Synthesis of N-(2-(Methylamino)ethyl) Derivatives of 2H-Phthalazin-1-ones

REFERENCES

• Kuroda , S. ; Takamura , F. ; Tenda , Y. ; Itani , H. ; Tomishima , Y. ; Akahane , A. ; Sakane , K. Design, synthesis, and biological evaluation of a novel series of potent, orally active adenosine A1 receptor antagonists with high blood–brain barrier permeability . Chem. Pharm. Bull. 2001 , 49 , 988 – 998 .
   PubMed Web of Science ®Google Scholar
• Dal Piaz , V. ; Cianini , G. ; Turco , G. ; Giovannoni , M.P. ; Mideli , M. ; Pirisino , R. ; Perretti , M. 5-Acyl-6-aryl-4-nitro-3(2H)-pyridazinones and related 4-amino compounds: synthesis and pharmacological evaluation . J. Pharm. Sci. 1991 , 80 , 341 – 348 .
   PubMed Web of Science ®Google Scholar
• Dal Piaz , V. ; Giovannoni , M. P. ; Ciciani , G. ; Barlocco , D. ; Giardina , G. ; Petrone , G. ; Clarke , G. D. 4,5-Functionalized 6-phenyl-3(2H)-pyridazinones: synthesis and evaluation of antinociceptive activity . Eur. J. Med. Chem. 1996 , 31 , 65 – 70 .
   Web of Science ®Google Scholar
• Takaya , M. ; Sato , M. ; Terashima , H. ; Tanizawa , H. ; Maki , Y. A new nonsteroidal analgesic-antiinflammatory agent: Synthesis and activity of 4-ethoxy-2-methyl-5-morpholino-3(2H)-pyridazinone and related compounds . J. Med. Chem. 1979 , 22 , 53 – 58 .
   PubMed Web of Science ®Google Scholar
• Montesano , F. ; Barlocco , D. ; Dal Piaz , V. ; Leonardi , A. ; Poggesi , E. ; Fanelli , F. ; De Benedetti , P. G. Isoxazolo-[3,4-d]-pyridazin-7-(6H)-ones and their corresponding 4,5-disubstituted-3-(2H)-pyridazinone analogues as new substrates for α1-adrenoceptor selective antagonists: synthesis, modeling, and binding studies . Bioorg. Med. Chem. 1998 , 6 , 925 – 935 .
   PubMed Web of Science ®Google Scholar
• (a) Strappaghetti , G. ; Brodi , C. ; Giannaccini , G. ; Betti , L. New 4-(4-methyl-phenyl)phthalazin-1(2H)-one derivatives and their effects on α1-receptors . Bioorg. Med. Chem. Lett. 2006 , 16 , 2575 – 2579 (b) Betti , L. ; Botta , M. ; Corelli , F. ; Floridi , M. ; Fossa , P. ; Giannaccini , G. ; Manetti , F. ; Strappaghetti , G. ; Corsano , S. α1-Adrenoceptor antagonists: Rational design, synthesis and biological evaluation of new trazodone-like compounds . Bioorg. Med. Chem. Lett. 2002 , 12 , 437 – 440 .
   PubMed Web of Science ®Google Scholar
• Tsubaki , K. ; Taniguchi , K. ; Tabuchi , S. ; Okitsu , O. ; Hattori , K. ; Seki , J. ; Sakanea , K. ; Tanaka , H. A novel pyridazinone derivative as a nonprostanoid PGI2 agonist . Bioorg. Med. Chem. Lett. 2000 , 10 , 2787 – 2790 .
   PubMed Web of Science ®Google Scholar
• Rohet , F. , Rubat , C. ; Coudert , P. ; Albuisson , E. ; Couquelet , J. Synthesis and trazodone-like analgesic activity of 4-phenyl-6-aryl-2-[3-(4-arylpiperazin-1-yl)propyl]pyriazin-3-ones . Chem. Pharm. Bull. 1996 , 44 , 980 – 986 .
   PubMed Web of Science ®Google Scholar
• Gokce , M. ; Dogruer , D. ; Fethi Sahin , M. Synthesis and antinociceptive activity of 6-substituted-3-pyridazinone derivatives . Farmaco 2001 , 56 , 233 – 237 .
   PubMedGoogle Scholar
• Dal Piaz , V. ; Vergelli , C. ; Giovannoni , M. P. ; Scheideler , M. A. ; Petrone , G. ; Zaratin , P. 4-Amino-3(2H)-pyridazinones bearing arylpiperazinylalkyl groups and related compounds: Synthesis and antinociceptive activity . Farmaco 2003 , 58 , 1063 – 1071 .
   PubMedGoogle Scholar
• Pakulska , W. ; Malinowski , Z. ; Szcześniak , A. K. ; Czarnecka , E. ; Epsztajn , J. Synthesis and pharmacological evaluation of N-(dimethylamino)ethyl derivatives of benzo- and pyridopyridazinones . Arch. Pharm. Chem. Life Sci. 2009 , 342 , 41 – 47 .
   PubMed Web of Science ®Google Scholar
• Epsztajn , J. ; Malinowski , Z. ; Urbaniak , P. ; Andrijewski , G. A practical approach for preparation of 2-[(dialkylamino)-methyl]-4-aryl-2H-phthalazin-1-ones via Mannich reaction of 4-aryl-2H-phthalazin-1-ones . Synth. Commun. 2005 , 35 , 179 – 192 .
   Web of Science ®Google Scholar
• Brzeziński , J. ; Epsztajn , J. ; Bakalarz , A. D. ; Łajszczak , A. ; Malinowski , Z. Application of organolithium and related reagents in synthesis, part 22: Synthetic strategies based on ortho-aromatic metallation: A concise regiospecific conversion of benzoic acids into the 4-pyridyl-2H-phthalazin-1-ones . Synth. Commun. 1999 , 29 , 457 – 473 .
   Web of Science ®Google Scholar
• Epsztajn , J. ; Malinowski , Z. ; Brzeziński , J. ; Karzatka , M. Application of organolithium and related reagents in synthesis, part 26: Synthetic strategies based on directed ortho- metalation: Synthesis of 4-methyl-2H-phthalazin-1-ones . Synthesis 2001 , 14 , 2085 – 2090 .
   Google Scholar
• Strappaghetti , G. ; Corsano , S. ; Barbaro , R. ; Lucacchini , A. ; Giannaccini , G. ; Betti , L. Adenosine receptors: Synthesis, structure–activity relationships, and biological activity of new 6-amino purine derivatives. Eur. J. Med. Chem. 1998, 33, 501–508.
   Web of Science ®Google Scholar
• Epsztajn , J. ; Czarnecka , E. ; Szcześniak , A. ; Pakulska , W. ; Malinowski , Z. Benzo- and pyridopyridazinones with analgesic and antiinflammatory activity. WO Patent Application 051504 A1, 2009 .
   Google Scholar
• Bencini , A. ; Bianchi , A. ; Garcia-Espana , E. ; Fusi , V. ; Micheloni , M ; Paoletti , P. ; Ramirez , J. A. ; Rodriguez A. ; Valtancolia , B. Synthesis and protonation behaviour of the macrocyclic ligand 1,4,7,13-tetramethyl-1,4,7,10,13,16-hexaazacyclooctadecane and of its bicyclic derivative 4,7,10,17,23-pentamethyl-1,4,7,10,13,17,23-heptaazabicyclo[11.7.5]-pentacosane: A potentiometric and 1H and 13C NMR study . J. Chem. Soc. Perkin Trans. 2 1992 , 1059 – 1065 .
   Google Scholar
• Herold , P. ; Mah , R. ; Tschinke , V. ; Behnke , D. ; Marti , Ch. ; Jotterand , N. ; Stutz , S. Substituted piperidines as therapeutic compounds. European Patent Application EP 1987834 A2, 2008 .
   Google Scholar
• Basel , Y. ; Hassner , A. Di-tert-butyl dicarbonate and 4-(dimethylamino)pyridine revisited: Their reactions with amines and alcohols . J. Org. Chem. 2000 , 65 , 6368 – 6380 .
   PubMed Web of Science ®Google Scholar
• Yadav , V. K. ; Ganesh Babu , K. Reactions on a solid surface: A simple, economical, and efficient acylation of alcohols and amines over Al2O3 . J. Org. Chem. 2004 , 69 , 577 – 580 .
   PubMed Web of Science ®Google Scholar
• Knaack , M. ; Fleischhauer , I. ; Charpentier , P. ; Emig , P. ; Kutcher , B. ; Mueller , A. Ringumlagerungen bei der Mitsunobu-alkylierung von phthalazinonen und indazololen . Liebigs Ann. 1996 , 9 , 1477 – 1482 .
   Google Scholar
• Procopiou , P. A. ; Browning , C. ; Buckley , J. M. ; Clark , K. L. ; Fechner , L. ; Gore , P. M. ; Hancock , A. P. ; Hodgson , S. T. ; Holmes , D. S. ; Kranz , M. ; Looker , B. E. ; Morriss , K. M. L. ; Parton , D. L. ; Russell , L. J. ; Slack , R. J. ; Sollis , S. L. ; Vile , S. ; Watts , C. J. The discovery of phthalazinone-based human H1 and H3 single-ligand antagonists suitable for intranasal administration for the treatment of allergic rhinitis . J. Med. Chem. 2011 , 54 , 2183 – 2195 .
   PubMed Web of Science ®Google Scholar
• Kim , Y. J. ; Park , Y. ; Park , K. K. Rotational isomers of N-alkyl-N-(o-acylphenyl)acetamides . J. Mol. Struct. 2006 , 783 , 61 – 65 .
   Web of Science ®Google Scholar