SU1786804A1 - Derivatives of 2,2-dimethyl-1,2-dihydro-4h-pyrano-[4,3d]-furo-[2,3-b]-pyridine showing antitumor activity - Google Patents

Derivatives of 2,2-dimethyl-1,2-dihydro-4h-pyrano-[4,3d]-furo-[2,3-b]-pyridine showing antitumor activity

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Publication number
SU1786804A1
SU1786804A1 SU4872432/04A SU4872432A SU1786804A1 SU 1786804 A1 SU1786804 A1 SU 1786804A1 SU 4872432/04 A SU4872432/04 A SU 4872432/04A SU 4872432 A SU4872432 A SU 4872432A SU 1786804 A1 SU1786804 A1 SU 1786804A1
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SU
USSR - Soviet Union
Prior art keywords
reagent
pyrano
dihydro
pyridine
dimethyl
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Application number
SU4872432/04A
Other languages
Russian (ru)
Inventor
Е.Г. Пароникян
А.Х. Оганесян
А.С. Норавян
Ф.Г. Арсенян
Г.М. Степанян
Б.Т. Гарибджанян
Original Assignee
Институт Тонкой Органической Химии Им.А.Л.Мнджояна
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Priority to SU4872432/04A priority Critical patent/SU1786804A1/en
Application granted granted Critical
Publication of SU1786804A1 publication Critical patent/SU1786804A1/en

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  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

FIELD: organic chemistry. SUBSTANCE: product: derivatives of 2,2-dimethyl-1,2-dihydro-4H-pyrano-[4,3-d] -furo-[2,3-b] -pyridine of the general formulawhere at R-CH, R=R-H; R-n-Br and R-H, R-H and R-C(O)-CH-CH= CH-O; where at R-CH, R=R-H; R-n-Br and R-H; R-H and R-C(O)-C=CH-CH=CH-O; R-n-Br and R-C(O)CH; R-n-Br and R-C(O)CCl. Maximal tolerated dose above >2500 mg/kg, degree of sarcoma 45 inhibition by 41-45% Walker carcinosarcoma by 30-43% Reagent 1: 3-phenacyloxy-5,6-dihydro-6,6-dimethyl-1-phenyl(methyl)-4-cyano-8H-pyrano-[3,4-c] -pyridine. Reagent 2: KOH. Reagent 3: phenacyl bromide. Conditions: boiling for 30 min in ethanol, ethanol distilling for drying, addition of reagent 3 and boiling in acetonitrile for 2 h. Reagent 4: CHONa.. Reagent 5: 3-phenacyloxy-5,6-dihydro-6,6-dimethyl-1-phenyl(methyl)-4-cyano-8H-pyrano-[3,4-c] -pyridine. Conditions: cyclization at boiling for 1 h, and compounds I-IV were obtained. Compounds I-VII were synthesized by conversion of compounds I-IV to the corresponding amides by carboxylic acid chloroanhydrides at boiling in dioxane for 25-30 h. Synthesized compounds where used in medicine as antitumor agents. EFFECT: improved method of synthesis. 3 tbl
SU4872432/04A 1990-08-20 1990-08-20 Derivatives of 2,2-dimethyl-1,2-dihydro-4h-pyrano-[4,3d]-furo-[2,3-b]-pyridine showing antitumor activity SU1786804A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
SU4872432/04A SU1786804A1 (en) 1990-08-20 1990-08-20 Derivatives of 2,2-dimethyl-1,2-dihydro-4h-pyrano-[4,3d]-furo-[2,3-b]-pyridine showing antitumor activity

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SU4872432/04A SU1786804A1 (en) 1990-08-20 1990-08-20 Derivatives of 2,2-dimethyl-1,2-dihydro-4h-pyrano-[4,3d]-furo-[2,3-b]-pyridine showing antitumor activity

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SU1786804A1 true SU1786804A1 (en) 1995-09-20

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SU4872432/04A SU1786804A1 (en) 1990-08-20 1990-08-20 Derivatives of 2,2-dimethyl-1,2-dihydro-4h-pyrano-[4,3d]-furo-[2,3-b]-pyridine showing antitumor activity

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SU (1) SU1786804A1 (en)

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