(E)-2-methyl-8-(3,4,5-trimethoxybenzylidene)-4-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydroquinazoline

ID: ALA3115731

PubChem CID: 76325172

Max Phase: Preclinical

Molecular Formula: C28H32N2O6

Molecular Weight: 492.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2\CCCc3c2nc(C)nc3-c2cc(OC)c(OC)c(OC)c2)cc(OC)c1OC

Standard InChI:  InChI=1S/C28H32N2O6/c1-16-29-25-18(11-17-12-21(31-2)27(35-6)22(13-17)32-3)9-8-10-20(25)26(30-16)19-14-23(33-4)28(36-7)24(15-19)34-5/h11-15H,8-10H2,1-7H3/b18-11+

Standard InChI Key:  BFTLDZSDIDHRER-WOJGMQOQSA-N

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
   13.1318   -8.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1306   -9.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8454   -9.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5619   -9.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5589   -8.2962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8436   -7.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2719   -7.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9879   -8.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9884   -9.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7003   -9.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4157   -9.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6981   -7.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4106   -8.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1223   -7.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1225   -7.0542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4053   -6.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6966   -7.0564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8359   -8.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8343   -9.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5478   -9.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2634   -9.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2610   -8.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5468   -7.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4021   -5.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4158   -9.5392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7016   -9.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9782   -9.5255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9791  -10.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4172   -7.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4170   -7.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9741   -7.8696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6899   -8.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8452  -10.3651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5472  -10.3511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8324  -10.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5596  -10.7778    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
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 12  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 14 18  1  0
 16 24  1  0
  2 25  1  0
 25 26  1  0
 21 27  1  0
 27 28  1  0
  1 29  1  0
 29 30  1  0
 22 31  1  0
 31 32  1  0
  3 33  1  0
 20 34  1  0
 34 35  1  0
 33 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3115731

   (8E)-2-methyl-4-(3,4,5-trimethoxyphenyl)-8-[(3,4,5-trimethoxyphenyl)methylidene]-6,7-dihydro-5H-quinazoline

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: 492.57

Molecular Weight (Monoisotopic): 492.2260

AlogP: 5.38

#Rotatable Bonds: 8

Polar Surface Area: 81.16

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.53

CX LogP: 5.14

CX LogD: 5.14

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.41

Np Likeness Score: -0.32

References

1. El-Subbagh HI, Hassan GS, El-Messery SM, Al-Rashood ST, Al-Omary FA, Abulfadl YS, Shabayek MI..  (2014)  Nonclassical antifolates, part 5. Benzodiazepine analogs as a new class of DHFR inhibitors: synthesis, antitumor testing and molecular modeling study.,  74  [PMID:24469112] [10.1016/j.ejmech.2014.01.004]

2. Khan I, Ibrar A, Ahmed W, Saeed A..  (2015)  Synthetic approaches, functionalization and therapeutic potential of quinazoline and quinazolinone skeletons: the advances continue.,  90  [PMID:25461317] [10.1016/j.ejmech.2014.10.084]

Source

Source(1):

• Scientific Literature