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RhII-Catalyzed De-symmetrization of Ethane-1,2-dithiol and Propane-1,3-dithiol Yields Metallo-β-lactamase Inhibitors. / Krasavin, Mikhail; Zhukovsky, Daniil; Solovyev, Igor; Barkhatova, Darina; Dar'in, Dmitry; Frank, Denia; Martinelli, Giada; Weizel, Lilia; Proschak, Anna; Rotter, Marco; Kramer, Jan S.; Brunst, Steffen; Wichelhaus, Thomas A.; Proschak, Ewgenij.

In: ChemMedChem, Vol. 16, No. 22, 19.11.2021, p. 3410-3417.

Research output: Contribution to journal › Article › peer-review

Harvard

Krasavin, M, Zhukovsky, D, Solovyev, I, Barkhatova, D, Dar'in, D, Frank, D, Martinelli, G, Weizel, L, Proschak, A, Rotter, M, Kramer, JS, Brunst, S, Wichelhaus, TA & Proschak, E 2021, 'RhII-Catalyzed De-symmetrization of Ethane-1,2-dithiol and Propane-1,3-dithiol Yields Metallo-β-lactamase Inhibitors', ChemMedChem, vol. 16, no. 22, pp. 3410-3417. https://doi.org/10.1002/cmdc.202100344

APA

Krasavin, M., Zhukovsky, D., Solovyev, I., Barkhatova, D., Dar'in, D., Frank, D., Martinelli, G., Weizel, L., Proschak, A., Rotter, M., Kramer, J. S., Brunst, S., Wichelhaus, T. A., & Proschak, E. (2021). RhII-Catalyzed De-symmetrization of Ethane-1,2-dithiol and Propane-1,3-dithiol Yields Metallo-β-lactamase Inhibitors. ChemMedChem, 16(22), 3410-3417. https://doi.org/10.1002/cmdc.202100344

Vancouver

Krasavin M, Zhukovsky D, Solovyev I, Barkhatova D, Dar'in D, Frank D et al. RhII-Catalyzed De-symmetrization of Ethane-1,2-dithiol and Propane-1,3-dithiol Yields Metallo-β-lactamase Inhibitors. ChemMedChem. 2021 Nov 19;16(22):3410-3417. https://doi.org/10.1002/cmdc.202100344

Author

Krasavin, Mikhail ; Zhukovsky, Daniil ; Solovyev, Igor ; Barkhatova, Darina ; Dar'in, Dmitry ; Frank, Denia ; Martinelli, Giada ; Weizel, Lilia ; Proschak, Anna ; Rotter, Marco ; Kramer, Jan S. ; Brunst, Steffen ; Wichelhaus, Thomas A. ; Proschak, Ewgenij. / RhII-Catalyzed De-symmetrization of Ethane-1,2-dithiol and Propane-1,3-dithiol Yields Metallo-β-lactamase Inhibitors. In: ChemMedChem. 2021 ; Vol. 16, No. 22. pp. 3410-3417.

BibTeX

@article{3d8cb65c75aa4c3482b21a1124d026a2,
title = "RhII-Catalyzed De-symmetrization of Ethane-1,2-dithiol and Propane-1,3-dithiol Yields Metallo-β-lactamase Inhibitors",
abstract = "Diversity-oriented synthesis (DOS) is a rich source for novel lead structures in Medicinal Chemistry. In this study, we present a DOS-compatible method for synthesis of compounds bearing a free thiol moiety. The procedure relies on Rh(II)-catalyzed coupling of dithiols to diazo building blocks. The synthetized library was probed against metallo-β-lactamases (MBLs) NDM-1 and VIM-1. Biochemical and biological evaluation led to identification of novel potent MBL inhibitors with antibiotic adjuvant activity.",
keywords = "diazo compounds, metallo β lactamases, multiresistant bacteria, Rh(II) catalysis, thiol inhibitors, DIAZO, KETONES, metallo beta lactamases",
author = "Mikhail Krasavin and Daniil Zhukovsky and Igor Solovyev and Darina Barkhatova and Dmitry Dar'in and Denia Frank and Giada Martinelli and Lilia Weizel and Anna Proschak and Marco Rotter and Kramer, {Jan S.} and Steffen Brunst and Wichelhaus, {Thomas A.} and Ewgenij Proschak",
note = "Publisher Copyright: {\textcopyright} 2021 The Authors. ChemMedChem published by Wiley-VCH GmbH.",
year = "2021",
month = nov,
day = "19",
doi = "10.1002/cmdc.202100344",
language = "English",
volume = "16",
pages = "3410--3417",
journal = "Farmaco",
issn = "1860-7179",
publisher = "Wiley-Blackwell",
number = "22",

}

RIS

TY - JOUR

T1 - RhII-Catalyzed De-symmetrization of Ethane-1,2-dithiol and Propane-1,3-dithiol Yields Metallo-β-lactamase Inhibitors

AU - Krasavin, Mikhail

AU - Zhukovsky, Daniil

AU - Solovyev, Igor

AU - Barkhatova, Darina

AU - Dar'in, Dmitry

AU - Frank, Denia

AU - Martinelli, Giada

AU - Weizel, Lilia

AU - Proschak, Anna

AU - Rotter, Marco

AU - Kramer, Jan S.

AU - Brunst, Steffen

AU - Wichelhaus, Thomas A.

AU - Proschak, Ewgenij

N1 - Publisher Copyright: © 2021 The Authors. ChemMedChem published by Wiley-VCH GmbH.

PY - 2021/11/19

Y1 - 2021/11/19

N2 - Diversity-oriented synthesis (DOS) is a rich source for novel lead structures in Medicinal Chemistry. In this study, we present a DOS-compatible method for synthesis of compounds bearing a free thiol moiety. The procedure relies on Rh(II)-catalyzed coupling of dithiols to diazo building blocks. The synthetized library was probed against metallo-β-lactamases (MBLs) NDM-1 and VIM-1. Biochemical and biological evaluation led to identification of novel potent MBL inhibitors with antibiotic adjuvant activity.

AB - Diversity-oriented synthesis (DOS) is a rich source for novel lead structures in Medicinal Chemistry. In this study, we present a DOS-compatible method for synthesis of compounds bearing a free thiol moiety. The procedure relies on Rh(II)-catalyzed coupling of dithiols to diazo building blocks. The synthetized library was probed against metallo-β-lactamases (MBLs) NDM-1 and VIM-1. Biochemical and biological evaluation led to identification of novel potent MBL inhibitors with antibiotic adjuvant activity.

KW - diazo compounds

KW - metallo β lactamases

KW - multiresistant bacteria

KW - Rh(II) catalysis

KW - thiol inhibitors

KW - DIAZO

KW - KETONES

KW - metallo beta lactamases

UR - http://www.scopus.com/inward/record.url?scp=85112073080&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/5993ce08-8619-3834-bbbe-d8bbbc29f6a8/

U2 - 10.1002/cmdc.202100344

DO - 10.1002/cmdc.202100344

M3 - Article

C2 - 34184833

AN - SCOPUS:85112073080

VL - 16

SP - 3410

EP - 3417

JO - Farmaco

JF - Farmaco

SN - 1860-7179

IS - 22

ER -

ID: 84793973