3,4,5-trimethoxystyrylarylaminopropenones as potential anticancer agents

US9487482B2 · US · B2

Patent metadata
FieldValue
Publication numberUS-9487482-B2
Application numberUS-201514689742-A
CountryUS
Kind codeB2
Filing dateApr 17, 2015
Priority dateMay 9, 2014
Publication dateNov 8, 2016
Grant dateNov 8, 2016

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Abstract

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The present invention relate to compounds of general formula A. The invention also provides the synthesis of 3,4,5-trimethoxystyrylarylaminopropenones useful as potential antitumor agents against human cancer cell lines and a process for the preparation thereof. wherein: R=H, OMe, Cl, F, OH, Me X=aryl, heteroaryl.

First claim

Opening claim text (preview).

We claim: 1. A novel 3,4,5-trimethoxystyrylarylaminopropenone of general formulae A wherein: R=H, OMe, Cl, F, OH, Me X=aryl, heteroaryl. 2. A novel 3,4,5-trimethoxystyrylarylaminopropenone of general formulae A as claimed in claim 1 selected from the compounds of 7a-7y, 8a-8y, 9a-9y, 10a-10y, 11a-11y, 12a-12y, 13a-13y, 14a-14y, 15a-15y, 16a-16y, 17a-17y, 18a-18y, 19a-19y, 20a-20y, and 21a-21y, X=aryl, heteroaryl. 3. A novel 3,4,5-trimethoxystyrylarylaminopropenone of general formulae A as claimed in claim 1 selected from the following compounds: (Z)-1-phenyl-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7a) (Z)-1-(4-methoxyphenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7b) (Z)-1-(3-methoxyphenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7c) (Z)-1-(2-methoxyphenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7d) (Z)-1-(4-hydroxyphenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7e) (Z)-1-(4-nitrophenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7f) (Z)-1-(4-aminophenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7g) (Z)-1-(2-nitrophenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7h) (Z)-1-(2-aminophenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7i) (Z)-1-(4-fluorophenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7J) (Z)-1-(4-(trifluoromethyl)phenyl)-3-(3-((3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7k) (Z)-1-(3-fluorophenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7l) (Z)-1-(3-chlorophenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7m) (Z)-1-(4-chlorophenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7n) (Z)-1-(4-(trifluoromethoxy)phenyl)-3-(3-((3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7o) (Z)-1-(3,4-dimethoxyphenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7p) (Z)-1-(3-hydroxy-4-methoxyphenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7q) (Z)-1-(3-fluoro-4-methoxyphenyl)-3-(3-((3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7r) (Z)-1-(3-chloro-4-methoxyphenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7s) (Z)-1-(4-methoxy-3-nitrophenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7t) (Z)-1-(3-amino-4-methoxyphenyl)-3-(3-((3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7u) (Z)-1-(1H-indol-3-yl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7v) (Z)-1-(1-methyl-1H-indol-3-yl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7w) (Z)-1-(3,4,5-trimethoxyphenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7x) (Z)-1-(2-bromo-3,4,5-trimethoxyphenyl)-3-(3-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (7y) (Z)-1-phenyl-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8a) (Z)-1-(4-methoxyphenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8b) (Z)-1-(3-methoxyphenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8c) (Z)-1-(2-methoxyphenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8d) (Z)-1-(4-hydroxyphenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8e) (Z)-1-(4-nitrophenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8f) (Z)-1-(4-aminophenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8g) (Z)-1-(2-nitrophenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8h) (Z)-1-(2-aminophenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8i) (Z)-1-(4-fluorophenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8j) (Z)-1-(4-(trifluoromethyl)phenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8k) (Z)-1-(3-fluorophenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8l) (Z)-1-(3-chlorophenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8m) (Z)-1-(4-chlorophenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8n) (Z)-1-(4-(trifluoromethoxy)phenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8o) (Z)-1-(3,4-dimethoxyphenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8p) (Z)-1-(3-hydroxy-4-methoxyphenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8q) (Z)-1-(3-fluoro-4-methoxyphenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8r) (Z)-1-(3-chloro-4-methoxyphenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8s) (Z)-1-(4-methoxy-3-nitrophenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8t) (Z)-1-(3-amino-4-methoxyphenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8u) (Z)-1-(1H-indol-3-yl)-3-(4-((3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (8v) (Z)-1-(1-methyl-1H-indol-3-yl)-3-(4-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (8w) (Z)-1-(3,4,5-trimethoxyphenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8x) (Z)-1-(2-bromo-3,4,5-trimethoxyphenyl)-3-((4-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (8y) (Z)-1-phenyl-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9a) (Z)-1-(4-methoxyphenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9b) (Z)-1-(3-methoxyphenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9c) (Z)-1-(2-methoxyphenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9d) (Z)-1-(4-hydroxyphenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9e) (Z)-1-(4-nitrophenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9f) (Z)-1-(4-aminophenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9g) (Z)-1-(2-nitrophenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9h) (Z)-1-(2-aminophenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9i) (Z)-1-(4-fluorophenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9j) (Z)-1-(4-(trifluoromethyl)phenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9k) (Z)-1-(3-fluorophenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9l) (Z)-1-(3-chlorophenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9m) (Z)-1-(4-chlorophenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9n) (Z)-1-(4-(trifluoromethoxy)phenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9o) (Z)-1-(3,4-dimethoxyphenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9p) (Z)-1-(3-hydroxy-4-methoxyphenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9q) (Z)-1-(3-fluoro-4-methoxyphenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9r) (Z)-1-(3-chloro-4-methoxyphenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9s) (Z)-1-(4-methoxy-3-nitrophenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9t) (Z)-1-(3-amino-4-methoxyphenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (9u) (Z)-1-(1H-indol-3-yl)-3-(2-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (9v) (Z)-1-(1-methyl-1H-indol-3-yl)-3-(2-(3,4,5-trimethoxystyryl)phenylamino)prop-2-en-1-one (9w) (Z)-1-(3,4,5-trimethoxyphenyl)-3-((2-((Z)-3,4,5-trimethoxystyryl)phenyl)ami

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Classifications

  • Antineoplastic agents · CPC title

  • with an alkyl or cycloalkyl radical attached to the ring nitrogen atom · CPC title

  • Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton · CPC title

  • having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton · CPC title

  • and containing six-membered aromatic rings · CPC title

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What does patent US9487482B2 cover?
The present invention relate to compounds of general formula A. The invention also provides the synthesis of 3,4,5-trimethoxystyrylarylaminopropenones useful as potential antitumor agents against human cancer cell lines and a process for the preparation thereof. wherein:…
Who is the assignee on this patent?
Council Scient Ind Res
What technology area does this patent fall under?
Primary CPC classification C07D209/14. Mapped technology areas include Chemistry & Metallurgy.
When was this patent published?
Publication date Tue Nov 08 2016 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
What related patents are in patentsdb?
We list 8 related publications on this page (citations in our corpus or others sharing the same primary CPC).