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N-{4-[(1-Phenyl-piperazin-2-ylmethyl)-amino]-phenyl}-methanesulfonamide

ID: ALA351183

PubChem CID: 14998853

Max Phase: Preclinical

Molecular Formula: C18H24N4O2S

Molecular Weight: 360.48

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)Nc1ccc(NCC2CNCCN2c2ccccc2)cc1

Standard InChI:  InChI=1S/C18H24N4O2S/c1-25(23,24)21-16-9-7-15(8-10-16)20-14-18-13-19-11-12-22(18)17-5-3-2-4-6-17/h2-10,18-21H,11-14H2,1H3

Standard InChI Key:  AFYXROQLTFFXOK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    6.7625   -5.0750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -3.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7625   -4.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -5.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2875   -5.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1250   -4.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -2.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792   -3.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1625   -3.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -4.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -3.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667   -5.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2292   -3.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -4.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000   -4.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6042   -4.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -4.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -5.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6042   -5.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1250   -5.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  4 10  1  0
  5  1  2  0
  6  1  2  0
  7  2  1  0
  8 15  1  0
  9 12  1  0
 10  9  1  0
 11  3  1  0
 12 19  2  0
 13  1  1  0
 14  2  1  0
 15  4  1  0
 16 11  1  0
 17 11  2  0
 18 16  2  0
 19 17  1  0
 20  8  1  0
 21  7  1  0
 22  7  2  0
 23 22  1  0
 24 21  2  0
 25 23  2  0
 12 18  1  0
 14 20  1  0
 25 24  1  0
M  END

Associated Targets(Human)

ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

ADRB2 Beta-2 adrenergic receptor (258 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Canis familiaris (36305 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

Biocomponents

Calculated Properties

Molecular Weight: 360.48Molecular Weight (Monoisotopic): 360.1620AlogP: 1.95#Rotatable Bonds: 6
Polar Surface Area: 73.47Molecular Species: BASEHBA: 5HBD: 3
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 11.85CX Basic pKa: 8.70CX LogP: 1.25CX LogD: -0.06
Aromatic Rings: 2Heavy Atoms: 25QED Weighted: 0.73Np Likeness Score: -1.05

References

1. Phillips GB, Morgan TK, Lumma WC, Gomez RP, Lind JM, Lis R, Argentieri T, Sullivan ME..  (1992)  Synthesis, cardiac electrophysiology, and beta-blocking activity of novel arylpiperazines with potential as class II/III antiarrhythmic agents.,  35  (4): [PMID:1347318] [10.1021/jm00082a016]
2. Uehling, David E DE and 16 more authors.  2006-05-04  Biarylaniline phenethanolamines as potent and selective beta3 adrenergic receptor agonists.  [PMID:16640337]
3. Lafontaine, Jennifer A JA and 10 more authors.  2007-09-15  Discovery of potent and orally bioavailable heterocycle-based beta3-adrenergic receptor agonists, potential therapeutics for the treatment of obesity.  [PMID:17632003]
4. Maruyama, Tatsuya T and 5 more authors.  2009-06  Discovery of novel acetanilide derivatives as potent and selective beta3-adrenergic receptor agonists.  [PMID:19232786]
5. Maruyama, Tatsuya T and 10 more authors.  2009-05-01  Synthesis and evaluation of novel phenoxypropanolamine derivatives containing acetanilides as potent and selective beta3-adrenergic receptor agonists.  [PMID:19362005]
6. Marquis, Robert W RW and 17 more authors.  2009-07-09  Antagonists of the calcium receptor I. Amino alcohol-based parathyroid hormone secretagogues.  [PMID:19492813]
7. Maruyama, Tatsuya T and 8 more authors.  2009-08-01  Discovery of novel thiourea derivatives as potent and selective beta3-adrenergic receptor agonists.  [PMID:19581100]
8. Senthil Kumar, P and Bharatam, Prasad V.  2010-12  Comparative 3D QSAR study on β(1)-, β(2)-, and β(3)-adrenoceptor agonists.  [PMID:21170122]
9. Bang-Andersen, Benny B and 10 more authors.  2011-05-12  Discovery of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine (Lu AA21004): a novel multimodal compound for the treatment of major depressive disorder.  [PMID:21486038]
10. Germain, Andrew R AR and 14 more authors.  2013-03-15  Cinnamides as selective small-molecule inhibitors of a cellular model of breast cancer stem cells.  [PMID:23403082]
11. Christopher, John A and 11 more authors.  2013-05-09  Biophysical fragment screening of the β1-adrenergic receptor: identification of high affinity arylpiperazine leads using structure-based drug design.  [PMID:23517028]
12. Nocentini, Alessio A and 15 more authors.  2018-06-28  Discovery of β-Adrenergic Receptors Blocker-Carbonic Anhydrase Inhibitor Hybrids for Multitargeted Antiglaucoma Therapy.  [PMID:29851481]
13. Xing, Gang; Woo, Anthony Yiu-Ho; Pan, Li; Lin, Bin and Cheng, Mao-Sheng.  2020-12-24  Recent Advances in β2-Agonists for Treatment of Chronic Respiratory Diseases and Heart Failure.  [PMID:33213146]

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