1-[(E)-{[6-(2,4-dichloro-5-nitrophenyl)-2-methylimidazo[2,1-b][1,3]thiazol-5-yl]methylidene}amino]guanidine

ID: ALA374050

Max Phase: Preclinical

Molecular Formula: C14H11Cl2N7O2S

Molecular Weight: 412.26

Molecule Type: Small molecule

Names and Identifiers

Synonyms from Alternative Forms(1): NSC-722870

Canonical SMILES:  Cc1cn2c(/C=N/NC(=N)N)c(-c3cc([N+](=O)[O-])c(Cl)cc3Cl)nc2s1

Standard InChI:  InChI=1S/C14H11Cl2N7O2S/c1-6-5-22-11(4-19-21-13(17)18)12(20-14(22)26-6)7-2-10(23(24)25)9(16)3-8(7)15/h2-5H,1H3,(H4,17,18,21)/b19-4+

Standard InChI Key:  QAQIMUUVPNQQJQ-RMOCHZDMSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    5.6909  -26.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4149  -25.9156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4330  -25.0901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1569  -24.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1751  -23.8675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8628  -25.1215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6699  -27.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6520  -28.4685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1451  -27.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9662  -27.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3689  -28.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1938  -28.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6171  -27.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2094  -27.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3859  -27.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8687  -28.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8853  -27.3827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1087  -27.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6122  -27.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0820  -28.4427    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.4427  -27.8522    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.6301  -26.4070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2243  -25.6878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4558  -26.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7866  -27.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9457  -29.2500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  4  6  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  9 10  1  0
 16 17  1  0
  2  3  1  0
  7  1  1  0
 16  8  2  0
  8  9  1  0
  9  7  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 16  1  0
  7 17  1  0
 13 21  1  0
  3  4  1  0
 10 11  2  0
 22 23  2  0
 22 24  1  0
 14 22  1  0
  4  5  1  0
 19 25  1  0
 11 12  1  0
 11 26  1  0
  1  2  2  0
 12 13  2  0
M  CHG  2  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA374050

   ---

2. Alternative Forms:

   

   ALA374050

   2-[(E)-[6-(2,4-dichloro-5-nitrophenyl)-2-methylimidazo[2,1-b][1,3]thiazol-5-yl]methylideneamino]guanidine

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: 412.26

Molecular Weight (Monoisotopic): 411.0072

AlogP: 3.40

#Rotatable Bonds: 4

Polar Surface Area: 134.70

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.35

CX LogP: 3.53

CX LogD: 3.50

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.26

Np Likeness Score: -1.93

References

1. Andreani A, Burnelli S, Granaiola M, Leoni A, Locatelli A, Morigi R, Rambaldi M, Varoli L, Farruggia G, Stefanelli C, Masotti L, Kunkel MW..  (2006)  Synthesis and antitumor activity of guanylhydrazones from 6-(2,4-dichloro-5-nitrophenyl)imidazo[2,1-b]thiazoles and 6-pyridylimidazo[2,1-b]thiazoles(1).,  49  (26): [PMID:17181173] [10.1021/jm061077m]

Source

Source(1):

• Scientific Literature