ID: ALA299112

Max Phase: Preclinical

Molecular Formula: C14H10N2O6S2

Molecular Weight: 366.38

Molecule Type: Small molecule

Representations

Synonyms (1): 3,4-Bis(Phenylsulfonyl)Furoxan
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=S(=O)(c1ccccc1)c1no[n+]([O-])c1S(=O)(=O)c1ccccc1

Standard InChI:  InChI=1S/C14H10N2O6S2/c17-16-14(24(20,21)12-9-5-2-6-10-12)13(15-22-16)23(18,19)11-7-3-1-4-8-11/h1-10H

Standard InChI Key:  PLIHJANRRMFJCC-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: 366.38

Molecular Weight (Monoisotopic): 365.9980

AlogP: 0.97

#Rotatable Bonds: 4

Polar Surface Area: 121.25

Molecular Species:

HBA: 7

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 1.05

CX LogD: 1.05

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.63

Np Likeness Score: -0.91

References

1. Moharram S, Zhou A, Wiebe LI, Knaus EE..  (2004)  Design and synthesis of 3'- and 5'-O-(3-benzenesulfonylfuroxan-4-yl)-2'-deoxyuridines: biological evaluation as hybrid nitric oxide donor-nucleoside anticancer agents.,  47  (7): [PMID:15027876] [10.1021/jm030544m]

2. Boiani L, Aguirre G, González M, Cerecetto H, Chidichimo A, Cazzulo JJ, Bertinaria M, Guglielmo S..  (2008)  Furoxan-, alkylnitrate-derivatives and related compounds as anti-trypanosomatid agents: mechanism of action studies.,  16  (17): [PMID:18706821] [10.1016/j.bmc.2008.07.077]

3. Fruttero R, Crosetti M, Chegaev K, Guglielmo S, Gasco A, Berardi F, Niso M, Perrone R, Panaro MA, Colabufo NA..  (2010)  Phenylsulfonylfuroxans as modulators of multidrug-resistance-associated protein-1 and P-glycoprotein.,  53  (15): [PMID:20684594] [10.1021/jm100066y]

4. Alvarez G, Aguirre-López B, Varela J, Cabrera M, Merlino A, López GV, Lavaggi ML, Porcal W, Di Maio R, González M, Cerecetto H, Cabrera N, Pérez-Montfort R, de Gómez-Puyou MT, Gómez-Puyou A..  (2010)  Massive screening yields novel and selective Trypanosoma cruzi triosephosphate isomerase dimer-interface-irreversible inhibitors with anti-trypanosomal activity.,  45  (12): [PMID:20889239] [10.1016/j.ejmech.2010.09.034]

5. Hernández P, Cabrera M, Lavaggi ML, Celano L, Tiscornia I, Rodrigues da Costa T, Thomson L, Bollati-Fogolín M, Miranda AL, Lima LM, Barreiro EJ, González M, Cerecetto H..  (2012)  Discovery of new orally effective analgesic and anti-inflammatory hybrid furoxanyl N-acylhydrazone derivatives.,  20  (6): [PMID:22356737] [10.1016/j.bmc.2012.01.034]

6. Liu MM, Chen XY, Huang YQ, Feng P, Guo YL, Yang G, Chen Y..  (2014)  Hybrids of phenylsulfonylfuroxan and coumarin as potent antitumor agents.,  57  (22): [PMID:25350923] [10.1021/jm500613m]

7. Duan W, Li J, Inks ES, Chou CJ, Jia Y, Chu X, Li X, Xu W, Zhang Y..  (2015)  Design, synthesis, and antitumor evaluation of novel histone deacetylase inhibitors equipped with a phenylsulfonylfuroxan module as a nitric oxide donor.,  58  (10): [PMID:25906087] [10.1021/acs.jmedchem.5b00317]

8. Fernandes GFDS, de Souza PC, Marino LB, Chegaev K, Guglielmo S, Lazzarato L, Fruttero R, Chung MC, Pavan FR, Dos Santos JL..  (2016)  Synthesis and biological activity of furoxan derivatives against Mycobacterium tuberculosis.,  123  [PMID:27508879] [10.1016/j.ejmech.2016.07.039]

9. Dutra LA, Guanaes JFO, Johmann N, Lopes Pires ME, Chin CM, Marcondes S, Dos Santos JL..  (2017)  Synthesis, antiplatelet and antithrombotic activities of resveratrol derivatives with NO-donor properties.,  27  (11): [PMID:28400236] [10.1016/j.bmcl.2017.04.007]

10. Ou Y,Sun P,Wu N,Chen H,Wu D,Hu W,Yang Z.  (2020)  Synthesis and biological evaluation of parthenolide derivatives with reduced toxicity as potential inhibitors of the NLRP3 inflammasome.,  30  (17): [PMID:32738997] [10.1016/j.bmcl.2020.127399]

11. Hu X, Gao X, Gao G, Wang Y, Cao H, Li D, Hua H..  (2021)  Discovery of β-carboline-(phenylsulfonyl)furoxan hybrids as potential anti-breast cancer agents.,  40  [PMID:33744443] [10.1016/j.bmcl.2021.127952]

12. Yu Z, Li M, Wang K, Gu Y, Guo S, Wang W, Ma Y, Liu H, Chen Y..  (2022)  Novel Hybrids of 3-Substituted Coumarin and Phenylsulfonylfuroxan as Potent Antitumor Agents with Collateral Sensitivity against MCF-7/ADR.,  65  (13.0): [PMID:35737669] [10.1021/acs.jmedchem.2c00608]

13. Huang X, Wang YS, Ma D, Wang YY, Bian SD, Zhang B, Qiao Y, He ZR, Lv M, Cai GL, Wang ZX, Liu XS, Shi JB, Liu MM..  (2022)  Synthesis and biological evaluation of novel hybrids of phenylsulfonyl furoxan and phenstatin derivatives as potent anti-tumor agents.,  230  [PMID:35065411] [10.1016/j.ejmech.2022.114112]

Source

Source(1):

• Scientific Literature