6-chloro-3-(1-(4-chlorobenzyl)-4-phenyl-1H-imidazol-5-yl)-1H-indole-2-carboxylic acid

ID: ALA1233798

Chembl Id: CHEMBL1233798

PubChem CID: 44825260

Max Phase: Preclinical

Molecular Formula: C25H17Cl2N3O2

Molecular Weight: 462.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1[nH]c2cc(Cl)ccc2c1-c1c(-c2ccccc2)ncn1Cc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C25H17Cl2N3O2/c26-17-8-6-15(7-9-17)13-30-14-28-22(16-4-2-1-3-5-16)24(30)21-19-11-10-18(27)12-20(19)29-23(21)25(31)32/h1-12,14,29H,13H2,(H,31,32)

Standard InChI Key:  QZJRNGXHRQJBJH-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1233798

   6-Chloro-3-(1-(4-chlorobenzyl)-4-phenyl-1H-imidazol-5-yl)-1H-indole-2-carboxylic acid

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: 462.34

Molecular Weight (Monoisotopic): 461.0698

AlogP: 6.75

#Rotatable Bonds: 5

Polar Surface Area: 70.91

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.32

CX Basic pKa: 4.96

CX LogP: 5.19

CX LogD: 3.07

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.30

Np Likeness Score: -0.88

References

1. Wang W, Cao H, Wolf S, Camacho-Horvitz MS, Holak TA, Dömling A..  (2013)  Benzimidazole-2-one: a novel anchoring principle for antagonizing p53-Mdm2.,  21  (14): [PMID:22789708] [10.1016/j.bmc.2012.06.020]

2. Slobbe P, Ruijter E, Orru RVA.  (2012)  Recent applications of multicomponent reactions in medicinal chemistry,  3  (10): [10.1039/C2MD20089A]

3. Khoury K, Popowicz GM, Holak TA, Dömling A..  (2011)  The p53-MDM2/MDMX axis - A chemotype perspective.,  2  (4): [PMID:24466404] [10.1039/c0md00248h]

4. Guo W, Wisniewski JA, Ji H..  (2014)  Hot spot-based design of small-molecule inhibitors for protein-protein interactions.,  24  (11): [PMID:24751445] [10.1016/j.bmcl.2014.03.095]

5. Zhao Y, Aguilar A, Bernard D, Wang S..  (2015)  Small-molecule inhibitors of the MDM2-p53 protein-protein interaction (MDM2 Inhibitors) in clinical trials for cancer treatment.,  58  (3): [PMID:25396320] [10.1021/jm501092z]

6. Neochoritis CG, Wang K, Estrada-Ortiz N, Herdtweck E, Kubica K, Twarda A, Zak KM, Holak TA, Dömling A..  (2015)  2,30-Bis(10H-indole) heterocycles: New p53/MDM2/MDMX antagonists.,  25  (24): [PMID:26584879] [10.1016/j.bmcl.2015.11.019]

7. Zhang S, Lou J, Li Y, Zhou F, Yan Z, Lyu X, Zhao Y..  (2021)  Recent Progress and Clinical Development of Inhibitors that Block MDM4/p53 Protein-Protein Interactions.,  64  (15.0): [PMID:34286973] [10.1021/acs.jmedchem.1c00940]

Source

Source(1):

• Scientific Literature