Journal of Medicinal Chemistry

, volume 45 , issue 4 , pages 919-929

New Type of Metalloproteinase Inhibitor: Design and Synthesis of New Phosphonamide-Based Hydroxamic Acids

Masaaki Sawa ¹

Takao Kiyoi ¹

Kiriko Kurokawa ¹

Hiroshi Kumihara ¹

Minoru YAMAMOTO ¹

Tomohiro Miyasaka ¹

Yasuko Ito ¹

RYOICHI HIRAYAMA ¹

Inoue Tomomi ¹

Yasuyuki Kirii ¹

Eiji NISHIWAKI ¹

Hiroshi Ohmoto ¹

Yu Maeda ¹

Etsuko Ishibushi ¹

Yoshimasa Inoue ¹

Kohichiro Yoshino ¹

Hirosato KONDO ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Department of Chemistry, R&D Laboratories, Nippon Organon K.K., 1-5-90, Tomobuchi-cho, Miyakojima-ku, Osaka 534-0016, Japan |

Publication type: Journal Article

Publication date: 2002-01-15

American Chemical Society (ACS)

Journal of Medicinal Chemistry

scimago Q1

wos Q1

SJR: 1.801

CiteScore: 11.5

Impact factor: 6.8

ISSN: 00222623, 15204804

DOI: 10.1021/jm0103211

Copy DOI

PubMed ID: 11831904

Drug Discovery

Molecular Medicine

Abstract

A series of phosphonamide-based hydroxamate derivatives were synthesized, and the inhibitory activities were evaluated against various metalloproteinases in order to clarify its selectivity profile. Among the four diastereomeric isomers resulting from the chirality at the C-3 and P atoms, the compound with a (R,R)-configuration both at the C-3 position and the phosphorus atom was found to be potently active, while the other diastereomeric isomers were almost inactive. A number of (R,R)-compounds synthesized here exhibited broad spectrum activities with nanomolar K(i) values against MMP-1, -3, -9, and TACE and also showed nanomolar IC(50) values against HB-EGF shedding in a cell-based inhibition assay. The modeling study using X-ray structure of MMP-3 suggested the possible binding mode of the phosphonamide-based inhibitors.

Found

1 citation

Budnikova Yulia

DSc in Chemistry, professor

260 publications, 4 537 citations, 54 reviews

h-index: 34

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Kazan Scientific Center of the Russian Academy of Sciences

Research interests

C-H functionalization

Catalysis

Charge transfer

Chemistry of organoelement compounds

1 citation

Chugunova Elena

🤝

DSc in Chemistry

62 publications, 537 citations, 1 review

h-index: 13

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Kazan National Research Technological University

Top-30

Journals

	1 2 3 4 5 6 7 8
Organic Letters	Organic Letters, 8, 7.34% Organic Letters 8 publications, 7.34%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 7, 6.42% Organic and Biomolecular Chemistry 7 publications, 6.42%
Journal of Organic Chemistry	Journal of Organic Chemistry, 6, 5.5% Journal of Organic Chemistry 6 publications, 5.5%
Bioorganic and Medicinal Chemistry Letters	Bioorganic and Medicinal Chemistry Letters, 5, 4.59% Bioorganic and Medicinal Chemistry Letters 5 publications, 4.59%
Tetrahedron Letters	Tetrahedron Letters, 5, 4.59% Tetrahedron Letters 5 publications, 4.59%
Tetrahedron	Tetrahedron, 3, 2.75% Tetrahedron 3 publications, 2.75%
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 3, 2.75% Angewandte Chemie - International Edition 3 publications, 2.75%
Angewandte Chemie	Angewandte Chemie, 3, 2.75% Angewandte Chemie 3 publications, 2.75%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 3, 2.75% Advanced Synthesis and Catalysis 3 publications, 2.75%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 3, 2.75% European Journal of Organic Chemistry 3 publications, 2.75%
ChemistrySelect	ChemistrySelect, 3, 2.75% ChemistrySelect 3 publications, 2.75%
RSC Advances	RSC Advances, 3, 2.75% RSC Advances 3 publications, 2.75%
Bioorganic and Medicinal Chemistry	Bioorganic and Medicinal Chemistry, 2, 1.83% Bioorganic and Medicinal Chemistry 2 publications, 1.83%
Journal of the American Chemical Society	Journal of the American Chemical Society, 2, 1.83% Journal of the American Chemical Society 2 publications, 1.83%
ACS Catalysis	ACS Catalysis, 2, 1.83% ACS Catalysis 2 publications, 1.83%
Chemical Science	Chemical Science, 2, 1.83% Chemical Science 2 publications, 1.83%
Chemical Communications	Chemical Communications, 2, 1.83% Chemical Communications 2 publications, 1.83%
New Journal of Chemistry	New Journal of Chemistry, 2, 1.83% New Journal of Chemistry 2 publications, 1.83%
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 2, 1.83% Organic Chemistry Frontiers 2 publications, 1.83%
Phosphorus, Sulfur and Silicon and the Related Elements	Phosphorus, Sulfur and Silicon and the Related Elements, 2, 1.83% Phosphorus, Sulfur and Silicon and the Related Elements 2 publications, 1.83%
Journal of Molecular Structure THEOCHEM	Journal of Molecular Structure THEOCHEM, 1, 0.92% Journal of Molecular Structure THEOCHEM 1 publication, 0.92%
Journal of Biological Chemistry	Journal of Biological Chemistry, 1, 0.92% Journal of Biological Chemistry 1 publication, 0.92%
Journal of Dental Research	Journal of Dental Research, 1, 0.92% Journal of Dental Research 1 publication, 0.92%
MolBank	MolBank, 1, 0.92% MolBank 1 publication, 0.92%
Pharmaceutical Chemistry Journal	Pharmaceutical Chemistry Journal, 1, 0.92% Pharmaceutical Chemistry Journal 1 publication, 0.92%
Journal of Computer-Aided Molecular Design	Journal of Computer-Aided Molecular Design, 1, 0.92% Journal of Computer-Aided Molecular Design 1 publication, 0.92%
Mendeleev Communications	Mendeleev Communications, 1, 0.92% Mendeleev Communications 1 publication, 0.92%
Russian Chemical Reviews	Russian Chemical Reviews, 1, 0.92% Russian Chemical Reviews 1 publication, 0.92%
Comptes Rendus Chimie	Comptes Rendus Chimie, 1, 0.92% Comptes Rendus Chimie 1 publication, 0.92%
	1 2 3 4 5 6 7 8

Publishers

	5 10 15 20 25
Wiley	Wiley, 22, 20.18% Wiley 22 publications, 20.18%
Elsevier	Elsevier, 21, 19.27% Elsevier 21 publications, 19.27%
American Chemical Society (ACS)	American Chemical Society (ACS), 21, 19.27% American Chemical Society (ACS) 21 publications, 19.27%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 18, 16.51% Royal Society of Chemistry (RSC) 18 publications, 16.51%
Taylor & Francis	Taylor & Francis, 3, 2.75% Taylor & Francis 3 publications, 2.75%
Springer Nature	Springer Nature, 2, 1.83% Springer Nature 2 publications, 1.83%
Pleiades Publishing	Pleiades Publishing, 2, 1.83% Pleiades Publishing 2 publications, 1.83%
American Society for Biochemistry and Molecular Biology	American Society for Biochemistry and Molecular Biology, 1, 0.92% American Society for Biochemistry and Molecular Biology 1 publication, 0.92%
SAGE	SAGE, 1, 0.92% SAGE 1 publication, 0.92%
MDPI	MDPI, 1, 0.92% MDPI 1 publication, 0.92%
OOO Zhurnal "Mendeleevskie Soobshcheniya"	OOO Zhurnal "Mendeleevskie Soobshcheniya", 1, 0.92% OOO Zhurnal "Mendeleevskie Soobshcheniya" 1 publication, 0.92%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 0.92% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 0.92%
Cellule MathDoc/Centre Mersenne	Cellule MathDoc/Centre Mersenne, 1, 0.92% Cellule MathDoc/Centre Mersenne 1 publication, 0.92%
American Association for the Advancement of Science (AAAS)	American Association for the Advancement of Science (AAAS), 1, 0.92% American Association for the Advancement of Science (AAAS) 1 publication, 0.92%
American Association for Cancer Research (AACR)	American Association for Cancer Research (AACR), 1, 0.92% American Association for Cancer Research (AACR) 1 publication, 0.92%
American Physiological Society	American Physiological Society, 1, 0.92% American Physiological Society 1 publication, 0.92%
Cold Spring Harbor Laboratory	Cold Spring Harbor Laboratory, 1, 0.92% Cold Spring Harbor Laboratory 1 publication, 0.92%
Georg Thieme Verlag KG	Georg Thieme Verlag KG, 1, 0.92% Georg Thieme Verlag KG 1 publication, 0.92%
	5 10 15 20 25

We do not take into account publications without a DOI.
Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.

Metrics

109

Cite this

GOST |

Cite this

GOST Copy

Sawa M. et al. New Type of Metalloproteinase Inhibitor: Design and Synthesis of New Phosphonamide-Based Hydroxamic Acids // Journal of Medicinal Chemistry. 2002. Vol. 45. No. 4. pp. 919-929.

GOST all authors (up to 50) Copy

Sawa M., Kiyoi T., Kurokawa K., Kumihara H., YAMAMOTO M., Miyasaka T., Ito Y., HIRAYAMA R., Tomomi I., Kirii Y., NISHIWAKI E., Ohmoto H., Maeda Yu., Ishibushi E., Inoue Y., Yoshino K., KONDO H. New Type of Metalloproteinase Inhibitor: Design and Synthesis of New Phosphonamide-Based Hydroxamic Acids // Journal of Medicinal Chemistry. 2002. Vol. 45. No. 4. pp. 919-929.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1021/jm0103211

UR - https://doi.org/10.1021/jm0103211

TI - New Type of Metalloproteinase Inhibitor: Design and Synthesis of New Phosphonamide-Based Hydroxamic Acids

T2 - Journal of Medicinal Chemistry

AU - Sawa, Masaaki

AU - Kiyoi, Takao

AU - Kurokawa, Kiriko

AU - Kumihara, Hiroshi

AU - YAMAMOTO, Minoru

AU - Miyasaka, Tomohiro

AU - Ito, Yasuko

AU - HIRAYAMA, RYOICHI

AU - Tomomi, Inoue

AU - Kirii, Yasuyuki

AU - NISHIWAKI, Eiji

AU - Ohmoto, Hiroshi

AU - Maeda, Yu

AU - Ishibushi, Etsuko

AU - Inoue, Yoshimasa

AU - Yoshino, Kohichiro

AU - KONDO, Hirosato

PY - 2002

DA - 2002/01/15

PB - American Chemical Society (ACS)

SP - 919-929

IS - 4

VL - 45

PMID - 11831904

SN - 0022-2623

SN - 1520-4804

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2002_Sawa,

author = {Masaaki Sawa and Takao Kiyoi and Kiriko Kurokawa and Hiroshi Kumihara and Minoru YAMAMOTO and Tomohiro Miyasaka and Yasuko Ito and RYOICHI HIRAYAMA and Inoue Tomomi and Yasuyuki Kirii and Eiji NISHIWAKI and Hiroshi Ohmoto and Yu Maeda and Etsuko Ishibushi and Yoshimasa Inoue and Kohichiro Yoshino and Hirosato KONDO},

title = {New Type of Metalloproteinase Inhibitor: Design and Synthesis of New Phosphonamide-Based Hydroxamic Acids},

journal = {Journal of Medicinal Chemistry},

year = {2002},

volume = {45},

publisher = {American Chemical Society (ACS)},

month = {jan},

url = {https://doi.org/10.1021/jm0103211},

number = {4},

pages = {919--929},

doi = {10.1021/jm0103211}

}

MLA

Cite this

MLA Copy

Sawa, Masaaki, et al. “New Type of Metalloproteinase Inhibitor: Design and Synthesis of New Phosphonamide-Based Hydroxamic Acids.” Journal of Medicinal Chemistry, vol. 45, no. 4, Jan. 2002, pp. 919-929. https://doi.org/10.1021/jm0103211.

Publisher

American Chemical Society (ACS)

Journal

Journal of Medicinal Chemistry

scimago Q1

wos Q1

SJR

1.801

CiteScore

11.5

Impact factor

6.8

ISSN

00222623 (Print)

15204804 (Electronic)