(5-Oxo-5,6-dihydro-indolo[1,2-a]quinazolin-7-yl)-acetic acid

ID: ALA92361

Cas Number: 391670-48-7

PubChem CID: 447682

Max Phase: Preclinical

Molecular Formula: C17H12N2O3

Molecular Weight: 292.29

Molecule Type: Small molecule

Names and Identifiers

Synonyms: CGP-029482 | 391670-48-7|(5-OXO-5,6-DIHYDRO-INDOLO[1,2-A]QUINAZOLIN-7-YL)-ACETIC ACID|CGP-029482|CHEMBL92361|2-(5-oxo-6H-indolo[1,2-a]quinazolin-7-yl)acetic acid|IQA|(5-oxo-5,6-dihydroindolo[1,2-a]quinazolin-7-yl)acetic acid|1om1|SCHEMBL263731|BDBM11319|HMS3229D05|HMS3674K13|CGP029482|AKOS005266257|DB01765|HY-117332|CS-0065327|NS00068927|EN300-24706391|Q27092917|Z2216890192|2-{5-oxo-5H,6H-indolo[1,2-a]quinazolin-7-yl}acetic acid|[5-oxo-5,6-dihydroindolo-(1,2-a)quinazolin-7-yl]acetic acid|2-(5-OxShow More⌵

Canonical SMILES:  O=C(O)Cc1c2ccccc2n2c1[nH]c(=O)c1ccccc12

Standard InChI:  InChI=1S/C17H12N2O3/c20-15(21)9-12-10-5-1-3-7-13(10)19-14-8-4-2-6-11(14)17(22)18-16(12)19/h1-8H,9H2,(H,18,22)(H,20,21)

Standard InChI Key:  INSBKYCYLCEBOD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   -2.2977    2.1967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224    1.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3710    0.7696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0985    1.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7232    0.6850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0918    0.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7324    1.0767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5029    0.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1435    1.3017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6328   -0.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033   -0.3277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5333   -1.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8927   -1.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1221   -1.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9922   -0.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2217   -0.2579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130   -0.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969   -0.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8936   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5223   -1.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7257   -1.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  2  0
  4  2  1  0
  4  5  1  0
  5  6  2  0
  5 18  1  0
  6  7  1  0
  6 16  1  0
  8  7  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 10 15  1  0
 12 11  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
 15 16  1  0
 17 16  1  0
 18 17  2  0
 22 17  1  0
 19 18  1  0
 20 19  2  0
 20 21  1  0
 21 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA92361

   (5-Oxo-5,6-dihydro-indolo[1,2-A]quinazolin-7-YL)-acetic 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: 292.29

Molecular Weight (Monoisotopic): 292.0848

AlogP: 2.56

#Rotatable Bonds: 2

Polar Surface Area: 74.57

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.17

CX Basic pKa: ┄

CX LogP: 2.80

CX LogD: -0.25

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.60

Np Likeness Score: -0.40

References

1. Vangrevelinghe E, Zimmermann K, Schoepfer J, Portmann R, Fabbro D, Furet P..  (2003)  Discovery of a potent and selective protein kinase CK2 inhibitor by high-throughput docking.,  46  (13): [PMID:12801229] [10.1021/jm030827e]

2. Sekiguchi Y, Nakaniwa T, Kinoshita T, Nakanishi I, Kitaura K, Hirasawa A, Tsujimoto G, Tada T..  (2009)  Structural insight into human CK2alpha in complex with the potent inhibitor ellagic acid.,  19  (11): [PMID:19414254] [10.1016/j.bmcl.2009.04.076]

3. Sarno S, de Moliner E, Ruzzene M, Pagano MA, Battistutta R, Bain J, Fabbro D, Schoepfer J, Elliott M, Furet P, Meggio F, Zanotti G, Pinna LA..  (2003)  Biochemical and three-dimensional-structural study of the specific inhibition of protein kinase CK2 by [5-oxo-5,6-dihydroindolo-(1,2-a)quinazolin-7-yl]acetic acid (IQA).,  374  (3): [PMID:12816539] [10.1042/bj20030674]

4. Pierre F, Chua PC, O'Brien SE, Siddiqui-Jain A, Bourbon P, Haddach M, Michaux J, Nagasawa J, Schwaebe MK, Stefan E, Vialettes A, Whitten JP, Chen TK, Darjania L, Stansfield R, Anderes K, Bliesath J, Drygin D, Ho C, Omori M, Proffitt C, Streiner N, Trent K, Rice WG, Ryckman DM..  (2011)  Discovery and SAR of 5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-8-carboxylic acid (CX-4945), the first clinical stage inhibitor of protein kinase CK2 for the treatment of cancer.,  54  (2): [PMID:21174434] [10.1021/jm101251q]

5. Fuchi N, Iura Y, Kaneko H, Nitta A, Suyama K, Ueda H, Yamaguchi S, Nishimura K, Fujii S, Sekiya Y, Yamada M, Takahashi T..  (2012)  Discovery and structure-activity relationship of 2,6-disubstituted pyrazines, potent and selective inhibitors of protein kinase CK2.,  22  (13): [PMID:22633690] [10.1016/j.bmcl.2012.05.006]

6. Nakanishi I, Murata K, Nagata N, Kurono M, Kinoshita T, Yasue M, Miyazaki T, Takei Y, Nakamura S, Sakurai A, Iwamoto N, Nishiwaki K, Nakaniwa T, Sekiguchi Y, Hirasawa A, Tsujimoto G, Kitaura K..  (2015)  Identification of protein kinase CK2 inhibitors using solvent dipole ordering virtual screening.,  96  [PMID:25912672] [10.1016/j.ejmech.2015.04.032]

7. Ostrynska OV, Balanda AO, Bdzhola VG, Golub AG, Kotey IM, Kukharenko OP, Gryshchenko AA, Briukhovetska NV, Yarmoluk SM..  (2016)  Design and synthesis of novel protein kinase CK2 inhibitors on the base of 4-aminothieno[2,3-d]pyrimidines.,  115  [PMID:27017545] [10.1016/j.ejmech.2016.03.004]

8.  (2013)  Use of dibenzofuranone derivatives to inhibit kinases, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data