N-(4-ethylphenyl)-N,5-dimethylfuro[2,3-d]pyrimidin-4-amine

ID: ALA4242522

PubChem CID: 145982785

Max Phase: Preclinical

Molecular Formula: C16H17N3O

Molecular Weight: 267.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc(N(C)c2ncnc3occ(C)c23)cc1

Standard InChI:  InChI=1S/C16H17N3O/c1-4-12-5-7-13(8-6-12)19(3)15-14-11(2)9-20-16(14)18-10-17-15/h5-10H,4H2,1-3H3

Standard InChI Key:  HZYHQHCKBTWZMB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   30.8455  -13.5125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8443  -14.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5524  -14.7410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.5506  -13.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2592  -13.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2640  -14.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0440  -14.5760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5214  -13.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0363  -13.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5482  -12.2865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.2546  -11.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9615  -12.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6675  -11.8746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6655  -11.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9516  -10.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2485  -11.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2843  -12.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8392  -11.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3714  -10.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0809  -11.0504    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
  9 17  1  0
 10 18  1  0
 14 19  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4242522

   ---

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: 267.33

Molecular Weight (Monoisotopic): 267.1372

AlogP: 3.86

#Rotatable Bonds: 3

Polar Surface Area: 42.16

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.90

CX LogP: 4.31

CX LogD: 4.31

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.72

Np Likeness Score: -0.74

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