CJ-14877
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| Category | Antibiotics |
| Catalog number | BBF-02770 |
| CAS | |
| Molecular Weight | 211.21 |
| Molecular Formula | C10H13NO4 |
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Description
It is originally isolated from Marasmiellus sp. CL21624. CJ-14877 inhibited human blood interleukin-1β (IL-1β) production induced by lipoglycan (LPS) with an IC50 of 0.1 μmol/L.
Specification
| Synonyms | 2-Pyridinecarboxylic acid, 5-[(1S,2S)-1,2-dihydroxypropyl]-, methyl ester |
| IUPAC Name | methyl 5-[(1S,2S)-1,2-dihydroxypropyl]pyridine-2-carboxylate |
| Canonical SMILES | CC(C(C1=CN=C(C=C1)C(=O)OC)O)O |
| InChI | InChI=1S/C10H13NO4/c1-6(12)9(13)7-3-4-8(11-5-7)10(14)15-2/h3-6,9,12-13H,1-2H3/t6-,9+/m0/s1 |
| InChI Key | XZXCYBBAXJQLFQ-IMTBSYHQSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 399.9±37.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. Novel cytokine production inhibitors produced by a basidiomycete, Marasmiellus sp
K Ichikawa, H Hirai, M Ishiguro, T Kambara, Y Kato, Y J Kim, Y Kojima, Y Matsunaga, H Nishida, Y Shiomi, N Yoshikawa, N Kojima J Antibiot (Tokyo). 2001 Sep;54(9):703-9. doi: 10.7164/antibiotics.54.703.
New cytokine production inhibitors, CJ-14,877 (I) and CJ-14,897 (II), were isolated from the fermentation broth of a basidiomycete, Marasmiellus sp. CL21624. Their structures were determined to be methyl-(7S,8S)-5-(7,8-dihydroxypropyl)pyridine-2-carboxylate and methyl-(7S,8S)-5-(8-acetoxy-7-hydroxypropyl)pyridine-2-carboxylate [corrected], respectively, by spectroscopic analyses. These compounds showed inhibitory activities for lipopolysaccharide-induced production of interleukin-1beta and tumor necrosis factor-alpha in human whole blood with IC50 values of the range from 0.059 to 2.6 microM.
2. First asymmetric synthesis of CJ-14877 and its enantiomer and their interleukin-1beta inhibitory activities
Yutaka Aoyagi, Yoshiyuki Adachi, Shunta Akagi, Naohito Ohno, Koichi Takeya Bioorg Med Chem Lett. 2009 Apr 1;19(7):1876-8. doi: 10.1016/j.bmcl.2009.02.064. Epub 2009 Feb 21.
A potent antiinflammatory methyl picolinate alkaloid CJ-14877 [(+)-1] and its enantiomer (-)-1 were synthesized in two steps starting from commercially available methyl 5-bromopicolinate. The synthesis includes microwave-assisted Suzuki coupling reaction and Sharpless asymmetric dihydroxylation.
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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 ╳
