A concise synthesis and the antibacterial activity of 5,6-dimethoxynaphthalene-2-carboxylic acid

Goksu S., UGUZ M. T., Ozdemir H., Secen H.

TURKISH JOURNAL OF CHEMISTRY, cilt.29, sa.2, ss.199-205, 2005 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 29 Sayı: 2
  • Basım Tarihi: 2005
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.199-205
  • Anahtar Kelimeler: naphthalene-2-carboxylic acids, 2-naphthol, bromination, haloform, antibacterial activity, HIV-1 INTEGRASE, INHIBITORS, SUBSTITUTION
  • Atatürk Üniversitesi Adresli: Evet

Özet

5,6-Dimethoxynaphthalene-2-carboxylic acid was synthesized in 7 steps and with an overall yield of 46%. Bromination of 2-naphthol, and methylation with dimethyl sulfate followed by Friedel-Crafts acylation with AcCl gave 2-acetyl-5-bromo-6-methoxynaphthalene. 2-Acetyl-5-bromo-6-methoxynaphthalene was converted to 5-bromo-6-methoxynaphthalene-2-carboxylic acid by a haloform reaction. The esterification of the acid with methanol, methoxylation with NaOCH3 in the presence of CuI and subsequent de-esterification with NaOH afforded 5,6-dimethoxynaphthalene-2-carboxylic acid. The 5-bromo6-methoxynaphthalene-2-carboxylic acid and 5,6-dimethoxynaphthalene-2-carboxylic acid were found to have in vitro antibacterial activity against some pathogenic bacteria.