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Literature summary for 1.1.1.62 extracted from

  • Perspicace, E.; Giorgio, A.; Carotti, A.; Marchais-Oberwinkler, S.; Hartmann, R.W.
    Novel N-methylsulfonamide and retro-N-methylsulfonamide derivatives as 17beta-hydroxysteroid dehydrogenase type 2 (17beta-HSD2) inhibitors with good ADME-related physicochemical parameters (2013), Eur. J. Med. Chem., 69, 201-215.
    View publication on PubMed

Application

Application Comment Organism
medicine inhibition of 17beta-hydroxysteroid dehydrogenase type 2 (17beta-HSD2) can help maintaining the appropriate bone mass density in osteoporosis by increasing the level of estradiol and testosterone in bone Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
(4S,5S)-5-[biphenyl-3-yl(hydroxy)methyl]-4-(2-fluorophenyl)-1-methylpyrrolidin-2-one
-
Homo sapiens
(4S,5S)-5-[biphenyl-4-yl(hydroxy)methyl]-4-(2-fluorophenyl)-1-methylpyrrolidin-2-one
-
Homo sapiens
(4S,5S)-5-[hydroxy[5-(pyridin-3-yl)thiophen-2-yl]methyl]-1-methyl-4-phenylpyrrolidin-2-one
-
Homo sapiens
2'-methoxy-N-(3-methoxyphenyl)-N-methyl-[1,1'-biphenyl]-4-sulfonamide 23% inhibition at 0.001 mM Homo sapiens
2'-methoxy-N-methyl-N-phenyl-[1,1'-biphenyl]-4-sulfonamide 10% inhibition at 0.001 mM Homo sapiens
3'-hydroxy-N-(3-hydroxybenzyl)-N-methyl-[1,10-biphenyl]-4-sulfonamide 57% inhibition at 0.001 mM Homo sapiens
3'-hydroxy-N-(3-hydroxybenzyl)-N-methylbiphenyl-4-carboxamide
-
Homo sapiens
3'-hydroxy-N-(3-hydroxyphenyl)-N-methyl-[1,10-biphenyl]-3-sulfonamide 42% inhibition at 0.001 mM; 68% inhibition at 0.001 mM Homo sapiens
3'-hydroxy-N-(3-hydroxyphenyl)-N-methyl-[1,10-biphenyl]-4-sulfonamide 14% inhibition at 0.001 mM; 50% inhibition at 0.001 mM Homo sapiens
3'-hydroxy-N-(3-hydroxyphenyl)-N-methylbiphenyl-4-carboxamide 13% inhibition at 0.001 mM Homo sapiens
3'-hydroxy-N-(3-methoxyphenyl)-N-methyl-[1,10-biphenyl]-4-sulfonamide 15% inhibition at 0.001 mM; 38% inhibition at 0.001 mM Homo sapiens
3'-methoxy-N-(2-methoxyphenyl)-N-methyl-[1,1'-biphenyl]-4-sulfonamide 10% inhibition at 0.001 mM; 17% inhibition at 0.001 mM Homo sapiens
3'-methoxy-N-(3-methoxybenzyl)-N-methyl-[1,10-biphenyl]-4-sulfonamide 45% inhibition at 0.001 mM Homo sapiens
3'-methoxy-N-(3-methoxybenzyl)-N-methylbiphenyl-4-carboxamide
-
Homo sapiens
3'-methoxy-N-(3-methoxyphenyl)-N-methyl-[1,1'-biphenyl]-4-sulfonamide 10% inhibition at 0.001 mM; 27% inhibition at 0.001 mM Homo sapiens
3'-methoxy-N-(3-methoxyphenyl)-N-methyl-[1,10-biphenyl]-3-sulfonamide 26% inhibition at 0.001 mM Homo sapiens
3'-methoxy-N-(3-methoxyphenyl)-N-methylbiphenyl-4-carboxamide 35% inhibition at 0.001 mM Homo sapiens
3'-methoxy-N-(4-methoxyphenyl)-N-methyl-[1,1'-biphenyl]-4-sulfonamide 22% inhibition at 0.001 mM Homo sapiens
3-hydroxy-N-(3'-hydroxy-[1,1'-biphenyl]-3-yl)-N-methylbenzenesulfonamide 17% inhibition at 0.001 mM; 88% inhibition at 0.001 mM Homo sapiens
3-hydroxy-N-(3'-hydroxy-[1,1'-biphenyl]-4-yl)-N-methylbenzenesulfonamide 22% inhibition at 0.001 mM; 66% inhibition at 0.001 mM Homo sapiens
3-methoxy-N-(3'-methoxy-[1,1'-biphenyl]-3-yl)-N-methylbenzenesulfonamide 14% inhibition at 0.001 mM; 68% inhibition at 0.001 mM Homo sapiens
3-methoxy-N-(3'-methoxy-[1,10-biphenyl]-4-yl)-Nmethylbenzenesulfonamide 18% inhibition at 0.001 mM; 25% inhibition at 0.001 mM Homo sapiens
4'-hydroxy-N-(3-hydroxybenzyl)-N-methylbiphenyl-3-carboxamide
-
Homo sapiens
4'-methoxy-N-(3-methoxybenzyl)-N-methylbiphenyl-3-carboxamide
-
Homo sapiens
4'-methoxy-N-(3-methoxyphenyl)-N-methyl-[1,1'-biphenyl]-4-sulfonamide 13% inhibition at 0.001 mM Homo sapiens
4-fluoro-3-hydroxy-N-(3'-hydroxybiphenyl-3-yl)-N-methylbenzenesulfonamide 80% inhibition at 0.001 mM; 96% inhibition at 0.001 mM Homo sapiens
4-fluoro-3-methoxy-N-(3'-methoxybiphenyl-3-yl)-N-methylbenzenesulfonamide 17% inhibition at 0.001 mM Homo sapiens
additional information synthesis, physicochemical properties, and biological evaluation of novel N-methylsulfonamide and retro-N-methylsulfonamide derivatives as 17beta-HSD2 inhibitors showing high potency with a good selectivity toward 17beta-HSD1 (the isoenzyme responsible of the reverse reaction), and a likely good in vitro ADME profile, overview; synthesis, physicochemical properties, and biological evaluation of novel N-methylsulfonamide and retro-N-methylsulfonamide derivatives as 17beta-HSD2 (the isoenzyme responsible of the reverse reaction) inhibitors showing high potency with a good selectivity toward 17beta-HSD1, and a likely good in vitro ADME profile, overview. No inhibition by 9b, 9c, 9e, 9f, 9g, 9h, 9k, 9o, and 10a Homo sapiens
N-(3-hydroxyphenyl)-3'-methoxy-N-methyl-[1,1'-biphenyl]-4-sulfonamide 18% inhibition at 0.001 mM Homo sapiens
N-(3-hydroxyphenyl)-N,3'-dimethyl-[1,1'-biphenyl]-4-sulfonamide 15% inhibition at 0.001 mM; 22% inhibition at 0.001 mM Homo sapiens
N-(3-hydroxyphenyl)-N-methyl-4-(thiophen-2-yl)benzenesulfonamide 31% inhibition at 0.001 mM Homo sapiens
N-(3-methoxyphenyl)-N-methyl-4-(thiophen-2-yl)benzenesulfonamide 32% inhibition at 0.001 mM Homo sapiens
N-(3-methoxyphenyl)-N-methyl-4-(thiophen-3-yl)benzenesulfonamide 23% inhibition at 0.001 mM Homo sapiens
N-(4-hydroxyphenyl)-N-methyl-4-(pyridin-3-yl)benzenesulfonamide 14% inhibition at 0.001 mM; 15% inhibition at 0.001 mM Homo sapiens

Localization

Localization Comment Organism GeneOntology No. Textmining
cytosol
-
Homo sapiens 5829
-
microsome
-
Homo sapiens
-
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
17beta-estradiol + NAD+ Homo sapiens
-
estrone + NADH + H+
-
?
estrone + NADH + H+ Homo sapiens
-
17beta-estradiol + NAD+
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens P14061
-
-
Homo sapiens P37059
-
-

Source Tissue

Source Tissue Comment Organism Textmining
placenta
-
Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
17beta-estradiol + NAD+
-
Homo sapiens estrone + NADH + H+
-
?
estrone + NADH + H+
-
Homo sapiens 17beta-estradiol + NAD+
-
?

Synonyms

Synonyms Comment Organism
17beta-HSD1
-
Homo sapiens
17beta-HSD2
-
Homo sapiens
17beta-hydroxysteroid dehydrogenase type 1
-
Homo sapiens
17beta-hydroxysteroid dehydrogenase type 2
-
Homo sapiens
HSD17B1
-
Homo sapiens
HSD17B2
-
Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
assay at Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
phosphate buffer, assay at Homo sapiens

Cofactor

Cofactor Comment Organism Structure
NAD+
-
Homo sapiens
NADH
-
Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000023
-
pH 7.4, 37°C Homo sapiens 4-fluoro-3-hydroxy-N-(3'-hydroxybiphenyl-3-yl)-N-methylbenzenesulfonamide
0.00005
-
pH 7.4, 37°C Homo sapiens (4S,5S)-5-[hydroxy[5-(pyridin-3-yl)thiophen-2-yl]methyl]-1-methyl-4-phenylpyrrolidin-2-one
0.000159
-
pH 7.4, 37°C Homo sapiens 3-hydroxy-N-(3'-hydroxy-[1,1'-biphenyl]-3-yl)-N-methylbenzenesulfonamide
0.00042
-
pH 7.4, 37°C Homo sapiens (4S,5S)-5-[biphenyl-3-yl(hydroxy)methyl]-4-(2-fluorophenyl)-1-methylpyrrolidin-2-one
0.000482
-
pH 7.4, 37°C Homo sapiens 4'-hydroxy-N-(3-hydroxybenzyl)-N-methylbiphenyl-3-carboxamide
0.000494
-
pH 7.4, 37°C Homo sapiens 3'-methoxy-N-(3-methoxybenzyl)-N-methylbiphenyl-4-carboxamide
0.000511
-
pH 7.4, 37°C Homo sapiens 3-hydroxy-N-(3'-hydroxy-[1,1'-biphenyl]-4-yl)-N-methylbenzenesulfonamide
0.000517
-
pH 7.4, 37°C Homo sapiens 3'-methoxy-N-(3-methoxyphenyl)-N-methylbiphenyl-4-carboxamide
0.00054
-
pH 7.4, 37°C Homo sapiens 3'-hydroxy-N-(3-hydroxyphenyl)-N-methyl-[1,10-biphenyl]-3-sulfonamide
0.000594
-
pH 7.4, 37°C Homo sapiens 3'-hydroxy-N-(3-hydroxybenzyl)-N-methylbiphenyl-4-carboxamide
0.000934
-
pH 7.4, 37°C Homo sapiens 3'-hydroxy-N-(3-hydroxybenzyl)-N-methyl-[1,10-biphenyl]-4-sulfonamide
0.00102
-
pH 7.4, 37°C Homo sapiens (4S,5S)-5-[biphenyl-4-yl(hydroxy)methyl]-4-(2-fluorophenyl)-1-methylpyrrolidin-2-one
0.001179
-
pH 7.4, 37°C Homo sapiens 3'-hydroxy-N-(3-hydroxyphenyl)-N-methyl-[1,10-biphenyl]-4-sulfonamide
0.002031
-
pH 7.4, 37°C Homo sapiens 3'-hydroxy-N-(3-hydroxyphenyl)-N-methyl-[1,10-biphenyl]-4-sulfonamide
0.004299
-
pH 7.4, 37°C Homo sapiens 3'-hydroxy-N-(3-hydroxybenzyl)-N-methyl-[1,10-biphenyl]-4-sulfonamide