11-Azaartemisinin

Base Information

• Chemical Name: 11-Azaartemisinin
• CAS No.: 162791-23-3
• Molecular Formula: C15H23NO4
• Molecular Weight: 281.352
• Mol file: 162791-23-3.mol

Synonyms:11-Azaartemisinin;(3R,5aS,6R,8aS,9R,12R,12aR)-Decahydro-3,6,9-triMethyl-3,12-epoxy-1,2-dioxepino[4,3-i]isoquinolin-10(3H)-one

Chemical Property of 11-Azaartemisinin

Chemical Property:

• Boiling Point: 431.0±45.0 °C(Predicted)
• PKA: 14.49±0.70(Predicted)
• PSA: 56.79000
• Density: 1.23±0.1 g/cm3(Predicted)
• LogP: 2.29670
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

11-Azaartemisinin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A nontoxic analog of Artemisinin

Technology Process of 11-Azaartemisinin

There total 5 articles about 11-Azaartemisinin 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: 73.0%

C12H13O2(CH3)3(O)(OO) (63968-64-9) → 1,5,9-trimethyl-14,15,16-trioxa-11-aza tetracyclo[10.3.1.04,13.08,13]hexadecan-10-one (162791-23-3)

Guidance literature:

C₁₂H₁₃O₂(CH₃)3(O)(OO); With ammonium hydroxide; In tetrahydrofuran; methanol; at -15 ℃; for 10h;

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1002/cmdc.201700599

Reference yield:

C12H13O2(CH3)3(O)(OO) (63968-64-9) → 10-azadeoxyartemisinin + 1,5,9-trimethyl-14,15,16-trioxa-11-aza tetracyclo[10.3.1.04,13.08,13]hexadecan-10-one (162791-23-3) + C15H23NO4

Guidance literature:

With ammonia; In methanol; Ambient temperature;

DOI:10.1021/np980142v

Reference yield:

C12H13O2(CH3)3(O)(OO) (63968-64-9) → 10-azadeoxyartemisinin + 1,5,9-trimethyl-14,15,16-trioxa-11-aza tetracyclo[10.3.1.04,13.08,13]hexadecan-10-one (162791-23-3)

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; sulfuric acid; ammonia; silica gel; Yield given. Multistep reaction. Yields of byproduct given; 1.) CH₃OH, RT, 1.5 h, 2.) CH₂Cl₂, RT, overnight;

DOI:10.1021/jm00026a012

upstream raw materials:

C₁₂H₁₃O₂(CH₃)3(O)(OO)

Refernces

• 1、 Haynes, Richard K.,Hendry Hung-On, Pai,Voerste, Arnd. "Ring opening of artemisinin (Qinghaosu) and dihydroartemisinin and interception of the open hydroperoxides with formation of N-oxides - A chemical model for antimalarial mode of action". . p. 4715 - 4718. Retrieved 1999.
• 2、 Torok,Ziffer,Meshnick,Pan,Ager. "Syntheses and antimalarial activities of N-substituted 11-azaartemisinins". . p. 5045 - 5050. Retrieved 1995.
• 3、 Nguyen, Dung Tien,Ngo, Thuong Hanh,Tran, Hien Thu,Dinh, Thao Phuong,Do, Phuong Thi,Nguyen, Hau Ba,Tran, Linh Thi Phuong,Ta, Hanh My. "Synthesis and Anticancer Activity of 11-azaartemisinin Derivatives Bearing 1,2,3-triazole Moiety". . p. 1037 - 1044. Retrieved 2021/11/03.