(Z)-4-[[(6-chloro-3-pyridinyl)methyl]ethylamino]-3-methyl-1-(2-pyridinyl)methyl-5-nitro-1,2,3,6-tetrahydropyrimidine

ID: ALA2251836

PubChem CID: 76315449

Max Phase: Preclinical

Molecular Formula: C19H23ClN6O2

Molecular Weight: 402.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(Cc1ccc(Cl)nc1)C1=C([N+](=O)[O-])CN(Cc2ccccn2)CN1C

Standard InChI:  InChI=1S/C19H23ClN6O2/c1-3-25(11-15-7-8-18(20)22-10-15)19-17(26(27)28)13-24(14-23(19)2)12-16-6-4-5-9-21-16/h4-10H,3,11-14H2,1-2H3

Standard InChI Key:  OLPXJXWCWSVBFY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   30.3778   -8.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3766   -9.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0914   -9.7527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.8079   -9.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8050   -8.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0896   -8.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6618   -9.7518    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.5179   -8.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2339   -8.5035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9468   -8.0883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6654   -8.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.3762   -8.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3774   -7.2661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.6615   -6.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9445   -7.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2370   -9.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5242   -9.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6660   -9.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2283   -6.8545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5144   -7.2677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2274   -6.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0918   -6.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8063   -7.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8014   -8.0886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.5150   -8.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2305   -8.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2279   -7.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5136   -6.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 15  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  9 16  1  0
 16 17  1  0
 11 18  1  0
 19 20  2  0
 19 21  1  0
 15 19  1  0
 13 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2251836

   N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-1-methyl-5-nitro-3-(pyridin-2-ylmethyl)-2,4-dihydropyrimidin-6-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: 402.89

Molecular Weight (Monoisotopic): 402.1571

AlogP: 2.80

#Rotatable Bonds: 7

Polar Surface Area: 78.64

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.20

CX LogP: 2.53

CX LogD: 2.53

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.40

Np Likeness Score: -1.72

References

1. Sun C, Jin J, Zhu J, Wang H, Yang D, Xing J..  (2010)  Discovery of bis-aromatic ring neonicotinoid analogues fixed as cis-configuration: Synthesis, insecticidal activities, and molecular docking studies.,  20  (11): [PMID:20452211] [10.1016/j.bmcl.2010.04.050]

Source

Source(1):

• Scientific Literature