3-{4-Methyl-2-[2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-1H-pyrrol-3-yl}-propionic acid

ID: ALA89363

Chembl Id: CHEMBL89363

Cas Number: 215543-92-3

PubChem CID: 5289418

Product Number: S133274

Max Phase: Preclinical

Molecular Formula: C17H16N2O3

Molecular Weight: 296.33

Molecule Type: Small molecule

Names and Identifiers

Synonyms: SU-5402 | 215543-92-3|su5402|SU-5402|SU 5402|3-[(3-(2-CARBOXYETHYL)-4-METHYLPYRROL-2-YL)METHYLENE]-2-INDOLINONE|3-[4-methyl-2-[(Z)-(2-oxo-1H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl]propanoic acid|2-[(1,2-Dihydro-2-oxo-3H-indol-3-ylidene)methyl]-4-methyl-1H-pyrrole-3-propanoic acid|3-[3-(2-Carboxyethyl)-4-methylpyrrol-2-methylidenyl]-2-indolinone|(Z)-3-(4-methyl-2-((2-oxoindolin-3-ylidene)methyl)-1H-pyrrol-3-yl)propanoic acid|CHEMBL89363|SU 5402 (GMP)|3-{[3-(2-carboxyethyl)-4-methylpyrrol-2-yl]metShow More⌵

Canonical SMILES:  Cc1c[nH]c(/C=C2\C(=O)Nc3ccccc32)c1CCC(=O)O

Standard InChI:  InChI=1S/C17H16N2O3/c1-10-9-18-15(11(10)6-7-16(20)21)8-13-12-4-2-3-5-14(12)19-17(13)22/h2-5,8-9,18H,6-7H2,1H3,(H,19,22)(H,20,21)/b13-8-

Standard InChI Key:  JNDVEAXZWJIOKB-JYRVWZFOSA-N

Alternative Forms

1. Parent:

   

   ALA89363

   3-[(3-(2-Carboxyethyl)-4-methylpyrrol-2-YL)methylene]-2-indolinone

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: 296.33

Molecular Weight (Monoisotopic): 296.1161

AlogP: 2.83

#Rotatable Bonds: 4

Polar Surface Area: 82.19

Molecular Species: ACID

HBA: 2

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.15

CX Basic pKa: ┄

CX LogP: 2.86

CX LogD: -0.21

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.76

Np Likeness Score: 0.04

References

1. Sun L, Tran N, Tang F, App H, Hirth P, McMahon G, Tang C..  (1998)  Synthesis and biological evaluations of 3-substituted indolin-2-ones: a novel class of tyrosine kinase inhibitors that exhibit selectivity toward particular receptor tyrosine kinases.,  41  (14): [PMID:9651163] [10.1021/jm980123i]

2. Sun L, Tran N, Liang C, Hubbard S, Tang F, Lipson K, Schreck R, Zhou Y, McMahon G, Tang C..  (2000)  Identification of substituted 3-[(4,5,6, 7-tetrahydro-1H-indol-2-yl)methylene]-1,3-dihydroindol-2-ones as growth factor receptor inhibitors for VEGF-R2 (Flk-1/KDR), FGF-R1, and PDGF-Rbeta tyrosine kinases.,  43  (14): [PMID:10893303] [10.1021/jm9906116]

3. Thompson AM, Connolly CJ, Hamby JM, Boushelle S, Hartl BG, Amar AM, Kraker AJ, Driscoll DL, Steinkampf RW, Patmore SJ, Vincent PW, Roberts BJ, Elliott WL, Klohs W, Leopold WR, Showalter HD, Denny WA..  (2000)  3-(3,5-Dimethoxyphenyl)-1,6-naphthyridine-2,7-diamines and related 2-urea derivatives are potent and selective inhibitors of the FGF receptor-1 tyrosine kinase.,  43  (22): [PMID:11063616] [10.1021/jm000161d]

4. Sun L, Tran N, Liang C, Tang F, Rice A, Schreck R, Waltz K, Shawver LK, McMahon G, Tang C..  (1999)  Design, synthesis, and evaluations of substituted 3-[(3- or 4-carboxyethylpyrrol-2-yl)methylidenyl]indolin-2-ones as inhibitors of VEGF, FGF, and PDGF receptor tyrosine kinases.,  42  (25): [PMID:10602697] [10.1021/jm9904295]

5. Yu H, Wang Z, Zhang L, Zhang J, Huang Q..  (2007)  Pharmacophore modeling and in silico screening for new KDR kinase inhibitors.,  17  (8): [PMID:17306530] [10.1016/j.bmcl.2007.01.089]

6. Mohammadi M, McMahon G, Sun L, Tang C, Hirth P, Yeh BK, Hubbard SR, Schlessinger J..  (1997)  Structures of the tyrosine kinase domain of fibroblast growth factor receptor in complex with inhibitors.,  276  (5314): [PMID:9139660] [10.1126/science.276.5314.955]

7. Virsodia V, Manvar A, Upadhyay K, Loriya R, Karia D, Jaggi M, Singh A, Mukherjee R, Shaikh MS, Coutinho EC, Shah A..  (2009)  Synthesis of 1-(2,6-dichlorophenyl)-3-methylene-1,3-dihydro-indol-2-one derivatives and in vitro anticancer evaluation against SW620 colon cancer cell line.,  44  (3): [PMID:18316139] [10.1016/j.ejmech.2008.01.012]

8. Luesch H, Chanda SK, Raya RM, DeJesus PD, Orth AP, Walker JR, Izpisúa Belmonte JC, Schultz PG..  (2006)  A functional genomics approach to the mode of action of apratoxin A.,  2  (3): [PMID:16474387] [10.1038/nchembio769]

9. Chen Z, Wang X, Zhu W, Cao X, Tong L, Li H, Xie H, Xu Y, Tan S, Kuang D, Ding J, Qian X..  (2011)  Acenaphtho[1,2-b]pyrrole-based selective fibroblast growth factor receptors 1 (FGFR1) inhibitors: design, synthesis, and biological activity.,  54  (11): [PMID:21517068] [10.1021/jm200258t]

10. Wang J, Wang X, Chen Y, Chen S, Chen G, Tong L, Meng L, Xie Y, Ding J, Yang C..  (2012)  Discovery and bioactivity of 4-(2-arylpyrido[3',2':3,4]pyrrolo[1,2-f][1,2,4]triazin-4-yl) morpholine derivatives as novel PI3K inhibitors.,  22  (1): [PMID:22130133] [10.1016/j.bmcl.2011.11.003]

11. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

12. Cheng W, Wang M, Tian X, Zhang X..  (2017)  An overview of the binding models of FGFR tyrosine kinases in complex with small molecule inhibitors.,  126  [PMID:27914362] [10.1016/j.ejmech.2016.11.052]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data