Mesatlantin C

Base Information

• Chemical Name: Mesatlantin C
• CAS No.: 84692-91-1
• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.306
• European Community (EC) Number: 851-932-7
• Wikipedia: Arglabin
• Wikidata: Q105279921
• Mol file: 84692-91-1.mol

Synonyms:arglabin

Chemical Property of Mesatlantin C

Chemical Property:

• Vapor Pressure: 9.34E-07mmHg at 25°C
• Melting Point: 100-102 °C
• Boiling Point: 404.6°C at 760 mmHg
• Flash Point: 171.3°C
• PSA: 38.83000
• Density: 1.22g/cm³
• LogP: 2.37190
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 246.125594432
• Heavy Atom Count: 18
• Complexity: 506

Purity/Quality:

99% ^*data from raw suppliers

Arglabin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC23C1C4C(CCC2(O3)C)C(=C)C(=O)O4
• Isomeric SMILES: CC1=CC[C@]23[C@H]1[C@@H]4[C@@H](CC[C@]2(O3)C)C(=C)C(=O)O4
• Description: Arglabin is a new antineoplastic agent launched in Russia for the treatment of a variety of cancers. It is a sesquiterpene gamma-lactone extracted from Artemisia glabella, a plant from Kazakstan; it was first developed in Kazakstan followed by US and other countries as an ethical pharmaceutical. Arglabin can be obtained by resin extraction from A.glabella, purification by chromatography and finally recrystallization. Arglabin is a potent and selective inhibitor of farnesyl transferase, an enzyme critical to the function of the Ras oncogene in cancer cell reproduction. It showed a strong Inhibitory effect against tumor cells proliferation in in vitro models of transformed mouse hepatocytes and splenocytes. This cytotoxic effect against tumor cells was 50-100 times higher than that on intact cells. In many patients with various cancers, Arglabin was shown to stop or inhibit the tumour development, alone or in combination with other anticancer agents, and was reportedly well tolerated with few sideeffects. Promising response rates were also reported with Arglabin after treating other 《difficult-to-treat cancers》 such as breast, ovarian, lung or colon cancers.
• Uses: Arglabin is a sesquiterpene lactone used in the inhibition of glucose induced NF-kB activation and MCP-1/TGF-β1 expression treating diabetic nephropathy. Cytocoxic.

Technology Process of Mesatlantin C

There total 6 articles about Mesatlantin C which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 67.0%

(1R,3aR,4aS,6aS,9aS,9bS)-1-hydroxy-1,4a-dimethyl-7-methyleneoctahydro-1H-oxireno[2',3':8,8a]azuleno[4,5-b]furan-8(4aH)-one (1343403-10-0) → 1β,10β-Epoxyguaia-3,11(13)-dien-12,6α-olide (137624-14-7,84692-91-1)

Guidance literature:

With Martins sulfurane; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jo300888s

Reference yield: 27.1%

kauniolide (81066-45-7) → C15H18O3 (137624-14-7) + C15H18O3 (157751-04-7) + 1β,10β-Epoxyguaia-3,11(13)-dien-12,6α-olide (137624-14-7,84692-91-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃;

DOI:10.1021/jo300888s

Reference yield:

(3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylene-3a,4,5,7,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2(3H)-one (68370-47-8) → 1β,10β-Epoxyguaia-3,11(13)-dien-12,6α-olide (137624-14-7,84692-91-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C

2: Martins sulfurane / dichloromethane / 24 h / 20 °C / Inert atmosphere

With Martins sulfurane; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jo300888s

upstream raw materials:

(1R,3aR,4aS,6aS,9aS,9bS)-1-hydroxy-1,4a-dimethyl-7-methyleneoctahydro-1H-oxireno[2',3':8,8a]azuleno[4,5-b]furan-8(4aH)-one

parthenolide

kauniolide

(3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylene-3a,4,5,7,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2(3H)-one

Downstream raw materials:

3α,4α-epoxyarglabin

3β,4β-epoxyarglabin

Refernces

• 1、 -. "Process for the preparation of Arglabin". Paragraph 0047-0048. . Retrieved 2017/04/07.
• 2、 -. "USES OF SESQUITERPENE LACTONE COMPOUNDS AND THEIR DERIVATIVES IN DRUGS PREPARATION". Paragraph 0143; 0144. . Retrieved 2017/04/13.