Compounds for the treatment of diseases associated with amyloid or amyloid-like proteins
US-9221812-B2 · Dec 29, 2015 · US
US9487482B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9487482-B2 |
| Application number | US-201514689742-A |
| Country | US |
| Kind code | B2 |
| Filing date | Apr 17, 2015 |
| Priority date | May 9, 2014 |
| Publication date | Nov 8, 2016 |
| Grant date | Nov 8, 2016 |
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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.
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
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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