Organic and Biomolecular Chemistry

, volume 19 , issue 16 , pages 3589-3594

Rh-Catalyzed C–H alkylation enabling modular synthesis of CF₃-substituted benzannulated macrocyclic inhibitors of B cell responses

Tao Sun ^{1, 2, 3, 4, 5}

Shijun He ^{5, 6, 7, 8, 9, 10, 11}

Zhongliang Xu ^{5, 6, 8, 9, 10, 11}

Jian-ping Zuo ^{6, 7}

Jianping Zuo ^{5, 8, 9, 10, 11}

Yang Yu ^{1, 2, 3, 4, 5}

Weibo Yang ^{5, 6, 7, 8, 9, 10, 11, 12}

Hide authors affiliations Show authors affiliations: 12 affiliations

Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, China |

Center for Supramolecular Chemistry and Catalysis and Department of Chemistry

Shanghai university |

⁴

Shanghai 200444 |

⁵

CHINA |

⁶

Chinese Academy of Sciences Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica (SIMM), Chinese Academy of Sciences, Shanghai, China |

⁷

University of Chinese Academy of sciences, Beijing 100049, China |

⁸

Chinese Academy of Sciences Key Laboratory of Receptor Research

⁹

Shanghai Institute of Materia Medica (SIMM) |

¹⁰

Chinese Academy of sciences

¹¹

Shanghai |

¹²

School of Pharmaceutical Science and Technology, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, China |

Publication type: Journal Article

Publication date: 2021-03-24

Royal Society of Chemistry (RSC)

Organic and Biomolecular Chemistry

scimago Q2

wos Q2

SJR: 0.600

CiteScore: 5.2

Impact factor: 2.7

ISSN: 14770520, 14770539

DOI: 10.1039/d1ob00296a

Copy DOI

PubMed ID: 33908550

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

Inspired by aspirin and chalcone, herein, we describe a modular biomimetic strategy to achieve a new class of CF3-bearing benzannulated macrolactams. The key to the success of macrolactams was the utilization of a highly chemoselective Rh(iii)-catalyzed native carboxylic acid-directed C-H alkylation. Moreover, the unique CF3-containing benzannulated macrocycles showed decent immunosuppressive effects on B cells in vitro, including proliferation, activation, and antibody production upon specific stimulation implicating TLR and BCR signaling.

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GOST |

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GOST Copy

Sun T. et al. Rh-Catalyzed C–H alkylation enabling modular synthesis of CF3-substituted benzannulated macrocyclic inhibitors of B cell responses // Organic and Biomolecular Chemistry. 2021. Vol. 19. No. 16. pp. 3589-3594.

GOST all authors (up to 50) Copy

Sun T., He S., Xu Z., Zuo J., Zuo J., Yu Y., Yang W. Rh-Catalyzed C–H alkylation enabling modular synthesis of CF3-substituted benzannulated macrocyclic inhibitors of B cell responses // Organic and Biomolecular Chemistry. 2021. Vol. 19. No. 16. pp. 3589-3594.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1039/d1ob00296a

UR - https://xlink.rsc.org/?DOI=D1OB00296A

TI - Rh-Catalyzed C–H alkylation enabling modular synthesis of CF3-substituted benzannulated macrocyclic inhibitors of B cell responses

T2 - Organic and Biomolecular Chemistry

AU - Sun, Tao

AU - He, Shijun

AU - Xu, Zhongliang

AU - Zuo, Jian-ping

AU - Zuo, Jianping

AU - Yu, Yang

AU - Yang, Weibo

PY - 2021

DA - 2021/03/24

PB - Royal Society of Chemistry (RSC)

SP - 3589-3594

IS - 16

VL - 19

PMID - 33908550

SN - 1477-0520

SN - 1477-0539

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2021_Sun,

author = {Tao Sun and Shijun He and Zhongliang Xu and Jian-ping Zuo and Jianping Zuo and Yang Yu and Weibo Yang},

title = {Rh-Catalyzed C–H alkylation enabling modular synthesis of CF3-substituted benzannulated macrocyclic inhibitors of B cell responses},

journal = {Organic and Biomolecular Chemistry},

year = {2021},

volume = {19},

publisher = {Royal Society of Chemistry (RSC)},

month = {mar},

url = {https://xlink.rsc.org/?DOI=D1OB00296A},

number = {16},

pages = {3589--3594},

doi = {10.1039/d1ob00296a}

}

MLA

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MLA Copy

Sun, Tao, et al. “Rh-Catalyzed C–H alkylation enabling modular synthesis of CF3-substituted benzannulated macrocyclic inhibitors of B cell responses.” Organic and Biomolecular Chemistry, vol. 19, no. 16, Mar. 2021, pp. 3589-3594. https://xlink.rsc.org/?DOI=D1OB00296A.

Publisher

Royal Society of Chemistry (RSC)

Journal

Organic and Biomolecular Chemistry

scimago Q2

wos Q2

SJR

0.600

CiteScore

5.2

Impact factor

2.7

ISSN

14770520 (Print)

14770539 (Electronic)

Profiles

Weibo Yang