(R)-3-Amino-1-((R)-2-benzyl-piperazin-1-yl)-4-(2-fluoro-phenyl)-butan-1-one

ID: ALA175872

Chembl Id: CHEMBL175872

PubChem CID: 10144962

Max Phase: Preclinical

Molecular Formula: C21H26FN3O

Molecular Weight: 355.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CC(=O)N1CCNC[C@H]1Cc1ccccc1)Cc1ccccc1F

Standard InChI:  InChI=1S/C21H26FN3O/c22-20-9-5-4-8-17(20)13-18(23)14-21(26)25-11-10-24-15-19(25)12-16-6-2-1-3-7-16/h1-9,18-19,24H,10-15,23H2/t18-,19-/m1/s1

Standard InChI Key:  JCRFZKKDIWRAQQ-RTBURBONSA-N

Alternative Forms

1. Parent:

   

   ALA175872

   (R)-3-amino-1-((R)-2-benzylpiperazin-1-yl)-4-(2-fluorophenyl)butan-1-one

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: 355.46

Molecular Weight (Monoisotopic): 355.2060

AlogP: 2.13

#Rotatable Bonds: 6

Polar Surface Area: 58.36

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.84

CX LogP: 2.48

CX LogD: 0.61

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.83

Np Likeness Score: -0.82

References

1. Kim D, Wang L, Beconi M, Eiermann GJ, Fisher MH, He H, Hickey GJ, Kowalchick JE, Leiting B, Lyons K, Marsilio F, McCann ME, Patel RA, Petrov A, Scapin G, Patel SB, Roy RS, Wu JK, Wyvratt MJ, Zhang BB, Zhu L, Thornberry NA, Weber AE..  (2005)  (2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine: a potent, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes.,  48  (1): [PMID:15634008] [10.1021/jm0493156]

2. Brockunier LL, He J, Colwell LF, Habulihaz B, He H, Leiting B, Lyons KA, Marsilio F, Patel RA, Teffera Y, Wu JK, Thornberry NA, Weber AE, Parmee ER..  (2004)  Substituted piperazines as novel dipeptidyl peptidase IV inhibitors.,  14  (18): [PMID:15324904] [10.1016/j.bmcl.2004.06.065]

3. Kim D, Kowalchick JE, Brockunier LL, Parmee ER, Eiermann GJ, Fisher MH, He H, Leiting B, Lyons K, Scapin G, Patel SB, Petrov A, Pryor KD, Roy RS, Wu JK, Zhang X, Wyvratt MJ, Zhang BB, Zhu L, Thornberry NA, Weber AE..  (2008)  Discovery of potent and selective dipeptidyl peptidase IV inhibitors derived from beta-aminoamides bearing subsituted triazolopiperazines.,  51  (3): [PMID:18201067] [10.1021/jm070330v]

4. Havale SH, Pal M..  (2009)  Medicinal chemistry approaches to the inhibition of dipeptidyl peptidase-4 for the treatment of type 2 diabetes.,  17  (5): [PMID:19217790] [10.1016/j.bmc.2009.01.061]

5. Kumar S, Mittal A, Mittal A..  (2021)  A review upon medicinal perspective and designing rationale of DPP-4 inhibitors.,  46  [PMID:34428715] [10.1016/j.bmc.2021.116354]

Source

Source(1):

• Scientific Literature