Carbazomycin A
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| Category | Antibiotics |
| Catalog number | BBF-00221 |
| CAS | 75139-39-8 |
| Molecular Weight | 255.31 |
| Molecular Formula | C16H17NO2 |
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Description
Carbazomycin A is a nitrogen-containing heterocyclic antibiotic produced by streptomyces H-1051-MY 10, which weakly inhibits a few fungi and bacteria.
Specification
| Synonyms | 4-O-Methylcarbazomycin B; 9H-Carbazole, 3,4-dimethoxy-1,2-dimethyl- |
| IUPAC Name | 3,4-dimethoxy-1,2-dimethyl-9H-carbazole |
| Canonical SMILES | CC1=C(C(=C(C2=C1NC3=CC=CC=C32)OC)OC)C |
| InChI | InChI=1S/C16H17NO2/c1-9-10(2)15(18-3)16(19-4)13-11-7-5-6-8-12(11)17-14(9)13/h5-8,17H,1-4H3 |
| InChI Key | CABZEVNLYSXBGW-UHFFFAOYSA-N |
Properties
| Appearance | Yellow needle Crystal |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 443.4°C at 760 mmHg |
| Melting Point | 143-146°C |
| Density | 1.179 g/cm3 |
Reference Reading
1. New antibiotics, carbazomycins A and B. II. Structural elucidation
K Sakano, S Nakamura J Antibiot (Tokyo) . 1980 Sep;33(9):961-6. doi: 10.7164/antibiotics.33.961.
The structures of carbazomycins A and B are elucidated to be 3,4-dimethoxy-1,2-dimethylcarbazole and 4-hydroxy-3-methoxy-1,2-dimethylcarbazole, respectively. Further, 13C-chemical shifts of carbazomycins and their derivatives are assigned simultaneously.
2. Diversity oriented convergent access for collective total synthesis of bioactive multifunctional carbazole alkaloids: synthesis of carbazomycin A, carbazomycin B, hyellazole, chlorohyellazole, and clausenaline D
Shivaji B Markad, Narshinha P Argade Org Lett . 2014 Oct 17;16(20):5470-3. doi: 10.1021/ol502721r.
Facile syntheses of imperative carbazole alkaloids carbazomycin A, carbazomycin B, hyellazole, chlorohyellazole, and clausenaline D have been demonstrated starting from readily available Boc-protected 3-formylindole and dimethyl maleate. The suitably substituted aromatic rings have been designed comprising three/four significant C-C bond forming reactions. The competent Wittig reaction, selective monoalkylations, one-pot regioselective Weinreb amide formation and Boc-deprotection, well designed Grignard reactions, dehydrative intramolecular cyclizations, and Baeyer-Villiger rearrangement of aromatic aldehydes were the main features.
3. A General Carbazole Synthesis via Stitching of Indole-Ynones with Nitromethanes: Application to Total Synthesis of Carbazomycin A, Calothrixin B, and Staurosporinone
Ramesh Samineni, Goverdhan Mehta, Srihari Pabbaraja, Shweta Singh Org Lett . 2019 May 3;21(9):3372-3376. doi: 10.1021/acs.orglett.9b01111.
A new, one-pot domino benzannulation reaction between indole-3-ynones and various nitromethane derivatives has been explored for a general entry to diversely functionalized carbazole frameworks (28 examples). The scope of this new benzannulation has been extended to variants like 2-chloroindole-3-ynones to eventuate in chemo-differentiated 1,2,3,4-tetrasubstituted carbazoles with retention of the nitro group. The efficacy of this strategy has been demonstrated through concise total synthesis of natural products, viz. carbazomycin A, calothrixin B, and staurosporinone (K252c).
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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 ╳
