N-((2,2-dimethyl-2H-chromen-6-yl)methyl)-3,4-dimethoxy-N-phenylbenzenesulfonamide

ID: ALA1823895

Chembl Id: CHEMBL1823895

Cas Number: 927823-01-6

PubChem CID: 16097752

Max Phase: Preclinical

Molecular Formula: C26H27NO5S

Molecular Weight: 465.57

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)N(Cc2ccc3c(c2)C=CC(C)(C)O3)c2ccccc2)cc1OC

Standard InChI:  InChI=1S/C26H27NO5S/c1-26(2)15-14-20-16-19(10-12-23(20)32-26)18-27(21-8-6-5-7-9-21)33(28,29)22-11-13-24(30-3)25(17-22)31-4/h5-17H,18H2,1-4H3

Standard InChI Key:  IPZJNJPAVPZHJM-UHFFFAOYSA-N

Associated Targets(Human)

HIF1A Tchem Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha (820 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HIF1A Tchem Hypoxia-inducible factor 1 alpha (6027 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EP300 Tchem Histone acetyltransferase p300 (1259 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LN-229 (376 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EP300 Tchem Histone acetyltransferase p300/Hypoxia-inducible factor 1-alpha (21 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Plasma (6361 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Liver (8163 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: 465.57Molecular Weight (Monoisotopic): 465.1610AlogP: 5.28#Rotatable Bonds: 7
Polar Surface Area: 65.07Molecular Species: NEUTRALHBA: 5HBD:
#RO5 Violations: 1HBA (Lipinski): 6HBD (Lipinski): #RO5 Violations (Lipinski): 1
CX Acidic pKa: CX Basic pKa: CX LogP: 4.99CX LogD: 4.99
Aromatic Rings: 3Heavy Atoms: 33QED Weighted: 0.47Np Likeness Score: -0.27

References

1. Tan C, de Noronha RG, Devi NS, Jabbar AA, Kaluz S, Liu Y, Mooring SR, Nicolaou KC, Wang B, Van Meir EG..  (2011)  Sulfonamides as a new scaffold for hypoxia inducible factor pathway inhibitors.,  21  (18): [PMID:21831638] [10.1016/j.bmcl.2011.06.099]
2. Mooring SR, Jin H, Devi NS, Jabbar AA, Kaluz S, Liu Y, Van Meir EG, Wang B..  (2011)  Design and synthesis of novel small-molecule inhibitors of the hypoxia inducible factor pathway.,  54  (24): [PMID:22032632] [10.1021/jm201018g]
3. Mun J, Jabbar AA, Devi NS, Liu Y, Van Meir EG, Goodman MM..  (2012)  Structure-activity relationship of 2,2-dimethyl-2H-chromene based arylsulfonamide analogs of 3,4-dimethoxy-N-[(2,2-dimethyl-2H-chromen-6-yl)methyl]-N-phenylbenzenesulfonamide, a novel small molecule hypoxia inducible factor-1 (HIF-1) pathway inhibitor and anti-cancer agent.,  20  (14): [PMID:22682301] [10.1016/j.bmc.2012.04.064]
4. Mun J, Jabbar AA, Devi NS, Yin S, Wang Y, Tan C, Culver D, Snyder JP, Van Meir EG, Goodman MM..  (2012)  Design and in vitro activities of N-alkyl-N-[(8-R-2,2-dimethyl-2H-chromen-6-yl)methyl]heteroarylsulfonamides, novel, small-molecule hypoxia inducible factor-1 pathway inhibitors and anticancer agents.,  55  (15): [PMID:22746274] [10.1021/jm300752n]
5. Shi Q, Yin S, Kaluz S, Ni N, Devi NS, Mun J, Wang D, Damera K, Chen W, Burroughs S, Mooring SR, Goodman MM, Van Meir EG, Wang B, Snyder JP..  (2012)  Binding Model for the Interaction of Anticancer Arylsulfonamides with the p300 Transcription Cofactor.,  (8): [PMID:24936238] [10.1021/ml300042k]
6. Ferguson J, De Los Santos Z, Devi N, Van Meir E, Zingales S, Wang B..  (2017)  Examining the structure-activity relationship of benzopyran-based inhibitors of the hypoxia inducible factor-1 pathway.,  27  (8): [PMID:28285917] [10.1016/j.bmcl.2017.02.073]
7. Li J, Xi W, Li X, Sun H, Li Y..  (2019)  Advances in inhibition of protein-protein interactions targeting hypoxia-inducible factor-1 for cancer therapy.,  27  (7): [PMID:30819620] [10.1016/j.bmc.2019.01.042]

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