Bioorganic and Medicinal Chemistry Letters

, том 59 , страницы 128550

Essential structure of orexin 1 receptor antagonist YNT-707: Conversion of the 16-cyclopropylmethyl group to the 16-sulfonamide group in d-nor-nalfurafine derivatives

Koki KATOH ¹

Noriki Kutsumura ^{1, 2}

Naoshi Yamamoto ²

Yasuyuki Nagumo ²

Tsuyoshi Saitoh ²

Yukiko Ishikawa ²

Yoko Irukayama-Tomobe ²

Ryuji Tanimura ³

Masashi Yanagisawa ^{2, 4, 5}

Tsuyoshi Saitoh ^{1, 2}

Скрыть аффилиации авторов Показать аффилиации авторов: 5 аффилиаций

Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan |

International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8575, Japan |

Pharmaceutical Research Laboratories, Toray Industries, Inc., 10-1, Tebiro 6-choume, Kamakura, Kanagawa 248-8555, Japan |

⁴

R&D Center for Frontiers of Mirai in Policy and Technology (F-MIRAI), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8575, Japan |

⁵

Department of Molecular Genetics, University of Texas Southwestern Medical Center, Dallas, TX75390, USA |

Тип публикации: Journal Article

Дата публикации: 2022-03-01

Elsevier

Bioorganic and Medicinal Chemistry Letters

scimago Q2

wos Q2

БС2

SJR: 0.472

CiteScore: 5.1

Impact factor: 2.2

ISSN: 0960894X, 14643405

DOI: 10.1016/j.bmcl.2022.128550

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PubMed ID: 35041942

Organic Chemistry

Drug Discovery

Biochemistry

Molecular Biology

Pharmaceutical Science

Clinical Biochemistry

Molecular Medicine

Краткое описание

The five-membered D-ring nalfurafine (d-nor-nalfurafine) derivatives with a 16-sulfonamide group were synthesized. Conversion of the 16-cyclopropylmethyl group to the 16-benzenesulfonamide group in the d-nor-nalfurafine derivatives drastically improved the orexin 1 receptor (OX1R) antagonist activities. The intramolecular hydrogen bond between the 14-hydroxy and the 16-sulfonamide groups may play an important role in increasing the probability that the 6-amide group would be located at the lower side of the C-ring, leading to an active conformation for OX1R. The assay results and the conformational analyses of the 14-OH, 14-H, and 14-dehydrated d-nor-nalfurafine derivatives suggested that the 14- and 16-substituents of the d-nor-nalfurafine derivatives had a greater effect on the affinities for the OX1R than did the 14- and 17-substituents of nalfurafine derivatives.

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Исламский университет Азад Отделение науки и технологий

Университет Урмии

Университет Бу-Али Сина

Университет Илама

Области научных интересов

Antimicrobial resistance

Инфекционные болезни животных

Инфекционные заболевания

Лабораторная диагностика

Продукты пчеловодства

Топ-30

Журналы

	1
Nature and Science of Sleep	Nature and Science of Sleep, 1, 20% Nature and Science of Sleep 1 публикация, 20%
Journal of the Electrochemical Society	Journal of the Electrochemical Society, 1, 20% Journal of the Electrochemical Society 1 публикация, 20%
Medicinal Research Reviews	Medicinal Research Reviews, 1, 20% Medicinal Research Reviews 1 публикация, 20%
Chemometrics and Intelligent Laboratory Systems	Chemometrics and Intelligent Laboratory Systems, 1, 20% Chemometrics and Intelligent Laboratory Systems 1 публикация, 20%
Synlett	Synlett, 1, 20% Synlett 1 публикация, 20%
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KATOH K. et al. Essential structure of orexin 1 receptor antagonist YNT-707: Conversion of the 16-cyclopropylmethyl group to the 16-sulfonamide group in d-nor-nalfurafine derivatives // Bioorganic and Medicinal Chemistry Letters. 2022. Vol. 59. p. 128550.

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KATOH K., Kutsumura N., Yamamoto N., Nagumo Y., Saitoh T., Ishikawa Y., Irukayama-Tomobe Y., Tanimura R., Yanagisawa M., Saitoh T. Essential structure of orexin 1 receptor antagonist YNT-707: Conversion of the 16-cyclopropylmethyl group to the 16-sulfonamide group in d-nor-nalfurafine derivatives // Bioorganic and Medicinal Chemistry Letters. 2022. Vol. 59. p. 128550.

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TY - JOUR

DO - 10.1016/j.bmcl.2022.128550

UR - https://doi.org/10.1016/j.bmcl.2022.128550

TI - Essential structure of orexin 1 receptor antagonist YNT-707: Conversion of the 16-cyclopropylmethyl group to the 16-sulfonamide group in d-nor-nalfurafine derivatives

T2 - Bioorganic and Medicinal Chemistry Letters

AU - KATOH, Koki

AU - Kutsumura, Noriki

AU - Yamamoto, Naoshi

AU - Nagumo, Yasuyuki

AU - Saitoh, Tsuyoshi

AU - Ishikawa, Yukiko

AU - Irukayama-Tomobe, Yoko

AU - Tanimura, Ryuji

AU - Yanagisawa, Masashi

AU - Saitoh, Tsuyoshi

PY - 2022

DA - 2022/03/01

PB - Elsevier

SP - 128550

VL - 59

PMID - 35041942

SN - 0960-894X

SN - 1464-3405

ER -

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@article{2022_KATOH,

author = {Koki KATOH and Noriki Kutsumura and Naoshi Yamamoto and Yasuyuki Nagumo and Tsuyoshi Saitoh and Yukiko Ishikawa and Yoko Irukayama-Tomobe and Ryuji Tanimura and Masashi Yanagisawa and Tsuyoshi Saitoh},

title = {Essential structure of orexin 1 receptor antagonist YNT-707: Conversion of the 16-cyclopropylmethyl group to the 16-sulfonamide group in d-nor-nalfurafine derivatives},

journal = {Bioorganic and Medicinal Chemistry Letters},

year = {2022},

volume = {59},

publisher = {Elsevier},

month = {mar},

url = {https://doi.org/10.1016/j.bmcl.2022.128550},

pages = {128550},

doi = {10.1016/j.bmcl.2022.128550}

}

Издатель

Elsevier

Журнал

Bioorganic and Medicinal Chemistry Letters

scimago Q2

wos Q2

БС2

SJR

0.472

CiteScore

5.1

Impact factor

2.2

ISSN

0960894X (Print)

14643405 (Electronic)