N-(3-(2,5-dimethylbenzyloxy)-4-(N-methylmethylsulfonamido)phenyl)cyclohexanecarboxamide

ID: ALA574422

Chembl Id: CHEMBL574422

Cas Number: 1021926-22-6

PubChem CID: 24873741

Max Phase: Preclinical

Molecular Formula: C24H32N2O4S

Molecular Weight: 444.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C)c(COc2cc(NC(=O)C3CCCCC3)ccc2N(C)S(C)(=O)=O)c1

Standard InChI:  InChI=1S/C24H32N2O4S/c1-17-10-11-18(2)20(14-17)16-30-23-15-21(12-13-22(23)26(3)31(4,28)29)25-24(27)19-8-6-5-7-9-19/h10-15,19H,5-9,16H2,1-4H3,(H,25,27)

Standard InChI Key:  NLBGXSHIKISRHR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA574422

   N-[3-[(2,5-dimethylphenyl)methoxy]-4-[methyl(methylsulfonyl)amino]phenyl]cyclohexanecarboxamide

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

Calculated Properties

Molecular Weight: 444.60

Molecular Weight (Monoisotopic): 444.2083

AlogP: 4.80

#Rotatable Bonds: 7

Polar Surface Area: 75.71

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.51

CX LogD: 4.51

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.67

Np Likeness Score: -1.61

References

1. Su B, Chen S..  (2009)  Lead optimization of COX-2 inhibitor nimesulide analogs to overcome aromatase inhibitor resistance in breast cancer cells.,  19  (23): [PMID:19854050] [10.1016/j.bmcl.2009.09.109]

2. Zhong B, Lama R, Smith KM, Xu Y, Su B..  (2011)  Design and synthesis of a biotinylated probe of COX-2 inhibitor nimesulide analog JCC76.,  21  (18): [PMID:21807508] [10.1016/j.bmcl.2011.07.025]

3. Zhong B, Cai X, Chennamaneni S, Yi X, Liu L, Pink JJ, Dowlati A, Xu Y, Zhou A, Su B..  (2012)  From COX-2 inhibitor nimesulide to potent anti-cancer agent: synthesis, in vitro, in vivo and pharmacokinetic evaluation.,  47  [PMID:22119125] [10.1016/j.ejmech.2011.11.012]

4. Yi X, Zhong B, Smith KM, Geldenhuys WJ, Feng Y, Pink JJ, Dowlati A, Xu Y, Zhou A, Su B..  (2012)  Identification of a class of novel tubulin inhibitors.,  55  (7): [PMID:22435708] [10.1021/jm300100d]

5. Lama R, Sandhu R, Zhong B, Li B, Su B..  (2012)  Identification of selective tubulin inhibitors as potential anti-trypanosomal agents.,  22  (17): [PMID:22850214] [10.1016/j.bmcl.2012.07.023]

6. Lama R, Zhang L, Naim JM, Williams J, Zhou A, Su B..  (2013)  Development, validation and pilot screening of an in vitro multi-cellular three-dimensional cancer spheroid assay for anti-cancer drug testing.,  21  (4): [PMID:23306053] [10.1016/j.bmc.2012.12.007]

7. Zhong B, Chennamaneni S, Lama R, Yi X, Geldenhuys WJ, Pink JJ, Dowlati A, Xu Y, Zhou A, Su B..  (2013)  Synthesis and anticancer mechanism investigation of dual Hsp27 and tubulin inhibitors.,  56  (13): [PMID:23767669] [10.1021/jm4004736]

8. Zhao A, Zheng Q, Orahoske CM, Idippily ND, Ashcraft MM, Quamine A, Su B..  (2018)  Synthesis and biological evaluation of anti-cancer agents that selectively inhibit Her2 over-expressed breast cancer cell growth via down-regulation of Her2 protein.,  28  (4): [PMID:29352646] [10.1016/j.bmcl.2018.01.016]

Source

Source(1):

• Scientific Literature