4-(1-pyridin-2-yl ethylene) N',N''-dimethyl thiosemicarbazone

ID: ALA223250

Cas Number: 71555-14-1

PubChem CID: 5843399

Max Phase: Preclinical

Molecular Formula: C10H14N4S

Molecular Weight: 222.32

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2-Acetylpyridine N,N-Dimethylthiosemicarbazone | 71555-14-1|NSC319725|KETONE, METHYL 2-PYRIDYL, 4,4-DIMETHYL-3-THIOSEMICARBAZONE|1,1-dimethyl-3-[(E)-1-pyridin-2-ylethylideneamino]thiourea|Thiosemicarbazone R|N,N-Dimethyl-2-(1-(pyridin-2-yl)ethylidene)hydrazine-1-carbothioamide|NSC 319725|BRN 1463083|NSC-319725|2-acetylpyridine N,N-dimethylthiosemicarbazone|starbld0002295|Semicarbazide, 4,4-dimethyl-1-(1-(2-pyridyl)ethylidine)-3-thio-|CHEMBL223250|SCHEMBL5839502|Hydrazinecarbothioamide, N,N-dimetShow More⌵

Canonical SMILES:  C/C(=N\NC(=S)N(C)C)c1ccccn1

Standard InChI:  InChI=1S/C10H14N4S/c1-8(9-6-4-5-7-11-9)12-13-10(15)14(2)3/h4-7H,1-3H3,(H,13,15)/b12-8+

Standard InChI Key:  ZMZIYBQONAEPNV-XYOKQWHBSA-N

Molfile:  

     RDKit          2D

 15 15  0  0  0  0  0  0  0  0999 V2000
   -3.4795  -15.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7673  -14.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0520  -15.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0522  -15.8341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3378  -16.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6246  -15.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304  -14.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3454  -14.5935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7704  -13.7782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4857  -13.3712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4888  -12.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1999  -12.1366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7765  -12.1312    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2029  -11.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9121  -12.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
  8  3  1  0
  2  9  2  0
  4  5  1  0
  9 10  1  0
  2  3  1  0
 10 11  1  0
  5  6  2  0
 11 12  1  0
  1  2  1  0
 11 13  2  0
  6  7  1  0
 12 14  1  0
  3  4  2  0
 12 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA223250

   1,1-dimethyl-3-[(E)-1-pyridin-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: 222.32

Molecular Weight (Monoisotopic): 222.0939

AlogP: 1.24

#Rotatable Bonds: 2

Polar Surface Area: 40.52

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.80

CX Basic pKa: 2.88

CX LogP: 1.13

CX LogD: 1.13

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.46

Np Likeness Score: -2.01

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. Klayman DL, Scovill JP, Bartosevich JF, Bruce J..  (1983)  2-Acetylpyridine thiosemicarbazones. 5. 1-[1-(2-Pyridyl)ethyl]-3-thiosemicarbazides as potential antimalarial agents.,  26  (1): [PMID:6338234] [10.1021/jm00355a008]

3. Kowol CR, Berger R, Eichinger R, Roller A, Jakupec MA, Schmidt PP, Arion VB, Keppler BK..  (2007)  Gallium(III) and iron(III) complexes of alpha-N-heterocyclic thiosemicarbazones: synthesis, characterization, cytotoxicity, and interaction with ribonucleotide reductase.,  50  (6): [PMID:17315858] [10.1021/jm0612618]

4. Richardson DR, Kalinowski DS, Richardson V, Sharpe PC, Lovejoy DB, Islam M, Bernhardt PV..  (2009)  2-Acetylpyridine thiosemicarbazones are potent iron chelators and antiproliferative agents: redox activity, iron complexation and characterization of their antitumor activity.,  52  (5): [PMID:19216562] [10.1021/jm801585u]

5. PubChem BioAssay data set, 

6. Gilleran JA, Yu X, Blayney AJ, Bencivenga AF, Na B, Augeri DJ, Blanden AR, Kimball SD, Loh SN, Roberge JY, Carpizo DR..  (2021)  Benzothiazolyl and Benzoxazolyl Hydrazones Function as Zinc Metallochaperones to Reactivate Mutant p53.,  64  (4.0): [PMID:33538587] [10.1021/acs.jmedchem.0c01360]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays