Porothramycin B
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| Category | Antibiotics |
| Catalog number | BBF-02050 |
| CAS | 110652-72-7 |
| Molecular Weight | 357.40 |
| Molecular Formula | C19H23N3O4 |
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Description
Porothramycin B is an antibiotic produced by Str.albus K731-113. It has activity against gram-positive bacteria and anaerobic bacteria.
Specification
| Synonyms | 2-Propenamide, N,N-dimethyl-3-(5,10,11,11a-tetrahydro-9,11-dimethoxy-5-oxo-1H-pyrrolo(2,1-c)(1,4)benzodiazepin-2-yl)-, (11R-(2(E),11-alpha,11a-beta))- |
| IUPAC Name | (E)-3-[(6R)-4,6-dimethoxy-11-oxo-5,6,6a,7-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-8-yl]-N,N-dimethylprop-2-enamide |
| Canonical SMILES | CN(C)C(=O)C=CC1=CN2C(C1)C(NC3=C(C2=O)C=CC=C3OC)OC |
| InChI | InChI=1S/C19H23N3O4/c1-21(2)16(23)9-8-12-10-14-18(26-4)20-17-13(19(24)22(14)11-12)6-5-7-15(17)25-3/h5-9,11,14,18,20H,10H2,1-4H3/b9-8+/t14?,18-/m1/s1 |
| InChI Key | XCFSBOSFMAOQAL-VOVBJCLESA-N |
Properties
| Appearance | Yellow Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 599.9°C at 760 mmHg |
| Melting Point | 164-166°C (dec.) |
| Density | 1.28 g/cm3 |
Reference Reading
1. Porothramycin, a new antibiotic of the anthramycin group: production, isolation, structure and biological activity
M Tsunakawa, H Kamei, M Konishi, T Miyaki, T Oki, H Kawaguchi J Antibiot (Tokyo). 1988 Oct;41(10):1366-73. doi: 10.7164/antibiotics.41.1366.
A new antitumor antibiotic porothramycin was produced by a new strain of Streptomyces albus. The antibiotic was isolated in two active forms, the natural free hydroxyl form (porothramycin A) or the crystalline methyl ether form (porothramycin B) depending upon the isolation process used. Structural studies established that porothramycin is a new member of the pyrrolo[1,4]benzodiazepine group antibiotics having only one substituent on the benzene ring. The antibiotic exhibited antimicrobial activity against Gram-positive bacteria and anaerobes and significantly prolonged the survival times of mice implanted with experimental tumors.
2. Synthesis and cytotoxicity on sensitive and doxorubicin-resistant cell lines of new pyrrolo[2,1-c][1,4]benzodiazepines related to anthramycin
N Langlois, A Rojas-Rousseau, C Gaspard, G H Werner, F Darro, R Kiss J Med Chem. 2001 Oct 25;44(22):3754-7. doi: 10.1021/jm010937q.
A new 7,8-methylenedioxy analogue (4) of (+)-porothramycin B (2) and its water-soluble sodium bisulfite derivative (15) have been synthesized in high yields and have been shown to exhibit high cytotoxic activities against several tumor cell lines. The new pyrrolo[2,1-c][1,4]benzodiazepine 4 was as effective against the resistant cell lines as against the doxorubicin-sensitive cell lines tested.
3. Concise formal synthesis of porothramycins A and B via Zincke pyridinium ring-opening/ring-closing cascade
Theo D Michels, Matthew J Kier, Aaron M Kearney, Christopher D Vanderwal Org Lett. 2010 Jul 2;12(13):3093-5. doi: 10.1021/ol101035p.
Short formal syntheses of the antitumor antibiotics porothramycins A and B from a commercially available ester of the unnatural amino acid 3-(3-pyridyl)alanine are presented. A rearrangement cascade that presumably involves a Zincke-type pyridinium ring-opening followed by cyclization of a pendant nucleophilic amide generates the salient pyrroline ring of the alkaloids.
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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 ╳
