35818-31-6

Basic information

• Product Name: Cladosporin
• Synonyms: Cladosporin;(3R)-3β-[[(2R)-6α-Methyltetrahydro-2H-pyran-2β-yl]methyl]-6,8-dihydroxy-3,4-dihydro-1H-2-benzopyran-1-one;(R)-3,4-Dihydro-3-[[(2R,6S)-6-methyltetrahydro-2H-pyran-2-yl]methyl]-6,8-dihydroxy-1H-2-benzopyran-1-one;(R)-3,4-Dihydro-6,8-dihydroxy-3-[[(2R)-tetrahydro-6α-methyl-2H-pyran-2-yl]methyl]-1H-2-benzopyran-1-one;Asperentin
• CAS NO: 35818-31-6
• Molecular Formula: C16H20O5
• Molecular Weight: 292.329
• Mol File: 35818-31-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 543.4°Cat760mmHg
• Flash Point: 204°C
• Appearance: /
• Density: 1.261g/cm³
• Vapor Pressure: 2.03E-12mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• CAS DataBase Reference: Cladosporin(CAS DataBase Reference)
• NIST Chemistry Reference: Cladosporin(35818-31-6)
• EPA Substance Registry System: Cladosporin(35818-31-6)

Safety Data

• Hazardous Substances Data: 35818-31-6(Hazardous Substances Data)

Usage

Description

Cladosporin, a member of the isocoumarin class, is a compound characterized by its 6,8-dihydroxy-3,4-dihydro-1H-isochromen-1-one structure, with a [6-methyltetrahydro-2H-pyran-2-yl]methyl group substitution at position 3. It has been isolated from the fungus Chaetomium globosum and Aspergillus flavus. Cladosporin exhibits potent antimalarial properties and acts as an inhibitor of Plasmodium falciparum lysyl-tRNA synthetase.

Uses

Used in Pharmaceutical Industry:
Cladosporin is used as an antimalarial drug for treating malaria, a life-threatening disease caused by Plasmodium parasites. It targets Plasmodium falciparum lysyl-tRNA synthetase, an essential enzyme for protein synthesis in the parasite, thereby inhibiting its growth and proliferation.
Additionally, Cladosporin's unique chemical structure and biological activity make it a potential candidate for further research and development in the pharmaceutical industry, possibly leading to the discovery of new therapeutic agents for various diseases.

InChI:InChI=1/C16H20O5/c1-9-3-2-4-12(20-9)8-13-6-10-5-11(17)7-14(18)15(10)16(19)21-13/h5,7,9,12-13,17-18H,2-4,6,8H2,1H3

Upstream product

• 852065-88-4 (S,E)-8-((tert-butyldimethylsilyl)oxy)non-3-en-2-one 
• 852065-89-5 (8S,E)-8-((tert-butyldimethylsilyl)oxy)non-3-en-2-ol 
• 393109-13-2 (S)-tert-butyl(hept-6-en-2-yloxy)dimethylsilane 
• 121785-62-4 (5S)-5-[1-(tert-butyl)-1,1-dimethylsilyl]oxyhexanal 
• 153595-06-3 (4S)-1-(1,3-dioxan-2-yl)pentan-4-ol 
• 35931-68-1 (R)-3,4-dihydro-3-(((2R,6S)-tetrahydro-6-methyl-2H-pyran-2-yl)methyl)-6,8-dimethoxyisochromen-1-one 
• 1381766-06-8 (R)-1-((2R,6S)-tetrahydro-6-methyl-2H-pyran-2-yl)-3-(3,5-dimethoxyphenyl)propan-2-ol 
• 1381766-10-4 (2S,6R)-tetrahydro-2-methyl-6-(((S)-oxiran-2-yl)methyl)-2H-pyran 
• 1381766-09-1 (2R,6S)-2-allyltetrahydro-6-methyl-2H-pyran 

Downstream Products

• 51484-09-4 4′(R)-hydroxyasperentin 
• 51484-09-4 (S)-4’-hydroxyasperentin 

Relevant articles and documents

Specific Stereoisomeric Conformations Determine the Drug Potency of Cladosporin Scaffold against Malarial Parasite

The dependence of drug potency on diastereomeric configurations is a key facet. Using a novel general divergent synthetic route for a three-chiral center antimalarial natural product cladosporin, we built its complete library of stereoisomers (cladologs) and assessed their inhibitory potential using parasite-, enzyme-, and structure-based assays. We show that potency is manifest via tetrahyropyran ring conformations that are housed in the ribose binding pocket of parasite lysyl tRNA synthetase (KRS). Strikingly, drug potency between top and worst enantiomers varied 500-fold, and structures of KRS-cladolog complexes reveal that alterations at C3 and C10 are detrimental to drug potency whereas changes at C3 are sensed by rotameric flipping of glutamate 332. Given that scores of antimalarial and anti-infective drugs contain chiral centers, this work provides a new foundation for focusing on inhibitor stereochemistry as a facet of antimicrobial drug development.

Asymmetric total synthesis of cladosporin and isocladosporin

The first asymmetric total syntheses of cladosporin and isocladosporin were accomplished in 8 steps with 8% overall yield and 10 steps with 26% overall yield, respectively. The relative configuration of isocladosporin was determined via this total synthes