Pimprinethine
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| Category | Antibiotics |
| Catalog number | BBF-03290 |
| CAS | 146426-35-9 |
| Molecular Weight | 212.25 |
| Molecular Formula | C13H12N2O |
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Description
Pimprinethine is a pyrazoloisoquinolinone antibiotic produced by Streptoverticillium griseocarneum. It has weak anti-Gram-positive bacteria activity.
Specification
| Related CAS | 73053-81-3 |
| Synonyms | APHE-1 |
| IUPAC Name | 2-ethyl-5-(1H-indol-3-yl)-1,3-oxazole |
| Canonical SMILES | CCC1=NC=C(O1)C2=CNC3=CC=CC=C32 |
| InChI | InChI=1S/C13H12N2O/c1-2-13-15-8-12(16-13)10-7-14-11-6-4-3-5-9(10)11/h3-8,14H,2H2,1H3 |
| InChI Key | QWRZPVDPCWVPBI-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 412.6±28.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Antiviral effects against EV71 of pimprinine and its derivatives isolated from Streptomyces sp
Yanhong Wei, Wei Fang, Zhongyi Wan, Kaimei Wang, Qingyu Yang, Xiaofeng Cai, Liqiao Shi, Ziwen Yang Virol J. 2014 Nov 20;11:195. doi: 10.1186/s12985-014-0195-y.
Background: The pimprinine family of compounds represent very important and promising microbial metabolites for drug discovery. However, their ability in inhibiting viral infections has not yet been tested. Methods: The antiviral activity of the pimprinine family of compounds was evaluated by determining the cytopathic effect (CPE), cell viability or plaque-forming unit (PFU), and virus yield. The mechanism of action against EV71 was determined from the virucidal activity, and effective stage and time-of-addition assays. The effects on EV71 replication were evaluated further by determining viral RNA synthesis, protein expression and cells apoptosis using the SYBR Green assays, immunofluorescence assays and flow cytometric assays, respectively. Results: Pimprinethine, WS-30581 A and WS-30581 B inhibited EV71-induced CPE, reduced progeny EV71 yields, as well as prevented EV71-induced apoptosis in human rhabdomyosarcoma (RD) cells. These compounds were found to target the early stages of the EV71 replication in cells including viral RNA replication and protein synthesis. They also showed antiviral activity against ADV-7, and were slightly active against CVB3, HSV-1 and H1N1 with a few exceptions. Pimprinine was slightly active or inactive against all the viruses tested. The mechanisms by which these compounds act against the viruses tested may be similar to that demonstrated for EV71. Conclusion: The data described herein demonstrate that the pimprinine family of compounds are inhibitors effective against the replication of EV71 and ADV-7, so they might be feasible therapeutic agents for the treatment of viral infections.
2. 2-Ethyl-5-(3-indolyl)oxazole from Streptomyces cinnamomeus discovered by chemical screening. Characterization and structure elucidation by X-ray analysis
M Noltemeyer, G M Sheldrick, H U Hoppe, A Zeeck J Antibiot (Tokyo). 1982 May;35(5):549-55. doi: 10.7164/antibiotics.35.549.
In the lipophilic extracts from Streptomyces cinnamomeus 2-ethyl-5-(3-indolyl)oxazole (1a) was detected by chemical screening methods. The structure of the crystalline 1a was determined by spectroscopic and X-ray analysis. The new mono- and dibromo derivatives 1b and 1c are described. 1a is identical with pimprinethine and belongs to a group of microbial indole alkaloids, which can be regarded as masked tryptamine derivatives.
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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 ╳
