Pyridindolol K1
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| Category | Antibiotics |
| Catalog number | BBF-02095 |
| CAS | |
| Molecular Weight | 342.35 |
| Molecular Formula | C18H18N2O5 |
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Description
Pyridindolol K1 is an alkaloid antibiotic produced by Str. sp. K93-0711.
Specification
| Synonyms | Pyridoindole K1 |
| IUPAC Name | [1-[(1R)-2-acetyloxy-1-hydroxyethyl]-9H-pyrido[3,4-b]indol-3-yl]methyl acetate |
| Canonical SMILES | CC(=O)OCC1=CC2=C(C(=N1)C(COC(=O)C)O)NC3=CC=CC=C32 |
| InChI | InChI=1S/C18H18N2O5/c1-10(21)24-8-12-7-14-13-5-3-4-6-15(13)20-17(14)18(19-12)16(23)9-25-11(2)22/h3-7,16,20,23H,8-9H2,1-2H3/t16-/m0/s1 |
| InChI Key | ULBLUJBIDCYVTD-INIZCTEOSA-N |
Properties
| Appearance | Colorless Oil |
| Boiling Point | 585.5±45.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Pyridindolols K1 and K2, new alkaloids from Streptomyces sp. K93-0711
Y P Kim, S Takamatsu, M Hayashi, K Komiyama, S Omura J Antibiot (Tokyo). 1997 Mar;50(3):189-93.
Two new alkaloids with the beta-carboline skeleton, pyridindolols K1 (C18H18N2O5) and K2 (C16H16N2O4), were isolated from the culture both of Streptomyces sp. K93-0711. The structure of pyridindolols were established by spectroscopic investigations and chemical transformations. Pyridindolol K2 inhibited the adhesion of HL-60 cells to LPS-activated HUVEC monolayer (IC50 = 75 micrograms/ml).
2. Total syntheses of beta-carboline alkaloids, (R)-(-)-pyridindolol K1, (R)-(-)-pyridindolol K2, and (R)-(-)-pyridindolol
N Kanekiyo, T Kuwada, T Choshi, J Nobuhiro, S Hibino J Org Chem. 2001 Dec 28;66(26):8793-8. doi: 10.1021/jo0105585.
The total syntheses of beta-carboline alkaloids, (R)-(-)-pyridindolols (1, 5, and 6) are described. The two key steps involved are (1) a thermal electrocyclic reaction of the 3-alkenylindole-2-aldoxime 10 and (2) a thermal cyclization of 3-alkynylindole-2-aldoxime 11 to construct the beta-carboline N-oxides 8, which upon heating with acetic anhydride and sequential treatment with trifluoromethanesulfonic anhydride gave the triflates 18. The Stille coupling reaction of 18 with vinylstannane, followed by cleavage of MOM ether, afforded the 1-ethenyl-3-hydroxymethyl-beta-carboline (7a). Subsequent acetylation of 7a yielded the acetate 7b, which was subjected to the Sharpless asymmetric 1,2-dihydroxylation by AD-mix-beta to produce (R)-(-)-pyridindolol K2 (6). Selective acetylation of 6 was effected by Ac(2)O and collidine to form (R)-(-)-pyridindolol K1 (5). By contrast, hydrolysis of 6 provided (R)-(-)-pyridindolol (1).
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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 ╳
