Synthesis, Crystal Structure and Antitumour Activity of Ethyl 2-[(2-Amino-3-Cyano-4-Phenethyl-4H-Naphtho[1,2-b]Pyran-8-yl)Oxy]acetate

Ethyl 2-[(2-amino-3-cyano-4-phenethyl-4H-naphtho[1,2-b]pyran-8-yl)oxy]acetate has been synthesised by condensation of ethyl 2-chloroacetate with the hydroxy group of 2-amino-8-hydroxy-4-phenethyl-4H-naphtho[1,2-b]pyran-3-carbonitrile. The latter was prepared from cinnamaldehyde, malononitrile and na...

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Bibliographic Details
Published inJournal of chemical research Vol. 42; no. 9; pp. 486 - 489
Main Authors Liu, Ju, Shi, Jian-Tao, Hao, Xue-Chen, Liu, Yu-Tong, Ding, Shi, Wang, Yang, Chen, Ye
Format Journal Article
LanguageEnglish
Published London, England SAGE Publications 01.09.2018
Sage
Sage Publications Ltd
Subjects
Anticancer properties
Chemistry
Chemistry, Multidisciplinary
Cinnamaldehyde
Condensation
Crystal structure
Malononitrile
Naphthalene
Physical Sciences
Science & Technology
X-ray diffraction
synthesis of 4H-chromenes
chromene
antitumour activity
KETENES
N,N-DISUBSTITUTED ALPHA-AMINOMETHYLENEKETONES
DERIVATIVES
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Summary:Ethyl 2-[(2-amino-3-cyano-4-phenethyl-4H-naphtho[1,2-b]pyran-8-yl)oxy]acetate has been synthesised by condensation of ethyl 2-chloroacetate with the hydroxy group of 2-amino-8-hydroxy-4-phenethyl-4H-naphtho[1,2-b]pyran-3-carbonitrile. The latter was prepared from cinnamaldehyde, malononitrile and naphthalene-1,6-diol through Knoevenagel condensation and cyclisation reaction and then reduction with hydrogen in the presence of Pd/C at room temperature. The crystal structure of the title compound was determined. In addition, the compound showed distinct inhibition of the proliferation of some cancer cell lines.
ISSN:1747-5198
2047-6507
DOI:10.3184/174751918X15365767693793