MSD-92

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MSD-92
Category Antibiotics
Catalog number BBF-03680
CAS 22712-32-9
Molecular Weight 223.19
Molecular Formula C8H9N5O3

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Description

It is originally isolated from Actinomyces sp. MSD-92 has anti-gram-positive and anti-gram-negative activity, and the MIC of it against Escherichia coli was 2 μg/mL.

Specification

Synonyms 2-Methylfervenulone; BRN 0540815; 2,8-Dihydro-2,6,8-trimethylpyrimido(5,4-e)-as-triazine-3,5,7-trione
IUPAC Name 2,6,8-trimethylpyrimido[5,4-e][1,2,4]triazine-3,5,7-trione
Canonical SMILES CN1C2=NN(C(=O)N=C2C(=O)N(C1=O)C)C
InChI InChI=1S/C8H9N5O3/c1-11-5-4(6(14)12(2)8(11)16)9-7(15)13(3)10-5/h1-3H3
InChI Key NLCDJWLDGSBUOQ-UHFFFAOYSA-N

Properties

Appearance Yellow Flake Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 298.6±23.0°C at 760 mmHg
Melting Point 183-183.5°C
Density 1.6±0.1 g/cm3

Reference Reading

1. Isolation of a novel protein tyrosine phosphatase inhibitor, 2-methyl-fervenulone, and its precursors from Streptomyces
H Wang, K L Lim, S L Yeo, X Xu, M M Sim, A E Ting, Y Wang, S Yee, Y H Tan, C J Pallen J Nat Prod. 2000 Dec;63(12):1641-6. doi: 10.1021/np000293+.
High-throughput screening identified an extract from Streptomyces sp. IM 2096 with inhibitory activity toward several protein tyrosine phosphatases (PTPs). Four 1,2,4-triazine compounds 2096A-D (1-4) were isolated from this extract and their structures elucidated by interpretation of spectroscopic data and confirmed by degradation and synthesis. The novel glycocyamidine derivatives 1 and 2 are diastereomers and may interconvert. Both are inactive in the PTP inhibition assay. Compounds 1 and 2 are unstable and partially decompose to 3 and glycocyamidine (5) at room temperature. Compound 3, known as MSD-92 or 2-methyl-fervenulone, is a broad-specificity PTP inhibitor with comparable potency to vanadate. The imidazo[4, 5-e]-1,2,4-triazine (4), inactive in the PTP-inhibition assay, may be a degradation product of 3.

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