Chalcones having antiproliferative activity
OwnerEzio Bombardelli, Piero Valentiinventors
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Abstract
The invention relates to a novel class of compounds that have structures related to certain naturally occurring or synthetic chalcones. The invention also relates to pharmaceutical compositions comprising the compounds and methods for treating certain disorders using the pharmaceutical compositions. The invention further relates to process for synthesizing the novel class of compounds.
Claims13
A compound of formula (A) ##STR2## wherein Ar represents 3-pyridyl;
- 4-pyridyl;
- or 3-indolyl;
- and
- R represents --OCH.sub.2 R.sub.1, in which R.sub.1 is selected from --CH.dbd.CMe.sub.2, --CMe.dbd.CH.sub.2, or --C.tbd.CH.
A compound selected from the group consisting of:
- 1-[2-hydroxy-4-(3-methylbut-2-enyloxy)-phenyl]-3-(pyridine-4-yl)-propen-1-o ne,
- 1-[2-hydroxy-4-(3-methylbut-2-enyloxy)-phenyl]-3-(pyridine-3-yl)-propen-1-o ne,
- 1-[2-hydroxy-4-(3-methylbut-2-enyloxy)-phenyl]-3-(indole-3-yl)-propen-1-one
- 1-[2-hydroxy-4-(2-methylallyloxy)-phenyl]-3-(indole-3-yl)-propen-1-one,
- 1-[2-hydroxy-4-(prop-2-ynyloxy)-phenyl]-3-(pyridine-3-yl)-propen-1-one,
- 1-[2-hydroxy-4-(2-methylallyloxy)-phenyl]-3-(indole-3-yl)-propen-1-one,
- 1-[2-hydroxy-4-(prop-2-ynyloxy)-phenyl]-3-(pyridine-3-yl)-propen-1-one.
A pharmaceutical composition comprising a compound of formula (A) ##STR3## and a pharmaceutically acceptable excepient, wherein, in formula (A), Ar represents 3-pyridyl;
- 4-pyridyl;
- or 3-indolyl;
- and
- R represents --OCH.sub.2 R.sub.1, in which R.sub.1 is selected from --CH.dbd.CMe.sub.2, --CMe.dbd.CH.sub.2, or --C.tbd.CH.
A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound selected from the group consisting of:
- 1-[2-hydroxy-4-(3-methylbut-2-enyloxy)-phenyl]-3-(pyridine-4-yl)-propen-1-o ne,
- 1-[2-hydroxy-4-(3-methylbut-2-enyloxy)-phenyl]-3-(pyridine-3-yl)-propen-1-o ne,
- 1-[2-hydroxy-4-(3-methylbut-2-enyloxy)-phenyl]-3-(indole-3-yl)-propen-1-one
- 1-[2-hydroxy-4-(2-methylallyloxy)-phenyl]-3-(indole-3-yl)-propen-1-one,
- 1-[2-hydroxy-4-(prop-2-ynyloxy)-phenyl]-3-(indole-3-yl)-propen-1-one,
- 1-[2-hydroxy-4-(2-methylallyloxy)-phenyl]-3-(pyridine-3-yl)-propen-1-one, and
- 1-[2-hydroxy-4-(prop-2-ynyloxy)-phenyl]-3-(pyridine-3-yl)-propen-1-one.
A method for treating or preventing neoplasms, menopausal disorders, and osteoporosis in a mammal, which comprises administering to the mammal a therapeutically effective amount of a compound of formula (A) ##STR4## wherein, in formula (A), Ar represents 3-pyridyl;
- 4-pyridyl;
- or 3-indolyl;
- and
- R represents --OCH.sub.2 R.sub.1, in which R.sub.1 is selected from --CH.dbd.CMe.sub.2, --CMe.dbd.CH.sub.2, or --C.tbd.CH.
A process for synthesizing a compound of formula (A) ##STR5## wherein Ar represents 3-pyridyl;
- 4-pyridyl;
- or 3-indolyl;
- and
- R represents --OCH.sub.2 R.sub.1, in which R.sub.1 is selected from --CH.dbd.CMe.sub.2, --CMe.dbd.CH.sub.2, or --C.tbd.CH;
- said process comprises
- (1) reacting equimolar solution of acetophenone and an aldehyde in ethyl alcohol in the presence of KOH;
- or
- (2) reacting equimolar solution of acetophenone and an aldehyde in ethyl alcohol in the presence of piperidine and acetic acid under weak countercurrent.
Dependencies are inferred from the claim text.