WO2011151789A3 - Aminoalkyl substituted chalcones and analogues and derivatives thereof - Google Patents

Aminoalkyl substituted chalcones and analogues and derivatives thereof Download PDF

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Publication number
WO2011151789A3
WO2011151789A3 PCT/IB2011/052396 IB2011052396W WO2011151789A3 WO 2011151789 A3 WO2011151789 A3 WO 2011151789A3 IB 2011052396 W IB2011052396 W IB 2011052396W WO 2011151789 A3 WO2011151789 A3 WO 2011151789A3
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WO
WIPO (PCT)
Prior art keywords
analogues
derivatives
aminoalkyl substituted
substituted chalcones
chalcones
Prior art date
Application number
PCT/IB2011/052396
Other languages
French (fr)
Other versions
WO2011151789A2 (en
Inventor
Jan Hendrik Van Der Westhuizen
Anwar Elbushra Mohammed Nor Eljaleel
Susanna Lucia Bonnet
Anke Wilhelm-Mouton
Original Assignee
University Of The Free State
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 University Of The Free State filed Critical University Of The Free State
Priority to AP2012006642A priority Critical patent/AP2012006642A0/en
Publication of WO2011151789A2 publication Critical patent/WO2011151789A2/en
Publication of WO2011151789A3 publication Critical patent/WO2011151789A3/en
Priority to ZA2012/09581A priority patent/ZA201209581B/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
    • C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
    • C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C07C225/18—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings the carbon skeleton containing also rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
    • C07C239/08—Hydroxylamino compounds or their ethers or esters
    • C07C239/14—Hydroxylamino compounds or their ethers or esters having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/24—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
    • C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

This invention relates to B-ring aminoalkyl substituted chalcones and analogues thereof. It also relates to processes for the synthesis of such compounds and to the use of such compounds as medicaments, in particular but not exclusively for the treatment of cancer and malaria.
PCT/IB2011/052396 2010-05-31 2011-05-31 Aminoalkyl substituted chalcones and analogues and derivatives thereof WO2011151789A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AP2012006642A AP2012006642A0 (en) 2010-05-31 2011-05-31 Aminoalkyl substituted chalcones and analogues andderivatives thereof
ZA2012/09581A ZA201209581B (en) 2010-05-31 2012-12-18 Aminoalkyl substituted chalcones and analogues and derivatives thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ZA201003897 2010-05-31
ZA2010/03897 2010-05-31

Publications (2)

Publication Number Publication Date
WO2011151789A2 WO2011151789A2 (en) 2011-12-08
WO2011151789A3 true WO2011151789A3 (en) 2012-05-24

Family

ID=44629425

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2011/052396 WO2011151789A2 (en) 2010-05-31 2011-05-31 Aminoalkyl substituted chalcones and analogues and derivatives thereof

Country Status (3)

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AP (1) AP2012006642A0 (en)
WO (1) WO2011151789A2 (en)
ZA (1) ZA201209581B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109734614B (en) * 2019-01-11 2022-04-22 四川大学 3-hydroxy chalcone Mannich base compound, preparation method and application thereof
CN109678736B (en) * 2019-01-11 2022-04-22 四川大学 Chalcone Mannich base compound, preparation method and application thereof

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102775288A (en) * 2012-07-12 2012-11-14 温州大学 Synthetic method of chalcone compounds
CN109665969B (en) * 2019-01-11 2022-04-22 四川大学 3-methoxy-4-hydroxychalcone bis-Mannich base compound, and preparation method and application thereof
CN109608346B (en) * 2019-01-11 2022-04-22 四川大学 Chalcone bis-Mannich base compound, and preparation method and application thereof
CN112694392B (en) * 2020-12-21 2022-11-22 青岛大学 TRPV3 inhibitor and preparation method thereof
CN112826812B (en) * 2020-12-21 2023-08-25 青岛大学 Pharmaceutical composition for treating colon cancer and application thereof

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
J. V. BRAUN ET.AL.: "Synthesen in der fettaromatische Reihe X: Derivate der Diarylparaffine", CHEMISCHE BERICHTE, 1913, pages 1511 - 1526, XP002671587 *
JONATHAN R. DIMMOCK ET AL: "Cytotoxic Activities of Mannich Bases of Chalcones and Related Compounds", JOURNAL OF MEDICINAL CHEMISTRY, vol. 41, no. 7, 1 March 1998 (1998-03-01), pages 1014 - 1026, XP055013705, ISSN: 0022-2623, DOI: 10.1021/jm970432t *
JULIUS V. BRAUN ET.AL.: "Die realtive Festigkeit cyclischer Basen, VII: Substituierte Tetrahydrochilolin Ringe", CHEMISCHE BERICHTE, 1922, pages 3803 - 3817, XP002671586 *
MICHAEL J. HALL ET AL: "A Modular Synthesis of Unsymmetrical Tetraarylazadipyrromethenes", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 70, no. 14, 1 July 2005 (2005-07-01), pages 5571 - 5578, XP055013649, ISSN: 0022-3263, DOI: 10.1021/jo050696k *
SIMON F. NIELSEN ET.AL.: "Cationic chalcone antibiotics. Design, synthesis, and mechanism of action", J. MED. CHEM., vol. 48, 2005, pages 2667 - 2677, XP002664898 *
SOON SUNG LIM ET.AL.: "In vitro antimalaian activity of flavonoids and chalcones", BULL. KOREAN CHEM. SOC., vol. 28, no. 12, 2007, pages 2495 - 2497, XP002664899 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109734614B (en) * 2019-01-11 2022-04-22 四川大学 3-hydroxy chalcone Mannich base compound, preparation method and application thereof
CN109678736B (en) * 2019-01-11 2022-04-22 四川大学 Chalcone Mannich base compound, preparation method and application thereof

Also Published As

Publication number Publication date
ZA201209581B (en) 2013-08-28
AP2012006642A0 (en) 2012-12-31
WO2011151789A2 (en) 2011-12-08

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