Synthesis of gamma-Aminobutyric Acid (GABA) Analogues Conformationally Restricted by Bicyclo[3.1.0]hexane/hexene or [4.1.0]Heptane/heptene Backbones as Potent Betaine/GABA Transporter Inhibitors

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Synthesis of gamma-Aminobutyric Acid (GABA) Analogues Conformationally Restricted by Bicyclo[3.1.0]hexane/hexene or [4.1.0]Heptane/heptene Backbones as Potent Betaine/GABA Transporter Inhibitors. / Mitsui, Keisuke; Lie, Maria E. K.; Saito, Naoki; Fujiwara, Koichi; Watanabe, Mizuki; Wellendorph, Petrine; Shuto, Satoshi.

In: Organic Letters, Vol. 24, No. 23, 2022, p. 4151-4154.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Mitsui, K, Lie, MEK, Saito, N, Fujiwara, K, Watanabe, M, Wellendorph, P & Shuto, S 2022, 'Synthesis of gamma-Aminobutyric Acid (GABA) Analogues Conformationally Restricted by Bicyclo[3.1.0]hexane/hexene or [4.1.0]Heptane/heptene Backbones as Potent Betaine/GABA Transporter Inhibitors', Organic Letters, vol. 24, no. 23, pp. 4151-4154. https://doi.org/10.1021/acs.orglett.2c01346

APA

Mitsui, K., Lie, M. E. K., Saito, N., Fujiwara, K., Watanabe, M., Wellendorph, P., & Shuto, S. (2022). Synthesis of gamma-Aminobutyric Acid (GABA) Analogues Conformationally Restricted by Bicyclo[3.1.0]hexane/hexene or [4.1.0]Heptane/heptene Backbones as Potent Betaine/GABA Transporter Inhibitors. Organic Letters, 24(23), 4151-4154. https://doi.org/10.1021/acs.orglett.2c01346

Vancouver

Mitsui K, Lie MEK, Saito N, Fujiwara K, Watanabe M, Wellendorph P et al. Synthesis of gamma-Aminobutyric Acid (GABA) Analogues Conformationally Restricted by Bicyclo[3.1.0]hexane/hexene or [4.1.0]Heptane/heptene Backbones as Potent Betaine/GABA Transporter Inhibitors. Organic Letters. 2022;24(23):4151-4154. https://doi.org/10.1021/acs.orglett.2c01346

Author

Mitsui, Keisuke ; Lie, Maria E. K. ; Saito, Naoki ; Fujiwara, Koichi ; Watanabe, Mizuki ; Wellendorph, Petrine ; Shuto, Satoshi. / Synthesis of gamma-Aminobutyric Acid (GABA) Analogues Conformationally Restricted by Bicyclo[3.1.0]hexane/hexene or [4.1.0]Heptane/heptene Backbones as Potent Betaine/GABA Transporter Inhibitors. In: Organic Letters. 2022 ; Vol. 24, No. 23. pp. 4151-4154.

Bibtex

@article{16921dee715d4005b147df84db05d9ae,
title = "Synthesis of gamma-Aminobutyric Acid (GABA) Analogues Conformationally Restricted by Bicyclo[3.1.0]hexane/hexene or [4.1.0]Heptane/heptene Backbones as Potent Betaine/GABA Transporter Inhibitors",
abstract = "Novel gamma-aminobutyric acid (GABA) analogues 3-5, having a bicyclo[3.1.0]hexene, [4.1.0]heptane, or [4.1.0]heptene backbone, respectively, were designed from the bioactive form analysis of the previous inhibitor 2 with a bicyclo[3.1.0]hexane backbone. Compounds 3-5 and 2 were synthesized from a common 1,7-diene intermediate 6 using ring-closing metathesis (RCM) to construct the key bicyclo backbones. Compounds 3-5 strongly inhibit betaine/GABA transporter 1 (BGT1) uptake, but compound 4 stands out with its selective low micromolar potency.",
keywords = "ISOMERIZATION, CYCLOISOMERIZATION, CARBENE",
author = "Keisuke Mitsui and Lie, {Maria E. K.} and Naoki Saito and Koichi Fujiwara and Mizuki Watanabe and Petrine Wellendorph and Satoshi Shuto",
year = "2022",
doi = "10.1021/acs.orglett.2c01346",
language = "English",
volume = "24",
pages = "4151--4154",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "23",

}

RIS

TY - JOUR

T1 - Synthesis of gamma-Aminobutyric Acid (GABA) Analogues Conformationally Restricted by Bicyclo[3.1.0]hexane/hexene or [4.1.0]Heptane/heptene Backbones as Potent Betaine/GABA Transporter Inhibitors

AU - Mitsui, Keisuke

AU - Lie, Maria E. K.

AU - Saito, Naoki

AU - Fujiwara, Koichi

AU - Watanabe, Mizuki

AU - Wellendorph, Petrine

AU - Shuto, Satoshi

PY - 2022

Y1 - 2022

N2 - Novel gamma-aminobutyric acid (GABA) analogues 3-5, having a bicyclo[3.1.0]hexene, [4.1.0]heptane, or [4.1.0]heptene backbone, respectively, were designed from the bioactive form analysis of the previous inhibitor 2 with a bicyclo[3.1.0]hexane backbone. Compounds 3-5 and 2 were synthesized from a common 1,7-diene intermediate 6 using ring-closing metathesis (RCM) to construct the key bicyclo backbones. Compounds 3-5 strongly inhibit betaine/GABA transporter 1 (BGT1) uptake, but compound 4 stands out with its selective low micromolar potency.

AB - Novel gamma-aminobutyric acid (GABA) analogues 3-5, having a bicyclo[3.1.0]hexene, [4.1.0]heptane, or [4.1.0]heptene backbone, respectively, were designed from the bioactive form analysis of the previous inhibitor 2 with a bicyclo[3.1.0]hexane backbone. Compounds 3-5 and 2 were synthesized from a common 1,7-diene intermediate 6 using ring-closing metathesis (RCM) to construct the key bicyclo backbones. Compounds 3-5 strongly inhibit betaine/GABA transporter 1 (BGT1) uptake, but compound 4 stands out with its selective low micromolar potency.

KW - ISOMERIZATION

KW - CYCLOISOMERIZATION

KW - CARBENE

U2 - 10.1021/acs.orglett.2c01346

DO - 10.1021/acs.orglett.2c01346

M3 - Journal article

C2 - 35674784

VL - 24

SP - 4151

EP - 4154

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 23

ER -

ID: 315267054