-
Je něco špatně v tomto záznamu ?
Synthesis of (purin-6-yl)acetates and their transformations to 6-(2-hydroxyethyl)- and 6-(carbamoylmethyl)purines
Zbyněk Hasník, Radek Pohl, Blanka Klepetářová and Michal Hocek
Jazyk angličtina Země Česko
- MeSH
- financování organizované MeSH
- nukleosidy chemická syntéza MeSH
- puriny chemická syntéza MeSH
- vztahy mezi strukturou a aktivitou MeSH
A novel approach to the synthesis of (purin-6-yl)acetates was developed based on Pd-catalyzed cross-coupling reactions of 6-chloropurines with a Reformatsky reagent. Their reduction with NaBH4 and treatment with MnO2 gave 6-(2-hydroxyethyl)purines, while reactions with amines in presence of NaCN afforded 6-(carbamoylmethyl)purines. Mesylation of the 6-(2-hydroxyethyl)purines followed by nucleophilic substitutions gave rise to several 6-(2-substituted ethyl)purines. This methodology was successfully applied to the synthesis of substituted purine bases and nucleosides for cytostatic and antiviral activity screening. None of the compounds exerted significant activity.
Citace poskytuje Crossref.org
Lit.: 32
- 000
- 00000naa 2200000 a 4500
- 001
- bmc09004754
- 003
- CZ-PrNML
- 005
- 20111210153936.0
- 008
- 091206s2009 xr e eng||
- 009
- AR
- 024 7_
- $a 10.1135/cccc2009042 $2 doi
- 040 __
- $a ABA008 $b cze $c ABA008 $d ABA008 $e AACR2
- 041 0_
- $a eng
- 044 __
- $a xr
- 100 1_
- $a Hasník, Zbyněk. $7 xx0269136
- 245 10
- $a Synthesis of (purin-6-yl)acetates and their transformations to 6-(2-hydroxyethyl)- and 6-(carbamoylmethyl)purines / $c Zbyněk Hasník, Radek Pohl, Blanka Klepetářová and Michal Hocek
- 314 __
- $a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic v.v.i., Gilead Sciences & IOCB Research Center, Flemingovo nám. 2, CZ-166 10 Prague 6, Czech Republic
- 504 __
- $a Lit.: 32
- 520 9_
- $a A novel approach to the synthesis of (purin-6-yl)acetates was developed based on Pd-catalyzed cross-coupling reactions of 6-chloropurines with a Reformatsky reagent. Their reduction with NaBH4 and treatment with MnO2 gave 6-(2-hydroxyethyl)purines, while reactions with amines in presence of NaCN afforded 6-(carbamoylmethyl)purines. Mesylation of the 6-(2-hydroxyethyl)purines followed by nucleophilic substitutions gave rise to several 6-(2-substituted ethyl)purines. This methodology was successfully applied to the synthesis of substituted purine bases and nucleosides for cytostatic and antiviral activity screening. None of the compounds exerted significant activity.
- 650 _2
- $a puriny $x chemická syntéza $7 D011687
- 650 _2
- $a nukleosidy $x chemická syntéza $7 D009705
- 650 _2
- $a vztahy mezi strukturou a aktivitou $7 D013329
- 650 _2
- $a financování organizované $7 D005381
- 700 1_
- $a Pohl, Radek
- 700 1_
- $a Klepetářová, Blanka $7 xx0119828
- 700 1_
- $a Hocek, Michal, $d 1969- $7 mzk2006368321
- 773 0_
- $w MED00010973 $t Collection of Czechoslovak chemical communications $g Roč. 74, č. 7-8 (2009), s. 1035-1059 $x 0010-0765
- 910 __
- $a ABA008 $b A 1006 $c 394 $y 9
- 990 __
- $a 20091206160512 $b ABA008
- 991 __
- $a 20091207075533 $b ABA008
- 999 __
- $a ok $b bmc $g 700571 $s 562987
- BAS __
- $a 3
- BMC __
- $a 2009 $b 74 $c 7-8 $d 1035-1059 $i 0010-0765 $m Collection of Czechoslovak Chemical Communications $x MED00010973
- LZP __
- $a 2009-63/vtmv
