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    In vitro antiproliferative/cytotoxic activity of 2,3 '-biindole against various cancer cell lines
    (Tubitak Scientific & Technical Research Council Turkey, 2015) Okten, Salih; Erenler, Ramazan; Koprulu, Tugba Kul; Tekin, Saban
    2,3'-Biindole (2) was synthesized via bromination of indole (1) with molecular bromine and underwent simultaneous dimerization. Antiproliferative and cytotoxic activity of 2 was investigated in vitro on C6 (rat brain tumor), HeLa (human cervix carcinoma), and HT29 (human colon carcinoma) cells lines by using BrdU cell proliferation ELISA and lactate dehydrogenase (LDH) assays. In contrast to 5-fluorouracil (5-FU), 2,3'-biindole (2) significantly inhibited proliferation of HeLa and HT29 cell lines. According to LDH assay, the cytotoxicity of compound 2 was low on HT29 cell lines and high on HeLa and C6 cell lines. Moreover, 2 did not cause any DNA laddering on the DNA of tested cells; therefore, it is suggested that the mechanism of action of this compound may not involve apoptosis. In addition, 2 inhibited relaxation of supercoiled plasmid DNA by topoisomerase activity. Results of the present study indicates that biindole (2) may have promising anticancer and antitopoisomerase potential with an unknown mechanism of action.
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    Simple and convenient preparation of novel 6,8-disubstituted quinoline derivatives and their promising anticancer activities
    (Scientific Technical Research Council Turkey-Tubitak, 2013) Okten, Salih; Cakmak, Osman; Erenler, Ramazan; Yuce, Onem; Tekin, Saban
    A short and easy route is described for 6,8-disubstituted derivatives of quinoline and 1,2,3,4-tetrahydroquinoline from 6,8-dibromoquinolines 2 and 7 by various substitution reactions. While copper-promoted substitution of 6,8-dibromide 2 produced monomethoxides 3 and 4, a prolonged reaction time mainly afforded dimethoxide 6 instead of 5, whose aromatization with DDQ and substitution reaction of dibromide 7 with NaOMe in the presence of CuI also gave rise to dimethoxide 6. Several 6,8-disubstituted quinolines were obtained by treatment of 6,8-dibromoquinoline (7) with n-BuLi followed by trapping with an electrophile [Si(Me)(3)Cl, S-2(Me)(2), and DMF]. Furthermore, 7 was also converted to mono and dicyano derivatives. The anticancer activities of compounds 2, 7, 6, 12, 13, 15, and 16 against HeLa, HT29, and C6 tumor cell lines were tested, and 6,8-dibromo-1,2,3,4-tetrahydroquinoline (2) and 6,8-dimethoxyquinoline (6) showed significant anticancer activities against the tumor cell lines.
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    Theoretical Study of Synthesis of 1,3-dibromonaphthanlene
    (Chem Soc Pakistan, 2018) Gokalp, Faik; Erenler, Ramazan
    Naphthalene derivatives have been attracted the interest for synthesis of natural products having biological properties. Elimination reaction of tetrabromonaphthalene (1) resulted in the formation of 1,3-dibromonaphthalene (2) rather than 1,4-dibomonaphthalene (3). This phenomenon was explained by theoretical investigation. The physical properties and optimization of tetrabromonaphthalene (1), 1,3-dibromonaphthalene (2) and 1,4-dibromonaphthalene (3) were evaluated by B3lyp/6-31+G(d,p) method. Due to the HOMO-LUMO gap of 1,3-dibromonaphthalene (2) was higher than that of the 1,4-dibomonaphthalene (3), the formation of 1,3-dibromonaphthalene (2) was favorable. Moreover, Higher dipole moment of 1,3-dibromonaphthalene (2) than 1,4-dibomonaphthalene (3) supported the synthesis of 1,3-dibromonaphthalene (2) properly.