Synthesis and antioxidant properties of some indole ethylamine derivatives as melatonin analogs

Pharmazie

Volumn 60, Issue 9, 2005, Pages 643-647

  Ates Alagoz, Z ^a   Buyukbingol, Z ^a   Buyukbingol, Erdem ^a  

^a ANKARA UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANT; BUTYLCRESOL; ETHYLAMINE; INDOLE DERIVATIVE; MELATONIN; MELATONIN DERIVATIVE;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; LIPID PEROXIDATION; LIVER MICROSOME; MALE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ACYLATION; ANIMALS; ANTIOXIDANTS; ETHYLAMINES; INDICATORS AND REAGENTS; INDOLES; LIPID PEROXIDATION; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MASS SPECTROMETRY; MELATONIN; MICROSOMES, LIVER; RATS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TRYPTAMINES;

EID: 25144450451     PISSN: 00317144     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (21)

1. Arendt J, Boberly AA, Franey C, Wright J (1984) The effects of chronic, small doses of melatonin given in the late afternoon on fatigue in man. Neurosci Lett 45: 317.
2. Avery D, Lenz M, Landis C (1998) Guidelines for prescribing melatonin. Ann Med 30: 122.
3. Bishayee S, Balasubramanian AS (1971) Lipid peroxide formation in rat brain. J Neurochem 18: 909-920.
4. Buyukbingol E, Suzen S, Klopman G (1994) Studies on the synthesis and structure-activity relationships of 5-(3′-indolal)-2-thio-hydantoin derivatives as aldose reductase enzyme inhibitors. Farmaco 49: 443-447.
5. Depreux P, Lesieur D, Mansour HA, Morgan P, Howell HE, Renard P, Caignard D-H, Pfeiffer B, Delagrange P, Guardiola B, Yous S, Demarque A, Adam G, Andrieux J (1994) Synthesis and structure-activity relationships of novel naphthalenic and bioisosteric related amidic derivatives as melatonin receptor ligands. J Med Chem 37: 3231-3239.
6. Faust R, Garratt P, Jones R, Yeh Li-K (2000) Mapping the melatonin receptor. 6. Melatonin agonist and antagonists derived from 6H-iso-indolo[2,1-a] indoles, 5,6-dihydroindolo[2,1-a]isoquinolines and 6,7-dihydro-5H-benzo[c] azepino [2,1-a]indoles. J Med Chem 43: 1050-1061.
7. Guardiola-Lemaitre B (1991) Development of melatonin analogues. Adv Pineal Res 351-353.
8. Iscan M, Arinc E, Vural N, Iscan MY (1984) In vivo effects of 3-methylcholanthrene, phenobarbital, pyrethrum and 2.4.5-T isooctylester on liver, lung and kidney microsomal mixed-function oxidase system of guinea-pig; a comparative study. Comp Biochem Physiol 77C: 177-190.
9. James PN, Synder HR (1930) Indole-3-aldehyde. Org Synthesis 539-541.
10. Jones MP, Melan MA, Witt-Enderby PA (2000) Melatonin decreases cell proliferation and transformation in a melatonin receptor-dependent manner. Cancer Lett 151: 133.
11. Lerner AB, Case JD, Takahaski Y, Lee TH, Mori W (1958) Isolation of melatonin the pineal gland factor that lightens melanocytes. J Am Chem Soc 80: 2587.
12. Li PK, Witt-Enderby PA (2000) Melatonin receptors as potential targets for drug discovery. Drugs Future 25: 945.
13. Lowry OH, Rosebrough NJ, Farr AL, Randall RT (1951) Protein measurement with the folin phenol reagent. J Biol Chem, 193: 265-275.
14. Mor M, Rivara S, Silva C, Bordi F, Plazzi PV, Spadoni G, Diamantini G, Balsamini C, Tarzia G (1998) Melatonin receptor ligands: synthesis of new melatonin derivatives and comprehensive comparative molecular field analysis (CoMFA) study. J Med Chem 41: 3831-3844.
15. Poeggler B, Reiter RJ, Tan DX, Chen LD, Manchester LG (1993) Melatonin hydroxy radical-mediated oxidative damage and aging: a hypothesis. J Pineal Res 14: 151.
16. Seltzer A, Viswanathan M, Sazwedra JM (1992) Melatonin-binding sites in brain and caudal arteries of the female rat during the estrous cycle and after estrogen administration. Endocrinology 30: 1890.
17. Shabica AC, Howe EE, Zeigler JB, Tishler M (1946) Improved synthesis of indole-3-aldehyde. J Am Chem Soc 68: 1156-1157.
18. Spadoni G, Balsamini C, Diamantini G, Di-Giacoma B, Tarzia G, Mor M, Plazzi PV, Rivara S, Lucini V, Nonno R, Pannacci M, Franschini F, Stankov BM (1997) Conformationally restrained melatonin analogues: synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity and molecular modeling study. J Med Chem 40: 1990-2002.
19. Wills ED (1966) Mechanism of lipid peroxide formation in animal tissues. Biochem J 99: 667-676.
20. Wills ED (1969) Lipid peroxide formation in microsomes. Relationship of hidroxylation to lipid peroxide formation. Biochem J 113: 333-341.
21. Witt-Enderby PA, Li PK (2000) Melatonin receptors and ligands. Vitam Horm 58: 321.