Synthesis and Structure–Activity Relationship Study of NBRI16716B, an Antitumor Natural Product

• Abe Hikaru

  Institute of Microbial Chemistry (BIKAKEN), Tokyo

• Sakashita Chiharu

  Institute of Microbial Chemistry (BIKAKEN), Tokyo

• Kawada Manabu

  Institute of Microbial Chemistry (BIKAKEN), Numazu

• Nomoto Akio

  Institute of Microbial Chemistry (BIKAKEN), Tokyo

• Watanabe Takumi

  Institute of Microbial Chemistry (BIKAKEN), Tokyo

• Shibasaki Masakatsu

  Institute of Microbial Chemistry (BIKAKEN), Tokyo

Abstract

The total synthesis of NBRI16716B (2), a naturally occurring modulator of tumor–stroma interactions, was successfully achieved. Using this synthetic route, a dehydroxy analogue (21) and a derivative lacking the 5-hydroxy-3-methylpentenoyl side chain (22) became accessible. A preliminary structure–activity relationship study to unveil the structural requirements for selective inhibition of tumor cells cocultured with stromal cells revealed that both of the hydroxamate structures of 2 are indispensable, whereas the 5-hydroxy-3-methylpentenoyl side chain is not essential.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 63 (6), 463-468, 2015

  The Pharmaceutical Society of Japan

Keywords

• antitumor agent
• natural product
• diketopiperazine
• tumor–stroma interaction
• structure–activity relationship

Details

• CRID: 1390001204178829440
• NII Article ID: 130005072098
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.c15-00200
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 026408284
• PubMed: 26027472
• Web Site: http://id.ndl.go.jp/bib/026408284
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I026408284
• Web Site: https://www.jstage.jst.go.jp/article/cpb/63/6/63_c15-00200/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/2016026436
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed