WO2011009826A3 - Novel chalcone derivatives with cytotoxic activity - Google Patents

Novel chalcone derivatives with cytotoxic activity Download PDF

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Publication number
WO2011009826A3
WO2011009826A3 PCT/EP2010/060368 EP2010060368W WO2011009826A3 WO 2011009826 A3 WO2011009826 A3 WO 2011009826A3 EP 2010060368 W EP2010060368 W EP 2010060368W WO 2011009826 A3 WO2011009826 A3 WO 2011009826A3
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
independently
chalcone derivatives
cytotoxic activity
carboxy
Prior art date
Application number
PCT/EP2010/060368
Other languages
French (fr)
Other versions
WO2011009826A2 (en
Inventor
Marek Konieczny
Andrzej Skladanowski
Krzysztof Lemke
Jerzy Pieczykolan
Original Assignee
ADAMED Sp.z o.o.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by ADAMED Sp.z o.o. filed Critical ADAMED Sp.z o.o.
Publication of WO2011009826A2 publication Critical patent/WO2011009826A2/en
Publication of WO2011009826A3 publication Critical patent/WO2011009826A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/64—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Abstract

Chalcone derivatives of the general formula (I), wherein two from among A, B and Z which are adjacent to each other are linked and form a moiety selected from -O-(CH2)n-S(O)m-, -S(O)m-(CH2)n-O- and -O-(CH2)n-O-, and the remaining one from among A, B and Z is H; or two from among A, B and Z, independently from each other, are selected from a group consisting of OH, -O-C1-C6-alkyl and -S(O)m-C1-C6-alkyl, and the remaining one from among A, B and Z is H; R is H, C1-C6-alkyl, carboxy-C1-C6-alkyl, -(CH2)P- NR1R2 or O(CH2)3NH(CO)CF3, where R1 and R2 both independently are C1-C6-alkyl; or R1 and R2 are linked together to form polymethylene group -(CH2)q-, and with N atom, to which they are attached, form a 5- or 6-membered ring, in which one of carbon atoms may be optionally replaced with O, N, or S; Y is -CH=CH-, -O-, -S- or -CH=N-; X1, X2, X3 independently are H, halogen atom, OH, -C1-C6-alkoxy, carboxy-C1-C6-alkoxyl, di(C1-C6- alkyl)amino-C1-C6-alkoxy, -0-PO(OH)2, NO2 or NH2; m = O, 1 or 2; n = 1 or 2; p = 2 to 6; q = 4 or 5; and acid addition salts, salts with bases and C1-C6-alkyl esters thereof. The compounds may be useful as cytotoxic drugs for the treatment of neoplastic diseases. Formula (I).
PCT/EP2010/060368 2009-07-21 2010-07-16 Novel chalcone derivatives with cytotoxic activity WO2011009826A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PLP-388593 2009-07-21
PL38859309 2009-07-21

Publications (2)

Publication Number Publication Date
WO2011009826A2 WO2011009826A2 (en) 2011-01-27
WO2011009826A3 true WO2011009826A3 (en) 2011-06-09

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2010/060368 WO2011009826A2 (en) 2009-07-21 2010-07-16 Novel chalcone derivatives with cytotoxic activity

Country Status (1)

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WO (1) WO2011009826A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103153053B (en) 2010-08-18 2015-02-18 萨穆梅德有限公司 Diketones and hydroxyketones as catenin signaling pathway activators
ME03296B (en) 2013-02-22 2019-07-20 Samumed Llc Gamma-diketones as wnt/beta -catenin signaling pathway activators
GB2534052A (en) * 2013-08-30 2016-07-13 Council Scient Ind Res Pyrazolochalcones as potential anticancer agents
CN103910691A (en) * 2014-04-18 2014-07-09 山东药品食品职业学院 Halogenated phenyl chalcone derivative as well as preparation method and application thereof
AU2015305373B2 (en) * 2014-08-20 2020-12-10 Samumed, Llc Gamma-diketones for treatment and prevention of aging skin and wrinkles
WO2017103637A1 (en) 2015-12-18 2017-06-22 Blirt S.A. Diphenylpropane compounds and their cytotoxic activity

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003076407A1 (en) * 2002-03-14 2003-09-18 The Walter And Eliza Hall Institute Of Medical Research Novel chalcone derivatives and uses thereof
US20090182058A1 (en) * 2006-01-17 2009-07-16 Ahcene Boumendjel Novel Chalcone Derivatives With Antimitotic Activity

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6462075B1 (en) 1999-12-23 2002-10-08 The University Of Georgia Research Foundation, Inc. Chalcone and its analogs as agents for the inhibition of angiogensis and related disease states
GB0007401D0 (en) 2000-03-27 2000-05-17 Cancer Res Campaign Tech Substituted chalcones as therapeeutic compounds
FR2817749A1 (en) 2000-12-13 2002-06-14 Aventis Pharma Sa NEW USE OF CHALCON CLASS COMPOUNDS
KR100567125B1 (en) 2001-11-01 2006-03-31 주식회사 안지오랩 Pharmaceutical composition for inhibiting matrix metalloproteinase activity comprising chalcone or its derivatives
CN1596240A (en) 2001-12-19 2005-03-16 阿特罗吉尼克斯公司 Chalcone derivatives and their use to treat diseases
US20030229136A1 (en) 2002-04-18 2003-12-11 Nurulain Zaveri Novel flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003076407A1 (en) * 2002-03-14 2003-09-18 The Walter And Eliza Hall Institute Of Medical Research Novel chalcone derivatives and uses thereof
US20090182058A1 (en) * 2006-01-17 2009-07-16 Ahcene Boumendjel Novel Chalcone Derivatives With Antimitotic Activity

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Publication number Publication date
WO2011009826A2 (en) 2011-01-27

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