Basic antiinflammatory compounds. N, N', N''-Trisubstituted guanidines

…, I Ahnfelt-Rønne, E Arrigoni-Martelli

Index: Rachlin, Schneur; Bramm, E.; Ahnfelt-Ronne, I.; Arrigoni-Martelli, E. Journal of Medicinal Chemistry, 1980 , vol. 23, # 1 p. 13 - 20

Full Text: HTML

Citation Number: 21

Abstract

A variety of basic N, N', N”-trisubstituted guanidines was prepared and tested for antiinflammatory activity. Compounds with a thiazolylguanidine moiety linked to the 4 position of the 2-methylquinoline ring exhibited fairly high antiinflammatory activity. Optimal activity was associated with the presence of N-cycloalkyl substituents on

 Related Synthetic Route
2-Methyl-4-quinolinamine Structure

6628-04-2

2-Methyl-4-quin...

N-tert-butyl-N-(thiazol-2-yl)methanediimine Structure

72042-12-7

N-tert-butyl-N-...

~46%

2-tert-butyl-1-(2-methylquinolin-4-yl)-3-(1,3-thiazol-2-yl)guanidine Structure

71079-32-8

2-tert-butyl-1-...

4-Methylthiazol-2-amine Structure

1603-91-4

4-Methylthiazol...

N-tert-butyl-N-(2-methylquinolin-4-yl)methanediimine Structure

71079-33-9

N-tert-butyl-N-...

~53%

2-tert-butyl-1-(2-methylquinolin-4-yl)-3-(4-methyl-1,3-thiazol-2-yl)guanidine Structure

71079-34-0

2-tert-butyl-1-...

N-tert-butyl-N-(2-methylquinolin-4-yl)methanediimine Structure

71079-33-9

N-tert-butyl-N-...

Structure

74497-02-2

~61%

2-tert-butyl-1-(2-methylquinolin-4-yl)-3-phenylguanidine Structure

72042-06-9

2-tert-butyl-1-...

2-Aminothiazole Structure

96-50-4

2-Aminothiazole

N-(cyclohexylcarbonimidoyl)-2-methylquinolin-4-amine Structure

71079-18-0

N-(cyclohexylca...

~78%

Timegadine Structure

71079-19-1

Timegadine

1-cyclohexyl-3-(2-methyl-4-quinolyl)urea Structure

71070-70-7

1-cyclohexyl-3-...

~%

Timegadine Structure

71079-19-1

Timegadine

N-tert-butyl-N-(thiazol-2-yl)methanediimine Structure

72042-12-7

N-tert-butyl-N-...

Naphthalen-2-amine Structure

91-59-8

Naphthalen-2-amine

~44%

Guanidine, 1-tert-butyl-2-(2-naphthyl)-3-(2-thiazolyl)- Structure

72041-76-0

Guanidine, 1-te...

4H-1,2,4-Triazol-4-amine Structure

584-13-4

4H-1,2,4-Triazo...

N-tert-butyl-N-(2-methylquinolin-4-yl)methanediimine Structure

71079-33-9

N-tert-butyl-N-...

~46%

2-tert-butyl-1-(2-methylquinolin-4-yl)-3-(1,2,4-triazol-4-yl)guanidine Structure

71079-39-5

2-tert-butyl-1-...

Aminothiazoline Structure

1779-81-3

Aminothiazoline

N-tert-butyl-N-(2-methylquinolin-4-yl)methanediimine Structure

71079-33-9

N-tert-butyl-N-...

~37%

2-tert-butyl-1-(4,5-dihydro-1,3-thiazol-2-yl)-3-(2-methylquinolin-4-yl)guanidine Structure

71079-75-9

2-tert-butyl-1-...

1-ISOQUINOLINAMINE Structure

1532-84-9

1-ISOQUINOLINAMINE

N-tert-butyl-N-(thiazol-2-yl)methanediimine Structure

72042-12-7

N-tert-butyl-N-...

~51%

2-tert-butyl-1-isoquinolin-1-yl-1-(1,3-thiazol-2-yl)guanidine Structure

72041-88-4

2-tert-butyl-1-...

N-(cyclohexylcarbonimidoyl)-2-methylquinolin-4-amine Structure

71079-18-0

N-(cyclohexylca...

~69%

2-cyclohexyl-1-(2-methylquinolin-4-yl)guanidine Structure

72042-07-0

2-cyclohexyl-1-...

1-cyclohexyl-3-(2-methyl-4-quinolyl)urea Structure

71070-70-7

1-cyclohexyl-3-...

~%

2-cyclohexyl-1-(2-methylquinolin-4-yl)guanidine Structure

72042-07-0

2-cyclohexyl-1-...

1-cyclohexyl-3-(2-methyl-4-quinolyl)urea Structure

71070-70-7

1-cyclohexyl-3-...

~%

2-cyclohexyl-1-(4,5-dihydro-1,3-thiazol-2-yl)-3-(2-methylquinolin-4-yl )guanidine Structure

72042-08-1

2-cyclohexyl-1-...

2-Methyl-4-quinolinamine Structure

6628-04-2

2-Methyl-4-quin...

N-(thiazol-2-yl)-N-(2,4,4-trimethylpentan-2-yl)methanediimine Structure

71079-44-2

N-(thiazol-2-yl...

~37%

1-(2-methylquinolin-4-yl)-3-(1,3-thiazol-2-yl)-2-(2,4,4-trimethylpentan-2-yl)guanidine Structure

71079-43-1

1-(2-methylquin...

N-tert-butyl-N-(2-methylquinolin-4-yl)methanediimine Structure

71079-33-9

N-tert-butyl-N-...

5-Amino-1,3,4-thiadiazole-2-thiol Structure

2349-67-9

5-Amino-1,3,4-t...

~53%

Guanidine, 1-tert-butyl-3-(5-mercapto-1,3,4-thiadiazol-2-yl)-2-(2-meth yl-4-quinolyl)- Structure

71253-69-5

Guanidine, 1-te...

3-Quinolinamine Structure

580-17-6

3-Quinolinamine

N-tert-butyl-N-(thiazol-2-yl)methanediimine Structure

72042-12-7

N-tert-butyl-N-...

~35%

2-tert-butyl-1-quinolin-3-yl-3-(1,3-thiazol-2-yl)guanidine Structure

72041-90-8

2-tert-butyl-1-...

Quinolin-5-amine Structure

611-34-7

Quinolin-5-amine

N-tert-butyl-N-(thiazol-2-yl)methanediimine Structure

72042-12-7

N-tert-butyl-N-...

~45%

2-tert-butyl-1-quinolin-5-yl-1-(1,3-thiazol-2-yl)guanidine Structure

72041-92-0

2-tert-butyl-1-...

8-Aminoquinoline Structure

578-66-5

8-Aminoquinoline

N-tert-butyl-N-(thiazol-2-yl)methanediimine Structure

72042-12-7

N-tert-butyl-N-...

~46%

2-tert-butyl-1-quinolin-8-yl-3-(1,3-thiazol-2-yl)guanidine Structure

72041-94-2

2-tert-butyl-1-...

Aminothiazoline Structure

1779-81-3

Aminothiazoline

N-(cyclohexylcarbonimidoyl)-2-methylquinolin-4-amine Structure

71079-18-0

N-(cyclohexylca...

~62%

2-cyclohexyl-1-(4,5-dihydro-1,3-thiazol-2-yl)-3-(2-methylquinolin-4-yl )guanidine Structure

72042-08-1

2-cyclohexyl-1-...

3-Chloro-2-methylaniline Structure

87-60-5

3-Chloro-2-meth...

N-tert-butyl-N-(thiazol-2-yl)methanediimine Structure

72042-12-7

N-tert-butyl-N-...

~78%

1-(3-Chloro-2-methylphenyl)-2-(2-methyl-2-propanyl)-3-(1,3-thiazo l-2-yl)guanidine Structure

72041-72-6

1-(3-Chloro-2-m...

1-cyclohexyl-3-(2-methyl-4-quinolyl)urea Structure

71070-70-7

1-cyclohexyl-3-...

~%

2-cyclohexyl-1-(2-methylquinolin-4-yl)-3-phenylguanidine Structure

72042-09-2

2-cyclohexyl-1-...

N-(cyclohexylcarbonimidoyl)-2-methylquinolin-4-amine Structure

71079-18-0

N-(cyclohexylca...

Structure

74497-02-2

~47%

2-cyclohexyl-1-(2-methylquinolin-4-yl)-3-phenylguanidine Structure

72042-09-2

2-cyclohexyl-1-...

1-cyclohexyl-3-(2-methyl-4-quinolyl)urea Structure

71070-70-7

1-cyclohexyl-3-...

~%

N-(cyclohexylcarbonimidoyl)-2-methylquinolin-4-amine Structure

71079-18-0

N-(cyclohexylca...

1-cyclohexyl-3-(2-methyl-4-quinolyl)urea Structure

71070-70-7

1-cyclohexyl-3-...

~%

2-cyclohexyl-1-(2-methylquinolin-4-yl)-3-(1,3,4-thiadiazol-2-yl)guanidine Structure

71079-28-2

2-cyclohexyl-1-...

2-Amino-1,3,4-thiadiazole Structure

4005-51-0

2-Amino-1,3,4-t...

N-(cyclohexylcarbonimidoyl)-2-methylquinolin-4-amine Structure

71079-18-0

N-(cyclohexylca...

~14%

2-cyclohexyl-1-(2-methylquinolin-4-yl)-3-(1,3,4-thiadiazol-2-yl)guanidine Structure

71079-28-2

2-cyclohexyl-1-...

1-Aminonaphthalene Structure

134-32-7

1-Aminonaphthalene

N-tert-butyl-N-(thiazol-2-yl)methanediimine Structure

72042-12-7

N-tert-butyl-N-...

~38%

2-tert-butyl-1-naphthalen-1-yl-1-(1,3-thiazol-2-yl)guanidine Structure

72041-73-7

2-tert-butyl-1-...

N-tert-butyl-N-(2-methylquinolin-4-yl)methanediimine Structure

71079-33-9

N-tert-butyl-N-...

~75%

2-tert-butyl-1-(2-methylquinolin-4-yl)guanidine Structure

72042-03-6

2-tert-butyl-1-...

2-Aminoethanol Structure

141-43-5

2-Aminoethanol

N-tert-butyl-N-(2-methylquinolin-4-yl)methanediimine Structure

71079-33-9

N-tert-butyl-N-...

~80%

1-tert-butyl-2-(2-hydroxyethyl)-3-(2-methylquinolin-4-yl)guanidine Structure

72042-04-7

1-tert-butyl-2-...

2-Aminothiazole Structure

96-50-4

2-Aminothiazole

N-tert-butyl-N'-pyridin-4-ylcarbodiimide Structure

60573-10-6

N-tert-butyl-N'...

~21%

2-tert-butyl-1-pyridin-4-yl-3-(1,3-thiazol-2-yl)guanidine Structure

72041-82-8

2-tert-butyl-1-...

2-Aminothiazole Structure

96-50-4

2-Aminothiazole

N/A Structure

60572-87-4

N/A

~51%

2-(2-methylbutan-2-yl)-3-pyridin-3-yl-1-(1,3-thiazol-2-yl)guanidine Structure

67026-82-8

2-(2-methylbuta...

Ethyl 2-aminothiazole-5-carboxylate Structure

32955-21-8

Ethyl 2-aminoth...

N-tert-butyl-N-(2-methylquinolin-4-yl)methanediimine Structure

71079-33-9

N-tert-butyl-N-...

~37%

ethyl 2-[[N'-tert-butyl-N-(2-methylquinolin-4-yl)carbamimidoyl]amino]-1,3-thiazole-5-carboxylate Structure

71132-06-4

ethyl 2-[[N'-te...

N-(cyclohexylcarbonimidoyl)-2-methylquinolin-4-amine Structure

71079-18-0

N-(cyclohexylca...

5-Amino-1,3,4-thiadiazole-2-thiol Structure

2349-67-9

5-Amino-1,3,4-t...

~59%

2-cyclohexyl-1-(2-methylquinolin-4-yl)-3-(2-sulfanylidene-3H-1,3,4-thiadiazol-5-yl)guanidine Structure

71253-70-8

2-cyclohexyl-1-...

1-cyclohexyl-3-(2-methyl-4-quinolyl)urea Structure

71070-70-7

1-cyclohexyl-3-...

~%

2-cyclohexyl-1-(2-methylquinolin-4-yl)-3-(2-sulfanylidene-3H-1,3,4-thiadiazol-5-yl)guanidine Structure

71253-70-8

2-cyclohexyl-1-...

2-Aminothiazole Structure

96-50-4

2-Aminothiazole

N-pyridin-4-yl-N'-1,1,3-trimethylbutylcarbodiimide Structure

60573-13-9

N-pyridin-4-yl-...

~30%

2-(2,4-dimethylpentan-2-yl)-1-pyridin-4-yl-3-(1,3-thiazol-2-yl)guanidine Structure

72041-83-9

2-(2,4-dimethyl...

Isoquinolin-5-amine Structure

1125-60-6

Isoquinolin-5-amine

N-tert-butyl-N-(thiazol-2-yl)methanediimine Structure

72042-12-7

N-tert-butyl-N-...

~39%

3-isoquinolin-5-yl-2-tert-butyl-1-(1,3-thiazol-2-yl)guanidine Structure

72041-87-3

3-isoquinolin-5...


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