Aspicilin
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| Category | Others |
| Catalog number | BBF-05430 |
| CAS | 52461-05-9 |
| Molecular Weight | 328.44 |
| Molecular Formula | C18H32O5 |
| Purity | 99% |
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Description
It is obtained from the lichens Aspicilia calcarea and A. gibbosa.
Specification
| Related CAS | 52461-07-1 (tri-Ac) 52461-08-2 (dihydro) |
| Synonyms | (-)-Aspicillin; (5R,6S,7R,18S,E)-5,6,7-trihydroxy-18-methyloxacyclooctadec-3-en-2-one; (3E,5R,6S,7R,18S)-5,6,7-Trihydroxy-18-methyloxacyclooctadeca-3-en-2-one; Oxacyclooctadec-3-en-2-one, 5,6,7-trihydroxy-18-methyl-, (3E,5R,6S,7R,18S)- |
| IUPAC Name | (3E,5R,6S,7R,18S)-5,6,7-trihydroxy-18-methyl-1-oxacyclooctadec-3-en-2-one |
| Canonical SMILES | CC1CCCCCCCCCCC(C(C(C=CC(=O)O1)O)O)O |
| InChI | InChI=1S/C18H32O5/c1-14-10-8-6-4-2-3-5-7-9-11-15(19)18(22)16(20)12-13-17(21)23-14/h12-16,18-20,22H,2-11H2,1H3/b13-12+/t14-,15+,16+,18-/m0/s1 |
| InChI Key | KECCBFYFEOTIBV-KHDHUXSVSA-N |
Properties
| Appearance | Platelet |
| Boiling Point | 512.1±50.0°C (Predicted) |
| Melting Point | 153-154°C (ethyl ether) |
| Density | 1.055±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Wittig Cyclization of ω-Hydroxy Hemiacetals: Synthesis of (+)-Aspicilin
René Schmidt, Michael Ostermeier, Rainer Schobert J Org Chem. 2017 Sep 1;82(17):9126-9132. doi: 10.1021/acs.joc.7b01702. Epub 2017 Aug 11.
The polyhydroxylated 18-membered lichen macrolide (+)-aspicilin was synthesized in 12 steps and 17% yield (longest linear sequence) starting from d-mannose and (S)-propylene oxide as the source of the stereogenic centers. Key steps were a palladium-catalyzed Csp3X-Csp3ZnX Negishi cross-coupling affording an ω-hydroxy hemiacetal which was macrocyclized via a domino addition-Wittig olefination reaction with the cumulated ylide Ph3PCCO. This synthetic approach also allowed a regioselective glycosylation of 6-OH of aspicilin with d-desosamine, a quick entry to chimeric macrolides with potential antibiotic activity.
2. Identification of potent Antigen 85C inhibitors of Mycobacterium tuberculosis via in-house lichen library and binding free energy studies Part-II
Ragini Pant, Amit Joshi, Tanuja Joshi, Priyanka Maiti, Mahesha Nand, Tushar Joshi, Veena Pande, Subhash Chandra J Mol Graph Model. 2021 Mar;103:107822. doi: 10.1016/j.jmgm.2020.107822. Epub 2020 Dec 8.
Tuberculosis remains the cause of mortality throughout the world. Currently, the available anti-tubercular drugs are not effective because of the existence of Multi-Drug resistant tuberculosis (MDR-TB) and Extensively-Drug resistant tuberculosis (XDR-TB). It has, therefore, become necessary to develop novel drugs that inhibit the activity of drug-resistant Mycobacterium tuberculosis. Due to the existence of MDR and XDR-TB, Mtb Ag85C has risen out as a propitious molecular drug target as it has importance in the synthesis of main components of the Mtb cell envelope which are essential for the virulence and survival of Mtb. In a previous paper, we studied a potential drug target by virtual high throughput screening of compounds and in continuation of the study on Mtb Ag85C, we further studied the role of lichen compounds in the inhibition of Ag85C. In the current research work, virtual screening of a lichen compounds library was performed against Ag85C. Further, ADMET analysis was employed to filter out the screened lichen compounds. Bioactivity score and toxicity prediction finalized four lichen compounds i.e. Portentol, Aspicilin, Parietinic acid and Polyporic acid as potential inhibitors of Ag85C. The stability and dynamic behavior of four compounds were analyzed by using Molecular dynamics simulation which indicated that they may be potential inhibitors of Ag85C. Therefore, based on the above results, Portentol, Aspicilin, Parietinic acid and Polyporic acid may be potential drug candidates against Mtb. We suggest that the use of these compounds can minimize the treatment time-period and the various side effects associated with the currently available anti-tubercular drugs.
3. Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis
Henok H Kinfe Org Biomol Chem. 2019 Apr 24;17(17):4153-4182. doi: 10.1039/c9ob00343f.
Glycals, 1,2-unsaturated sugar derivatives, are versatile starting materials for the synthesis of natural products and the generation of novel structural features in Diversity Oriented Synthesis (DOS). The versatility of glycals in synthesis emanates, among others, from the presence of the ring oxygen and the enol-ether type unsaturation, the different types of stable conformations they can adopt depending on the nature of the protecting groups present and the ease with which the protecting groups of the three hydroxy groups could be tailored to suite for a desired manipulation. This review summarizes the literature on the different transformations of the endo glycals into biologically relevant compounds such as chromans, thiochromans, chromenes, thiochromenes, peptidomimetics, bridged benzopyrans etc., as well as on the use of glycals as chiral building blocks for the synthesis of various natural products such as aspicilin, reblastatin, diospongins, decytospolides, osmundalactones, paclitaxel, isatisine, d-fagomine, and spliceostatin, reported post 2014.
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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
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
