Synthesis and antitumor activity against HepG-2, PC-3, and HCT-116 cells of some naphthyridine and pyranopyridinecarbonitrile derivatives
- Авторлар: Mohamed S.1, Abdel-Hafez N.1, Amr A.1,2, Awad H.3
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Мекемелер:
- Applied Organic Chemistry Department
- Pharmaceutical Chemistry Department, Drug Exploration & Development Chair (DEDC), College of Pharmacy
- Department of Tanning Materials and Leather Technology
- Шығарылым: Том 87, № 6 (2017)
- Беттер: 1264-1274
- Бөлім: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/220321
- DOI: https://doi.org/10.1134/S1070363217060226
- ID: 220321
Дәйексөз келтіру
Аннотация
A series of substituted and fused heterocyclic derivatives 2–17 were synthesized using 3,5-bis(4-methoxybenzylidene)-1-propylpiperidin-4-one (1) as starting material. Treatment of 1 with malononitrile or semicarbazide afforded compounds 2 and 3, respectively. Condensation of 1 with ethyl cyanoacetate afforded naphthyridine-3-carbonitrile derivative 4, which reacted with phosphorus pentachloride and phosphoryl chloride to give chloro derivative 5. Treatment of 5 with thiosemicarbazide afforded compound 6. The reaction of 1 with malononitrile gave cyano aminopyrane derivative 7 which was condensed with pyromellitic dianhydride, phthalic anhydride, succinic anhydride, or morpholine in glacial acetic acid to obtain imide derivatives 8–11. Additionally, the reaction of 7 with aromatic aldehydes gave derivatives 12a–12c. Acetylation of 7 with acetic anhydride in boiling acetic acid gave N-acetyl derivative 13 which was cyclized to pyridine derivative 14 by refluxing in dioxane in the presence of triethylamine. Treatment of 7 with hydrazine hydrate gave pyrazolo derivative 15. Finally, the reaction of 7 with triethyl orthoformate in the presence of acetic anhydride gave formimidate 16 which was treated with hydrazine hydrate to form N-amino derivative 17. Some of the synthesized compounds were examined in vitro for their antitumor activity against HepG-2, PC-3, and HCT-116 human carcinoma cell lines using MTT assay.
Авторлар туралы
S. Mohamed
Applied Organic Chemistry Department
Хат алмасуға жауапты Автор.
Email: drsalwafahim@yahoo.com
Египет, Dokki, Cairo, 12622
N. Abdel-Hafez
Applied Organic Chemistry Department
Email: drsalwafahim@yahoo.com
Египет, Dokki, Cairo, 12622
A. Amr
Applied Organic Chemistry Department; Pharmaceutical Chemistry Department, Drug Exploration & Development Chair (DEDC), College of Pharmacy
Email: drsalwafahim@yahoo.com
Египет, Dokki, Cairo, 12622; Riyadh, 11451
H. Awad
Department of Tanning Materials and Leather Technology
Email: drsalwafahim@yahoo.com
Египет, Dokki, Cairo