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Title: The synthesis of enantiomers of 8-amino-7-[2-hydroxyl-3(morpholin-4 yl)propyl]teophylline and preliminary evaluation of their pharmacological activity

Author:

Potaczek, Joanna

Date:

2006

Type:

Praca doktorska

Abstract:

The invented path of synthesis started with the connection of chiral synthon - 4-(2,3-epoxypropyl)morpholine (2) to 8-bromotheophylline ( 1 ). The synthon was received m reaction of morpholine with enantiomers of epichlorohydrin. Connecting the epoxide derivative to C-7 position of methyloxanthine results in chiral oxazolopurine - 7-(morpholinomethyl)-6, 7-dihydrooxazolo[2,3-f]purine-2,4(1H,3.H)-dione (3). The subsequent reaction with ammonia gives the desired product-8-amino-7-[2-hydroxy 1-3-( morpholin-4 yl) propyl]theophylline (4). The proposed method let to obtain 77 and 79 percentage of ( +) and (-) enantiomers (4), respectively. The synthesis by using of another synthon - glycidyl p-toluenesulfonate does not succeed. The pharmacological tests revealed that the both enantiomers 8-amino-7-[2-hydroxyl-3(morpholin-4-yl)propyl]theophylline (4) exhibit hypothensive activity. lt has been shown that this activity is not linked with the affinity to adrenergic receptors nor spazmolitic activity. During the reaction of 8-bromotheophy lline (1) with 4-(2,3-epoxypropyl) morpholine (2) an interesting rearrangement occur: the obtained oxazolopurine (3)is transformed to an isomeric compound 7-(morpholino )-7 ,8-dihydro-6H-[ 1,3 ]oxazino [2,3-f]purine-2,4(1H,3H)-dione (5).

Place of publishing:

Kraków

Level of degree:

2 - studia doktoranckie

Degree discipline:

farmakologia

Degree grantor:

Wydział Farmaceutyczny

Promoter:

Cegła, Marek

Date issued:

2006

Identifier:

oai:dl.cm-uj.krakow.pl:1083

Call number:

ZB-105320

Language:

pol; eng

Access rights:

tylko w bibliotece

Subject and keywords:

8-amino-7-[2-hydroxyl-3(morpholin-4 yl)propyl]teophylline synthon C3 hypotensive activity rearrangement enantiomer

Object collections:

Last modified:

Jun 26, 2023

In our library since:

Nov 21, 2012

Number of object content hits:

3 112

Number of object content views in PDF format

0

All available object's versions:

http://dl.cm-uj.krakow.pl:8080/publication/1083

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ZB-105320 Jun 26, 2023

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