Ethyl 9-(4-Methoxybenzyl)-4,5,6,9-tetrahydropyrrolo[2',3':3,4]-cyclohepta[1,2-d][1,2]oxazole-8-carboxylate

ID: ALA4788281

PubChem CID: 155811362

Max Phase: Preclinical

Molecular Formula: C21H22N2O4

Molecular Weight: 366.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc2c(n1Cc1ccc(OC)cc1)-c1oncc1CCC2

Standard InChI:  InChI=1S/C21H22N2O4/c1-3-26-21(24)18-11-15-5-4-6-16-12-22-27-20(16)19(15)23(18)13-14-7-9-17(25-2)10-8-14/h7-12H,3-6,13H2,1-2H3

Standard InChI Key:  FPUBMLGVFKUDFD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    5.8068   -9.2152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9930   -9.1249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6570   -9.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1413  -11.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7374  -11.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5374  -11.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2576  -10.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9714  -10.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7689  -10.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9952  -11.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7887  -11.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0528  -10.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4226   -9.8777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4432   -9.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8436  -10.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0352   -9.3224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4427  -10.6920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8260   -9.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0177   -8.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1678   -8.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8717   -9.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5963   -8.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6170   -7.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9130   -7.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1885   -7.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3415   -7.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3622   -6.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  7  3  1  0
  8  1  1  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  8  9  1  0
 10  6  1  0
  7  8  2  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  9  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 18 19  1  0
 14 20  1  0
 20 21  1  0
 20 25  2  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4788281

   ---

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: 366.42

Molecular Weight (Monoisotopic): 366.1580

AlogP: 3.87

#Rotatable Bonds: 5

Polar Surface Area: 66.49

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.10

CX LogP: 3.98

CX LogD: 3.98

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: -0.91

References

1. Spanò V,Rocca R,Barreca M,Giallombardo D,Montalbano A,Carbone A,Raimondi MV,Gaudio E,Bortolozzi R,Bai R,Tassone P,Alcaro S,Hamel E,Viola G,Bertoni F,Barraja P.  (2020)  Pyrrolo[2',3':3,4]cyclohepta[1,2-d][1,2]oxazoles, a New Class of Antimitotic Agents Active against Multiple Malignant Cell Types.,  63  (20.0): [PMID:32986419] [10.1021/acs.jmedchem.0c01315]

Source

Source(1):

• Scientific Literature