120020-26-0

Basic information

• Product Name: ARTELINIC ACID
• Synonyms: artelinic acid;(3R,5aα,8aα,12aR)-Decahydro-3,6α,9β-trimethyl-10α-(4-carboxybenzyloxy)-3β,12α-epoxypyrano[4,3-j]-1,2-benzodioxepin;(3R,5aα,8aα,12aR)-Decahydro-10β-(4-carboxybenzyloxy)-3,6α,9β-trimethyl-3β,12α-epoxypyrano[4,3-j]-1,2-benzodioxepin;beta-Artelinic acid
• CAS NO: 120020-26-0
• Molecular Formula: C23H30O7
• Molecular Weight: 418.4801
• Mol File: 120020-26-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 537.1°Cat760mmHg
• Flash Point: 181.3°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 2.28E-12mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: ARTELINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: ARTELINIC ACID(120020-26-0)
• EPA Substance Registry System: ARTELINIC ACID(120020-26-0)

Safety Data

• Hazardous Substances Data: 120020-26-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C23H30O7/c1-13-4-9-18-14(2)20(26-12-15-5-7-16(8-6-15)19(24)25)27-21-23(18)17(13)10-11-22(3,28-21)29-30-23/h5-8,13-14,17-18,20-21H,4,9-12H2,1-3H3,(H,24,25)/t13-,14-,17+,18+,20+,21-,22+,23?/m1/s1

Upstream product

• 63968-64-9 artemisinin 
• 6908-41-4 4-(methoxycarbonyl)benzyl alcohol 
• 63968-64-9 artemisinin 
• 71939-50-9 dihydroartemisinin 
• 85031-59-0 dihydroartemisinic acid 
• 3006-96-0 3-hydroxymethyl-benzoic acid 
• 216963-48-3 methyl p-<(10-dihydroartemisininoxy)methyl>benzoate 
• 71939-50-9 dihydroartemisinin 
• 81496-81-3 dihydroartesiminin 
• 63968-64-9 C₁₂H₁₃O₂(CH₃)3(O)(OO) 

Relevant articles and documents

Synthesis, Antiplasmodial, and Antileukemia Activity of Dihydroartemisinin–HDAC Inhibitor Hybrids as Multitarget Drugs

Artemisinin-based combination therapies (ACTs) are the gold standard for the treatment of malaria, but the efficacy is threatened by the development of parasite resistance. Histone deacetylase inhibitors (HDACis) are an emerging new class of potential antiplasmodial drugs. In this work, we present the design, synthesis, and biological evaluation of a mini library of dihydroartemisinin–HDACi hybrid molecules. The screening of the hybrid molecules for their activity against selected human HDAC isoforms, asexual blood stage P. falciparum parasites, and a panel of leukemia cell lines delivered important structure–activity relationships. All synthesized compounds demonstrated potent activity against the 3D7 and Dd2 line of P. falciparum with IC50 values in the single-digit nanomolar range. Furthermore, the hybrid (α)-7c displayed improved activity against artemisinin-resistant parasites compared to dihydroartemisinin. The screening of the compounds against five cell lines from different leukemia entities revealed that all hydroxamate-based hybrids (7a–e) and the ortho-aminoanilide 8 exceeded the antiproliferative activity of dihydroartemisinin in four out of five cell lines. Taken together, this series of hybrid molecules represents an excellent starting point toward the development of antimalarial and antileukemia drug leads.

Synthesis of water soluble c-10-phenoxy artemisinin-chitosan conjugate

A sort of C-10-phenoxy artemisinin-chitosan conjugate, in which C-10-phenoxy artemisinin was covalently bound to chitosan, was prepared and its aqueous solubility was evaluated. The results indicated that the conjugate (1.013 mg/mL) had much higher aqueous solubility than artemisinin (0.0084 mg/mL) and C-10-phenoxy artemisinin (0.0245 mg/mL). The conjugate will be potentially useful for their application as the prodrug of artemisinin.

Artemisinin-dipeptidyl vinyl sulfone hybrid molecules: Design, synthesis and preliminary SAR for antiplasmodial activity and falcipain-2 inhibition

A series of artemisinin-vinyl sulfone hybrid molecules with the potential to act in the parasite food vacuole via endoperoxide activation and falcipain inhibition was synthesized and screened for antiplasmodial activity and falcipain-2 inhibition. All conjugates were active against the Plasmodium falciparum W2 strain in the low nanomolar range and those containing the Leu-hPhe core inhibited falcipain-2 in low micromolar range.