SYNTHESIS OF ANTIMALARIAL 3-(2-HYDROXYETHYL)-2-METHYL-1,10-PHENANTHROLINE-4-OL FROM 8-AMINOQUINOLINE

https://doi.org/10.22146/ijc.21858

Ruslin Hadanu(1*), Chairil Anwar(2), Jumina Jumina(3), Iqmal Tahir(4), Mustofa Mustofa(5)

(1) Chemistry Department, Pattimura University, Ambon
(2) Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta 55281
(3) Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta 55281
(4) Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta 55281
(5) Faculty of Medicine, Universitas Gadjah Mada, Yogyakarta 55281
(*) Corresponding Author

Abstract


It has been conducted the synthesis of 3-(2-hydroxyethyl)-2-methyl-1,10-phenanthroline-4-ol was carried out from 8-aminoquinoline which are expected to posses antimalarial activity. The experiment perfomed consisted of two steps i.e (1) reaction of 8-aminoquinoline with 2-acetyl-butyrolactone and (2) cyclization of the resulted 3-[1-(quinolin-8-ylamino)-ethylidene]-4,5-dihydro-furan-2-one. The reaction of 8-aminoquinoline with 2-acetyl-butyrolactone was performed in toluene at reflux for 6 hours in the presence of p-toluensulfonic acid as catalyst. This reaction gave 3-[1-(quinolin-8-ilamino)-etiliden]-4,5-dihidro-furan-2-on in 60.6% yield. The cyclization of 3-[1-(quinoline-8-ylamino)-ethyliden]-4,5-dihydro-furan-2-one was conducted in cloroform at reflux for 4 hours in the presence of H2SO4 as catalyst and also tween 80 as transfer phase catalyst to give 3-(2-hydroxy-ethyl)-2-methyl-1,10-phenanthroline-4-ol in 76.2% yield. Identification of the products were carried out by means of infra red (IR) spectroscopy, proton nuclear magnetic resonance (1H-NMR) spectroscopy, and mass spectroscopy (MS).


Keywords


antimalarial; 8-aminoquinoline; cyclization; 1,10-phenantroline

Full Text:

Full Text Pdf


References

[1] Wilson and Gisvold, 1982, Kimia Farmasi dan Medisinal Organik, Edisi ketujuh (diterjemahkan Fatah, A.M), Gadjah Mada University Press, Yogyakarta

[2] Humberstone, A.J., Porter, C.J., and Charman, W.N. 1996, J. Pharm. Sci. 85, 5, 525-529.

[3] Yapi, A. D., Mustofa, Valentin, A., Chavignon, O., and Teulade, J. C., J. Chem. Pharm. Bull, 48, 12, 1886 -1889.

[4] Mustofa, Yapi, A. D., Valentin, A., and Tahir, I, 2003, Berkala Umum Kedokteran, 35, 2, 67-64.

[5] Mustofa, Tahir I., and Jumina, 2002, Indo. J. Chem, 2, 2, 91-96



DOI: https://doi.org/10.22146/ijc.21858

Article Metrics

Abstract views : 1362 | views : 2506


Copyright (c) 2010 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 

Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web Analytics View The Statistics of Indones. J. Chem.