Literature DB >> 1819704

PAF inhibitory activity of diketopiperazines: structure-activity relationships.

N Shimazaki1, I Shima, M Okamoto, K Yoshida, K Hemmi, M Hashimoto.   

Abstract

FR900452, a natural product isolated from the culture broth of Streptomyces phaeofaciens No. 7739, was found to inhibit PAF-induced rabbit platelet aggregation with an IC50 of 3.7 x 10(-7)M. FR900452, 1-methyl-3-[1-[5- methylthiomethyl-6-oxo-3-(2-oxo-3-cyclopenten-1-yli- dene)-2-piperazinyl]ethyl]-2-indoline, has an oxocylopentylidene group incorporated as a vinylogous amide in a diketopiperazine skeleton. This unique structure led us to synthesize diketopiperazine derivatives, 3-arylalkyl- 6-substituted-piperazine-2,5-diones. Their observed PAF inhibitory activity suggest that the D-D configuration of diketopiperazine is an important factor for anti-PAF activity and that the hydrophobic aromatic portion may play a specific role in the binding of the diketopiperazine to the PAF receptor.

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Year:  1991        PMID： 1819704     DOI： 10.1007/BF02536526

Source DB:  PubMed          Journal:  Lipids        ISSN： 0024-4201            Impact factor:   1.880


  6 in total

1.  Studies of platelet activating factor (PAF) antagonists from microbial products. II. Pharmacological studies of FR-49175 in animal models.

Authors:  M Okamoto; K Yoshida; I Uchida; M Kohsaka; H Aoki
Journal:  Chem Pharm Bull (Tokyo)       Date:  1986-01       Impact factor: 1.645

2.  Studies of platelet activating factor (PAF) antagonists from microbial products. I. Bisdethiobis(methylthio)gliotoxin and its derivatives.

Authors:  M Okamoto; K Yoshida; I Uchida; M Nishikawa; M Kohsaka; H Aoki
Journal:  Chem Pharm Bull (Tokyo)       Date:  1986-01       Impact factor: 1.645

3.  Diketopiperazine derivatives, a new series of platelet-activating factor inhibitors.

Authors:  N Shimazaki; I Shima; K Hemmi; Y Tsurumi; M Hashimoto
Journal:  Chem Pharm Bull (Tokyo)       Date:  1987-08       Impact factor: 1.645

4.  Studies of platelet activating factor (PAF) antagonists from microbial products. III. Pharmacological studies of FR-900452 in animal models.

Authors:  M Okamoto; K Yoshida; M Nishikawa; K Hayashi; I Uchida; M Kohsaka; H Aoki
Journal:  Chem Pharm Bull (Tokyo)       Date:  1986-07       Impact factor: 1.645

5.  Diketopiperazines as a new class of platelet-activating factor inhibitors.

Authors:  N Shimazaki; I Shima; K Hemmi; M Hashimoto
Journal:  J Med Chem       Date:  1987-10       Impact factor: 7.446

Review 6.  Perspectives in platelet-activating factor research.

Authors:  P Braquet; L Touqui; T Y Shen; B B Vargaftig
Journal:  Pharmacol Rev       Date:  1987-06       Impact factor: 25.468
  6 in total
  5 in total

Review 1.  Platelet-activating factor antagonists.

Authors:  M Koltai; P G Braquet
Journal:  Clin Rev Allergy       Date:  1994

2.  Influence of Open Chain and Cyclic Structure of Peptidomimetics on Antibacterial Activity in E. coli Strains.

Authors:  Parul Sahrawat; Paweł Kowalczyk; Dominik Koszelewski; Mateusz Szymczak; Karol Kramkowski; Aleksandra Wypych; Ryszard Ostaszewski
Journal:  Molecules       Date:  2022-06-06       Impact factor: 4.927

Review 3.  Rational and combinatorial tailoring of bioactive cyclic dipeptides.

Authors:  Tobias W Giessen; Mohamed A Marahiel
Journal:  Front Microbiol       Date:  2015-07-30       Impact factor: 5.640

4.  Global analysis of prokaryotic tRNA-derived cyclodipeptide biosynthesis.

Authors:  Michael A Skinnider; Chad W Johnston; Nishanth J Merwin; Chris A Dejong; Nathan A Magarvey
Journal:  BMC Genomics       Date:  2018-01-15       Impact factor: 3.969

5.  Morphology-Controlled Self-Assembly and Synthesis of Biopolyimide Particles from 4-Amino-l-phenylalanine.

Authors:  Thawinda Hirayama; Amit Kumar; Kenji Takada; Tatsuo Kaneko
Journal:  ACS Omega       Date:  2020-02-03
  5 in total

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