4-Phenyl-1-[(S)-2-(pyrrolidine-1-carbonyl)-pyrrolidin-1-yl]-butan-1-one

ID: ALA289651

Chembl Id: CHEMBL289651

Cas Number: 112603-82-4

PubChem CID: 3081017

Max Phase: Preclinical

Molecular Formula: C19H26N2O2

Molecular Weight: 314.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: SUAM-1221 | Suam 1221|N-(N-(Phenyl)butyryl-L-prolyl)pyrrolidine|112603-82-4|Suam-1221|4-phenyl-1-[(2S)-2-(pyrrolidine-1-carbonyl)pyrrolidin-1-yl]butan-1-one|CHEMBL289651|Pyrrolidine, 1-(1-oxo-4-phenylbutyl)-2-(1-pyrolidinylcarbonyl)-, (S)-|SCHEMBL6285952|DTXSID40150119|HDRSLHFTJYMQIL-KRWDZBQOSA-N|BDBM50051539|N-[N-(gamma-phenyl)butyryl-L-prolyl]pyrrolidine|(S)-4-phenyl-1-(2-(pyrrolidine-1-carbonyl)pyrrolidin-1-yl)butan-1-one|4-Phenyl-1-[(S)-2-(pyrrolidine-1-carbonyl)-pyrrolidin-1-yl]-butan-1-oneShow More⌵

Canonical SMILES:  O=C([C@@H]1CCCN1C(=O)CCCc1ccccc1)N1CCCC1

Standard InChI:  InChI=1S/C19H26N2O2/c22-18(12-6-10-16-8-2-1-3-9-16)21-15-7-11-17(21)19(23)20-13-4-5-14-20/h1-3,8-9,17H,4-7,10-15H2/t17-/m0/s1

Standard InChI Key:  HDRSLHFTJYMQIL-KRWDZBQOSA-N

Alternative Forms

1. Parent:

   

   ALA289651

   N-(N-(Phenyl)butyryl-L-prolyl)pyrrolidine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 314.43

Molecular Weight (Monoisotopic): 314.1994

AlogP: 2.62

#Rotatable Bonds: 5

Polar Surface Area: 40.62

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.28

CX LogD: 2.28

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.84

Np Likeness Score: -0.98

References

1. Karoly K, Sandor E, Edit S, Miklos F, Judit S, Benjamin P, Andrea S, Istvan H.  (1997)  Prolyl endopeptidase inhibitors1: N-acyl derivatives of L-thioproline-pyrrolidine,  7  (13): [10.1016/S0960-894X(97)00295-3]

2. Tanaka Y, Niwa S, Nishioka H, Yamanaka T, Torizuka M, Yoshinaga K, Kobayashi N, Ikeda Y, Arai H..  (1994)  New potent prolyl endopeptidase inhibitors: synthesis and structure-activity relationships of indan and tetralin derivatives and their analogues.,  37  (13): [PMID:8027988] [10.1021/jm00039a019]

3. Portevin B, Benoist A, Rémond G, Hervé Y, Vincent M, Lepagnol J, De Nanteuil G..  (1996)  New prolyl endopeptidase inhibitors: in vitro and in vivo activities of azabicyclo[2.2.2]octane, azabicyclo[2.2.1]heptane, and perhydroindole derivatives.,  39  (12): [PMID:8691432] [10.1021/jm950858c]

4. Vendeville S, Bourel L, Davioud-Charvet E, Grellier P, Deprez B, Sergheraert C..  (1999)  Automated parallel synthesis of a tetrahydroisoquinolin-based library: potential prolyl endopeptidase inhibitors.,  9  (3): [PMID:10091698] [10.1016/s0960-894x(99)00003-7]

5. Wallén EA, Christiaans JA, Forsberg MM, Venäläinen JI, Männistö PT, Gynther J..  (2002)  Dicarboxylic acid bis(L-prolyl-pyrrolidine) amides as prolyl oligopeptidase inhibitors.,  45  (20): [PMID:12238937] [10.1021/jm020966g]

6. Jarho EM, Venäläinen JI, Huuskonen J, Christiaans JA, Garcia-Horsman JA, Forsberg MM, Järvinen T, Gynther J, Männistö PT, Wallén EA..  (2004)  A cyclopent-2-enecarbonyl group mimics proline at the P2 position of prolyl oligopeptidase inhibitors.,  47  (23): [PMID:15509157] [10.1021/jm049503w]

7. Jarho EM, Wallén EA, Christiaans JA, Forsberg MM, Venäläinen JI, Männistö PT, Gynther J, Poso A..  (2005)  Dicarboxylic acid azacycle l-prolyl-pyrrolidine amides as prolyl oligopeptidase inhibitors and three-dimensional quantitative structure-activity relationship of the enzyme-inhibitor interactions.,  48  (15): [PMID:16033257] [10.1021/jm0500020]

8. Jarho EM, Venäläinen JI, Juntunen J, Yli-Kokko AL, Vepsäläinen J, Christiaans JA, Forsberg MM, Järvinen T, Männistö PT, Wallén EA..  (2006)  An introduction of a pyridine group into the structure of prolyl oligopeptidase inhibitors.,  16  (21): [PMID:16919454] [10.1016/j.bmcl.2006.08.029]

9. Kánai K, Arányi P, Böcskei Z, Ferenczy G, Harmat V, Simon K, Bátori S, Náray-Szabo G, Hermecz I..  (2008)  Prolyl oligopeptidase inhibition by N-acyl-pro-pyrrolidine-type molecules.,  51  (23): [PMID:19006380] [10.1021/jm800944x]

10. Lawandi J, Gerber-Lemaire S, Juillerat-Jeanneret L, Moitessier N..  (2010)  Inhibitors of prolyl oligopeptidases for the therapy of human diseases: defining diseases and inhibitors.,  53  (9): [PMID:20058865] [10.1021/jm901104g]

11. Van der Veken P, Fülöp V, Rea D, Gerard M, Van Elzen R, Joossens J, Cheng JD, Baekelandt V, De Meester I, Lambeir AM, Augustyns K..  (2012)  P2-substituted N-acylprolylpyrrolidine inhibitors of prolyl oligopeptidase: biochemical evaluation, binding mode determination, and assessment in a cellular model of synucleinopathy.,  55  (22): [PMID:23121075] [10.1021/jm301060g]

12. Kallinen A, Todorov B, Kallionpää R, Bäck S, Sarparanta M, Raki M, García-Horsman JA, Bergström KA, Wallén EA, Männistö PT, Airaksinen AJ..  (2014)  Synthesis and biological evaluation of novel (123)I-labeled 4-(4-iodophenyl)butanoyl-L-prolyl-(2S)-pyrrolidines for imaging prolyl oligopeptidase in vivo.,  79  [PMID:24763264] [10.1016/j.ejmech.2014.04.014]

13. Kilpeläinen TP, Tyni JK, Lahtela-Kakkonen MK, Eteläinen TS, Myöhänen TT, Wallén EAA..  (2019)  Tetrazole as a Replacement of the Electrophilic Group in Characteristic Prolyl Oligopeptidase Inhibitors.,  10  (12): [PMID:31857839] [10.1021/acsmedchemlett.9b00394]

Source

Source(1):

• Scientific Literature