To find novel histone deacetylase 6 (HDAC6)-selective inhibitors and clarify the structural requirements for HDAC6-selective inhibition, we prepared thiolate analogues designed based on the structure of an HDAC6-selective substrate and evaluated the histone/α-tubulin acetylation selectivity by Western blot analysis. Aliphatic compounds 17b−20b selectively caused α-tubulin acetylation over histone H4 acetylation. In enzyme assays using HDAC1, HDAC4, and HDAC6, compounds 17a−19a exhibited HDAC6-selective inhibition over HDAC1 and HDAC4.

10.1021/jm060554y

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Citations (104)

Synthesis of a 6-CF₃-Substituted 2-Amino-dihydro-1,3-thiazine β-Secretase Inhibitor by N,N-Diethylaminosulfur Trifluoride-Mediated Chemoselective Cyclization

The Journal of Organic Chemistry (2018)

Takuya Oguma Kosuke Anan Shinji Suzuki Shinya Hisakawa Akihiro Takada

The synthesis of a 6-CF3-substituted 2-amino-dihydro-1,3-thiazine via N, N-diethylaminosulfur trifluoride (DAST)-mediated cyclization of N-hydroxypropyl thiourea 6 is described. This reaction gave 6-CF3-1,3-thiazine 7 with high chemical yield and chemoselectivity, suppressing the common byproduct of oxazine 8. This new protocol enabled access to 6-CF3-substituted 1,3-thiazine β-secretase inhibitor 2.

Thiazine

10.1021/acs.joc.8b02179

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Identification of a potent and stable antiproliferative agent by the prodrug formation of a thiolate histone deacetylase inhibitor

Bioorganic & Medicinal Chemistry Letters (2007)

Takayoshi Suzuki Shinya Hisakawa Yukihiro Itoh Sakiko Maruyama Mineko Kurotaki

Histone deacetylase inhibitor

10.1016/j.bmcl.2006.12.117

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Citations (17)

Design, synthesis, and biological activity of folate receptor-targeted prodrugs of thiolate histone deacetylase inhibitors

Bioorganic & Medicinal Chemistry Letters (2007)

Takayoshi Suzuki Shinya Hisakawa Yukihiro Itoh Nobuaki Suzuki Katsumasa Takahashi

Folate receptor

Moiety

Histone deacetylase inhibitor

Hydroxamic acid

10.1016/j.bmcl.2007.05.040

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Citations (49)

CCDC 1861093: Experimental Crystal Structure Determination

The Cambridge Structural Database (2019)

Takuya Oguma Kosuke Anan Shinji Suzuki Shinya Hisakawa Akihiro Takada

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc20gm8d

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Cefiderocol (S-649266), A new siderophore cephalosporin exhibiting potent activities against Pseudomonas aeruginosa and other gram-negative pathogens including multi-drug resistant bacteria: Structure activity relationship

European Journal of Medicinal Chemistry (2018)

Toshiaki Aoki Hidenori Yoshizawa Kenji Yamawaki Katsuki Yokoo Jun Sato

Stenotrophomonas maltophilia

Acinetobacter baumannii

10.1016/j.ejmech.2018.06.014

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Citations (132)