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Literature summary for 3.4.14.5 extracted from

  • Pei, Z.; Li, X.; Longenecker, K.; von Geldern, T.W.; Wiedeman, P.E.; Lubben, T.H.; Zinker, B.A.; Stewart, K.; Ballaron, S.J.; Stashko, M.A.; Mika, A.K.; Beno, D.W.; Long, M.; Wells, H.; Kempf-Grote, A.J.; Madar, D.J.; McDermott, T.S.; Bhagavatula, L.; Fickes, M.G.; Pireh, D.; Solomon, L.R.; Lake, M.R.; Edalji, R.; Fry, E.H.; Sham, H.L.; Trevillyan, J.M.
    Discovery, structure-activity relationship, and pharmacological evaluation of (5-substituted-pyrrolidinyl-2-carbonyl)-2-cyanopyrrolidines as potent dipeptidyl peptidase IV inhibitors (2006), J. Med. Chem., 49, 3520-3535.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)-N-phenylpyrrolidine-2-carboxamide
-
Homo sapiens
(2R,5S)-N-(4-bromophenyl)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidine-2-carboxamide
-
Homo sapiens
(2S)-1-(((2S,5R)-5-[(1,3-benzodioxol-4-yloxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-(((2S,5R)-5-[(1-naphthyloxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-(((2S,5R)-5-[(2,4-dichlorophenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-(((2S,5R)-5-[(2,6-dichlorophenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-(((2S,5R)-5-[(2-chloro-4-cyanophenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-(((2S,5R)-5-[(2-chlorophenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-(((2S,5R)-5-[(2-methylphenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-(((2S,5R)-5-[(4-bromophenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-(((2S,5R)-5-[(4-cyanophenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-(((2S,5R)-5-[(4-methoxyphenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-(((2S,5R)-5-[(4-methylphenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-(((2S,5R)-5-[(benzyloxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-([(2S,5R)-5-(([2-chloro-5-(dihydroxymethyl)pyridin-3-yl]oxy)methyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-([(2S,5R)-5-(([dihydroxy(phenyl)-'4-sulfanyl]amino)methyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-([(2S,5R)-5-(anilinomethyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-([(2S,5R)-5-(morpholin-4-ylmethyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-([(2S,5R)-5-(phenoxymethyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-([(2S,5R)-5-([(2-chloropyridin-3-yl)oxy]methyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-([(2S,5R)-5-([(4-bromophenyl)amino]methyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-([(2S,5R)-5-([(6-bromo-1,3-benzodioxol-5-yl)oxy]methyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-([(2S,5R)-5-([2,4-dichloro-5-(dihydroxyamino)phenoxy]methyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-([(2S,5R)-5-([2-bromo-4-(methylsulfonodithioyl)phenoxy]methyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-([(2S,5R)-5-([2-chloro-4-(methylsulfonodithioyl)phenoxy]methyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-[(2S)-pyrrolidin-2-ylcarbonyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
1-([(5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methyl)-3-phenylurea
-
Homo sapiens
3-bromo-4-([(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methoxy)benzoic acid
-
Homo sapiens
3-chloro-4-([(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methoxy)benzoic acid
-
Homo sapiens
4-([(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methoxy)-3-methoxybenzoic acid
-
Homo sapiens
4-bromo-3-([(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methoxy)benzoic acid
-
Homo sapiens
4-chloro-3-([(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methoxy)benzoic acid
-
Homo sapiens
5-chloro-2-([(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methoxy)benzoic acid
-
Homo sapiens
5-chloro-6-([(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methoxy)nicotinic acid
-
Homo sapiens
cis-(2S)-1-([(2S)-5-(2-hydroxyethyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
cis-(2S)-1-([(2S)-5-ethylpyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
cis-(2S)-1-([(2S)-5-methylpyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
cis-(2S)-1-([(2S)-5-phenylpyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
cis-(2S)-1-([(2S)-5-prop-2-yn-1-ylpyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
cis-(2S)-1-([(2S)-5-propylpyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
N-([(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methyl)benzamide
-
Homo sapiens
trans-(2S)-1-([(2S)-5-(2-hydroxyethyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
trans-(2S)-1-([(2S)-5-ethylpyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
trans-(2S)-1-([(2S)-5-prop-2-yn-1-ylpyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile
-
Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens P27487
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
Gly-Pro-4-methylcoumarin 7-amide + H2O
-
Homo sapiens Gly-Pro + 7-amino-4-methylcoumarin
-
?

Synonyms

Synonyms Comment Organism
DPPIV
-
Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00000041
-
(2S)-1-([(2S,5R)-5-([(6-bromo-1,3-benzodioxol-5-yl)oxy]methyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.00000045
-
5-chloro-6-([(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methoxy)nicotinic acid pH 7.5 Homo sapiens
0.0000006
-
(2S)-1-(((2S,5R)-5-[(2-chloro-4-cyanophenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.00000063
-
(2S)-1-([(2S,5R)-5-([2,4-dichloro-5-(dihydroxyamino)phenoxy]methyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.00000066
-
3-bromo-4-([(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methoxy)benzoic acid pH 7.5 Homo sapiens
0.00000068
-
(2S)-1-([(2S,5R)-5-([2-bromo-4-(methylsulfonodithioyl)phenoxy]methyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.00000072
-
(2S)-1-([(2S,5R)-5-([(2-chloropyridin-3-yl)oxy]methyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.00000082
-
4-chloro-3-([(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methoxy)benzoic acid pH 7.5 Homo sapiens
0.00000085
-
(2S)-1-(((2S,5R)-5-[(2-chlorophenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.00000093
-
3-chloro-4-([(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methoxy)benzoic acid pH 7.5 Homo sapiens
0.000001
-
4-bromo-3-([(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methoxy)benzoic acid pH 7.5 Homo sapiens
0.0000014
-
(2S)-1-([(2S,5R)-5-([2-chloro-4-(methylsulfonodithioyl)phenoxy]methyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.0000016
-
4-([(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methoxy)-3-methoxybenzoic acid pH 7.5 Homo sapiens
0.0000016
-
(2S)-1-(((2S,5R)-5-[(2,4-dichlorophenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.0000025
-
(2S)-1-(((2S,5R)-5-[(1-naphthyloxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.0000027
-
(2S)-1-(((2S,5R)-5-[(1,3-benzodioxol-4-yloxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.0000035
-
(2S)-1-(((2S,5R)-5-[(2-methylphenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.0000044
-
(2S)-1-(((2S,5R)-5-[(4-cyanophenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.0000046
-
(2S)-1-(((2S,5R)-5-[(4-bromophenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.0000068
-
(2S)-1-([(2S,5R)-5-(phenoxymethyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.0000068
-
(2S)-1-([(2S,5R)-5-(([2-chloro-5-(dihydroxymethyl)pyridin-3-yl]oxy)methyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.0000072
-
(2S)-1-(((2S,5R)-5-[(4-methylphenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.0000083
-
cis-(2S)-1-([(2S)-5-methylpyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.0000089
-
(2S)-1-([(2S,5R)-5-([(4-bromophenyl)amino]methyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.00001
-
5-chloro-2-([(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methoxy)benzoic acid pH 7.5 Homo sapiens
0.000011
-
(2S)-1-(((2S,5R)-5-[(4-methoxyphenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.000012
-
(2S)-1-([(2S,5R)-5-(anilinomethyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.000015
-
1-([(5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methyl)-3-phenylurea
-
Homo sapiens
0.00002
-
(2S)-1-[(2S)-pyrrolidin-2-ylcarbonyl]pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.00002
-
N-([(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidin-2-yl]methyl)benzamide pH 7.5 Homo sapiens
0.000021
-
cis-(2S)-1-([(2S)-5-prop-2-yn-1-ylpyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.00003
-
(2S)-1-(((2S,5R)-5-[(benzyloxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.000033
-
cis-(2S)-1-([(2S)-5-ethylpyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.000044
-
(2S)-1-([(2S,5R)-5-(([dihydroxy(phenyl)-'4-sulfanyl]amino)methyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.000076
-
(2S)-1-(((2S,5R)-5-[(2,6-dichlorophenoxy)methyl]pyrrolidin-2-yl)carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.000103
-
trans-(2S)-1-([(2S)-5-ethylpyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.000143
-
trans-(2S)-1-([(2S)-5-prop-2-yn-1-ylpyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.000317
-
cis-(2S)-1-([(2S)-5-propylpyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.00072
-
cis-(2S)-1-([(2S)-5-phenylpyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.000764
-
cis-(2S)-1-([(2S)-5-(2-hydroxyethyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.000867
-
trans-(2S)-1-([(2S)-5-(2-hydroxyethyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens
0.00128
-
(2R,5S)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)-N-phenylpyrrolidine-2-carboxamide pH 7.5 Homo sapiens
0.00131
-
(2R,5S)-N-(4-bromophenyl)-5-([(2S)-2-cyanopyrrolidin-1-yl]carbonyl)pyrrolidine-2-carboxamide pH 7.5 Homo sapiens
0.00161
-
(2S)-1-([(2S,5R)-5-(morpholin-4-ylmethyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carbonitrile pH 7.5 Homo sapiens