N-isopropyl-N-(4-methoxyphenyl)-5-methylfuro[2,3-d]pyrimidin-4-amine

ID: ALA4250273

PubChem CID: 145983389

Max Phase: Preclinical

Molecular Formula: C17H19N3O2

Molecular Weight: 297.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(N(c2ncnc3occ(C)c23)C(C)C)cc1

Standard InChI:  InChI=1S/C17H19N3O2/c1-11(2)20(13-5-7-14(21-4)8-6-13)16-15-12(3)9-22-17(15)19-10-18-16/h5-11H,1-4H3

Standard InChI Key:  WXUQFXPVDDHAIZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   16.0452  -13.7519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0441  -14.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7521  -14.9804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7504  -13.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4590  -13.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4638  -14.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2438  -14.8154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7212  -14.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2361  -13.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7479  -12.5258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4544  -12.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1612  -12.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8672  -12.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8652  -11.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1513  -10.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4482  -11.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5712  -10.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2806  -11.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4840  -12.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0390  -12.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0366  -11.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3325  -12.5301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 14 17  1  0
 17 18  1  0
  9 19  1  0
 10 20  1  0
 20 21  1  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4250273

   ---

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: 297.36

Molecular Weight (Monoisotopic): 297.1477

AlogP: 4.09

#Rotatable Bonds: 4

Polar Surface Area: 51.39

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.69

CX LogP: 3.96

CX LogD: 3.96

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.73

Np Likeness Score: -0.47

References

1. Devambatla RKV, Choudhary S, Ihnat M, Hamel E, Mooberry SL, Gangjee A..  (2018)  Design, synthesis and preclinical evaluation of 5-methyl-N4-aryl-furo[2,3-d]pyrimidines as single agents with combination chemotherapy potential.,  28  (18): [PMID:30098869] [10.1016/j.bmcl.2018.07.039]

2. Devambatla RK, Namjoshi OA, Choudhary S, Hamel E, Shaffer CV, Rohena CC, Mooberry SL, Gangjee A..  (2016)  Design, Synthesis, and Preclinical Evaluation of 4-Substituted-5-methyl-furo[2,3-d]pyrimidines as Microtubule Targeting Agents That Are Effective against Multidrug Resistant Cancer Cells.,  59  (12): [PMID:27213719] [10.1021/acs.jmedchem.6b00237]

Source

Source(1):

• Scientific Literature