YM-181741

YM-181741

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Category Antibiotics
Catalog number BBF-01558
CAS
Molecular Weight 322.3
Molecular Formula C19H14O5

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Description

YM-181741 is a novel benz[a]anthraquinone antibiotic isolated from the culture broth of actinomycete strain Q57219. It showed selective anti-Helicobacterpylori activity with a MIC value of 0.2 microg/ml.

Specification

IUPAC Name 8-hydroxy-3-(hydroxymethyl)-3,4-dihydro-2H-benzo[a]anthracene-1,7,12-trione
Canonical SMILES C1C(CC(=O)C2=C1C=CC3=C2C(=O)C4=C(C3=O)C(=CC=C4)O)CO
InChI InChI=1S/C19H14O5/c20-8-9-6-10-4-5-12-17(15(10)14(22)7-9)19(24)11-2-1-3-13(21)16(11)18(12)23/h1-5,9,20-21H,6-8H2
InChI Key UXSDRWXYYLSCOY-UHFFFAOYSA-N

Properties

Appearance Yellow Powder
Antibiotic Activity Spectrum Gram-negative bacteria

Reference Reading

1. Angucyclinone antibiotics: total syntheses of YM-181741, (+)-ochromycinone, (+)-rubiginone B2, (-)-tetrangomycin, and MM-47755
Krishna P Kaliappan, Velayutham Ravikumar J Org Chem. 2007 Aug 3;72(16):6116-26. doi: 10.1021/jo070709p. Epub 2007 Jul 11.
A concise and highly enantioselective route has been developed for the synthesis of angucyclinone-type natural products. Utilizing this strategy, total syntheses of five natural products YM-181741, (+)-ochromycinone, (+)-rubiginone B2, (-)-tetrangomycin, and MM-47755 have been accomplished in 22%, 23%, 19%, 18%, and 12% overall yields, respectively. Our approach for the synthesis of these natural products having the benz[a]anthraquinone skeleton is based on a sequential intramolecular enyne metathesis, intermolecular Diels-Alder reaction (DAR), and aromatization. The intramolecular enyne metathesis reaction was employed for the synthesis of enantiopure 1,3-dienes in excellent yields. Furthermore, the synthesis of YM-181741 as well as structurally similar angucyclinones such as (+)-ochromycinone and (+)-rubiginone B2 was achieved via asymmetric enolate alkylation of an oxazolidinone in excellent de. The related angucyclinones (-)-tetrangomycin and MM-47755, bearing a labile tertiary alcohol, were synthesized via Sharpless asymmetric epoxidation of a known allylic alcohol followed by opening the epoxide with Red-Al. The introduction of oxygen functionality at C-1 in all these natural products was accomplished by photooxygenation under a positive pressure of oxygen.
2. YM-181741, a novel benz[a]anthraquinone antibiotic with anti-Helicobacter pylori activity from Streptomyces sp
Masatoshi Taniguchi, Koji Nagai, Masato Watanabe, Nami Nimura, Ken-ichi Suzuki, Akihiro Tanaka J Antibiot (Tokyo). 2002 Jan;55(1):30-5. doi: 10.7164/antibiotics.55.30.
A novel benz[a]anthraquinone, YM-181741, was isolated from the culture broth of actinomycete strain Q57219. The strain was identified as Streptomyces sp. by morphological and chemotaxonomic characterization. YM-181741 was purified from the culture supernatant by serial column chromatography. The structure of YM-181741 was determined by spectroscopic analysis including one- and two-dimensional NMR experiments. YM-181741 showed selective anti-Helicobacterpylori activity with a MIC value of 0.2 microg/ml.

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