Construction of reaction-development-based
chemical library
Nitrogen-containing molecules are known to have various biological activities. Our laboratory aims to discover new bioactive molecules from our molecular library that are synthesized through the development of new reactions. So far, we have found arylamine molecules named SIM that inhibit the stomatal opening of plant stomata. SIM molecules were originally synthesized through our C–H amination reactions. Currently, we have found multiple bioactive molecules, which will be reported soon.
(2) ITC project
In collaboration with Prof. Toshinori Kinoshita, Prof. Yusuke Aihara, and Prof. Ayato Sato of Nagoya University, we have developed a molecule that inhibits stomatal opening. In this study, we identified benzyl isothiocyanate (BITC: Bn-NCS) from a chemical library as a stomatal-opening inhibitor. Furthermore, we have synthesized BITC derivatives with multiple NCS groups (multi-ITCs), which demonstrate stronger inhibitory activity.
“Identification of stomatal-regulating molecules from de novo arylamine collection through aromatic C–H amination”
Yosuke Toda, * Gregory JP Perry, † Shimpei Inoue, † Eri Ito, † Takahiro Kawakami, Mina R. Narouz, Koji Takahashi, Yusuke Aihara, Bumpei Maeda, Toshinori Kinoshita, Kenichiro Itami, Kei Murakami * († Equal contribution)
Sci. Rep. 2022 , 12 , 949. DOI: 10.1038 / s41598-022-04947-z.
[Related work]
“Catalytic Dehydrogenative C–H Imidation of Arenes Enabled by Photo-generated Hole Donation to Sulfonimide”
Eri Ito, Tomohiro Fukushima, Takahiro Kawakami, Kei Murakami, * Kenichiro Itami *
Chem 2017 , 2 , 383–392. [OPEN ARCHIVE]
“Catalytic Dehydrogenative C–H Imidation of Arenes Enabled by Photo-generated Hole Donation to Sulfonimide”
Eri Ito, Tomohiro Fukushima, Takahiro Kawakami, Kei Murakami, * Kenichiro Itami *
Chem 2017 , 2 , 383–392. [OPEN ARCHIVE]
(1) SIM project
We constructed an imidized aromatic ring library from the developed aromatic amination reaction. When Dr. Toshinori Kinoshita and Dr. Yosuke Toda of Nagoya University evaluated these biological activities, we found a molecule (SIM1: imidized oxazole) that inhibits stomatal opening. By synthesizing these derivatives and conducting structure-activity relationship studies, it was clarified that the sulfonamided oxazole SIM3 * has better activity .
“Identification of stomatal-regulating molecules from de novo arylamine collection through aromatic C–H amination”
Yosuke Toda, * Gregory JP Perry, † Shimpei Inoue, † Eri Ito, † Takahiro Kawakami, Mina R. Narouz, Koji Takahashi, Yusuke Aihara, Bumpei Maeda, Toshinori Kinoshita, Kenichiro Itami, Kei Murakami * († Equal contribution)
Sci. Rep. 2022 , 12 , 949. DOI: 10.1038 / s41598-022-04947-z.
[Related work]
“Catalytic Dehydrogenative C–H Imidation of Arenes Enabled by Photo-generated Hole Donation to Sulfonimide”
Eri Ito, Tomohiro Fukushima, Takahiro Kawakami, Kei Murakami, * Kenichiro Itami *
Chem 2017 , 2 , 383–392. [OPEN ARCHIVE]