4-{N'-[5-Bromo-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-hydrazino}-benzenesulfonamide

ID: ALA411491

Chembl Id: CHEMBL411491

Max Phase: Preclinical

Molecular Formula: C14H11BrN4O3S

Molecular Weight: 395.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1ccc(N/N=C2\C(=O)Nc3ccc(Br)cc32)cc1

Standard InChI:  InChI=1S/C14H11BrN4O3S/c15-8-1-6-12-11(7-8)13(14(20)17-12)19-18-9-2-4-10(5-3-9)23(16,21)22/h1-7,18H,(H2,16,21,22)(H,17,19,20)

Standard InChI Key:  ODZNNZYRBRRREX-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA411491

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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: 395.24

Molecular Weight (Monoisotopic): 393.9735

AlogP: 1.86

#Rotatable Bonds: 3

Polar Surface Area: 113.65

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.52

CX Basic pKa: 0.36

CX LogP: 2.44

CX LogD: 2.41

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.69

Np Likeness Score: -1.56

References

1. Tominaga Y, Jorgensen WL..  (2004)  General model for estimation of the inhibition of protein kinases using Monte Carlo simulations.,  47  (10): [PMID:15115396] [10.1021/jm0304358]

2. Bramson HN, Corona J, Davis ST, Dickerson SH, Edelstein M, Frye SV, Gampe RT, Harris PA, Hassell A, Holmes WD, Hunter RN, Lackey KE, Lovejoy B, Luzzio MJ, Montana V, Rocque WJ, Rusnak D, Shewchuk L, Veal JM, Walker DH, Kuyper LF..  (2001)  Oxindole-based inhibitors of cyclin-dependent kinase 2 (CDK2): design, synthesis, enzymatic activities, and X-ray crystallographic analysis.,  44  (25): [PMID:11728181] [10.1021/jm010117d]

3. Kolb P, Huang D, Dey F, Caflisch A..  (2008)  Discovery of kinase inhibitors by high-throughput docking and scoring based on a transferable linear interaction energy model.,  51  (5): [PMID:18271520] [10.1021/jm070654j]

4. Anderson PC, De Sapio V, Turner KB, Elmer SP, Roe DC, Schoeniger JS..  (2012)  Identification of binding specificity-determining features in protein families.,  55  (5): [PMID:22289061] [10.1021/jm200979x]

5. Ibrahim HS, Abou-Seri SM, Abdel-Aziz HA..  (2016)  3-Hydrazinoindolin-2-one derivatives: Chemical classification and investigation of their targets as anticancer agents.,  122  [PMID:27391135] [10.1016/j.ejmech.2016.06.034]

6. Hazlitt RA, Teitz T, Bonga JD, Fang J, Diao S, Iconaru L, Yang L, Goktug AN, Currier DG, Chen T, Rankovic Z, Min J, Zuo J..  (2018)  Development of Second-Generation CDK2 Inhibitors for the Prevention of Cisplatin-Induced Hearing Loss.,  61  (17): [PMID:30091915] [10.1021/acs.jmedchem.8b00669]

7. Jorda R, Hendrychová D, Voller J, Řezníčková E, Gucký T, Kryštof V..  (2018)  How Selective Are Pharmacological Inhibitors of Cell-Cycle-Regulating Cyclin-Dependent Kinases?,  61  (20): [PMID:30234987] [10.1021/acs.jmedchem.8b00049]

8. Abo-Ashour MF, Eldehna WM, Nocentini A, Bonardi A, Bua S, Ibrahim HS, Elaasser MM, Kryštof V, Jorda R, Gratteri P, Abou-Seri SM, Supuran CT..  (2019)  3-Hydrazinoisatin-based benzenesulfonamides as novel carbonic anhydrase inhibitors endowed with anticancer activity: Synthesis, in vitro biological evaluation and in silico insights.,  184  [PMID:31629164] [10.1016/j.ejmech.2019.111768]

9. Tadesse S, Caldon EC, Tilley W, Wang S..  (2019)  Cyclin-Dependent Kinase 2 Inhibitors in Cancer Therapy: An Update.,  62  (9): [PMID:30543440] [10.1021/acs.jmedchem.8b01469]

Source

Source(1):

• Scientific Literature