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Journal

2005 | 3 | 4 | 683-704

Article title

Synthesis, structural and conformational study of selected N-substituted phthalimides

Content

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EN

Abstracts

EN
This paper synthesizes N-substituted phthalimides derived from nitrogen heterocycles as potential 5-HT4 ligands by using the Mitsunobu reaction. Conformational studies of some of the new compounds have been conducted using 1H and 13C-NMR spectroscopy. Proton and carbon resonances were achieved through the application of one-dimensional selective NOE, two-dimensional NMR techniques-homonuclear COSY-45, NOESY and heteronuclear 1H-13C HMQC correlated spectroscopy- and double resonance experiments. The crystal structure of compound 1 was determined by X-ray diffraction.

Publisher

Journal

Year

Volume

3

Issue

4

Pages

683-704

Physical description

Dates

published
1 - 12 - 2005
online
1 - 12 - 2005

Contributors

author
  • Dpto. Química Orgánica, Universidad de Alcalá, Ctra. Madrid-Barcelona Km. 33.600, 28871, Alcalá de Henares, Madrid, Spain
  • Dpto. Química Orgánica, Universidad de Alcalá, Ctra. Madrid-Barcelona Km. 33.600, 28871, Alcalá de Henares, Madrid, Spain
  • Dpto. Química Orgánica, Universidad de Alcalá, Ctra. Madrid-Barcelona Km. 33.600, 28871, Alcalá de Henares, Madrid, Spain
  • Universidad Complutense de Madrid, 28006, Madrid, Spain
  • Universidad Complutense de Madrid, 28006, Madrid, Spain
author
  • Instituto de Química Fisica Rocasolano, (CSIC), 28006, Madrid, Spain

References

  • [1] M.K. Hargreaves, J.G. Pritchard and H.R. Dave: “Cyclic Carboxylic Monimimides”, Chem. Rev., Vol. 70, (1970), pp. 439–469. http://dx.doi.org/10.1021/cr60266a001[Crossref]
  • [2] R. Antunes, H. Batista, R.M. Srivastava, G. Tomas, C.C. Araujo, R.L. Lango H. Magallaes, M.B.C. Leao and A.C. Pavao: “Synthesis, Characterization and Interaction Mechanism of New Oxadiazolo-phthalimides as Peripheral Analgesics. IV”, J. Mol. Struct., Vol. 660, (2003), pp. 1–13. http://dx.doi.org/10.1016/S0022-2860(03)00418-6[Crossref]
  • [3] V.L.M. Sena, R.M. Srivastava, R.O. Silva and V.L.M. Lima: “Synthesis and Hypolipidemic Activity of N-substituted Phthalimides. Part IV”, Il Farmaco, Vol. 58, (2003), pp. 1283–1288. http://dx.doi.org/10.1016/S0014-827X(03)00185-X[Crossref]
  • [4] L.M. Lima, P. Castro, A.L. Machado, C.A.M., Fraga, C. Lugnier, V.L. Gonçalves de Moraes and E.J. Barreiro: “Synthesis and Anti-Inflammatory Activity of Phthalimide Derivatives, Designed as New Thalidomide Analogues”, Bioorg. Med. Chem. Lett., Vol. 10, (2002), pp. 3067–3073. http://dx.doi.org/10.1016/S0968-0896(02)00152-9[Crossref]
  • [5] X. Collin, J. M. Robert, G. Wielgosz, G. Le Baut, C. Bobin-Dubigeon, N. Grimaud and J.Y. Petit: “New Anti-inflammatory N-pyridinyl(alkyl)phthalimides Acting as Tumour Necrosis Factor-α Production Inhibitors”, Eur. J. Med. Chem., Vol. 36, (2001), pp. 639–649. http://dx.doi.org/10.1016/S0223-5234(01)01254-5[Crossref]
  • [6] L.M. Lima, F.C.F. De Brito, S.D. De Souza, A.L.P. Miranda, C.R. Rodriguez, C.A.M. Fraga and E.J. Barreiro: “Novel Phthalimide Derivatives, Designed as Leukotriene D4 Receptor Antagonists”, Bioorg. Med. Chem. Lett., Vol. 12, (2002), pp. 1533–1535. http://dx.doi.org/10.1016/S0960-894X(02)00203-2[Crossref]
  • [7] U. Holazabe and E. Heller: “A New Synthetic Route to Compounds of the AFDX-type with Affinity to Muscarinic M2-Receptor”, Tetrahedron, Vol. 59, (2002), pp. 781–787.
  • [8] M.A. Walker: “The Mitsunobu Reaction: A Novel Method for the Synthesis of Bifunctional MaleimideLinkers”, Tetrahedron Lett., Vol. 35, (1994), pp. 665–668. http://dx.doi.org/10.1016/S0040-4039(00)75785-6[Crossref]
  • [9] M. Ohkubo, T. Nishimura, H. Jona, T. Honma and H. Morishima: “Practical Synthesis of Indolopyrrolocarbazoles”, Tetrahedron, Vol. 52. (1996), pp. 8099–8112. http://dx.doi.org/10.1016/0040-4020(96)00372-9[Crossref]
  • [10] A.R. Chamberlain and J.Y.L. Chung: “Enantioselective Synthesis of Seven Pyrrolizidine Diols from Single Precursor”, J. Org. Chem., Vol. 50, (1985), pp. 4425–4431. http://dx.doi.org/10.1021/jo00223a002[Crossref]
  • [11] J. Behniafar and A. Banihashemi: “Synthesis and Characterization of New Soluble and Termally Stable Aromatic Poly(amide-imide)s based on N-3,5-bis(N-trimellitoyl)phenyl]phthalimide”, Eur. Polym. J., Vol. 40, (2004), pp. 1409–1415. http://dx.doi.org/10.1016/j.eurpolymj.2004.02.006[Crossref]
  • [12] J. García, J. Vilarrasa, X. Bordas and A. Banaszek: “New Synthetic “tricks” Onepot Preparation of N-substituted Phthalimides from Azides and Phthalic Anhidride”, Tetrahedron Lett., Vol. 27 (1986), pp. 639–640. http://dx.doi.org/10.1016/S0040-4039(00)84061-7[Crossref]
  • [13] T. Aubert, M. Farnier and R. Guilard: “Reactivity of Iminophosphoranes Towards Some Symmetrical Dicarbonyl Dichlorides: Syntheses and Mechanisms”, Tetrahedron, Vol. 47, (1991), pp. 53–60. http://dx.doi.org/10.1016/0040-4020(91)80007-O[Crossref]
  • [14] T. Vidal, A. Petit, A. Loupy and R.N. Gedye: “Re-examination of Microwave-Induced Synthesis of Phthalimides”, Tetrahedron, Vol. 56, (2000), pp. 5473–5478. http://dx.doi.org/10.1016/S0040-4020(00)00445-2[Crossref]
  • [15] S. Chandrasekhar, M. Takhi and G. Uma: “Solvent Free N-Alkyl and N-Arylimides Preparation from Anhydrides Catalyzed by TaCl5-Silica Gel”, Tetrahedron Lett., Vol. 38 (1997), pp. 8089–8092. http://dx.doi.org/10.1016/S0040-4039(97)10116-2[Crossref]
  • [16] A. Kamal, E. Laxman, N. Laxman and N.V. Rao: “Efficient One-Pot Synthesis of N-substituted Phthalimides/Naphthalimides from Azides and Anhidrides by Iodo trimethylsilane”, Tetrahedron Lett., Vol. 39, (1998), pp. 8733–8734. http://dx.doi.org/10.1016/S0040-4039(98)01937-6[Crossref]
  • [17] M.S. Gibson and R.W. Bradshaw: “The Gabriel Synthesis of Primary Amines”, Angew. Chem. Internat. Edit., Vol. 7, (1968), pp. 919–930. http://dx.doi.org/10.1002/anie.196809191[Crossref]
  • [18] J.C. Sheehan and W.A. Bolhofer: “An Improved Procedure for the Condensation of Potassium Phthalimide with Organic Halides”, J. Am. Chem. Soc., Vol. 72, (1950), pp. 2786–2788. http://dx.doi.org/10.1021/ja01162a527[Crossref]
  • [19] D. Landini and F. Rolla: “A Convenient Synthesis of N-Alkylphthalimides in a Solid-Liquid Two-Phase System in the Presence of Phase-Transfer Catalysts”, Synthesis, (1976), pp. 389–391.
  • [20] O. MItsunobu: “The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products”, Synthesis, (1981), pp. 1–28.
  • [21] D.L. Hughes: “The Mitsunobu Reaction”, Org. Reactions, Vol. 42, (1992), pp. 335–656.
  • [22] Z. Li, Z. Zhou, L. Wang, Q. Zhou and C. Tang: “Enantioselective Reaction of Secondary Alcohols with Phthalimide in the Presence of a Chiral Tri-coordinate Phosphorus Reagent in Mitsunobu Reaction”, Tetrahedron: Asymmetr., Vol. 13, (2002), pp. 145–148. http://dx.doi.org/10.1016/S0957-4166(02)00054-X[Crossref]
  • [23] D.Q. Yuan, C. Yang, T. Fukuda and K. Fujita: “An Efficient Strategy for the Modification of α-Cyclodextrin: Direct Conversion of One or Two Adjacent 6-OHs to Phthalimides”, Tetrahedron Lett., Vol. 44, (2003), pp. 565–568. http://dx.doi.org/10.1016/S0040-4039(02)02503-0[Crossref]
  • [24] T. Suzuki, N. Imanishi, H. Itahana, S. Watanuki, K. Miyata, M. Ohta, H. Nakahara, Y. Yamagiwa and T. Mase: “Novel 5-Hidroxytryptamine 4 (5-HT4) Receptor Agonists. Synthesis and Gastroprokinetic Activity of 4-Amino-N-[2-(1-aminocycloalkan-1-yl)ethyl]-5-chloro-2-methoxybenzamides”, Chem. Pharm. Bull., Vol. 46, (1998), pp. 1116–1124. [Crossref]
  • [25] G.L. Grunewald, V.M. Paradkar, B. Pazhenchevsky, M.A. Pleiss, D.J. Sall, W.L. Seibel and T.J. Reitz: “Synthesis of Conformationally Defined Analogues of Norfenfluramine. A Highly Stereospecific Synthesis of Amines from Alcohols in the Benzobicyclo[2.2.1]heptene System”, J. Org. Chem., Vol. 48, (1983), pp. 2321–2327. http://dx.doi.org/10.1021/jo00162a005[Crossref]
  • [26] A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M.C. Burla, G. Polidori and M. Camalli: “SIR92”, J. Appl. Cryst., Vol. 27, (1994) pp. 435. http://dx.doi.org/10.1107/S002188989400021X[Crossref]
  • [27] J.M. Stewart, F.A. Kundell and J.C. Baldwin: The XRAY80 System, Computer Science Center, University of Maryland, College Park, Maryland, 1980.
  • [28] G.M. Sheldrick: SHELXL-93, Program for the Refinement of Crystal Structures, University of Gottingen, Germany, 1993.
  • [29] M. Nardelli: “PARST”, Comput. Chem., Vol. 7, (1983), pp. 95–98. http://dx.doi.org/10.1016/0097-8485(83)85001-3[Crossref]
  • [30] A.H. Beckett, N.J. Harper, A.D.J. Balon and T.H.E. Watts: “Stereochemistry of the Reduction of Tropine”, Tetrahedron, Vol. 6, (1959), pp. 319–330. http://dx.doi.org/10.1016/0040-4020(59)80012-0[Crossref]
  • [31] L.F. Werner: “Analogs of Atropine and Homatropine”, J. Am. Chem. Soc., Vol. 40, (1918), pp. 669–674. http://dx.doi.org/10.1021/ja02237a010[Crossref]
  • [32] I. Iriepa, A. Lorente, M.S. Arias, E. Galvez, F. Florencio and J. Sanz-Aparicio: “Synthesis and Structural Study of 9-(2′-Hydroxyethyl)-9-azabicyclo[3.3.1]nonan-3α-ol”, J. Mol. Struct., Vol. 174, (1988), pp. 273–280. http://dx.doi.org/10.1016/0022-2860(88)80170-4[Crossref]
  • [33] M.J. Fernandez, R. Huertas, M.S. Toledano, E. Galvez, F.H. Cano, I. Fonseca and J. Sanz-Aparicio: “Synthesis and Structural Study of Esters Derived from 2-Methyl-2-azabicyclo[2.2.2]octan-6-syn(anti)-ols by NMR Spectroscopy and X-ray Crystallography”, J. Phys. Org. Chem., Vol. 12, (1999), pp. 69–77. http://dx.doi.org/10.1002/(SICI)1099-1395(199901)12:1<69::AID-POC92>3.0.CO;2-0[Crossref]
  • [34] G.R. Krow, R. Rodebaugh, M. Grippi and R. Carmosin: “Dioscorone. Regioselective Oxymercuriation of 2-Azabicyclo[2.2.2]oct-5-ene”, Synth. Commun., Vol. 2, (1972), pp. 211–214.
  • [35] E. Matzat: “Die Kristallstruktur des Phthalimids (Kladnoit)”, Acta Cryst. B, Vol. 28, (1972), pp. 415–418. http://dx.doi.org/10.1107/S056774087200250X[Crossref]
  • [36] W. Seik: “Crystal Structure of Tributyltin (IV) N-methyl-N-phenylditiocarbamylacetate, (n-C4H9)3SnOC(O)CH2SC(S)N(CH3)(C6H5)”, Acta Cryst. C, Vol. 48, (1992), pp. 1694–1695. http://dx.doi.org/10.1107/S0108270192000957[Crossref]
  • [37] A. Albert and F.H. Cano: CONTACTOS. A Program for Systematic Study of Aromatic Rings Interactions, Instituto Rocasolano, CSIC, Madrid, 1987.
  • [38] M.S. Arias, E. Galvez, M.L. Izquierdo and C. Burgos: “Conformational Study of N-substituted 8-Azabicyclo[3.2.1]octan-3-ones”, J. Mol. Struct., Vol. 147, (1986), pp. 381–388. http://dx.doi.org/10.1016/0022-2860(86)80392-1[Crossref]
  • [39] M.L. Izquierdo, E. Galvez, C. Burgos, M.S. Arias, J. Sanz-Aparicio, I. Fonseca and J. Bellanato: “Structural and Conformational Study of some N-substituted Benzoyl Derivatives of the 3β-Amino-3α-carbamoyl-N-8-substituted Nortropanes”, J. Mol. Struct., Vol. 147, (1993), pp. 1–10. http://dx.doi.org/10.1016/0022-2860(93)80251-P[Crossref]
  • [40] E. Galvez, M.L. Izquierdo, C. Burgos, M.S. Arias, J. Sanz-Aparićio, I. Fonseca, F. Gago, G. Baldominos, P. López and J.C. Prieto: “Synthesis and Structural, Biomedical and Pharmacological Study of 3β-Acyloxy-3α-methoxycarbonyltropane Derivatives”, J. Pharm. Sci., Vol. 82, (1993), pp. 794–798. http://dx.doi.org/10.1002/jps.2600820808[Crossref]
  • [41] J.R. Wiseman and H.O. Krabbenhoff: “Carbon-13 Nuclear Magnetic Resonance Spectroscopy in Conformational Analysis of 9-Azabicyclo[3.3.1]nonane derivatives”, J. Org. Chem., Vol. 40, (1975), pp. 3222–3224. http://dx.doi.org/10.1021/jo00910a012[Crossref]
  • [42] I. Iriepa, M.S. Arias, A. Lorente, E. Galvez, F. Florencio and J. Sanz-Aparicio: “Structural and Conformational Study of 9-(2′-Hydroxyethyl)-9-azabicyclo[3.3.1]nonan-3β-ol”, J. Mol. Struct., Vol. 192, (1989), pp. 15–27. http://dx.doi.org/10.1016/0022-2860(89)87002-4
  • [43] I. Iriepa, B. Gil-Alberdi, E. Galvez, J. Bellanato and P. Carmona: “Synthesis, Structural, Conformational and Pharmacological Study of some Carbamates Derived from 3-Methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9α-ol”, J. Mol. Struct., Vol. 406, (1997), pp. 233–240. http://dx.doi.org/10.1016/S0022-2860(96)09619-6
  • [44] I. Iriepa, B. Gil-Alberdi, E. Galvez, J. Sanz-Aparicio, I. Fonseca, A. Orjales, A. Berisa and L. Labeaga: “Synthesis, Structural, Conformational and Pharmacological Study of Esters Derived from 3-Methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9α-ol as Potential analgesics”, J. Phys. Org. Chem., Vol. 11, (1998), pp. 125–132. http://dx.doi.org/10.1002/(SICI)1099-1395(199802)11:2<125::AID-POC979>3.0.CO;2-#

Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.-psjd-doi-10_2478_BF02475197
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