METHOD FOR PREPARING 2,5,7,8-TETRAMETHYL-2-(2'-CARBOXYETHYL)-6-ACETOXYCHROMANE AS PRECURSOR OF ALPHA-SENS Russian patent published in 2006 - IPC C07D311/72 

Abstract RU 2290402 C1

FIELD: organic chemistry, chemical technology, medicine.

SUBSTANCE: invention relates to a method for synthesis of biologically active substances, namely to a method for synthesis 2,5,7,8-tetramthyl-2-(2'-carboxyethyl)-6-acetoxychromane (α-SENS). Method involves the condensation reaction of trimethylhydroquinone with linalool in the boiling n-octane medium in the presence of p-toluenesulfoacid or (+)-camphor-10-sulfoacid as a catalyst for 3 h in the mole ratio trimethylhydroquinone : linalool : catalyst = 1:1:0.1, respectively. Then the method involves the acetylation reaction of the synthesized substance with acetic anhydride in pyridine medium at room temperature for 0.5 h, ozonization in acetone medium in the presence of Ba(OH)2, oxidation with the Johns reagent in acetone medium and the following isolation by column chromatography on silica gel. This compound is acetate derivative of the main metabolite of α-tocopherol, i. e. α-SENS that shows the high effectiveness in treatment of the central nervous system diseases.

EFFECT: improved method of synthesis, valuable medicinal properties of compound.

1 cl, 2 ex

Similar patents RU2290402C1

Title Year Author Number
METHOD OF PRODUCING (2RS)-2,5,7,8-TETRAMETHYL-2-[(4RS,8RS)-4,8,12-TRIMETHYLTRIDECYL]-CHROMAN-6-YL-N-[3-OXOLUP-20(29)-EN-28-OYL]-GLYCINATE 2008
  • Dzhemilev Usein Memetovich
  • Odinokov Viktor Nikolaevich
  • Spivak Anna Jul'Evna
  • Khabibrakhmanova Oksana Valer'Evna
  • Mufazzalova Rezeda Rafisovna
RU2440366C2
BIOCONJUGATES OF LUPANE-SERIES TRITERPENIC ACIDS WITH "TROLOX" ACID HYDRAZIDE, PRODUCTION METHOD AND USE AS IMMUNOTROPIC AND ANTI-INFLAMMATORY SUBSTANCES 2010
  • Spivak Anna Jul'Evna
  • Khalitova Rezeda Rafisovna
  • Shakurova Ehl'Vira Rifovna
  • Odinokov Viktor Nikolaevich
  • Danilets Marina Grigor'Evna
  • Bel'Skaja Natalija Vital'Evna
  • Bel'Skij Jurij Pavlovich
  • Ivanova Alena Nikolaevna
RU2464273C2
TOCOPHEROLS, TOCOTRIENOLS, OTHER CHROMANS AND DERIVATIVES BY SIDE CHAINS AND THEIR USING 2001
  • Sanderz Robert Dzh.
  • Klajn Kimberli
  • Kherli Lorens
  • Gardner Robb
  • Menchaka Marla
  • Ju Vejping
  • Ramanan Putkhukod N.
  • Liu Shenkuan
  • Izraehl Karen
RU2263672C2
TOCOPHEROLS, TOCOTRIENOLS AND OTHER DERIVATIVES OF CHROMAN AND BY-SIDE CHAINS AND METHODS FOR TREATMENT WITH THEIR USING 1999
  • Klajn Kimberli
  • Sanderz Bob G.
  • Kherli Lorens
  • Gardner Robb
  • Menchaka Marla
  • Ju Vejping
  • Ramanan Putkhukode N.
  • Liu Shenkvuan
  • Izrael Karen
RU2232758C2
METHOD OF PREPARING (6R,10R)-6,10,14-TRIMETHYLPENTADECAN-2-ONE (PHYTON) 2001
  • Odinokov V.N.
  • Malljabaeva M.I.
  • Emel'Janova G.A.
  • Spivak A.Ju.
RU2197465C2
METHOD OF PRODUCING (S)-(-)-6-BENZYLOXY-3,4-DIHYDRO-2,5,7,8-TETRAMETHYL-2H-1-BENZOPYRAN-2-YLMETHANOL 2010
  • Shafikov Ruslan Vavisovich
  • Spivak Anna Jul'Evna
  • Odinokov Viktor Nikolaevich
RU2443695C1
METHOD FOR PREPARING CONJUGATE OF (6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-YL)ACETALDEHYDE AND 20-HYDROXYECDYSONE AND USING IT AS ANTIOXIDANT AGENT INHIBITING LIPID PEROXIDATION PROCESS 2010
  • Odinokov Viktor Nikolaevich
  • Savchenko Rimma Gafurovna
  • Urazaeva Jana Rustamovna
  • Afon'Kina Svetlana Razifovna
  • Syrov Vladimir Nikolaevich
  • Khushbaktova Zajnab Abdurakhmanovna
  • Tsaruk Anastasija Viktorovna
RU2490267C2
SYNTHESIS OF CHROMANOL DERIVATIVES 2019
  • Weingarten, Melanie
  • Siegel, Wolfgang
  • Puhl, Michael
RU2795497C2
FLUORESCENTLY-LABELED DEOXYURIDINE TRIPHOSPHATES 2016
  • Chudinov Aleksandr Vasilevich
  • Kuznetsova Viktoriya Evgenevna
  • Shershov Valerij Evgenevich
  • Spitsyn Maksim Anatolevich
  • Gusejnov Tejmur Oktaevich
  • Lapa Sergej Anatolevich
  • Zasedatelev Aleksandr Sergeevich
RU2637310C1
PHENYLACETIC ACID DERIVATIVES AS COG-2 (CYCLOOXYGENASE-2) INHIBITORS 2007
  • Monovich Loren G.
  • Mugrejdzh Bendzhamin Biro
RU2454402C2

RU 2 290 402 C1

Authors

Spivak Anna Jul'Evna

Odinokov Viktor Nikolaevich

Knyshenko Oksana Valer'Evna

Dates

2006-12-27Published

2005-06-16Filed