ID: ALA2203744

Max Phase: Preclinical

Molecular Formula: C19H23N5S

Molecular Weight: 353.50

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN(C(=S)NN=C(c1ccccn1)c1ccccn1)C1CCCCC1

Standard InChI:  InChI=1S/C19H23N5S/c1-24(15-9-3-2-4-10-15)19(25)23-22-18(16-11-5-7-13-20-16)17-12-6-8-14-21-17/h5-8,11-15H,2-4,9-10H2,1H3,(H,23,25)

Standard InChI Key:  GNLZNQJBZNOUBM-UHFFFAOYSA-N

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

Properties

Molecular Weight: 353.50

Molecular Weight (Monoisotopic): 353.1674

AlogP: 3.37

#Rotatable Bonds: 4

Polar Surface Area: 53.41

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.65

CX Basic pKa: 2.38

CX LogP: 4.00

CX LogD: 4.00

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.52

Np Likeness Score: -1.34

References

1. Lovejoy DB, Sharp DM, Seebacher N, Obeidy P, Prichard T, Stefani C, Basha MT, Sharpe PC, Jansson PJ, Kalinowski DS, Bernhardt PV, Richardson DR..  (2012)  Novel second-generation di-2-pyridylketone thiosemicarbazones show synergism with standard chemotherapeutics and demonstrate potent activity against lung cancer xenografts after oral and intravenous administration in vivo.,  55  (16): [PMID:22861499] [10.1021/jm300768u]

2. Stacy AE, Palanimuthu D, Bernhardt PV, Kalinowski DS, Jansson PJ, Richardson DR..  (2016)  Structure-Activity Relationships of Di-2-pyridylketone, 2-Benzoylpyridine, and 2-Acetylpyridine Thiosemicarbazones for Overcoming Pgp-Mediated Drug Resistance.,  59  (18): [PMID:27524608] [10.1021/acs.jmedchem.6b01050]

3. de Siqueira LRP, de Moraes Gomes PAT, de Lima Ferreira LP, de Melo Rêgo MJB, Leite ACL..  (2019)  Multi-target compounds acting in cancer progression: Focus on thiosemicarbazone, thiazole and thiazolidinone analogues.,  170  [PMID:30904782] [10.1016/j.ejmech.2019.03.024]

4. He Z, Qiao H, Yang F, Zhou W, Gong Y, Zhang X, Wang H, Zhao B, Ma L, Liu HM, Zhao W..  (2019)  Novel thiosemicarbazone derivatives containing indole fragment as potent and selective anticancer agent.,  184  [PMID:31614257] [10.1016/j.ejmech.2019.111764]

5. Zhang XH,Bo-Wang null,Tao YY,Ma Q,Wang HJ,He ZX,Wu HP,Li YH,Zhao B,Ma LY,Liu HM.  (2020)  Thiosemicarbazone-based lead optimization to discover high-efficiency and low-toxicity anti-gastric cancer agents.,  199  [PMID:32438199] [10.1016/j.ejmech.2020.112349]

6. He ZX,Huo JL,Gong YP,An Q,Zhang X,Qiao H,Yang FF,Zhang XH,Jiao LM,Liu HM,Ma LY,Zhao W.  (2021)  Design, synthesis and biological evaluation of novel thiosemicarbazone-indole derivatives targeting prostate cancer cells.,  210  [PMID:33153765] [10.1016/j.ejmech.2020.112970]

7. Li JQ, Gao H, Zhai L, Sun LY, Chen C, Chigan JZ, Ding HH, Yang KW..  (2021)  Dipyridyl-substituted thiosemicarbazone as a potent broad-spectrum inhibitor of metallo-β-lactamases.,  38  [PMID:33862468] [10.1016/j.bmc.2021.116128]

Source

Source(1):

• Scientific Literature