10-Decarbamoyloxy-9-dehydromitomycin B
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| Category | Antibiotics |
| Catalog number | BBF-02012 |
| CAS | 74148-44-0 |
| Molecular Weight | 288.30 |
| Molecular Formula | C15H16N2O4 |
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Description
10-Decarbamoyloxy-9-dehydromitomycin B is a mitane antibiotic produced by Streptomyces caespitosus KY 2072. It has anti-Gram-positive bacteria and anti-tumor cell activity.
Specification
| Synonyms | Mitomycin H; Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 1,1a,2,8,8a,8b-hexahydro-1,5-dimethyl-8a-hydroxy-6-methoxy-8-methylene-, (1aS-(1a-alpha,8a-alpha,8b-alpha))- |
| IUPAC Name | (4S,6S,7R)-7-hydroxy-11-methoxy-5,12-dimethyl-8-methylidene-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-diene-10,13-dione |
| Canonical SMILES | CC1=C(C(=O)C2=C(C1=O)N3CC4C(C3(C2=C)O)N4C)OC |
| InChI | InChI=1S/C15H16N2O4/c1-6-11(18)10-9(12(19)13(6)21-4)7(2)15(20)14-8(16(14)3)5-17(10)15/h8,14,20H,2,5H2,1,3-4H3/t8-,14-,15+,16?/m0/s1 |
| InChI Key | VZIAQNJZWSNNKZ-ZDAIXBBBSA-N |
Properties
| Appearance | Blue purple Needle-like Crystals |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Boiling Point | 494.8±45.0°C at 760 mmHg |
| Melting Point | 125°C |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. Preparation and biological activities of 10-decarbamoyloxy-9-dehydromitomycin B and its analogs
C Urakawa, H Tsuchiya, K Nakano, N Nakamura J Antibiot (Tokyo). 1981 Sep;34(9):1152-6. doi: 10.7164/antibiotics.34.1152.
A new naturally occurring mitomycin, 10-decarbamoyloxy-9-dehydromitomycin B (1), was prepared by treating mitomycin B with sodium hydride. Its analogs having an exo-cyclic double bond in their structure were also synthesized. These compounds showed antibacterial and cytotoxic activities. Among them, 7-amino-10-decarbamoyloxy-9-dehydro-7-demethoxymitomycin B (2) was the most potent growth inhibitor of KB cells in vitro and, accordingly, it appears to be a potential antitumor agent.
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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 ╳
