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Pregled bibliografske jedinice broj: 82299

Synthesis, photochemical synthesis and antitumor evaluation of novel derivatives of thieno(3', 2':4, 5)thieno(2, 3-c)quinolones


Dogan Koružnjak, Jasna; Slade, Neda; Zamola, Branimir; Pavelić, Kresimir; Karminski-Zamola, Grace
Synthesis, photochemical synthesis and antitumor evaluation of novel derivatives of thieno(3', 2':4, 5)thieno(2, 3-c)quinolones // Chemical and Pharmaceutical Bulletin, 50 (2002), 5; 656-660 (međunarodna recenzija, članak, znanstveni)


Naslov
Synthesis, photochemical synthesis and antitumor evaluation of novel derivatives of thieno(3', 2':4, 5)thieno(2, 3-c)quinolones

Autori
Dogan Koružnjak, Jasna ; Slade, Neda ; Zamola, Branimir ; Pavelić, Kresimir ; Karminski-Zamola, Grace

Izvornik
Chemical and Pharmaceutical Bulletin (0009-2363) 50 (2002), 5; 656-660

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Quinolone; thiophene; antitumor activity; heck reaction; photocyclization; alkylation

Sažetak
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-carbonyl 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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Ustanove
Institut "Ruđer Bošković", Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE