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Pregled bibliografske jedinice broj: 82299

Časopis

Autori: Dogan Koružnjak, Jasna; Slade, Neda; Zamola, Branimir; Pavelić, Kresimir; Karminski-Zamola, Grace
Naslov: Synthesis, photochemical synthesis and antitumor evaluation of novel derivatives of thieno(3', 2':4, 5)thieno(2, 3-c)quinolones
Izvornik: Chemical and Pharmaceutical Bulletin (0009-2363) 50 (2002), 5; 656-660
Vrsta rada: članak
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.
Projekt / tema: 0098092, 0098093, 00981103, 00981104, 0125005
Izvorni jezik: ENG
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
MEDLINE
Scopus
SCI-EXP, SSCI i/ili A&HCI
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Kemija,Temeljne medicinske znanosti
URL cjelovitog teksta:
Google Scholar: Synthesis, photochemical synthesis and antitumor evaluation of novel derivatives of thieno(3', 2':4, 5)thieno(2, 3-c)quinolones



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