Synthesis, Photochemical Synthesis and Antitumor Evaluation of Novel Derivatives of Thieno [3',2' : 4,5]thieno [2,3-c] quinolones

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概要

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• The novel derivatives of thieno[3',2':4,5]thieno[2,3-c]quinolones 6a, 6b, 7, 10a and 10b were synthesized in multistep synthesis starting from thiophene-3-carboxaldehyde and malonic acid reacting in aldol condensation or from 3-bromothiophenes or methyl 4-bromothiophene-2-carboxylate reacting in Heck reaction. They resulted in corresponding substituted thienylacrylic acids 3a-c, which were cyclized into thieno[2,3-c]thiophene-2-car-bonyl chlorides 4a-c and converted into thieno[2,3-c]thiophene-2-carboxamides 5a-d. Prepared carboxamides were photochemically dehydrohalogenated into corresponding substituted thieno[3',2' :4,5]thieno[2,3-c]-quinolones 6a-d. Compound 7 was prepared from 6d by alkylation with N-[3-(dimethylamino)propyl]chloride hydrochloride in the presence of NaH. Compounds 10a and 10b were prepared from 6c in the multistep synthesis over acid 8 and acid chloride 9. Compounds 6a, 6b, 7, 10a and 10b were found to exert cytostatic activities against malignant cell lines: pancreatic carcinoma (MiaPaCa2), breast carcinoma (MCF7), cervical carcinoma (HeLa), laryngeal carcinoma (Hep2), colon carcinoma (CaCo-2), melanoma (HBL), and human fibroblast cell lines (WI-38). The compound 6b, which bears the 3-dimethylaminopropyl substituent on quinolone nitrogen and methoxycarbonyl substituent on position 9, exhibiedt marked antitumor activity. On the contrary, compound 7, which also bears the 3-dimethylaminopropyl substituent on the quinolone nitrogen but anilido substituent on position 9, exhibited less antitumor activity than the others.

• 公益社団法人日本薬学会の論文
• 2002-05-01

著者

• Karminski‐zamola G

  Univ. Zagreb Zagreb Hrv

• Slade Neda

  Division Of Molecular Medicine Ruder Boskovic Institute

• DOGANKORUZNJAK Jasna

  Department of Organic Chemistry, Faculty of Chemical Engineering and Technology University of Zagreb

• ZAMOLA Branimir

  Department of Biochemical Engineering, Faculty of Food and Biotechnology, University of Zagreb

• PAVELIC Kresimir

  Division of Molecular Medicine, Ruder Boskovic Institute

• KARMINSKI-ZAMOLA Grace

  Department of Organic Chemistry, Faculty of Chemical Engineering and Technology University of Zagreb

• Zamola B

  Univ. Zagreb Zagreb Hrv

• Zamola Branimir

  Department Of Biochemical Engineering Faculty Of Food Technology And Biotechnology University Of Zag

• Pavelic Kresimir

  Division Of Molecular Medicine Ruder Boskovic Institute

• Dogankoruznjak Jasna

  Department Of Organic Chemistry Faculty Of Chemical Engineering And Technology University Of Zagreb

• Karminski-zamola Grace

  Department Of Organic Chemistry Faculty Of Chemical Engineering And Technology University Of Zagreb

関連論文

• Synthesis, Photochemical Synthesis and Antitumor Evaluation of Novel Derivatives of Thieno [3',2' : 4,5]thieno [2,3-c] quinolones
• New Amidino-benzimidazolyl Derivatives of Tylosin and Desmycosin

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