3-(indole-3-yl)-4-(3,4,5-trimethoxyphenyl)-1H-pyrrole-2,5-dione

ID: ALA201511

Chembl Id: CHEMBL201511

Cas Number: 863223-52-3

PubChem CID: 11530963

Max Phase: Preclinical

Molecular Formula: C21H18N2O5

Molecular Weight: 378.38

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Maleimide | CHEMBL201511|863223-52-3|3-(1H-indol-3-yl)-4-(3,4,5-trimethoxyphenyl)pyrrole-2,5-dione|SCHEMBL1155440|BDBM47167|DTXSID40468140|US8957103, Z1|3-(1H-Indol-3-yl)-4-(3,4,5-trimethoxyphenyl)-2,5-dihydro-1H-pyrrole-2,5-dione

Canonical SMILES:  COc1cc(C2=C(c3c[nH]c4ccccc34)C(=O)NC2=O)cc(OC)c1OC

Standard InChI:  InChI=1S/C21H18N2O5/c1-26-15-8-11(9-16(27-2)19(15)28-3)17-18(21(25)23-20(17)24)13-10-22-14-7-5-4-6-12(13)14/h4-10,22H,1-3H3,(H,23,24,25)

Standard InChI Key:  CZGMEOAMQWAJOY-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA201511

   MALEIMIDE

2. Alternative Forms:

   

   ALA201511

   3-(3,5-dimethoxy-4-(111C)methoxyphenyl)-4-(1H-indol-3-yl)pyrrole-2,5-dione

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: 378.38

Molecular Weight (Monoisotopic): 378.1216

AlogP: 2.76

#Rotatable Bonds: 5

Polar Surface Area: 89.65

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.72

CX Basic pKa: ┄

CX LogP: 2.33

CX LogD: 2.32

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.67

Np Likeness Score: 0.28

References

1. Peifer C, Stoiber T, Unger E, Totzke F, Schächtele C, Marmé D, Brenk R, Klebe G, Schollmeyer D, Dannhardt G..  (2006)  Design, synthesis, and biological evaluation of 3,4-diarylmaleimides as angiogenesis inhibitors.,  49  (4): [PMID:16480264] [10.1021/jm0580297]

2. Peifer C, Krasowski A, Hämmerle N, Kohlbacher O, Dannhardt G, Totzke F, Schächtele C, Laufer S..  (2006)  Profile and molecular modeling of 3-(indole-3-yl)-4-(3,4,5-trimethoxyphenyl)-1 H-pyrrole-2,5-dione (1) as a highly selective VEGF-R2/3 inhibitor.,  49  (25): [PMID:17149885] [10.1021/jm0609871]

3. Fedorov O, Marsden B, Pogacic V, Rellos P, Müller S, Bullock AN, Schwaller J, Sundström M, Knapp S..  (2007)  A systematic interaction map of validated kinase inhibitors with Ser/Thr kinases.,  104  (51): [PMID:18077363] [10.1073/pnas.0708800104]

4. Peifer C, Selig R, Kinkel K, Ott D, Totzke F, Schächtele C, Heidenreich R, Röcken M, Schollmeyer D, Laufer S..  (2008)  Design, synthesis, and biological evaluation of novel 3-aryl-4-(1H-indole-3yl)-1,5-dihydro-2H-pyrrole-2-ones as vascular endothelial growth factor receptor (VEGF-R) inhibitors.,  51  (13): [PMID:18529047] [10.1021/jm8001185]

5. Ilovich O, Billauer H, Dotan S, Mishani E..  (2010)  Labeled 3-aryl-4-indolylmaleimide derivatives and their potential as angiogenic PET biomarkers.,  18  (2): [PMID:20031417] [10.1016/j.bmc.2009.12.004]

6. Ganser C, Lauermann E, Maderer A, Stauder T, Kramb JP, Plutizki S, Kindler T, Moehler M, Dannhardt G..  (2012)  Novel 3-Azaindolyl-4-arylmaleimides exhibiting potent antiangiogenic efficacy, protein kinase inhibition, and antiproliferative activity.,  55  (22): [PMID:23088521] [10.1021/jm301217c]

7.  (2015)  Conjugated 3-(indolyl)- and 3-(azaindolyl)-4-arylmaleimide compounds and their use in tumor treatment, 

8.  (2016)  3-(indolyl)- or 3-(azaindolyl)- 4-arylmaleimide derivatives for use in the treatment of colon and gastric adenocarcinoma, 

Source

Source(2):

• Scientific Literature
• BindingDB Database