Melatonin analogue new indole hydrazide/hydrazone derivatives with antioxidant behavior: Synthesis and structure–activity relationships

References

• DV Ratnam, DD Ankola, V Bhardwaj, DK Sahana, and MN Kumar. (2006). Role of antioxidants in prophylaxis and therapy: A pharmaceutical perspective. J Control Release 113:189–207.
   PubMed Web of Science ®Google Scholar
• S Suzen. (2006). Recent developments of melatonin related antioxidant compounds. Chem High Throughput Screen 9:409–419.
   PubMed Web of Science ®Google Scholar
• S Suzen. Antioxidant activities of synthetic indole derivatives and possible activity mechanisms. In: MTH Khan, editor. Topics in Heterocyclic Chemistry., V11 Berlin/Heidelberg: Springer; (2007). p 145–178.
   Google Scholar
• S Dominici, L Pieri, A Paolicchi, V De Tata, F Zunino, and A Pompella. (2004). Endogenous oxidative stress induces distinct redox forms of tumor necrosis factor receptor-1 in melanoma cells. Ann NY Acad Sci 1030:62–68.
   PubMedGoogle Scholar
• B Malpaux, M Migaud, H Tricoire, and PJ Chemineau. (2001). Biology of mammalian photoperiodism and the critical role of the pineal gland and melatonin. Biol Rhythms 16:336–347.
   PubMed Web of Science ®Google Scholar
• JM Guerrero, and RJ Reiter. (2002). Melatonin-immune system relationships. Curr Top Med Chem 2:167–179.
   PubMedGoogle Scholar
• Z Ates-Alagoz, T Coban, and S Suzen. (2005). A comparative study: Evaluation of antioxidant activity of melatonin and some indole derivatives. Med Chem Res 14 (3):169–179.
   Google Scholar
• S Suzen, and E Buyukbingol. (2000). Anti-cancer activity studies of indolalthiohydantoin (PIT) on certain cancer cell lines. Farmaco 55 (4):246–248.
   PubMedGoogle Scholar
• S Suzen, and E Buyukbingol. (1998). Evaluation of anti-HIV activity of 5-(2-phenyl-3′-indolal)-2-thiohydantoin. Il Farmaco 53:525–527.
   PubMedGoogle Scholar
• P Sreejith, RS Beyo, L Divya, AS Vijayasree, M Manju, and OV Oommen. (2007). Triiodothyronine and melatonin influence antioxidant defense mechanism in a teleost Anabas testudineus (Bloch): in vitro study. Indian J Biochem Biophys 44 (3):164–168.
   PubMedGoogle Scholar
• H Okutan, C Savas, and N Delibas. (2004). The antioxidant effect of melatonin in lung injury after aortic occlusion-reperfusion. Interact Cardiovasc Thorac Surg 3 (3):519–522.
   PubMedGoogle Scholar
• PJ Leaden, and A Catala. (2007). Melatonin and N-acetyl serotonin inhibit selectively enzymatic and non-enzymatic lipid peroxidation of rat liver microsomes. Prostaglandins Leukot Essent Fatty Acids 77 (1):29–35.
   PubMedGoogle Scholar
• DS Maharaj, BD Glass, and S Daya. (2007). Melatonin: New places in therapy. Biosci Rep 27 (6):299–320.
   PubMedGoogle Scholar
• DX Tan, LD Chen, B Poeggeler, LC Manchester, and RJ Reiter. (1993). Melatonin: A potent endogenous hydroxyl radical scavenger. Endocr J 1:57–60.
   Google Scholar
• P Depreux, D Lesieur, HA Mansour, P Morgan, HE Howell, P Renard, DH Caignard, B Pfeiffer, P Delagrange, B Guardiola, S Yous, A Demarque, G Adam, and JJ Andrieux. (1994). Synthesis and structure-activity relationships of novel naphthalenic and bioisosteric related amidic derivatives as melatonin receptor ligands. Med Chem 37:3231–3239.
   Google Scholar
• M Mor, C Silva, F Vacondio, PV Plazzi, S Bertoni, G Spadoni, G Diamantini, A Bedini, G Tarzia, M Zusso, D Franceschini, and P Giusti. (2004). Indole-based analogs of melatonin: in vitro antioxidant and cytoprotective activities. J Pineal Res 36:95–102.
   PubMed Web of Science ®Google Scholar
• RJ Reiter. (2000). Melatonin: Lowering the high price of free radicals. News Physiol Sci 15:246–250.
   PubMedGoogle Scholar
• DX Tan, RJ Reiter, LC Manchester, MT Yan, M El-sawi, RM Sainz, JC Mayo, R Kohen, M Allegra, and R Hardeland. (2002). Chemical and physical properties and potential mechanisms: Melatonin as a broad spectrum antioxidant and free radical scavenger. Curr Top Med Chem 2:181–197.
   PubMedGoogle Scholar
• S Suzen, P Bozkaya, T Coban, and D Nebioglu. (2006). Investigation of the in vitro antioxidant behaviour of some 2-phenylindole derivatives: Discussion on possible antioxidant mechanisms and comparison with melatonin. J Enzyme Inhib Med Chem 21 (4):405–411.
   PubMed Web of Science ®Google Scholar
• P Bozkaya, B Dogan, S Suzen, D Nebioglu, and SA Ozkan. (2006). Determination and investigation of electrochemical behaviour of 2-phenylindole derivatives: Discussion on possible mechanistic pathways. Can J Anal Sci Spec 51 (3):125–139.
   Google Scholar
• S Suzen, T Demircigil, E Buyukbingol, and SA Ozkan. (2003). Electroanalitical Evaluation and Determination of 5-(3′-indolyl)-2-thiohydantoin derivatives by voltammetric studies: Possible relevance to in vitro metabolism. New J Chem 27:1007–1011.
   Web of Science ®Google Scholar
• S Suzen, Z Ateş-Alagöz, T Demircigil, and SA Ozkan. (2001). Synthesis and analytical evaluation by voltammetric studies of some new indole-3-propionamide derivatives. Farmaco 56:835–840.
   PubMedGoogle Scholar
• S Härtter, M Grözinger, H Weigmann, J Röschke, and C Hiemke. (2000). Increased bioavailability of oral melatonin after fluvoxamine coadministration. Clin Pharmacol Ther 67 (1):1–6.
   PubMedGoogle Scholar
• B Guardiola-Lemaitre. (1997). Toxicology of melatonin. J Biol Rhythms 12 (6):697–706.
   PubMedGoogle Scholar
• M Kidwai, N Negi, and SD Gupta. (1994). Synthesis and antifertility activity of 1,5-diaryl-3-(3′-indolyl)formazans. Chem Pharm Bull (Tokyo) 42 (11):2363–2364.
   PubMedGoogle Scholar
• RL Clevenger. (1962). Aldehyde hydrazone derivatives in cancer chemotherapy. Cllenlotherapy J Med Pharm Chem 5:1367–1371.
   Google Scholar
• A Alemany, PM Bernabe, AE Fernandez, M Lora-Tamayo, and LO Nieto. (1966). Potential psychotropic agents. I. Synthesis of 1-(2-indolylcarbonyl)-2-alkylhydrazines, 1-(3-indolylcarbonyl)-2-alkylhydrazines and 1-(3-indolylacetyl)-2-alkylhydrazines, and measurement, in vitro, of their monoamine oxidase inhibitory activity. Bull Soc Chim Fr 8:2486–2497.
   PubMedGoogle Scholar
• FD Popp. (1984). Potential anticonvulsants. VIII. Some hydrazones of indole-3-carboxaldehyde. J Heterocycl Chem 21:617.
   Google Scholar
• DL Rector, GA Conder, and SD Folz. (1987). Preparation of antihelmintic acylhydrazones, method of use and compositions. PCT Int Appl 57. CODEN: PIXXD2 WO 8706133 A1 19871022 CAN 108:101381 AN 1988:101381 caplus
   Google Scholar
• NP Buu-Hoi, and G Saint-Ruf. (1967). Thermal decomposition of aromatic aldizines. Applications to preparative chemistry. Bull Soc Chim Fr 955.
   Google Scholar
• B Kocyigit-Kaymakcioglu, E Oruc, S Unsalan, F Kandemirli, N Shvets, S Rollas, and D Anatholy. (2006). Synthesis and characterization of novel hydrazide-hydrazones and the study of their structure-antituberculosis activity. Eu J Med Chem 41 (11):1253–1261.
   PubMedGoogle Scholar
• MS Blois. (1958). Antioxidant determinations by the use of a free radical. Nature 181:1199–1200.
   Web of Science ®Google Scholar
• ZJ Cheng, SC Kuo, SC Chan, FN Ko, and CM Teng. (1998). Antioxidant properties of butein isolated from Dalbergia odorifera. Biochim Biophys Acta 1392:291–299.
   PubMed Web of Science ®Google Scholar
• NT Huong, K Matsumoto, R Kasai, K Yamasaki, and H Watanabe. (1998). In vitro antioxidant activity of Vietnamese ginseng saponin and its components. Biol Pharm Bull 21:978–981.
   PubMed Web of Science ®Google Scholar
• M Mihara, M Uchiyama, and K Fukuzawa. (1980). Thiobarbituric acid value on fresh homogenate of rat as a parameter of lipid peroxidation in aging, CCl4 intoxication, and vitamin E deficiency. Biochem Med 23:302–311.
   PubMed Web of Science ®Google Scholar
• B Poeggeler, S Thuermann, A Dose, M Schoenke, S Burkhardt, and RJ Hardeland. (2002). Melatonin's unique radical scavenging properties—roles of its functional substituents as revealed by a comparison with its structural analogs. Pineal Res 33:20–30.
   PubMed Web of Science ®Google Scholar
• B Poeggeler, MA Pappolla, R Hardeland, A Rassoulpour, S Hodgkins, P Guidetti, and R Schwarcz. (1999). Indole-3-propionate: A potent hydroxyl radical scavenger in rat brain. Brain Res 815:382–388.
   PubMed Web of Science ®Google Scholar
• M Allegra, RJ Reiter, DX Tan, C Gentile, L Tesoriere, and MA Livrea. (2003). The chemistry of melatonin's interaction with reactive species. J Pineal Res 34:1–10.
   PubMed Web of Science ®Google Scholar
• RJ Reiter. (1998). Cytoprotective properties of melatonin: Presumed association with oxidative damage and aging. Nutrition 14 (9):691–696.
   PubMedGoogle Scholar
• SH Benabadji, R Wen, JB Zheng, XC Dong, and SG Yuan. (2004). Acta Pharmacol Sin 25 (5):666.
   PubMedGoogle Scholar