Synthesis, antibacterial, and antifungal activities of biolabile (E)-1-(4-morpholinophenyl)-3-aryl-prop-2-en-1-ones

Medicinal Chemistry Research

Volumn 18, Issue 5, 2009, Pages 341-350

  Gopalakrishnan, M ^a   Thanusu, J ^a   Kanagarajan, V ^a   Govindaraju, R ^a  

^a ANNAMALAI UNIVERSITY   (India)

Author keywords

(E) 1 (4 morpholinophenyl) 3 aryl prop 2 en 1 ones; Antibacterial activity; Antifungal activity; NaHSO4 Al2O3; Synthesis

Indexed keywords

1 (4 MORPHOLINOPHENYL) 3 (3 NITROPHENYL)PROP 2 EN 1 ONE; 1 (4 MORPHOLINOPHENYL) 3 4 TOLYL PROP 2 EN 1 ONE; 1 (4 MORPHOLINOPHENYL) 3 PHENYL PROP 2 EN 1 ONE; 3 (4 CHLOROPHENYL) 1 (4 MORPHOLINOPHENYL)PROP 2 EN 1 ONE; 3 (4 FLUOROPHENYL) 1 (4 MORPHOLINOPHENYL)PROP 2 EN 1 ONE; 3 (4 METHOXYPHENYL) 1 (4 MORPHOLINOPHENYL)PROP 2 EN 1 ONE; ANTIFUNGAL AGENT; FLUCONAZOLE; MORPHOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FLAVUS; BACTERIAL STRAIN; BETA HEMOLYTIC STREPTOCOCCUS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; FUNGAL STRAIN; INFRARED SPECTROSCOPY; KLEBSIELLA PNEUMONIAE; MASS SPECTROMETRY; MELTING POINT; MICROSPORUM; MUCOR; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS; REACTION TIME; RHIZOPUS; STAPHYLOCOCCUS AUREUS;

EID: 67349194279     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00044-008-9131-2     Document Type: Article

References (24)

1. R Agarwal KC Chaudhary VS Misra 1984 Substituted morpholines compounds possessing central nervous system activities J Chem Soc Pak 6 308 310
2. Avramova P, Danchev N, Buyukliev R, Bogoslovova T (1998) Synthesis, toxicological, and pharmacological assessment of derivatives of 2-aryl-4-(3-arylpropyl)morpholines. Arch Pharm (Weinheim) 331:342-346. doi:10.1002/(SICI)1521-4184(199811)331:11<342::AID-ARDP342>3.0.CO;2-6
3. G Combes PH Vassort F Winternitz 1970 Structure de la rubranine, chalcone isolee de l'Aniba rosaeodora ducke Tetrahedron 26 5981 5992 10.1016/0040-4020(70)80036-9
4. J Deli T Lorand D Szabo A Foldesi 1984 Cyclic and alicyclic ketones as precursors for pyrimidine synthesis Pharmaz 39 539 542
5. Dorn CP, Hale JJ, MacCoss M, Mills SG (1997) Morpholine compounds are prodrugs useful as tachykinin receptor antagonists. US patent 5691336:82. Chem Abstr 128:48231
6. Fisher MH, Wyvratt MJ (1991) Morpholine derivatives compositions and uses. US Patent 5077290:10. Chem Abstr 116:214513
7. M Gopalakrishnan P Sureshkumar J Thanusu V Kanagarajan 2005 Organic synthesis in solid media. Aluminium supported sodium hydrogen sulfate as an effective and reusable catalyst for 'one-pot' synthesis of amides from ketones in dry media under microwave irradiation Lett Org Chem 2 444 446 10.2174/1570178054405904
8. M Gopalakrishnan P Sureshkumar J Thanusu V Kanagarajan 2007 Design, 'one-pot' synthesis, characterization, antibacterial and antifungal activities of novel 6-aryl-1,2,4,5-tetrazinan-3-thiones in dry media J Sulfur Chem 28 383 392 10.1080/17415990701415650
9. M Gopalakrishnan P Sureshkumar J Thanusu V Kanagarajan R Govindaraju G Jayasri 2007 A convenient one-pot synthesis and in vitro microbiological evaluation of novel 2,7-diaryl-[1,4]-diazepan-5-ones J Enzyme Inhib Med Chem 22 709 715 10.1080/14756360701270618 (Pubitemid 350215074)
10. M Gopalakrishnan J Thanusu V Kanagarajan 2007 Synthesis and biological evaluation of 5,7-diaryl-4,4-dimethyl-4,5,6,7-tetrahydropyridino[3,4-d]-1,2,3- thiadiazoles Med Chem Res 16 392 401 10.1007/s00044-007-9051-6
11. JJ Hale SG Mills M [tmp] MacCross CP Dorn PE Finke RJ Budhu 2000 Phosphorylated morpholine acetal human neurokinin-1 receptor antagonists as water-soluble prodrugs J Med Chem 43 1234 1237 10.1021/jm990617v (Pubitemid 30173749)
12. Hester JB, Nidy EG, Perricone SC, Poel TJ (2001) Derivatives of 4-phenyl morpholines possessing antimicrobial activity. PCT Int Appl W00144188
13. L Lafen 1970 Pharmacophoric activity of some substituted propenones Chem Abstr 7 120342s
14. XC Li D Ferreira MR Jacob Q Zhang SI Khan HN ElSohly DG Nagle TJ Smillie IA Khan LA Walker AM Clark 2004 Antifungal cyclopentenediones from Piper coruscans J Am Chem Soc 126 6872 6873 10.1021/ja048081c (Pubitemid 38855378)
15. 13C NMR spectra of N-substituted morpholines Eur Pat Appl EP 334146 28 Chem Abstr 112:178999
16. 13C NMR spectra of N-substituted morpholines Ger Offen DE 3729285 17 Chem Abstr 111:134172
17. JC Maruzella AH Percival 1958 Antibacterial activity of essential oil vapors J Am Pharm Assoc 47 471 473 (Pubitemid 27445806)
18. SS Misra RS Tewari 1973 Chalcones as agrochemical agents J Indian Chem Soc 50 68 70
19. VS Misra S Singh R Agarwal KC Chaudhary 1981 Substituted morpholines derivatives as potent anti-inflammators J Chem Soc Pak 3 209 211
20. S Mukherjee V Kumar AK Prasad HG Raj ME Bracke CE Olsen 2001 Synthetic and biological activity evaluation studies on novel 1,3-diarylpropenones Bioorg Med Chem 9 337 345 10.1016/S0968-0896(00)00249-2 (Pubitemid 32244032)
21. RS Varma R Prakash CR Prasad 1986 N-functionalised morpholine derivatives as CNS stimulants J Chem Soc Pak 8 117 119
22. RS Varma R Prakash MM Khan A Ali 1986 4-phenyl morpholines as potent antimicrobial agents Indian Drugs 23 345 349
23. MG Verma VR Sharma AK Saxena TN Bhalla JN Sinha KP Bhargava 1984 Antiinflammatory activity of amino acyl benzoates Pharmacol Res Commun 16 9 13 10.1016/S0031-6989(84)80100-9 (Pubitemid 14177531)
24. S Won C Liu L Tsao J Weng H Ko J Wang 2005 Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents Eur J Med Chem 40 103 107 10.1016/j.ejmech.2004.09.006 (Pubitemid 40092383)