3,4-Bis-benzenesulfonyl-furazan 2-oxide

ID: ALA299112

Chembl Id: CHEMBL299112

Cas Number: 66074-00-8

PubChem CID: 12405466

Max Phase: Preclinical

Molecular Formula: C14H10N2O6S2

Molecular Weight: 366.38

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: 3,4-Bis(Phenylsulfonyl)Furoxan | 66074-00-8|3,4-bis(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide|3,4-bis(benzenesulfonyl)-2-oxido-1,2,5-oxadiazol-2-ium|3,4-Bis(Phenylsulfonyl)Furoxan|1,2,5-Oxadiazole, 3,4-bis(phenylsulfonyl)-, 2-oxide|CHEMBL299112|MFCD29042396|SCHEMBL1460605|DTXSID20496704|PLIHJANRRMFJCC-UHFFFAOYSA-N|BCP30768|AC8997|BDBM50324369|3,4-Bis-benzenesulfonyl-furazan 2-oxide|AS-77350|SY253266|3,4-bis(phenylsulfonyl)-1,2,5-oxadiazole2-oxide|3,4-bis(phenylsulphonyl)-1,2,5-oxadiazole 2-oxide|Show More

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

Alternative Forms

Associated Targets(Human)

143B (353 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hs-578T (29457 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCB1 Tchem P-glycoprotein 1 (14716 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCC1 Tchem Multidrug resistance-associated protein 1 (2587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HT-29 (80576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A2780 (11979 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HUVEC (11049 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC1 Tclin Histone deacetylase (HDAC1 and HDAC2) (618 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEL (6614 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NLRP3 Tchem NACHT, LRR and PYD domains-containing protein 3 (908 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK-293T (167025 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-231 (73002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

KBALB cell line (25 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EMT6 (738 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma cruzi (99888 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Triosephosphate isomerase, glycosomal (493 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium tuberculosis (203094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nlrp3 NACHT, LRR and PYD domains-containing protein 3 (641 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
J774.A1 (2436 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 366.38Molecular Weight (Monoisotopic): 365.9980AlogP: 0.97#Rotatable Bonds: 4
Polar Surface Area: 121.25Molecular Species: HBA: 7HBD:
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: 1.05CX LogD: 1.05
Aromatic Rings: 3Heavy Atoms: 24QED Weighted: 0.63Np 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]

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