4-(5-bromofuran-2-carbonyl)-5-(4-fluorophenyl)-7-methyl-4,5-dihydro-1H-benzo[e][1,4]diazepin-2(3H)-one

ID: ALA5089738

PubChem CID: 4339968

Max Phase: Preclinical

Molecular Formula: C21H16BrFN2O3

Molecular Weight: 443.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)C(c1ccc(F)cc1)N(C(=O)c1ccc(Br)o1)CC(=O)N2

Standard InChI:  InChI=1S/C21H16BrFN2O3/c1-12-2-7-16-15(10-12)20(13-3-5-14(23)6-4-13)25(11-19(26)24-16)21(27)17-8-9-18(22)28-17/h2-10,20H,11H2,1H3,(H,24,26)

Standard InChI Key:  IPHKQIFYQWJQAB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    5.6231   -8.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6220   -9.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3367   -9.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3350   -7.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9073   -9.4844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0485   -9.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0503   -8.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6985   -7.7233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6976   -9.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5055   -7.9032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5060   -9.3974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8627   -8.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0222  -10.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7229  -10.8098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8375   -9.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4206  -10.4981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1574  -10.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0323   -9.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2180   -9.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5147  -10.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8906  -10.5051    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.7260  -10.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5429  -11.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1485  -11.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9398  -11.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1192  -10.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9667  -12.7999    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.0189   -7.2575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  7  4  2  0
  4  1  1  0
  2  5  1  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  8 10  1  0
  9 11  1  0
 10 12  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 15  2  0
  9 20  1  0
 17 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 20  1  0
 24 27  1  0
 10 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5089738

   4-(5-bromo-2-furoyl)-5-(4-fluorophenyl)-7-methyl-1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 443.27

Molecular Weight (Monoisotopic): 442.0328

AlogP: 4.67

#Rotatable Bonds: 2

Polar Surface Area: 62.55

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.22

CX Basic pKa: ┄

CX LogP: 3.90

CX LogD: 3.90

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: -1.47

References

1. Shen Y, Li F, Szewczyk MM, Halabelian L, Chau I, Eram MS, Dela Seña C, Park KS, Meng F, Chen H, Zeng H, Dong A, Wu H, Trush VV, McLeod D, Zepeda-Velázquez CA, Campbell RM, Mader MM, Watson BM, Schapira M, Arrowsmith CH, Al-Awar R, Barsyte-Lovejoy D, Kaniskan HÜ, Brown PJ, Vedadi M, Jin J..  (2021)  A First-in-Class, Highly Selective and Cell-Active Allosteric Inhibitor of Protein Arginine Methyltransferase 6.,  64  (7.0): [PMID:33591753] [10.1021/acs.jmedchem.0c02160]

2. Xiong B..  (2021)  Allosteric Modulation: Dynamics is Double-"E"dged.,  64  (7.0): [PMID:33761250] [10.1021/acs.jmedchem.1c00473]

Source

Source(1):

• Scientific Literature