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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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.
Specification
| 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 |
Properties
| 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 |
Reference Reading
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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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
