Derivatives of propane diyl dicinnamate
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Publication Number
US-10052301-B2
Publication Date
2018-08-21
Expiration Date
Abstract
The present invention provides a method for treating a cancer in a subject involving administering to the subject a compound of formula (II) or (II′): wherein R1, R2, R3, R4, R5, R6 and R7 are independently H, OH, alkoxy or alkylcarbonyloxy, or a pharmaceutically acceptable salt thereof. Also provided is a compound of formula (II) or (II)′, wherein R1 and R2 are independently OH, alkoxy or alkylcarbonyloxy, R3 and R4 are independently H, OH, alkoxy or alkylcarbonyloxy, R6 is H, alkoxy or alkylcarbonyloxy, R5 is H, OH or alkylcarbonyloxy, R6 is H or alkoxy, and R7 is H, or a pharmaceutically acceptable salt thereof.
Core Innovation
The invention relates to propane diyl dicinnamate derivative compounds described by general formulas (I)/(I′) and (II)/(II′), with variable substituent definitions and pharmaceutically acceptable salts. The disclosed subject matter includes selected structures, exclusions of specific cinnamate derivative compounds, and related structural variants within the defined chemical framework.
The invention addresses cancer treatment by providing compounds for use in treating cancer, and states that the compounds exhibit anticancer activity and are related to apoptosis of cancer cells. It also describes a pharmaceutical composition and cancer treatment use of the compounds.
The document further describes cinnamate- and glycidyl-related intermediate structures and derived compounds, including glycidyl cinnamate and glycidyl cinnamate epoxide derivatives, as well as corresponding cinnamoyl/glycidyl intermediates and potassium salts. Representative exemplified compounds include (Id), (Ie), (If), (Ig), (IIb), (IIc), (IId), and (IIe), including (2E,2′E)-2-hydroxypropane-1,3-diyl bis(3-(3,4-dihydroxyphenyl)acrylate) (IIb) and other substituted (E)-acrylate/cinnamate variants.
The description includes in-vitro anticancer evaluation results using B-16 melanoma EC50 and MTT-based IC50/EC50 across multiple human and normal cell lines, reporting entries including “no significant inhibitory effect” for some compounds. The results are compared to paclitaxel and include evaluation for specific exemplified compounds such as (Id), (IIb), (Ie), and (Id′).
Claims Coverage
The provided independent claims cover methods of inducing apoptosis of cancer cells by administering an effective amount of a compound defined by formula (II) with multiple allowable substituent options, or by administering a specific formula member (IIb or IIc). Across the independent claims, the inventive features are the apoptosis-inducing administration and the structural definition of the administered compound by formula (II) substituent constraints or by specified formula members (IIb/IIc).
Apoptosis-inducing administration to a subject
Administering to a subject in need thereof an effective amount of a compound.
A compound of formula (II) with specified R substituent options
Administering an effective amount of a compound of formula (II), wherein R4 is OH; R1 is H; R7 is H; R2 is H, OH, alkoxy or alkylcarbonyloxy; R6 is H, OH, alkoxy or alkylcarbonyloxy; R3 is OH, alkoxy or alkylcarbonyloxy; and R5 is OH or alkylcarbonyloxy, or a pharmaceutically acceptable salt thereof.
A method using the specific formula (IIb) compound
Administering an effective amount of a compound of formula (II), wherein the compound is the designated formula (IIb), or a pharmaceutically acceptable salt thereof.
A compound of formula (IIc)
Administering an effective amount of a compound of formula (IIc) to induce apoptosis of cancer cells in a subject in need thereof.
Overall, the independent claims define apoptosis-inducing methods that rely on administering an effective amount of a compound whose structure is specified either generally by formula (II) substituent constraints, or specifically by designated members formula (IIb) and formula (IIc), including pharmaceutically acceptable salts.
Stated Advantages
The compounds exhibit anticancer activity.
The compounds are associated with apoptosis of cancer cells.
In vitro evaluation includes EC50/IC50/EC50 results compared with paclitaxel.
Documented Applications
Cancer treatment use of the described compounds in connection with apoptosis of cancer cells.
In-vitro anticancer evaluation of exemplified compounds using B-16 melanoma EC50 and MTT-based IC50/EC50 across multiple human and normal cell lines, with comparisons to paclitaxel.
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