2, 4-Diaminopyrimidines as inhibitors of leishmanial and trypanosomal dihydrofolate reductase

…, I Leal, F Zuccotto, C Boussard, R Brun, SL Croft…

Index: Pez, Didier; Leal, Isabel; Zuccotto, Fabio; Boussard, Cyrille; Brun, Reto; Croft, Simon L.; Yardley, Vanessa; Ruiz Perez, Luis M.; Gonzalez Pacanowska, Dolores; Gilbert, Ian H. Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 22 p. 4693 - 4711

Full Text: HTML

Citation Number: 52

Abstract

This paper describes the synthesis of 4′-substituted and 3′, 4′-disubstituted 5-benzyl-2, 4-diaminopyrimidines as selective inhibitors of leishmanial and trypanosomal dihydrofolate reductase. Compounds were then assayed against the recombinant parasite and human enzymes. Some of the compounds showed good activity. They were also tested against the intact parasites using in vitro assays. Good activity was found against Trypanosoma cruzi, ...

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3,4-Dihydro-2H-pyran Structure

110-87-2

3,4-Dihydro-2H-pyran

4-hydroxybenzaldehyde Structure

123-08-0

4-hydroxybenzal...

~98%

4-(2-NAPHTHYLOXY)ANILINE HYDROCHLORIDE Structure

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4-(2-NAPHTHYLOX...

3',4'-(DIOCTYLOXY)BENZALDEHYDE Structure

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3',4'-(DIOCTYLO...

3-Ethoxypropanenitrile Structure

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3-Ethoxypropane...

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3-(3,4-dioctoxyphenyl)-2-(ethoxymethyl)prop-2-enenitrile Structure

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3-(3,4-dioctoxy...

1-Iodooctane Structure

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1-Iodooctane

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3-(3,4-dioctoxyphenyl)-2-(ethoxymethyl)prop-2-enenitrile Structure

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3-(3,4-dioctoxy...

3,4-Dihydroxybenzaldehyde Structure

139-85-5

3,4-Dihydroxybe...

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3-(3,4-dioctoxyphenyl)-2-(ethoxymethyl)prop-2-enenitrile Structure

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3-(3,4-dioctoxy...

Guanidine hydrochloride Structure

50-01-1

Guanidine hydro...

2-(ethoxymethyl)-3-(4-hexoxyphenyl)prop-2-enenitrile Structure

650606-13-6

2-(ethoxymethyl...

~49%

5-[(4-hexoxyphenyl)methyl]pyrimidine-2,4-diamine Structure

80407-61-0

5-[(4-hexoxyphe...

4-Hexoxybenzaldehyde Structure

5736-94-7

4-Hexoxybenzaldehyde

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5-[(4-hexoxyphenyl)methyl]pyrimidine-2,4-diamine Structure

80407-61-0

5-[(4-hexoxyphe...

4-hydroxybenzaldehyde Structure

123-08-0

4-hydroxybenzal...

~%

5-[(4-hexoxyphenyl)methyl]pyrimidine-2,4-diamine Structure

80407-61-0

5-[(4-hexoxyphe...

1-Iodohexane Structure

638-45-9

1-Iodohexane

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5-[(4-hexoxyphenyl)methyl]pyrimidine-2,4-diamine Structure

80407-61-0

5-[(4-hexoxyphe...

Benzyl bromide Structure

100-39-0

Benzyl bromide

4-[(2,4-diaminopyrimidin-5-yl)methyl]phenol Structure

30077-67-9

4-[(2,4-diamino...

~78%

5-[(4-Benzyloxy)benzyl]-2,4-diaminopyrimidine Structure

49873-11-2

5-[(4-Benzyloxy...

4-(2-NAPHTHYLOXY)ANILINE HYDROCHLORIDE Structure

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4-(2-NAPHTHYLOX...

~%

5-[(4-Benzyloxy)benzyl]-2,4-diaminopyrimidine Structure

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5-[(4-Benzyloxy...

4-hydroxybenzaldehyde Structure

123-08-0

4-hydroxybenzal...

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5-[(4-Benzyloxy)benzyl]-2,4-diaminopyrimidine Structure

49873-11-2

5-[(4-Benzyloxy...

(E)-2-(ethoxymethyl)-3-[4-(tetrahydro-2-pyranyloxy)phenyl]-2-propenenitrile Structure

650606-19-2

(E)-2-(ethoxyme...

~%

5-[(4-Benzyloxy)benzyl]-2,4-diaminopyrimidine Structure

49873-11-2

5-[(4-Benzyloxy...

5-(4-((tetrahydro-2H-pyran-2-yl)oxy)benzyl)pyrimidine-2,4-diamine Structure

650606-20-5

5-(4-((tetrahyd...

~%

5-[(4-Benzyloxy)benzyl]-2,4-diaminopyrimidine Structure

49873-11-2

5-[(4-Benzyloxy...

2-METHYLACRYLICACID-2-(4-BENZOYL-3-HYDROXYPHENOXY)ETHYLESTER Structure

118468-34-1

2-METHYLACRYLIC...

3-Ethoxypropanenitrile Structure

2141-62-0

3-Ethoxypropane...

~50%

3-(3,4-didecoxyphenyl)-2-(ethoxymethyl)prop-2-enenitrile Structure

650606-25-0

3-(3,4-didecoxy...

1-iodo-Decane Structure

2050-77-3

1-iodo-Decane

~%

3-(3,4-didecoxyphenyl)-2-(ethoxymethyl)prop-2-enenitrile Structure

650606-25-0

3-(3,4-didecoxy...

3,4-Dihydroxybenzaldehyde Structure

139-85-5

3,4-Dihydroxybe...

~%

3-(3,4-didecoxyphenyl)-2-(ethoxymethyl)prop-2-enenitrile Structure

650606-25-0

3-(3,4-didecoxy...

1-Iodooctane Structure

629-27-6

1-Iodooctane

4-hydroxybenzaldehyde Structure

123-08-0

4-hydroxybenzal...

~91%

4-Octyloxybenzaldehyde Structure

24083-13-4

4-Octyloxybenza...

Benzyl bromide Structure

100-39-0

Benzyl bromide

3,4-Dihydroxybenzaldehyde Structure

139-85-5

3,4-Dihydroxybe...

~76%

3-Hydroxy-4-benzyloxy benzaldehyde Structure

4049-39-2

3-Hydroxy-4-ben...

4-Pentoxybenzaldehyde Structure

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4-Pentoxybenzal...

3-Ethoxypropanenitrile Structure

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3-Ethoxypropane...

~64%

2-(ethoxymethyl)-3-(4-pentoxyphenyl)prop-2-enenitrile Structure

650606-12-5

2-(ethoxymethyl...

1-Iodopentane Structure

628-17-1

1-Iodopentane

~%

2-(ethoxymethyl)-3-(4-pentoxyphenyl)prop-2-enenitrile Structure

650606-12-5

2-(ethoxymethyl...

4-hydroxybenzaldehyde Structure

123-08-0

4-hydroxybenzal...

~%

2-(ethoxymethyl)-3-(4-pentoxyphenyl)prop-2-enenitrile Structure

650606-12-5

2-(ethoxymethyl...

4-Hexoxybenzaldehyde Structure

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4-Hexoxybenzaldehyde

3-Ethoxypropanenitrile Structure

2141-62-0

3-Ethoxypropane...

~82%

2-(ethoxymethyl)-3-(4-hexoxyphenyl)prop-2-enenitrile Structure

650606-13-6

2-(ethoxymethyl...

4-hydroxybenzaldehyde Structure

123-08-0

4-hydroxybenzal...

~%

2-(ethoxymethyl)-3-(4-hexoxyphenyl)prop-2-enenitrile Structure

650606-13-6

2-(ethoxymethyl...

1-Iodohexane Structure

638-45-9

1-Iodohexane

~%

2-(ethoxymethyl)-3-(4-hexoxyphenyl)prop-2-enenitrile Structure

650606-13-6

2-(ethoxymethyl...

4-Octyloxybenzaldehyde Structure

24083-13-4

4-Octyloxybenza...

3-Ethoxypropanenitrile Structure

2141-62-0

3-Ethoxypropane...

~69%

2-(ethoxymethyl)-3-(4-octoxyphenyl)prop-2-enenitrile Structure

650606-14-7

2-(ethoxymethyl...

1-Iodooctane Structure

629-27-6

1-Iodooctane

~%

2-(ethoxymethyl)-3-(4-octoxyphenyl)prop-2-enenitrile Structure

650606-14-7

2-(ethoxymethyl...

4-hydroxybenzaldehyde Structure

123-08-0

4-hydroxybenzal...

~%

2-(ethoxymethyl)-3-(4-octoxyphenyl)prop-2-enenitrile Structure

650606-14-7

2-(ethoxymethyl...

1-Bromohexane Structure

111-25-1

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3-Hydroxy-4-benzyloxy benzaldehyde Structure

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3-Hydroxy-4-ben...

~85%

3-hexoxy-4-phenylmethoxybenzaldehyde Structure

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3-hexoxy-4-phenylmethoxybenzaldehyde Structure

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3-hexoxy-4-phen...

3,4-Dihydroxybenzaldehyde Structure

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3,4-Dihydroxybe...

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3-hexoxy-4-phenylmethoxybenzaldehyde Structure

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3-hexoxy-4-phen...

p-Decyloxybenzaldehyde Structure

24083-16-7

p-Decyloxybenza...

3-Ethoxypropanenitrile Structure

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3-(4-decoxyphenyl)-2-(ethoxymethyl)prop-2-enenitrile Structure

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3-(4-decoxyphen...

1-iodo-Decane Structure

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1-iodo-Decane

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3-(4-decoxyphenyl)-2-(ethoxymethyl)prop-2-enenitrile Structure

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3-(4-decoxyphen...

4-hydroxybenzaldehyde Structure

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4-hydroxybenzal...

~%

3-(4-decoxyphenyl)-2-(ethoxymethyl)prop-2-enenitrile Structure

650606-15-8

3-(4-decoxyphen...

3-hexoxy-4-phenylmethoxybenzaldehyde Structure

650606-30-7

3-hexoxy-4-phen...

~86%

3-hexoxy-4-hydroxybenzaldehyde Structure

650606-31-8

3-hexoxy-4-hydr...

3-Hydroxy-4-benzyloxy benzaldehyde Structure

4049-39-2

3-Hydroxy-4-ben...

~%

3-hexoxy-4-hydroxybenzaldehyde Structure

650606-31-8

3-hexoxy-4-hydr...

3,4-Dihydroxybenzaldehyde Structure

139-85-5

3,4-Dihydroxybe...

~%

3-hexoxy-4-hydroxybenzaldehyde Structure

650606-31-8

3-hexoxy-4-hydr...

1-Bromopropane Structure

106-94-5

1-Bromopropane

3-hexoxy-4-hydroxybenzaldehyde Structure

650606-31-8

3-hexoxy-4-hydr...

~75%

3-hexoxy-4-propoxybenzaldehyde Structure

650606-32-9

3-hexoxy-4-prop...

3-Hydroxy-4-benzyloxy benzaldehyde Structure

4049-39-2

3-Hydroxy-4-ben...

~%

3-hexoxy-4-propoxybenzaldehyde Structure

650606-32-9

3-hexoxy-4-prop...

3,4-Dihydroxybenzaldehyde Structure

139-85-5

3,4-Dihydroxybe...

~%

3-hexoxy-4-propoxybenzaldehyde Structure

650606-32-9

3-hexoxy-4-prop...

3-hexoxy-4-phenylmethoxybenzaldehyde Structure

650606-30-7

3-hexoxy-4-phen...

~%

3-hexoxy-4-propoxybenzaldehyde Structure

650606-32-9

3-hexoxy-4-prop...

1-Iodooctane Structure

629-27-6

1-Iodooctane

3-hexoxy-4-hydroxybenzaldehyde Structure

650606-31-8

3-hexoxy-4-hydr...

~75%

3-hexoxy-4-octoxybenzaldehyde Structure

650606-33-0

3-hexoxy-4-octo...

3-Hydroxy-4-benzyloxy benzaldehyde Structure

4049-39-2

3-Hydroxy-4-ben...

~%

3-hexoxy-4-octoxybenzaldehyde Structure

650606-33-0

3-hexoxy-4-octo...

1-Iodopentane Structure

628-17-1

1-Iodopentane

4-hydroxybenzaldehyde Structure

123-08-0

4-hydroxybenzal...

~78%

4-Pentoxybenzaldehyde Structure

5736-91-4

4-Pentoxybenzal...

3,4-Dihydroxybenzaldehyde Structure

139-85-5

3,4-Dihydroxybe...

~%

3-hexoxy-4-octoxybenzaldehyde Structure

650606-33-0

3-hexoxy-4-octo...

3-hexoxy-4-phenylmethoxybenzaldehyde Structure

650606-30-7

3-hexoxy-4-phen...

~%

3-hexoxy-4-octoxybenzaldehyde Structure

650606-33-0

3-hexoxy-4-octo...

5-(4-((tetrahydro-2H-pyran-2-yl)oxy)benzyl)pyrimidine-2,4-diamine Structure

650606-20-5

5-(4-((tetrahyd...

~99%

4-[(2,4-diaminopyrimidin-5-yl)methyl]phenol Structure

30077-67-9

4-[(2,4-diamino...

4-hydroxybenzaldehyde Structure

123-08-0

4-hydroxybenzal...

~%

4-[(2,4-diaminopyrimidin-5-yl)methyl]phenol Structure

30077-67-9

4-[(2,4-diamino...

(E)-2-(ethoxymethyl)-3-[4-(tetrahydro-2-pyranyloxy)phenyl]-2-propenenitrile Structure

650606-19-2

(E)-2-(ethoxyme...

~%

4-[(2,4-diaminopyrimidin-5-yl)methyl]phenol Structure

30077-67-9

4-[(2,4-diamino...

3,4-dipropoxybenzaldehyde Structure

34841-08-2

3,4-dipropoxybe...

3-Ethoxypropanenitrile Structure

2141-62-0

3-Ethoxypropane...

~56%

3-(3,4-dipropoxyphenyl)-2-(ethoxymethyl)prop-2-enenitrile Structure

650606-22-7

3-(3,4-dipropox...

3,4-Dihydroxybenzaldehyde Structure

139-85-5

3,4-Dihydroxybe...

~%

3-(3,4-dipropoxyphenyl)-2-(ethoxymethyl)prop-2-enenitrile Structure

650606-22-7

3-(3,4-dipropox...

3,4-dihexoxybenzaldehyde Structure

64000-53-9

3,4-dihexoxyben...

3-Ethoxypropanenitrile Structure

2141-62-0

3-Ethoxypropane...

~65%

3-(3,4-dihexoxyphenyl)-2-(ethoxymethyl)prop-2-enenitrile Structure

650606-23-8

3-(3,4-dihexoxy...

1-Bromohexane Structure

111-25-1

1-Bromohexane

~%

3-(3,4-dihexoxyphenyl)-2-(ethoxymethyl)prop-2-enenitrile Structure

650606-23-8

3-(3,4-dihexoxy...

3,4-Dihydroxybenzaldehyde Structure

139-85-5

3,4-Dihydroxybe...

~%

3-(3,4-dihexoxyphenyl)-2-(ethoxymethyl)prop-2-enenitrile Structure

650606-23-8

3-(3,4-dihexoxy...

1-Iodoheptane Structure

4282-40-0

1-Iodoheptane

4-[(2,4-diaminopyrimidin-5-yl)methyl]phenol Structure

30077-67-9

4-[(2,4-diamino...

~94%

5-[(4-heptoxyphenyl)methyl]pyrimidine-2,4-diamine Structure

80407-60-9

5-[(4-heptoxyph...

4-(2-NAPHTHYLOXY)ANILINE HYDROCHLORIDE Structure

74189-56-3

4-(2-NAPHTHYLOX...

~%

5-[(4-heptoxyphenyl)methyl]pyrimidine-2,4-diamine Structure

80407-60-9

5-[(4-heptoxyph...

4-hydroxybenzaldehyde Structure

123-08-0

4-hydroxybenzal...

~%

5-[(4-heptoxyphenyl)methyl]pyrimidine-2,4-diamine Structure

80407-60-9

5-[(4-heptoxyph...

(E)-2-(ethoxymethyl)-3-[4-(tetrahydro-2-pyranyloxy)phenyl]-2-propenenitrile Structure

650606-19-2

(E)-2-(ethoxyme...

~%

5-[(4-heptoxyphenyl)methyl]pyrimidine-2,4-diamine Structure

80407-60-9

5-[(4-heptoxyph...

5-(4-((tetrahydro-2H-pyran-2-yl)oxy)benzyl)pyrimidine-2,4-diamine Structure

650606-20-5

5-(4-((tetrahyd...

~%

5-[(4-heptoxyphenyl)methyl]pyrimidine-2,4-diamine Structure

80407-60-9

5-[(4-heptoxyph...

4-(2-NAPHTHYLOXY)ANILINE HYDROCHLORIDE Structure

74189-56-3

4-(2-NAPHTHYLOX...

~%

4-[(2,4-diaminopyrimidin-5-yl)methyl]phenol Structure

30077-67-9

4-[(2,4-diamino...

1-iodo-Decane Structure

2050-77-3

1-iodo-Decane

3,4-Dihydroxybenzaldehyde Structure

139-85-5

3,4-Dihydroxybe...

~34%

2-METHYLACRYLICACID-2-(4-BENZOYL-3-HYDROXYPHENOXY)ETHYLESTER Structure

118468-34-1

2-METHYLACRYLIC...


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