SUCCINIMIDES: SYNTHESIS, REACTION AND BIOLOGICAL ACTIVITY
Keywords:
Succinimides, Biological activity, Dichlorodiformyl, Cyclic imidesAbstract
This review summarizes the synthetic methods, reactions and biological application of important pharmacological succinimides and summarizes recent developments in their derivatives such as dichlorodiformyl, Schiff base, chalcone, Barbier type allylation etc. Over the last years. The biological activity of the cyclic imides is also briefly discussed. Formation of succinimidyl radicals and Single crystal studies on this type of compounds are beyond the scope of this review and will not be discussed. Nor referenced.
Downloads
References
Hargreaves MK, Pritchard JG, Dave HR. Cyclic carboxylic monoimides. Chem Rev 1970;70(4):439-69.
Aeberli P, Gogerty JH, Houlihan WJ, Iorio LC. Synthesis and central nervous system depressant activity of some bicyclic amides. J Med Chem 1976;19(3):436-8.
Correa R, Filho VC, Rosa PW, Pereira CI, Schlemper V, Nunes RJ. Synthesis of new succinimides and sulphonated derivatives with analgesic action in mice. Pharm Pharmacol Comm 1997;3(2):67-71.
Hall IH, Wong OT, Scovill JP. The cytotoxicity of N-pyridinyl and N-quinolinyl substituted derivatives of phthalimide and succinimide. Biomed Pharmacother 1995;49(5):251-8.
Crider AM, Kolczynski TM, Yates KM. Synthesis and anticancer activity of nitrosourea derivatives of phensuximide. J Med Chem 1980;23(3):324-6.
Rich DH, Gardner JH. Synthesis of the cytostatic cyclic tetrapeptide, chlamydocin. Tetrahedron Lett 1983;24(48):5305-8.
Kaczorowski GJ, McManus OB, Priest BT, Garcia ML. Ion channels as drug targets: The next GPCRs. J Gen Physiol 2008;131(5):399-405.
Filho VC, Nunes RJ, Calixto JB, Yunes RA. Inhibition of Guinea-pig ileum contraction by phyllanthimide analogues: Structure-activity relationships. Pharm Pharmacol Comm 1995;1(8):399-401.
Johnston TP, Piper JR, Stringfellow CR. Terminal dicarboximido analogs of S-2-. omega.-aminoalkylamino) ethyl dihydrogen phosphorothioates and related compounds as potential antiradiation agents. 2. Succinimides, glutarimides, and cis-1,2-cyclohexanedicarboximides. J Med Chem 1971;14(4):350-4.
Musso DL, Cochran FR, Kelley JL, McLean EW, Selph JL, Rigdon GC, et al. Design and synthesis of (E)-2-(4,6-Difluoro-1-indanylidene)acetamide, a potent, centrally acting muscle relaxant with antiinflammatory and analgesic activity. J Med Chem 2003;46(3):399-408.
Pennington FC, Guercio PA, Solomons I A. The antihypertensive effect of a selective central muscarinic cholinergic antagonist: N-(4-diethylamino-2-butynyl)-succinimide. J Am Chem Soc 1953;75(9):2261-1.
Zentz F, Valla A, Guillou RL, Labia R, Mathot AG, Sirot D. Synthesis and antimicrobial activities of N-substituted imides. Il Farmaco 2002;57(5):421-6.
Hazra BG, Pore VS, Day SK, Datta S, Darokar MP, Saikia D, et al. Bile acid amides derived from chiral amino alcohols: novel antimicrobials and antifungals. Bioorg Med Chem Lett 2004;14(3):773-7.
Kornet MJ, Crider AM, Magarian EO. Potential long-acting anticonvulsants. J Med Chem 1977;20(3):405-9.
Isaka M, Prathumpai W, Wongsa P, Tanticharoen M. Hirsutellone F, a dimer of antitubercular alkaloids from the seed fungus Trichoderma species BCC 7579. Org Lett 2006;8(13):2815-7.
Rajput AP, Rajput SS. Preparation and antimicrobial activity of 2,5-dichloro-3,4-diformyl-(N-substituted phenyl)Pyroles. Asian J Chem 2007;19(6):4939-41.
Raddy PY, Kondu S, Toru T, Ueno Y. Lewis Acid and Hexamethyldisilazane promoted efficient synthesis of N-alkyl-and N-arylimide derivatives. J Org Chem 1997;62(8):2652-4.
Shetgiri NP, Nayak BK. Synthesis and antimicrobial activity of some succinimides. Indian J Chem B Org 2005;44B:1933-6.
Martin SF, Limberakis C. Diprotection of primary amines as N-substituted-2,5-bis[(triisopropylsilyl)oxy]pyrroles (BIPSOP). Tetrahedron Lett 1997;38(15):2617-20.
Zentz F, Labia R, Sirot D, Faure O, Grllot R, Valla A. Syntheses, in vitro antibacterial and antifungal activities of a series of N-alkyl, 1,4-dithiines. Il Farmaco 2005;60(11-12):944-7.
Chandrasekhar S, Thakhi M, Uma G. Solvent free N-alkyl and N-arylimides preparation from anhydrides catalyzed by TaCl5-Silica gel. Tetrahedron Lett 1997;38(46):8089-92.
Red-Moghadam K, Kheyrkhan L. Solid-phase synthesis of N-aryl succinimides. Synthetic Comm 2009;39(12):2108-15.
Walker MA. A high yielding synthesis of N-alkyl maleimides using a novel modification of the mitsunobu reaction. J Org Chem 1995;60(16):5352-5.
Upadhyay SK, Pingali SRK, Jursic BS. Comparison of microwave-assisted and conventional preparation of cyclic imides. Tetrahedron Lett 2010;51(17):2215-7.
Alpman SF, Koldas S, Giray ES. Clean and efficient synthesis of N-aryl and N-alkyl succinimides in sub-critical water. Eur J Med Chem 2003;60(3):8099-104.
Dabiri M, Salehi P, Baghbanzadeh M, Shakouri M, Otiokhesh S, Ekrami T, et al. Efficient and eco-friendly synthesis of dihydropyrimidinones, bis(indolyl)methanes, and N-alkyl and N-arylimides in ionic liquids. J Iran Chem Soc 2007;4(4):393-401.
Xie Y, Hou R, Wang H, Kang I, Chen L. An efficient protocol for the synthesis of N-alkyl-and N-arylimides using the lewis acidic ionic liquid Choline Chloride.2ZnCl2. J Chin Chem Soc 2009;56(4):839-42.
Shinde SB, Tekale SU, Kauthale SS, Deshamukh SU, Marathe RP, Nawale RB, et al. A facile and efficient synthesis of N-aryl imides using trifluoroacetic acid. Int J Ind Chem 2011;2(2):112-6.
Langade MM. Efficient one pot synthesis of N-alkyl and N-aryl imides. Der Pharm Chem 2011;3(2):283-6.
Kumar R, Jain S, Jain N, Singh M. Synthesis and biological evaluation of some novel analogue of p-Hydroxyaniline. Acta Pharm Sci 2008;50:183-8.
Marulashiddaiah R, Kalkhambar RG, Kulkarni MV. Synthesis and biological evaluation of cyclic imides with coumarins and azacoumarins. Open J Med Chem 2012;2(3):89-97.
Katigawa O, Izawa H, Sato K, Dobashi A, Taguchi T. Optically active axially chiral anilide and maleimide derivatives as new chiral reagents: synthesis and application to asymmetric Diels−Alder reaction. J Org Chem 1998;63(8):2634-40.
Brahma S, Ray JK. Halovinyl aldehydes: useful tools in organic synthesis. Tetrahedron 2008;64(13):2883-96.
Bennamane N, Kaoua R, Hammal L, Nedjar-Kolli B. Synthesis of new amino-1,5-benzodiazepine and benzotriazole derivatives from dimedone. Org Commun 2008;1(3):62-8.
Kivitko IY, Panfilova EA. Chloroformylation of N-succinimide and synthesis of enamines-pyrrolone derivative, Khim Geterotsikl Soedin 1973;4:507-10.
Schulte KE, Reisch J, Stoess U. Chloroformylation of α-Pyrrolones. Angew Chem Int Ed 1965;4(12):1081-2.
Ranadive VB, Samant SD. Reactions of amines with N-hydroxy-, N-(2,3-epoxypropoxy) succinimide and –naphthalimide. Indian J Chem B Org 1995;34B(2):102-6.
Kutto K. Synthesis of N-Vinylsuccinamides. Bull Chem Soc Jap 1962;35(10):1736-7.
Collado MI, Lete E, Sotomayor N, Villa MJ. Synthesis of 5-arylpyrrolo[2,1-a]isoquinolin-3(2H)-ones from N-phenethylsuccinimides and organolithium reagents. Tetrahedron 1995;51(16):4701-10.
Pearson RG, Songstad J. Application of the principle of hard and soft acids and bases to organic chemistry. J Am Chem Soc 1967;89(8):1827-36.
Sekhiya M, Terao Y. Reactions of N-(N', N'-Dialkylaminomethyl) amides with Grignard Reagents. Chem Pharm Bull 1970;18(5):947-56.
Sekhiya M, Terao Y, Zasshi Y. Reactions of potassium pthalimide with Grignard reagents. Chem Pharm Bull 1968;88(8):1085-9.
Rocco VP, Danishefsky SJ. Substrate specificity in enzymatically mediated trans acetylation reactions of calicheamicinone intermediates. Tetrahedron Lett 1991;32(46):6671-4.
Zaleska BJ. A new convenient route of synthesis of 1H-Pyrrole-2,3-Dione derivatives. J Prakt Chemie 1988;330(5):841-6.
Bryant LRB, Coyle JD. Photochemical hydrogen abstraction and cyclisation in maleimide derivatives. Tetrahedron Lett 1983;24(17):1841-4.
Guzman A, Romero M, Muchowski JM. Vilsmeier-Haack reaction with succinamidals: a convenient synthesis of 5-chloropyrrole-2-carboxaldehydes and 5-chloropyrrole-2,4-dicarboxaldehydesl. Can J Chem 1990;68(5):791-4.
El-Saied AA, Mohamed AA, Atif AE. A convenient synthesis of some Pyrazolinone and Pyrazole derivatives. J Chin Chem Soc 2004;51(5A):983-90.
Rajput SS. Synthesis and characterization of bis-heteroyclic derivatives of 1-(3-Chlorophenyl)-Pyrrolidine-2, 5-Dione. IJAPBC 2012;1(2):242-6.