Title:
METHOD FOR PRODUCING KAKEROMYCIN AND DERIVATIVES THEREOF
Document Type and Number:
WIPO Patent Application WO/2016/136963
Kind Code:
A1
Abstract:
Provided is a method for producing, through chemical synthesis, kakeromycin and derivatives thereof which exhibit antifungal activity and cytotoxicity, and are expected to serve as novel antifungal agents or anticancer agents. Said method includes a step in which a compound represented by formula (2) [wherein, R represents an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, and n represents 0 or 1] or a salt thereof is subjected to an oxidation reaction, and a compound represented by formula (1) [wherein, R and n are as defined above] or a salt thereof is produced.
Inventors:
ISHIKAWA TERUHIKO (JP)
IWAMI MORITA (JP)
IWAMI MORITA (JP)
Application Number:
PCT/JP2016/055891
Publication Date:
September 01, 2016
Filing Date:
February 26, 2016
Export Citation:
Assignee:
ISHIKAWA TERUHIKO (JP)
IWAMI MORITA (JP)
OP BIO FACTORY CO LTD (JP)
IWAMI MORITA (JP)
OP BIO FACTORY CO LTD (JP)
International Classes:
C07D498/04; C07C225/06; C07C271/18; C07D261/04
Domestic Patent References:
| WO2015030197A1 | 2015-03-05 | |||
| WO2009096996A1 | 2009-08-06 | |||
| WO2015042201A2 | 2015-03-26 | |||
| WO2016040515A1 | 2016-03-17 |
Foreign References:
| JPS63250352A | 1988-10-18 | |||
| JPH111472A | 1999-01-06 | |||
| JPH06319574A | 1994-11-22 | |||
| JP2003505452A | 2003-02-12 | |||
| JP2004516320A | 2004-06-03 |
Other References:
MATSUMOTO Y ET AL.: "A novel antifungal agent discovered from Streptomyces sp. in sea sand", POSTER PR, XP009505753
"Heisei 25 Nendo Senryakuteki Kiban Gijutsu Kodoka Shien Jigyo 'Aratana Bunrigen Shoriho Oyobi Hakko Baiyoho no Kaihatsu ni yoru Kaiyosei Biseibutsu · Bisai Sorui kara no Koritsuteki na Shinki Soyaku Seed Kagobutsu Tansakuho no Kaihatsu", KENKYU KAIHATSU SEIKA TO HOKOKUSHO, March 2014 (2014-03-01), XP055479817, Retrieved from the Internet [retrieved on 20160310]
SCHURINK,M. ET AL.: "Substrate Specificity and Stereoselectivity of Two Sulfolobus 2-Keto-3- deoxygluconate Aldolases towards Azido- Substituted Aldehydes", CHEMCATCHEM, vol. 6, no. 4, 2014, pages 1073 - 1081, XP055479826
WEISS,J.M. ET AL.: "6-Aryl-3- pyrrolidinylpyridines as mGlu5 receptor negative allosteric modulators", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 21, no. 16, 2011, pages 4891 - 4899, XP028247210, doi:10.1016/j.bmcl.2011.06.014
HECHT,S.S. ET AL.: "Metabolic beta-hydroxylation and N-oxidation of n'-nitrosonornicotine", JOURNAL OF MEDICINAL CHEMISTRY, vol. 23, no. 11, 1980, pages 1175 - 1178, XP055479839
WITKOP,B.: "Infrared diagnosis of the hydrochlorides of organic bases. III. Imine- enamine systems and the mechanism of their oxidation", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 78, 1956, pages 2873 - 2882, XP009505785
PUDER,C. ET AL.: "New co-metabolites of the streptazolin pathway", JOURNAL OF NATURAL PRODUCTS, vol. 64, no. 1, 2001, pages 42 - 45, XP055479867
GHABRIAL,S.S. ET AL.: "Synthesis of biheteroaromatic compounds via the isoxazoline route", ACTA CHEMICA SCANDINAVICA , SERIES B: ORGANIC CHEMISTRY AND BIOCHEMISTRY, vol. B41, no. 6, 1987, pages 426 - 434, XP002045744
BALACHANDRAN,S. ET AL.: "Novel derivatives of ISO-1 as potent inhibitors of MIF biological function", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 19, no. 16, 2009, pages 4773 - 4776, XP026419076
"Heisei 25 Nendo Senryakuteki Kiban Gijutsu Kodoka Shien Jigyo 'Aratana Bunrigen Shoriho Oyobi Hakko Baiyoho no Kaihatsu ni yoru Kaiyosei Biseibutsu · Bisai Sorui kara no Koritsuteki na Shinki Soyaku Seed Kagobutsu Tansakuho no Kaihatsu", KENKYU KAIHATSU SEIKA TO HOKOKUSHO, March 2014 (2014-03-01), XP055479817, Retrieved from the Internet
SCHURINK,M. ET AL.: "Substrate Specificity and Stereoselectivity of Two Sulfolobus 2-Keto-3- deoxygluconate Aldolases towards Azido- Substituted Aldehydes", CHEMCATCHEM, vol. 6, no. 4, 2014, pages 1073 - 1081, XP055479826
WEISS,J.M. ET AL.: "6-Aryl-3- pyrrolidinylpyridines as mGlu5 receptor negative allosteric modulators", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 21, no. 16, 2011, pages 4891 - 4899, XP028247210, doi:10.1016/j.bmcl.2011.06.014
HECHT,S.S. ET AL.: "Metabolic beta-hydroxylation and N-oxidation of n'-nitrosonornicotine", JOURNAL OF MEDICINAL CHEMISTRY, vol. 23, no. 11, 1980, pages 1175 - 1178, XP055479839
WITKOP,B.: "Infrared diagnosis of the hydrochlorides of organic bases. III. Imine- enamine systems and the mechanism of their oxidation", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 78, 1956, pages 2873 - 2882, XP009505785
PUDER,C. ET AL.: "New co-metabolites of the streptazolin pathway", JOURNAL OF NATURAL PRODUCTS, vol. 64, no. 1, 2001, pages 42 - 45, XP055479867
GHABRIAL,S.S. ET AL.: "Synthesis of biheteroaromatic compounds via the isoxazoline route", ACTA CHEMICA SCANDINAVICA , SERIES B: ORGANIC CHEMISTRY AND BIOCHEMISTRY, vol. B41, no. 6, 1987, pages 426 - 434, XP002045744
BALACHANDRAN,S. ET AL.: "Novel derivatives of ISO-1 as potent inhibitors of MIF biological function", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 19, no. 16, 2009, pages 4773 - 4776, XP026419076
Attorney, Agent or Firm:
TAKASHIMA, HAJIME (JP)
Takashima 1 (JP)
Takashima 1 (JP)
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