WO2009019616A3 - Isoprekinamycin analogs and syntheses thereof - Google Patents

Isoprekinamycin analogs and syntheses thereof Download PDF

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Publication number
WO2009019616A3
WO2009019616A3 PCT/IB2008/003117 IB2008003117W WO2009019616A3 WO 2009019616 A3 WO2009019616 A3 WO 2009019616A3 IB 2008003117 W IB2008003117 W IB 2008003117W WO 2009019616 A3 WO2009019616 A3 WO 2009019616A3
Authority
WO
WIPO (PCT)
Prior art keywords
isoprekinamycin
syntheses
analogs
present
natural products
Prior art date
Application number
PCT/IB2008/003117
Other languages
French (fr)
Other versions
WO2009019616A2 (en
Inventor
Brian B. Hasinoff
Wei Liu
Otunola Adedayo
Gary I. Dmitrienko
Original Assignee
University Of Manitoba
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 Manitoba filed Critical University Of Manitoba
Publication of WO2009019616A2 publication Critical patent/WO2009019616A2/en
Publication of WO2009019616A3 publication Critical patent/WO2009019616A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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
    • 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
    • C07C225/22—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 carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/56—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and doubly-bound oxygen atoms bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/30—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/86—Ring systems containing bridged rings containing four rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention relates to the preparation of various benzo[α]fluorenes The benzo[α]fluorene moiety appears in a variety of natural products, some of which have been shown to exhibit anticancer and antibacterial effects Methods of the present invention provide facile access to some of these natural products as well as derivatives thereof.
PCT/IB2008/003117 2007-08-08 2008-08-08 Isoprekinamycin analogs and syntheses thereof WO2009019616A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US95480607P 2007-08-08 2007-08-08
US60/954,806 2007-08-08
US95518707P 2007-08-10 2007-08-10
US60/955,187 2007-08-10

Publications (2)

Publication Number Publication Date
WO2009019616A2 WO2009019616A2 (en) 2009-02-12
WO2009019616A3 true WO2009019616A3 (en) 2011-04-28

Family

ID=40341835

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2008/003117 WO2009019616A2 (en) 2007-08-08 2008-08-08 Isoprekinamycin analogs and syntheses thereof

Country Status (1)

Country Link
WO (1) WO2009019616A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102603520A (en) * 2012-03-23 2012-07-25 中国药科大学 Method for preparing 1H-indene-1-ketone-3-methanoic acid compound

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
GOGITIDZE, N. O. ET AL.: "Benzophenanthridines. XIII. Synthesis of Ethyl 2,3,8,9-tetramethoxy-6-methyl-3H-indeno[1,2-c]isoquinoline-11-carboxylate", ZHURNAL ORGANICHESKOI KHIMII, vol. 26, no. 10, 1990, pages 2218 - 2222 *
HARADA, Y. ET AL.: "Rh(I)-Catalyced Carbonylative Cyclization Reactions of Alkynes with 2-Bromophenylboronic Acids Leading to Indenones", J. AM. CHEM. SOC., vol. 129, 2007, pages 5766 - 5771 *
LAUFER, R. S. ET AL.: "Diazo Group Electrophilicity in Kinamycins and Lomaiviticin A: Potential Insights into the Molecular Mechanism of Antibacterial and Antitumor Activity", J. AM. CHEM. SOC., vol. 124, no. 9, pages 1854 - 1855 *
LIU, W. ET AL.: "Total Synthesis of Isoprekinamycin: Structural Evidence for Enhanced Diazonium Ion Character and Growth Inhibitory Activity toward Cancer Cells", ORG. LETT., vol. 9, no. 15, 2007, pages 2915 - 2918 *
PROTEAU, P.J. ET AL.: "Isoprekinamycin is a Diazobenzo[a]fluorene Rather than a Diazobenzo[beta]fluorene", J. AM. CHEM. SOC., vol. 122, 2000, pages 8325 - 8326 *

Also Published As

Publication number Publication date
WO2009019616A2 (en) 2009-02-12

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