J. A. ; Samano , V. ; Sefler , A. M. ; Thompson , J. B. ; Travis , B. R. ; Boros , E. E. Stereocontrolled synthesis of cis-dibenzoquinolizine chlorofumarates: Curare-like agents of ultrashort duration . J. Org. Chem. 2001 , 66 , 3495 – 3501 .
   Google Scholar
• (a) Snow , R. J. ; Cardozo , M. G. ; Morwick , T. M. ; Busacca , C. A. ; Dong , Y. ; Eckner , R. J. ; Jacober , S. ; Jakes , S. ; Kapadia , S. ; Lukas , S. ; Panzenbeck , M. ; Peet , G. W. ; Peterson , J. D. ; Prokopowicz , A. S. ; Sellati , R. ; Tolbert , R. M. ; Tschantz , M. A. ; Moss , N. Discovery of 2-phenylamino-imidazo[4,5-h]isoquinolin-9-ones: A new class of inhibitors of lack kinase. J. Med. Chem. 2002, 45, 3394–3405; (b) Wells , G. J. ; Tao , M. ; Josef , K. A. ; Bibovsky , R. 1,2-Benzothiazine 1,1-dioxide P(2)–P(3) peptide mimetic aldehyde calpain I inhibitors. J. Med. Chem. 2001, 44, 3488–3503.
   PubMed Web of Science ®Google Scholar
• (a) Kozekov , I. D. ; Koleva , R. I. ; Palamareva , M. D. New trans/cis tetrahydroisoquinolines, 1-trans-2-benzyl-3-91-methyl-1H-pyriol-2-yl)-4-substituted-1,2,3,4-tetrahydroisoquinolin-1-ones, and corresponding tetrahydroisoquinolines . J. Heterocyclic Chem. 2002 , 39 , 229 ; (b) Yu , N. ; Poulain , R. ; Gesquiere , J. C. A one-pot synthesis of tetra-hydroisoquinolonic acids from aldehydes and amines in trimethylorthoformate . Synlett 2000 , 355 ; (c) Xu , X. Y. ; Qin , G. W. ; Xu , R. S. ; Zhu , X. Z. Total synthesis of decumbenine B . Tetrahedron 1998 , 54 , 14179 – 14188 ; (d) Banik , B. K. ; Raju , V. S. ; Manhas , M. S. ; Bose , A. K. Tetracyclic isoquinolones and quinazolones via aryl radical cyclizations . Heterocycles 1998 , 47 , 639 – 642 ; (e) Yu , N. ; Bourel , L. ; Deprez , B. ; Gesquiere , J. C. Lewis acid-induced reaction of homophthalic anhydride with imines: A convenient synthesis of trans-isoquinolonic acids . Tetrahedron Lett. 1998 , 39 , 829 – 832 ; (f) Heaney , H. ; Taha , M. O. A concise route to tetrahydro-phenanthridinones and functionalised isoquinolones . Synlett 1996 , 820 .
   Web of Science ®Google Scholar
• Mahmoud , M. R. ; El-Shahawi , M. M. ; Farahat , S. E. Novel isocoumarin and isoquinoline derivatives . J. Chem. Res. 2008 , 86 – 88 .
   Google Scholar
• Mahmoud , M. R. ; El-Shahawi , M. M. ; Farahat , S. E. Novel 1H-2-benzopyran-1-one and 2,3-benzodiazepin-1-one derivatives . J. Chem. Res. 2008 , 59 – 60 .
   Google Scholar
• Mackay , S. ; Gilmore , C. J. ; Edwards , C. ; Stewart , N. ; Shankland , K. Maxus computer program for the solution and refinement of crystal structures ; Bruker Nonius : The Netherlands , Mac Science: Japan, and the University of Glasgow . 1999 .
   Google Scholar
• Altomare , A. ; Cascarano , G. ; Giacovazzo , C. ; Guagliardi , A. ; Burla , M. C. ; Polidori , G. ; Camalli , M. SIR92, a program for automatic solution of crystal structures by direct methods . J. Appl. Cryst. 1994 , 27 , 435 .
   Web of Science ®Google Scholar
• Johnson , C. K. ORTEP II, a fortran thermal–ellipsoid plot program (Report ORNL-5138) ; Oak Ridge National Laboratory : Oak Ridge , TN , 1976 .
   Google Scholar