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Derivatii pteridinei

pi ri mi d in p i razi n

4 3 2

N N
1

N N
8

6 7

OH N H2N N N N

pteridina

pterina

OH

Acidul folic

NaOH H2N

N N

N N

O OH +

aci du l p teri n i c

H2N

C - NH - CH - C O CH2 CH2 C

O OH O OH

H2SO4

Aci du l p -ami n ob en zoi l gl u tami c

H2N

C - OH O

H2N - CH - C CH2 CH2 C

O OH O OH

Acidul
p -amin ob en zoi c

acidul
gl u tami c

Acidum folicum Acid folic


OH N H2N N N N CH2 - NH C - NH - CH - C O CH2 CH2 C O OH
1

O OH

Acidul N-[n-[(2-amino-4-hidroxi-6-pteridinil -metil!amino-!benzoil-4-"(# -glutamic

OH N H2N N N N OH H2N N

OH N N N OH OH

xantopterina

leucopterina

OH N H2N N N N
Acidul pteroic
H N N N C CH2 - N C - OH O O

CH2 - NH

C - OH O

OH N H2N

rizopterina

OH N H2N N

C N N H

O H CH2 - NH C - NH - CH - C O CH2 CH2 C O OH

O OH

Acidul folinic

$b%inerea acidului folic&


(Cl - CH - CO - CH2Cl NH2 + NH2 Br - CH - CH2 - Br
1 2 3

37 %) O OH

OH N3 H2N
4 5

21 6

C H

+ H2N

C - NH - CH - C O CH2 CH2 C O OH

15%

OH N H2N N

H N N

CH2 - NH

C - NH - CH - C O CH2 CH2 C O OH

O OH I2

OH N H2N N N N CH2 - NH C - NH - CH - C O CH2 CH2 C


OH N H2N N N N CH2 - NH C - NH - CH - C O CH2 CH2 C OH N H2N N N N C O OH O OH

O OH

O OH

O OH KMnO4 NaOH ; t0

'dentificarea&
H2N N O R N N N M N N N R O N NH2

(u 2 # ) precipitat verde (o2 # ) precipitat galben-verzui *e2 # ) precipitat rosu

OH N3 H2N
4

OH N
5 6

!H" !O" H2N

N3

N
5 6

21

21

N H

Aci d fol i c (coloratie galbena)


OH N H2N N N N CH2 - NH

+,-- aci d ul d ih i d rofol i c (incolor)


OH KMnO4 NaOH ; t0 H2N N N N N C O OH

C - NH - CH - C O CH2 CH2 C O OH

O OH

Aci du l p teri n - 6-carb oxi l i c

Dozarea& Acid folic


KMnO4 H2O H2N N

OH N N N C O OH + H2N C - NH - CH - C O CH2 CH2 C R O OH O OH

NH2 NaNO2 HCl R

Aci d para- ami n ob en zoi l gl tami c N

#
R

Cl

HNO2 +

H2N - S - ONH4 O O

N2

+ NH4HSO4 + H2O

NH - (CH2)2 - NH2 Cl +

NH - (CH2)2 - NH2 N N

#
R

N- (.-n afti l - eti l en di ami n

2 KMnO4 + 5 NaNO2 + 6 HCl


OH N H2N N N N C O H !O"

5 NaNO3 + 2 KCl + 2 MnCl2 + 3 H2O


OH N H2N N N N C O OH

6-formi l fte ri n

acid p teri n i c

/ethotrexat um
NH2 N H2N N N N CH3 CH2 - N C - NH - CH - C O CH2 CH2 C O OH

Metotrexat
O OH

Aci d u l 4-d ezh id roxi - 4-ami n o-N . 0 - meti l fol i c

$btinirea&
NH2 N H2N N NH2 + NH2 H2O CH2 - Cl C O + CH - Cl2 CH3 HN C - NH - CH - C O CH2 CH2 C O O O O Ba

# H2SO4 # 2
2,4,1,6-tetra amin op i ri mi di n a

.,.,2-tri cl orace ton a NH2 N N N CH3 CH2 - N

3area d e bari u a aci du l ui p -meti l ami n ob en zoi l glu tami c

C - NH - CH - C O CH2 CH2 C O OH

O OH

H2N

metot rexat

/edicamente derivati a izoaloxazinei


N N pi razi n
N N O H N O NH

N N
p i ri mi in
N N N

N N

N N

p teri d i n

2,4-d ioxop teri d i n a


$ 8 7 6 5

b ezop teri d i n a
H N

H N N
10

2 3

N N

O NH

NH
4

i zoal oxazi n

al oxazin

4iboflavinum
OH OH OH H2C - CH - CH - CH - CH2OH H3C H3C N N O N O NH

Riboflavin
5i tami nu m 6 2

6,+-d i meti l - 7-(D- .- ri b i ti l - i zoal oxazi n

4iboflavinum mononucleotidum Riboflavin mononucleotid


OH OH OH O NH O O H2C - CH - CH - CH - CH2 - O - % - ONa H3C H3C N N N

OH 2 H2O

ri b ofl avin - 1-mon ofo3fat 3od i c

$btinerea&
H3C H3C NH2 +

O
H C - (CHOH)3 - CH2OH H2O

H3C H3C

CH - (CHOH)3 - CH2OH

2,4-d i mi til an il i n

D-ri b oza

i mi n

!C6H5 - N

N" #Cl

H3C H3C

N N

CH - (CHOH)3 - CH2OH N - C6H5

!H"

O H3 C H3 C NH - CH - (CHOH)3 - CH2OH NH2 O

H N

O NH

HO O

O NH

8l oxan ari l rib ami n


H2C - (CHOH)3 - CH2OH H3C H3C N N O N O NH

ri b ofl avin a

R H3C H3C N N O N O NH !H" !O" H3C H3C

R N N H

H N

O NH

4-fragmen tu l ri b i til u lu i

l eu cori b ofl avin (in col or


OH OH OH H2C - CH - CH - CH - CH2OH O NH O OH CH3 N N O N O NH

H3C H3C H N N O H N
+

N N

h
O NH

h
H3C H3C

H3C H3C

lu mi crom

l u mi fl avin

Dozarea&
OH OH OH H2C - CH - CH - CH - CH2OH H3C H3C N N O O H2C - C H3C + H3C N N O N H O + H-C O + H-C H N O NH + 3 NaIO4

O OH

+ 3 NaIO3 + H2O

NH

O H-C OH

O + NaOH H-C ONa

H2O

1 Na' # Na'$2 # 2 92:$4 2 '2 # 2 Na2:$4 # 2 92$ '2 # 2Na2:2$2 2Na' # Na2:4$6

O H2C - (CHOH)3 - CH2 - O - % - OH H3C H3C N N O N O NH OH

*l avi n mon on u cl eoti d (*/N


NH2 N O O N O N N

H2C - (CHOH)3 - CH2 - O - % - O - % - O - H2C H3C H3C N N O N O NH OH OH

OH OH

*l avi n ad eni nd i nu cl eoti d (*AD


R H3C H3C N N O N O NH !H" !O" H3C H3C R N N H H N

O NH

*AD

*AD;2

(forma oxidata )

(forma redu3a )

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