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US 6,828,450 B2Granted
Triptycene analogs
AssigneeKansas State University Research Foundation
InventorsDuy Hua, Jean-Pierre Perchellet
Life of this patent
Estimating the term…
Abstract
This invention provides analogs of triptycene which are useful as anticancer drugs, as well as for other uses. The potency of these compounds is in a similar magnitude as daunomycin, a currently used anticancer drug. Each compound of the invention produces one or more desired effects (blocking nucleoside transport, inhibiting nucleic acid or protein syntheses, decreasing the proliferation and viability of cancer cells, inducing DNA fragmentation or retaining their effectiveness against multidrug-resistant tumor cells).
Claims40
A triptycene analog comprising a compound of formula:
- wherein
- X is selected from the group consisting of:
- H, R, SR and NR2;
- Y is selected from the group consisting of:
- halogen, R, NR2, SR and H;
- R and R1-2 are independently selected from the group consisting of:
- H, halogen, OR, and hydrocarbyl;
- R3-4, independently of one another, are selected from the group consisting of:
- H, bromine, R, SR, and NR2;
- R5, independently of other R5s, is selected from the group consisting of:
- ═O, ═N—OH and ═CHR;
- and reduced forms thereof, wherein in reduced forms, either ring A or ring C or both is replaced with
- and wherein reduced form, each R5 is
- independently H, C1-C8 alkyl or —OR;
- and pharmaceutically acceptable salts of the forgoing, as well as optical isomers thereof;
- wherein when all of R5 are ═O, at least one of X, Y, R1—R4 is not H.
13 more elements
A triptycene analog having the formula:
- wherein
- X is selected from the group consisting of:
- H, R, SR and NR2
- Y is selected from the group consisting of:
- halogen, NR2, R, SR and H;
- R and R1-2, are independently selected from the group consisting of:
- H, halogen, OR, and hydrocarbyl;
- R3-4, independently of one another, are selected from the group consisting of:
- H, bromine, R, SR, and NR2;
- R5, independently of other R5s, is selected from the group consisting of:
- ═O, ═N—OH, and ═CHR;
- R21 and R22 are independently selected from the group consisting of:
- H, R, and OR;
- and
- reduced forms thereof and pharmaceutically acceptable salts of the foregoing, as well as optical isomers thereof.
12 more elements
A triptycene analog having the formula:
- wherein
- R5 is selected from the group consisting of:
- R, halogen, NR2, SR, and H;
- R6 is selected from the group consisting of:
- H, R, SR and NR2;
- R7 and R8 are independently selected from the group consisting of:
- H, halogen, and hydrocarbyl;
- R17 and R18 are independently are selected from the group consisting of:
- H, bromine, R, SR, and NR2;
- R19 and R20 are, independently of one another, H, R, or OR;
- (R9 and R10) and (R11 and R12) and (R13 and R14) and (R15 and R16) are independently together ═O or are independently H or —OR;
- R is selected from the group consisting of:
- H, halogen, OR, and hydrocarbyl;
- and reduced forms thereof;
- and pharmaceutically acceptable salts of the foregoing, as well as optical isomers thereof.
12 more elements
A method of brominating a triptycene derivative of formula (I):
- wherein X is selected from the group consisting of:
- H, R, SR and NR2;
- Y is selected from the group consisting of:
- halogen, R, NR2, SR and H;
- R and R1-2 are independently selected from the group consisting of:
- H, halogen, OR, and hydrocarbyl;
- R3-4, independently of one another, are selected from the group consisting of:
- H, bromine, R, SR, and NR2;
- R5, independently of other R5s, is selected from the group consisting of:
- ═O, ═N—OH and ═CHR;
- and reduced forms thereof, wherein in reduced forms, either ring A or ring C or both is replaced with
- and wherein in reduced forms, each R5 is independently H, C1-C8 alkyl or —OR;
- and pharmaceutically acceptable salts of the foregoing, as well as optical isomers thereof;
- wherein when all of R5 are ═O, at least one of X, Y, R1—R4 is not H;
- and
- wherein either:
- (a) Y is a hydrogen and X is a methoxy group;
- (b) R1 is a hydrogen and R2 is a methoxy group;
- or
- (c) R2 is a hydrogen and R1 is a methoxy group,
- by reacting a triptycene derivative of formula (I) with N-bromosuccinimide, wherein the Y, R1 or R2 that is hydrogen is replaced with a bromine.
18 more elements
A triptycene analog comprising a compound of formula:
- wherein X is —NW(CW2)nZ, where the Ws are independently selected from the group consisting of:
- H, C1-C8 alkyl, and C1-C8 alkenyl;
- n is an integer from 1 to 8;
- and Z is selected from the group consisting of:
- R, COR, COOR, CONR2, OOCR and NRCOR;
- Y is selected from the group consisting of:
- halogen, C1-C8 alkyl, C1-C8 alkenyl, OR, NR2, SR, H, COR, OCOR and NRCOR;
- R and R1-2, are independently selected from the group consisting of:
- H, OR, and hydrocarbyl;
- R3-4, independently of one another, are selected from the group consisting of:
- H, OR, SR, and NR2;
- R5, is ═O;
- and reduced forms thereof and pharmaceutically acceptable salts of the foregoing, as well as optical isomers thereof.
10 more elements
A triptycene analog of formula:
- and the reduced forms thereof, wherein in said reduced forms, either ring A or ring C or both is reduced to
- wherein all but one of X, Y, R1 and R2 is independently H, C1-C6 alkyl, C1-C6 alkenyl, OR, SR or NR2 wherein each R is independently H or C1-C6 alkyl and the other R1 or R2 is a solubilizing group;
- and each R5 is independently H, C1-C6 alkyl or OR.
Dependencies are inferred from the claim text.