Discovery of Plant Growth Stimulants by C-H Arylation of 2-Azahypoxanthine

Hiroyuki Kitano; Jae-Hoon Choi; Ayaka Ueda; Hideto Ito; Shinya Hagihara; Toshiyuki Kan; Hirokazu Kawagishi; Kenichiro Itami

doi:10.1021/acs.orglett.8b02407

Discovery of Plant Growth Stimulants by C-H Arylation of 2-Azahypoxanthine

Org Lett. 2018 Sep 21;20(18):5684-5687. doi: 10.1021/acs.orglett.8b02407. Epub 2018 Sep 4.

Authors

Hiroyuki Kitano¹, Jae-Hoon Choi², Ayaka Ueda¹, Hideto Ito^{1

3}, Shinya Hagihara^{1

4}, Toshiyuki Kan⁵, Hirokazu Kawagishi^{2

6}, Kenichiro Itami^{1

3}

Affiliations

¹ Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science , Nagoya University , Chikusa, Nagoya 464-8601 , Japan.
² Research Institute of Green Science and Technology , Shizuoka University , 836 Ohya , Suruga-ku, Shizuoka 422-8529 , Japan.
³ JST-ERATO, Itami Molecular Nanocarbon Project , Nagoya University , Chikusa, Nagoya 464-8602 , Japan.
⁴ Center for Sustainable Resource Science , RIKEN , 2-1 Hirosawa , Wako , Saitama 351-0198 , Japan.
⁵ School of Pharmaceutical Sciences , University of Shizuoka , 52-1 Yada , Suruga-ku, Shizuoka 422-8526 Japan.
⁶ Graduate School of Agriculture , Shizuoka University , 836 Ohya , Suruga-ku, Shizuoka 422-8529 , Japan.

PMID: 30179492
DOI: 10.1021/acs.orglett.8b02407

Abstract

A series of new AHX derivatives were synthesized by Pd-catalyzed C-H arylation. Their rice-growth-promoting activity was evaluated in vivo. Among the synthesized compounds, C8 phenyl-substituted AHX showed remarkable growth-promoting activity on rice. The present study shows the power and significant opportunity of C-H functionalization chemistry to rapidly transform biologically active natural products into more active compounds.

Publication types

Research Support, Non-U.S. Gov't