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

ID: ALA4241638

PubChem CID: 132942957

Max Phase: Preclinical

Molecular Formula: C16H17N3O2

Molecular Weight: 283.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(c1ccc(OC)cc1)c1ncnc2occ(C)c12

Standard InChI:  InChI=1S/C16H17N3O2/c1-4-19(12-5-7-13(20-3)8-6-12)15-14-11(2)9-21-16(14)18-10-17-15/h5-10H,4H2,1-3H3

Standard InChI Key:  GDYIJFHOFSZSLG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    8.7401  -13.8427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7389  -14.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4470  -15.0712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4452  -13.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1538  -13.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1586  -14.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9386  -14.9061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4160  -14.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9309  -13.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4427  -12.6166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1492  -12.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8560  -12.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5620  -12.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5600  -11.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8461  -10.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1430  -11.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2660  -10.9751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9754  -11.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1788  -12.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7338  -12.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7314  -11.3930    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
M  END

Alternative Forms

1. Parent:

   

   ALA4241638

   ---

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: 283.33

Molecular Weight (Monoisotopic): 283.1321

AlogP: 3.70

#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: 1.82

CX LogP: 3.55

CX LogD: 3.55

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.73

Np Likeness Score: -0.59

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