Tylophorine

Base Information

• Chemical Name: Tylophorine
• CAS No.: 482-20-2
• Molecular Formula: C24H27 N O4
• Molecular Weight: 393.483
• NSC Number: 717335,76387
• UNII: O41630Y8V3
• DSSTox Substance ID: DTXSID30964025
• Nikkaji Number: J1.826.262B
• Wikidata: Q27108498
• ChEMBL ID: CHEMBL250426
• Mol file: 482-20-2.mol

Synonyms:2,3,6,7-tetramethoxyphenanthro(9,10:6,7')indolizidine;dehydrotylophorine;tylophorine

Chemical Property of Tylophorine

Chemical Property:

• Vapor Pressure: 1.44E-12mmHg at 25°C
• Melting Point: 125-130 °C (decomp)
• Boiling Point: 559.9°C at 760 mmHg
• PKA: 7.63±0.20(Predicted)
• Flash Point: 160.5°C
• PSA: 40.16000
• Density: 1.26g/cm³
• LogP: 4.48580
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 393.19400834
• Heavy Atom Count: 29
• Complexity: 573

Purity/Quality:

99%, ^*data from raw suppliers

(+)-(S)-Tylophorine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C3=C(CN4CCCC4C3)C5=CC(=C(C=C52)OC)OC)OC
• Isomeric SMILES: COC1=C(C=C2C(=C1)C3=C(CN4CCC[C@H]4C3)C5=CC(=C(C=C52)OC)OC)OC
• Uses: (+)-(S)-Tylophorine is a a major alkaloid of Tylophora indica. (+)-(S)-Tylophorine is an immunosuppressant and inflammation inhibitor. (+)-(S)-Tylophorine showed antiproliferative activity and induction of apoptosis in tumor cells.

Technology Process of Tylophorine

There total 132 articles about Tylophorine 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: 96.0%

(S)-2,3,6,7-tetramethoxyphenanthro<9,10-b>-11-indolizidinone (87302-61-2) → (S)-(+)-tylophorine (482-20-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Heating;

DOI:10.1021/jo00171a014

Reference yield: 94.0%

(14S)-14-hydroxy-2,3,6,7-tetramethoxyphenanthro<9,10-b>indolizidine (87302-58-7) → (S)-(+)-tylophorine (482-20-2)

Guidance literature:

With triethylsilane; trifluoroacetic acid; at 20 ℃; for 10h; Darkness;

DOI:10.1002/ejoc.200900920

Reference yield: 92.0%

(S)-2,3,6,7-tetramethoxy-12,13,13a,14-tetrahydrodibenzo[f,h]-pyrrolo[1,2-b]isoquinolin-9(11H)-one (933982-91-3) → (S)-(+)-tylophorine (482-20-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

DOI:10.1021/acs.joc.6b01161

upstream raw materials:

formaldehyd

(S)-2-<(2,3,6,7-tetramethoxyphenanthren-9-yl)methyl>pyrrolidine

(S)-2,3,6,7-tetramethoxyphenanthro<9,10-b>-11-indolizidinone

2,3,6,7-tetramethoxyphenanthrene

Refernces

• 1、 Abdalla, Ashraf N.,Abdullah, Omeima,Chen, Linwei,Fischer, Peter M.,Guise, Chris P.,Liu, Yuxiu,Omran, Ziad,Patterson, Adam V.,Rauch, Cyril,Sindi, Ikhlas A.,Smaill, Jeff B.,Wang, Qingmin. "Design, synthesis and in-vitro biological evaluation of antofine and tylophorine prodrugs as hypoxia-targeted anticancer agents". . . Retrieved 2021/06/21.
• 2、 -. "Two NK007 optical pure isomers and synthesis and application thereof". Paragraph 0037; 0042; 0043. . Retrieved 2016/11/28.