4-[(3,5-diamino-1H-pyrazol-4-yl)diazenyl]phenol

ID: ALA215205

Chembl Id: CHEMBL215205

Max Phase: Preclinical

Molecular Formula: C9H10N6O

Molecular Weight: 218.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1n[nH]c(N)c1/N=N/c1ccc(O)cc1

Standard InChI:  InChI=1S/C9H10N6O/c10-8-7(9(11)15-14-8)13-12-5-1-3-6(16)4-2-5/h1-4,16H,(H5,10,11,14,15)/b13-12+

Standard InChI Key:  AYZRKFOEZQBUEA-OUKQBFOZSA-N

Alternative Forms

1. Parent:

   

   ALA215205

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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: 218.22

Molecular Weight (Monoisotopic): 218.0916

AlogP: 1.70

#Rotatable Bonds: 2

Polar Surface Area: 125.67

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.90

CX Basic pKa: 4.59

CX LogP: 1.41

CX LogD: 1.29

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.57

Np Likeness Score: -0.35

References

1. Krystof V, Cankar P, Frysová I, Slouka J, Kontopidis G, Dzubák P, Hajdúch M, Srovnal J, de Azevedo WF, Orság M, Paprskárová M, Rolcík J, Látr A, Fischer PM, Strnad M..  (2006)  4-arylazo-3,5-diamino-1H-pyrazole CDK inhibitors: SAR study, crystal structure in complex with CDK2, selectivity, and cellular effects.,  49  (22): [PMID:17064068] [10.1021/jm0605740]

2. Kryštof V, Rárová L, Liebl J, Zahler S, Jorda R, Voller J, Cankař P..  (2011)  The selective P-TEFb inhibitor CAN508 targets angiogenesis.,  46  (9): [PMID:21777997] [10.1016/j.ejmech.2011.06.035]

3. Hole AJ, Baumli S, Shao H, Shi S, Huang S, Pepper C, Fischer PM, Wang S, Endicott JA, Noble ME..  (2013)  Comparative structural and functional studies of 4-(thiazol-5-yl)-2-(phenylamino)pyrimidine-5-carbonitrile CDK9 inhibitors suggest the basis for isotype selectivity.,  56  (3): [PMID:23252711] [10.1021/jm301495v]

4. Jorda R, Schütznerová E, Cankař P, Brychtová V, Navrátilová J, Kryštof V..  (2015)  Novel arylazopyrazole inhibitors of cyclin-dependent kinases.,  23  (9): [PMID:25835357] [10.1016/j.bmc.2015.03.025]

5. Jing L, Tang Y, Xiao Z..  (2018)  Discovery of novel CDK inhibitors via scaffold hopping from CAN508.,  28  (8): [PMID:29550093] [10.1016/j.bmcl.2018.02.054]

6. Said MA,Eldehna WM,Nocentini A,Fahim SH,Bonardi A,Elgazar AA,Kryštof V,Soliman DH,Abdel-Aziz HA,Gratteri P,Abou-Seri SM,Supuran CT.  (2020)  Sulfonamide-based ring-fused analogues for CAN508 as novel carbonic anhydrase inhibitors endowed with antitumor activity: Design, synthesis, and in vitro biological evaluation.,  189  [PMID:31972394] [10.1016/j.ejmech.2019.112019]

7. Huang Z, Wang T, Wang C, Fan Y..  (2022)  CDK9 inhibitors in cancer research.,  13  (6.0): [PMID:35814933] [10.1039/d2md00040g]

Source

Source(1):

• Scientific Literature