147384-69-8

Basic information

• Product Name: kynostatin
• Synonyms: kynostatin;kynostatin 227
• CAS NO: 147384-69-8
• Molecular Formula: C35H45N5O6S2
• Molecular Weight: 695.8917
• Mol File: 147384-69-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 1030.4°Cat760mmHg
• Flash Point: 577°C
• Appearance: /
• Density: 1.261g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.609
• PKA: 12.44±0.46(Predicted)
• CAS DataBase Reference: kynostatin(CAS DataBase Reference)
• NIST Chemistry Reference: kynostatin(147384-69-8)
• EPA Substance Registry System: kynostatin(147384-69-8)

Safety Data

• Hazardous Substances Data: 147384-69-8(Hazardous Substances Data)

Usage

General Description

Kynostatin is an antimalarial chemical compound that was discovered in a study of natural products from marine microorganisms. It exhibits potent antimalarial activity against both chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum, the parasite responsible for malaria. Kynostatin works by targeting the parasite's mitochondria, disrupting its energy production and causing the parasite to die. kynostatin shows promise as a potential new drug for the treatment of malaria, particularly in regions where resistance to conventional antimalarial drugs is prevalent. Further research and development are needed to fully understand its mechanism of action and potential for clinical use.

InChI:InChI=1/C35H45N5O6S2/c1-34(2,3)39-32(44)30-35(4,5)48-21-40(30)33(45)29(42)25(17-22-11-8-7-9-12-22)38-31(43)26(20-47-6)37-28(41)19-46-27-14-10-13-23-18-36-16-15-24(23)27/h7-16,18,25-26,29-30,42H,17,19-21H2,1-6H3,(H,37,41)(H,38,43)(H,39,44)/t25-,26-,29-,30+/m0/s1

Upstream product

• 80278-25-7 5-isoquinolinyloxyacetic acid 
• 159000-72-3 (R)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(tert-butoxycarbonyl)amino-3-methylthiopropionyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide 
• 130292-81-8 methyl 5-isoquinolyloxyacetate 
• 2439-04-5 5-hydroxyisoquinoline 
• 159000-71-2 Boc-Apns-Dmt-NHtBu 
• 184955-18-8 (R)-N-tert-butyl-3-<(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl>-5,5-dimethyl-1,3-thiazolidine-4-carboxamide 
• 148983-13-5 (R)-4-tert-Butylcarbamoyl-5,5-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 117918-23-7 (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid 
• 158941-58-3 (R)-N-tert-butyl-5,5-dimethyl-1,3-thiazolidine-4-carboxamide 

Relevant articles and documents

New water-soluble prodrugs of HIV protease inhibitors based on O→N intramolecular acyl migration

To improve the low water-solubility of HIV protease inhibitors, we synthesized water-soluble prodrugs of KNI-272 and KNI-279 which are potent HIV-1 protease inhibitors consisting of an Apns-Thz core structure (Apns; allophenylnorstatine, Thz; thiazolidine-4-carboxylic acid) as an inhibitory machinery. The prodrugs, which contained an O-acyl peptidomimetic structure with an ionized amino group leading to the increase of water-solubility, were designed to regenerate the corresponding parent drugs based on the O→N intramolecular acyl migration reaction at the α-hydroxy-β-amino acid residue, that is allophenylnorstatine. The synthetic prodrugs 3, 4, 6, and 7 improved the water-solubility (>300 mg/mL) more than 4000-fold in comparison with the parent compounds, which is the practically acceptable value as water-soluble drugs. These prodrugs were stable as an HCl salt and in a strongly acidic solution corresponding to gastric juice (pH 2.0), and could be converted to the parent compounds promptly in the aqueous condition from slightly acidic to basic pH at 37°C, with the suitable migration rate, via a five-membered ring intermediate. Using a similar method, we synthesized a prodrug (12) of ritonavir, a clinically useful HIV-1 protease inhibitor as an anti-AIDS drug. In contrast to the prodrugs 3, 4, 6, and 7, the prodrug 12 was very slowly converted to ritonavir probably through a six-membered ring intermediate, with the t1/2 value of 32 h that may not be suitable for practical use.