4-(1-pyrazin-2-yl ethylene) N'-methyl thiosemicarbazone

ID: ALA113086

PubChem CID: 5375900

Max Phase: Preclinical

Molecular Formula: C8H11N5S

Molecular Weight: 209.28

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2-Acetylpyrazinen(4)-Methylthiosemicarbazone | CHEMBL113086|2-Acetylpyrazinen(4)-Methylthiosemicarbazone|1-methyl-3-[(E)-1-pyrazin-2-ylethylideneamino]thiourea|BDBM50341555|2-Acetylpyrazine 4-methylthiosemicarbazone|4-(1-pyrazin-2-yl ethylene) N''-methyl thiosemicarbazone|(E)-N-Methyl-2-(1-(pyrazin-2-yl)ethylidene)hydrazinecarbothioamide|Hydrazinecarbothioamide, N-methyl-2-(1-pyrazinylethylidene)-, (2E)-

Canonical SMILES:  C/N=C(\S)N/N=C(\C)c1cnccn1

Standard InChI:  InChI=1S/C8H11N5S/c1-6(12-13-8(14)9-2)7-5-10-3-4-11-7/h3-5H,1-2H3,(H2,9,13,14)/b12-6+

Standard InChI Key:  GLPQYBREVOHZTO-WUXMJOGZSA-N

Molfile:  

     RDKit          2D

 14 14  0  0  0  0  0  0  0  0999 V2000
    0.9125   -1.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500   -1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9042   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3875   -0.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292   -1.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500   -0.8792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -0.8792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333    0.3208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667   -1.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3875    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292   -0.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500   -0.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875   -1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  1  2  0
  4  3  1  0
  5  1  1  0
  6  2  1  0
  7  4  2  0
  8 10  2  0
  9  2  2  0
 10  4  1  0
 11  3  1  0
 12  7  1  0
 13  8  1  0
 14  9  1  0
 13 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA113086

   1-methyl-3-[(E)-1-pyrazin-2-ylethylideneamino]thiourea

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: 209.28

Molecular Weight (Monoisotopic): 209.0735

AlogP: 0.71

#Rotatable Bonds: 2

Polar Surface Area: 62.53

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.52

CX Basic pKa: 4.56

CX LogP: 0.17

CX LogD: -0.47

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.33

Np Likeness Score: -1.58

References

1. Easmon J, Heinisch G, Holzer W, Rosenwirth B..  (1992)  Novel thiosemicarbazones derived from formyl- and acyldiazines: synthesis, effects on cell proliferation, and synergism with antiviral agents.,  35  (17): [PMID:1354751] [10.1021/jm00095a027]

2. Li MX, Chen CL, Ling CS, Zhou J, Ji BS, Wu YJ, Niu JY..  (2009)  Cytotoxicity and structure-activity relationships of four alpha-N-heterocyclic thiosemicarbazone derivatives crystal structure of 2-acetylpyrazine thiosemicarbazone.,  19  (10): [PMID:19369075] [10.1016/j.bmcl.2009.03.135]

3. Zeglis BM, Divilov V, Lewis JS..  (2011)  Role of metalation in the topoisomerase IIα inhibition and antiproliferation activity of a series of α-heterocyclic-N4-substituted thiosemicarbazones and their Cu(II) complexes.,  54  (7): [PMID:21391686] [10.1021/jm101532u]

Source

Source(1):

• Scientific Literature