(S)-4-(6,7-Dimethoxy-quinazolin-4-yl)-piperazine-1-carbothioic acid (1-phenyl-ethyl)-amide

ID: ALA1788249

PubChem CID: 10906260

Max Phase: Preclinical

Molecular Formula: C23H27N5O2S

Molecular Weight: 437.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2ncnc(N3CCN(/C(S)=N\[C@@H](C)c4ccccc4)CC3)c2cc1OC

Standard InChI:  InChI=1S/C23H27N5O2S/c1-16(17-7-5-4-6-8-17)26-23(31)28-11-9-27(10-12-28)22-18-13-20(29-2)21(30-3)14-19(18)24-15-25-22/h4-8,13-16H,9-12H2,1-3H3,(H,26,31)/t16-/m0/s1

Standard InChI Key:  JJICUGUAKGHFQB-INIZCTEOSA-N

Molfile:  

     RDKit          2D

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    2.4167   -4.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -1.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -3.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9917   -4.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1250   -0.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -4.5500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917   -5.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2792   -5.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4250   -5.7917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -0.4292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7000   -2.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4333   -4.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375   -5.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417    0.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1500   -5.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -4.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542    0.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792    0.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4 18  1  0
  5  2  1  0
  6  1  1  0
  7  1  2  0
  8  3  2  0
  9  2  2  0
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 13  6  1  0
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 15 13  2  0
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 22 11  1  0
 23 12  1  0
 16 24  1  6
 25 21  1  0
 26 21  2  0
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 30 25  2  0
 31 29  2  0
 12 10  1  0
  9 15  1  0
  4 17  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1788249

   4-(6,7-dimethoxyquinazolin-4-yl)-N-[(1S)-1-phenylethyl]piperazine-1-carbothioamide

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: 437.57

Molecular Weight (Monoisotopic): 437.1885

AlogP: 3.82

#Rotatable Bonds: 5

Polar Surface Area: 63.08

Molecular Species: ZWITTERION

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.06

CX Basic pKa: 13.36

CX LogP: 5.04

CX LogD: 5.04

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.37

Np Likeness Score: -0.92

References

1. Matsuno K, Nakajima T, Ichimura M, Giese NA, Yu JC, Lokker NA, Ushiki J, Ide S, Oda S, Nomoto Y..  (2002)  Potent and selective inhibitors of PDGF receptor phosphorylation. 2. Synthesis, structure activity relationship, improvement of aqueous solubility, and biological effects of 4-[4-(N-substituted (thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline derivatives.,  45  (20): [PMID:12238930] [10.1021/jm0201114]

Source

Source(1):

• Scientific Literature