(S)-Lisofylline

Base Information

• Chemical Name: (S)-Lisofylline
• CAS No.: 100324-80-9
• Molecular Formula: C13H20N4O3
• Molecular Weight: 280.32300
• Mol file: 100324-80-9.mol

Synonyms:Amendol;Di-O-methyl-osajetin;

Chemical Property of (S)-Lisofylline

Chemical Property:

• PSA: 82.05000
• LogP: -0.01520
• Solubility.: ≤15mg/ml in ethanol;3mg/ml in DMSO;12mg/ml in dimethyl formamide

Purity/Quality:

98%min ^*data from raw suppliers

(S)-Lisofylline ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: LSF, a chiral metabolite of pentoxifylline, acts as a potent anti-inflammatory agent. (S)-LSF is the pharmacologically inactive optical enantiomer of (R)-LSF, the biologically active isomer. When metabolized by isolated human liver cells, pentoxifylline is exclusively reduced to (S)-LSF in the cytosol, while reduction in liver microsomes is 85% stereoselective in favor of (S)-LSF formation. Thus, pentoxifylline is an inefficient prodrug for the delivery of therapeutically relevant lisofylline.
• Uses: LSF, a chiral metabolite of pentoxifylline, acts as a potent anti-inflammatory agent. (S)-LSF is the pharmacologically inactive optical enantiomer of (R)-LSF, the biologically active isomer. When metabolized by isolated human liver cells, pentoxifylline is exclusively reduced to (S)-LSF in the cytosol, while reduction in liver microsomes is 85% stereoselective in favor of (S)-LSF formation. Thus, pentoxifylline is an inefficient prodrug for the delivery of therapeutically relevant lisofylline.[Cayman Chemical]

Technology Process of (S)-Lisofylline

There total 21 articles about (S)-Lisofylline 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: 100.0%

1-(5,6-oxidohexyl)-3,7-dimethylxanthine (154719-57-0) + ammonium chloride → 1-(5-hydroxyhexyl)theobromine (6493-06-7,100324-80-9,100324-81-0)

Guidance literature:

With sodium borohydrid; In ethanol;

Reference yield: 95.0%

pentoxyphylline (6493-05-6) → 1-(5-hydroxyhexyl)theobromine (6493-06-7,100324-80-9,100324-81-0)

Guidance literature:

With methanol; sodium tetrahydroborate; In acetonitrile; at 0 - 20 ℃; for 3.33333h;

DOI:10.1002/ejoc.202001602

Reference yield: 95.0%

pentoxyphylline (6493-05-6) → lisofylline (100324-81-0) + (+)-(S)-3,7-dimethyl-1-(5-hydroxyhexyl)-3,7-dihydropurine-2,6-dione (100324-80-9)

Guidance literature:

With Saccharomyces cerevisiae KKPU; In phosphate buffer; at 30 ℃; for 120h; Further Variations:; Solvents; Temperatures; Reagents; time; Product distribution;

upstream raw materials:

pentoxyphylline

1-(5,6-oxidohexyl)-3,7-dimethylxanthine

methanol

isopropyl alcohol

Downstream raw materials:

3-Methyl-5-methylamino-3H-imidazole-4-carboxylic acid (5-methoxy-hexyl)-amide; compound with picric acid

lisofylline

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate

Refernces

• 1、 Raoul, Jennifer M.,Peterson, Marc R.,Peterson, Theresa C.. "A novel drug interaction between the quinolone antibiotic ciprofloxacin and a chiral metabolite of pentoxifylline". . p. 639 - 646. Retrieved 2007.
• 2、 Borowiecki, Pawe?,Zdun, Beata,Dranka, Maciej. "Chemoenzymatic enantioselective and stereo-convergent syntheses of lisofylline enantiomers via lipase-catalyzed kinetic resolution and optical inversion approach". . . Retrieved 2021.
• 3、 Chen, Yuming,He, Ru,Song, Hongjian,Yu, Guoqing,Li, Chenglin,Liu, Yuxiu,Wang, Qingmin. "Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols". supporting information. p. 1179 - 1183. Retrieved 2021/02/01.