Halogenation of Indoles with Copper(II) Halides: Selective Synthesis of 2‐Halo‐, 3‐Halo‐, and 2,3‐Dibromoindoles.

Tang, Shi; Li, Jin‐Heng; Xie, Ye‐Xiang; Wang, Nai‐Xing

doi:10.1002/chin.200740116

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“…In contrast to the accepted wisdom, the indole (1) nucleus has not been challenged to realize a nucleophilic substitution reaction (Yamada et al, 2003(Yamada et al, , 2012. In 1, electrophilic substitution is preferred in position 3 with almost all reagents including halogens (Tang et al, 2007), nitrate (Gribble, 2003), sulfur (Gilow et al, 1991), Friedel-Crafts acyls (Ottoni et al, 2001), and alkyls (Zhang et al, 2012). Bromination of indole poses a dimeric product (2; Figure 1); as a result, 3-haloindoles and 2-haloindoles are unstable structures (Robertson et al, 2000;Joule and Mills, 2010;Kianmehr et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

In vitro antiproliferative/cytotoxic activity of 2,3ʹ-biindole againstvarious cancer cell lines

Ökten

Erenler²,

Köprülü³

et al. 2015

Turk J Biol

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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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Section: Introductionmentioning

confidence: 99%

In vitro antiproliferative/cytotoxic activity of 2,3ʹ-biindole againstvarious cancer cell lines

Ökten

Erenler²,

Köprülü³

et al. 2015

Turk J Biol

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Halogenation of Indoles with Copper(II) Halides: Selective Synthesis of 2‐Halo‐, 3‐Halo‐, and 2,3‐Dibromoindoles.

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Cited by 1 publication

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In vitro antiproliferative/cytotoxic activity of 2,3ʹ-biindole againstvarious cancer cell lines

In vitro antiproliferative/cytotoxic activity of 2,3ʹ-biindole againstvarious cancer cell lines

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