CU22858A1 - PROCEDURE FOR OBTAINING SUBSTITUTED N-ALENIL ACRIDONS - Google Patents
PROCEDURE FOR OBTAINING SUBSTITUTED N-ALENIL ACRIDONSInfo
- Publication number
- CU22858A1 CU22858A1 CU1998120A CU1998120A CU22858A1 CU 22858 A1 CU22858 A1 CU 22858A1 CU 1998120 A CU1998120 A CU 1998120A CU 1998120 A CU1998120 A CU 1998120A CU 22858 A1 CU22858 A1 CU 22858A1
- Authority
- CU
- Cuba
- Prior art keywords
- acridones
- alenyl
- derivatives
- alkylation
- obtaining
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 abstract 4
- 230000029936 alkylation Effects 0.000 abstract 2
- 238000005804 alkylation reaction Methods 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- -1 nitro, amino Chemical group 0.000 abstract 2
- 238000009825 accumulation Methods 0.000 abstract 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000003266 anti-allergic effect Effects 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 230000004071 biological effect Effects 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- 239000007809 chemical reaction catalyst Substances 0.000 abstract 1
- 150000001993 dienes Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000011835 investigation Methods 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 238000004611 spectroscopical analysis Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Esta invención está relacionada con el campo de la síntesis orgánica y tiene como objetivo desarrollar un procedimiento para la obtención de acridonas n-alenil sustituidas de fórmula general: En la cual R1, R2, R3, R4, R5, R6, R7 y R8 es un átomo de hidrógeno o halógeno o un grupo nitro, amino, alquilo, triclorometil, trifluorometil, alcoxilo, alquilamino, acetamido, ariloxi, ciano, hidroxilo, y Rl0 es un grupo alenilo. Las acridonas son una familia de compuestos heterocíclicos que presentan tres anillos fusionados entre sí, que caracterizan a su estructura base. Recientemente ha existido un desarrollo en las investigaciones biológicas de esta familia, comprobando que algunos derivados poseen actividad antialérgica, antiviral, antitumoral. Dada la importancia de sus propiedades biológicas, la presente invención proporciona un nuevo método para la obtención de N-alenil derivados de acridonas que permitan mejorar la solubilidad así como realizar otras transformaciones químicas en su estructura. La alquilación de las acridonas se realizó con el empleo de la catálisis por transferencia de fases liquido-líquido utilizando sales cuaternaria de amonio como catalizador de la reacción. Como producto de la alquilación con bromuro de propargilo no se obtiene una estructura R-CH2-C-CH como debía esperarse y sí una esrtructura de dienos acumulados R-CH=C=CH2 lo cual se demuestra por métodos espectroscópicos. No tenemos conocimiento que estos derivados hayan sido obtenidos en las condiciones de reacción descritas en esta invención.This invention is related to the field of organic synthesis and aims to develop a process for obtaining substituted n-alenyl acridones of the general formula: In which R1, R2, R3, R4, R5, R6, R7 and R8 is a hydrogen or halogen atom or a nitro, amino, alkyl, trichloromethyl, trifluoromethyl, alkoxy, alkylamino, acetamido, aryloxy, cyano, hydroxyl group, and R0 is an alenyl group. Acridones are a family of heterocyclic compounds that have three rings fused together, which characterize their base structure. Recently there has been a development in the biological investigations of this family, proving that some derivatives have antiallergic, antiviral, antitumor activity. Given the importance of its biological properties, the present invention provides a new method for obtaining N-alenyl derivatives of acridones that allow improving solubility as well as performing other chemical transformations in its structure. The alkylation of the acridones was carried out with the use of catalysis by liquid-liquid phase transfer using quaternary ammonium salts as the reaction catalyst. As a product of the alkylation with propargyl bromide, an R-CH2-C-CH structure is not obtained as expected, but an accumulation of accumulated dienes R-CH = C = CH2 which is demonstrated by spectroscopic methods. We are not aware that these derivatives have been obtained under the reaction conditions described in this invention.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CU1998120A CU22858A1 (en) | 1998-08-14 | 1998-08-14 | PROCEDURE FOR OBTAINING SUBSTITUTED N-ALENIL ACRIDONS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CU1998120A CU22858A1 (en) | 1998-08-14 | 1998-08-14 | PROCEDURE FOR OBTAINING SUBSTITUTED N-ALENIL ACRIDONS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CU22858A1 true CU22858A1 (en) | 2003-05-26 |
Family
ID=46599440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CU1998120A CU22858A1 (en) | 1998-08-14 | 1998-08-14 | PROCEDURE FOR OBTAINING SUBSTITUTED N-ALENIL ACRIDONS |
Country Status (1)
| Country | Link |
|---|---|
| CU (1) | CU22858A1 (en) |
-
1998
- 1998-08-14 CU CU1998120A patent/CU22858A1/en unknown
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