(S)-2'-(neopentyloxy)-7'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

ID: ALA3354688

Chembl Id: CHEMBL3354688

PubChem CID: 45256109

Max Phase: Preclinical

Molecular Formula: C24H24N4O3

Molecular Weight: 416.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)COc1ccc2c(c1)[C@]1(COC(N)=N1)c1cc(-c3cncnc3)ccc1O2

Standard InChI:  InChI=1S/C24H24N4O3/c1-23(2,3)12-29-17-5-7-21-19(9-17)24(13-30-22(25)28-24)18-8-15(4-6-20(18)31-21)16-10-26-14-27-11-16/h4-11,14H,12-13H2,1-3H3,(H2,25,28)/t24-/m0/s1

Standard InChI Key:  CHZHWZAKWGFQNL-DEOSSOPVSA-N

Alternative Forms

1. Parent:

   

   ALA3354688

   (4s)-2'-(2,2-Dimethylpropoxy)-7'-(Pyrimidin-5-Yl)spiro[1,3-Oxazole-4,9'-Xanthen]-2-Amine

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: 416.48

Molecular Weight (Monoisotopic): 416.1848

AlogP: 4.26

#Rotatable Bonds: 3

Polar Surface Area: 91.85

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.65

CX LogP: 3.69

CX LogD: 3.68

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.69

Np Likeness Score: -0.21

References

1. Epstein O, Bryan MC, Cheng AC, Derakhchan K, Dineen TA, Hickman D, Hua Z, Human JB, Kreiman C, Marx IE, Weiss MM, Wahl RC, Wen PH, Whittington DA, Wood S, Zheng XM, Fremeau RT, White RD, Patel VF..  (2014)  Lead optimization and modulation of hERG activity in a series of aminooxazoline xanthene β-site amyloid precursor protein cleaving enzyme (BACE1) inhibitors.,  57  (23): [PMID:25389560] [10.1021/jm501266w]

2. Dineen TA, Chen K, Cheng AC, Derakhchan K, Epstein O, Esmay J, Hickman D, Kreiman CE, Marx IE, Wahl RC, Wen PH, Weiss MM, Whittington DA, Wood S, Fremeau RT, White RD, Patel VF..  (2014)  Inhibitors of β-site amyloid precursor protein cleaving enzyme (BACE1): identification of (S)-7-(2-fluoropyridin-3-yl)-3-((3-methyloxetan-3-yl)ethynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-2'-amine (AMG-8718).,  57  (23): [PMID:25363711] [10.1021/jm5012676]

3. Maia M, Resende DISP, Durães F, Pinto MMM, Sousa E..  (2021)  Xanthenes in Medicinal Chemistry - Synthetic strategies and biological activities.,  210  [PMID:33310284] [10.1016/j.ejmech.2020.113085]

Source

Source(1):

• Scientific Literature