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Epoxyquinomicin B

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Category Antibiotics
Catalog number BBF-00857
CAS 175448-32-5
Molecular Weight 289.24
Molecular Formula C14H11NO6

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Product Description

Epoxyquinomicin B is an antibiotic produced by Amycolatopsis sp. MK299-95F4. It has moderate antibacterial activity against Pasteurella. It has a strong inhibitory effect on arthritis induced by oral collagen and is cytotoxic to several tumor cells.

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Synonyms (1S)-2-Hydroxy-N-(6-(hydroxymethyl)-2,5-dioxo-7-oxabicyclo(4.1.0)hept-3-en-3-yl)benzamide; Benzamide, 2-hydroxy-N-(6-(hydroxymethyl)-2,5-dioxo-7-oxabicyclo(4.1.0)hept-3-en-3-yl)-, (1S)-
IUPAC Name 2-hydroxy-N-[(1S,6R)-6-(hydroxymethyl)-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzamide
Canonical SMILES C1=CC=C(C(=C1)C(=O)NC2=CC(=O)C3(C(C2=O)O3)CO)O
InChI InChI=1S/C14H11NO6/c16-6-14-10(18)5-8(11(19)12(14)21-14)15-13(20)7-3-1-2-4-9(7)17/h1-5,12,16-17H,6H2,(H,15,20)/t12-,14+/m1/s1
InChI Key VIGCRVLJRHAWJR-OCCSQVGLSA-N
Appearance Light Yellow Powder
Antibiotic Activity Spectrum Gram-positive bacteria
Boiling Point 625.7°C at 760 mmHg
Melting Point 178-184°C
Density 1.63 g/cm3
1. Epoxyquinomicins A, B, C and D, new antibiotics from Amycolatopsis. II. Effect on type II collagen-induced arthritis in mice
N Matsumoto, H Iinuma, T Sawa, T Takeuchi, S Hirano, T Yoshioka, M Ishizuka J Antibiot (Tokyo). 1997 Nov;50(11):906-11. doi: 10.7164/antibiotics.50.906.
The anti-arthritic effects of epoxyquinomicins on type II collagen-induced arthritis in DBA/1J mice were examined. Prophylactic treatment with epoxyquinomicins A, B, C and D (1-4 mg/kg) had potent inhibitory effects on type II collagen-induced arthritis. In contrast to nonsteroidal anti-inflammatory drugs (NSAIDs), epoxyquinomicin C (1-30 mg/kg) had neither an anti-inflammatory effect on carrageenan-induced paw edema in rats nor an analgesic effect on acetic acid-induced writhing in mice. These results suggest that the mode of action of epoxyquinomicins is different from that of NSAIDs and that epoxyquinomicins may become useful drugs for the treatment of rheumatoid arthritis.
2. Epoxyquinomicins A, B, C and D, new antibiotics from Amycolatopsis. III. Physico-chemical properties and structure determination
N Matsumoto, T Tsuchida, R Sawa, H Iinuma, H Nakamura, H Naganawa, T Sawa, T Takeuchi J Antibiot (Tokyo). 1997 Nov;50(11):912-5. doi: 10.7164/antibiotics.50.912.
The structures of epoxyquinomicins A (1), B (2), C (3) and D (4) were determined by spectroscopic studies. Compound 1 was determined to be (5R,6S)-2-(3-chloro-2-hydroxybenzoylamino)-5-hydroxymethyl-5,6-epo xy- 2-cyclohexene-1,4-dione. Compound 2 was revealed to be the dechlorinated derivative of 1. Compounds 3 and 4 were determined to be the reduced derivative of 2 and 1, respectively.
3. Synthesis of anti-rheumatic agent epoxyquinomicin B
N Matsumoto, H Iinuma, T Sawa, T Takeuchi Bioorg Med Chem Lett. 1998 Nov 3;8(21):2945-8. doi: 10.1016/S0960-894X(98)00529-0.
Anti-rheumatic agent (+/-)-epoxyquinomicin B was synthesized for a 22% overall yield in eight steps from commercially available 3-hydroxy-4-nitrobenzaldehyde via the intermediate quinone 6 prepared by selective phenol oxidation of 5 by use of Fremy's salt as the key step.

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