Anti-tumor and anti-inflammatory dicinnamoyl-glycerol esters and their analogues
OwnerHenry Lowe, Joseph L. Bryantinventors
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Abstract
Synthetic dicinnamate compounds and their analogues are disclosed that exhibit anti-tumor activity and/or an anti-inflammatory activity, and have beneficial activity principally in destroying cancer cells. Furthermore, methods for the extraction of the extracts are disclosed.
Claims10
A method for the synthesis of an anti-cancer pharmaceutical dimethoxy-dicinnamate compound comprising the steps of:
- i) providing a first reactant comprising phosphonium bromide [((E)-(2-(3-(3-(3,4-dimethoxyphenyl)acryloyloxy) -2-hydroxypropoxy)-2-oxoethyl)triphenylphosphonium bromide)];
- ii) converting said first reactant to a triphenylphosphonium ylide [(E)-(2-(3-(3-(3,4-dimethoxyphenyl)acryloyloxy) -2-hydroxypropoxy)-2-oxoethyl)triphenylphosphonium ylide];
- iii) providing a second reactant comprising benzaldehyde;
- iv) reacting the triphenyl phosphonium ylide provided in step ii) with the second reactant provided in step iv) to form one or more covalent bond(s) coupling said triphenyl phosphonium ylide with the second reactant to yield an anti-cancer pharmaceutical dimethoxy-dicinnamate compound of the formula (E)-3-(cinnamoyloxy)-2-hydroxypropyl 3-(3,4-dimethoxyphenyl)acrylate.
A method for the synthesis of an anti-cancer pharmaceutical dihydroxy-dicinnamate compound comprising the steps of:
- i) providing a first reactant comprising caffeic acid;
- ii) reacting said first reactant with acetic anhydride to produce 2,3-diacetyl caffeic acid;
- iii) vary the molar ratio of said 2,3-diacetyl caffeic acid to produce oxiran-2-ylmethyl cinnamate;
- iii) converting said oxiran-2-ylmethyl cinnamate to a tertiary anti-cancer pharmaceutical dihydroxy-dicinnamate compound of the formula (E)-3-(cinnamoyloxy)-2-hydroxypropyl 3-(3,4-dihydroxyphenyl)acrylate.
A method for the synthesis of an anti-cancer pharmaceutical compound comprising the steps of:
- i) providing a first reactant comprising 3,4-Dimethoxycaffeic acid;
- ii) converting said first reactant to 3,4-Dimethoxycaffeic acid chloride;
- iii) providing a second reactant comprising 1,2-isoprpylideneglycerol;
- iv) reacting said 3,4-Dimethoxycaffeic acid chloride with said second reactant to form one or more covalent bond(s) coupling said 3,4-Dimethoxycaffeic acid chloride with the second reactant to provide a first molecule having an isopropylidene group;
- v) removing said isopropylidene group to form a terminal hydroxyl group;
- vi) reacting said first molecule with bromoacetyl bromide to form one or more covalent bond(s) coupling said first molecule by said terminal hydroxyl group to said bromoacetyl bromide;
- vii) reacting said first molecule with triphenyphosphine to form phosphonium bromide;
- viii) converting said phosphonium bromide to a ylide;
- ix) employing a Wittig reaction to form a third reactant coupling said phosphonium bromide ylide to one of 4-formyl-2-hydroxybenzoic acid or 2-formyl-5-hydroxybenzoic acid;
- x) reacting sad third reactant with, acetic anhydride (Ac2O) and triethylamine (TEA) to yield an anti-cancer pharmaceutical compound of the formula 2-acetoxy-4-((E)-3-(3-((E)-3-(3,4-dimethoxyphenyl)acryloyloxy) -2-hydroxypropoxy)-3-oxoprop-1-enyl)benzoic acid.
A method of treating cancer, comprising administering a pharmaceutically effective amount of a dicinnamate composition of the formula (E)-3-(cinnamoyloxy)-2-hydroxypropyl 3-(3,4-dihydroxyphenyl)acrylate.
A method of treating cancer, compiling administering a pharmaceutically effective amount of a dicinnamate composition of the formula 2-acetoxy-4-((E)-3-(3-((E)-3-(3,4-dimethoxyphenyl)acryloyloxy) -2-hydroxypropoxy)-3-oxoprop-1-enyl)benzoic acid.
A method of synthesizing a therapeutic drug comprising the steps of:
- producing a ylide;
- and
- coupling the ylide with an aldehyde.
A method of synthesizing a therapeutic drug comprising the steps of:
- treating caffeic acid with acetic anhydride to yield 2,3-diacetyl caffeic acid;
- and forming a glycerol backbone using oxiran-2-ylmethyl cinnamate.
Dependencies are inferred from the claim text.