(Z)-4-(8-bromo-(E)-2-styrylbenzo[b]furo[3,2-d][1,3]oxazin-4-ylideno)but-(E)-2-enoic acid ethyl este

ID: ALA375808

PubChem CID: 11858405

Max Phase: Preclinical

Molecular Formula: C24H18BrNO4

Molecular Weight: 464.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)/C=C/C=C1\OC(/C=C/c2ccccc2)=Nc2c1oc1ccc(Br)cc21

Standard InChI:  InChI=1S/C24H18BrNO4/c1-2-28-22(27)10-6-9-20-24-23(18-15-17(25)12-13-19(18)30-24)26-21(29-20)14-11-16-7-4-3-5-8-16/h3-15H,2H2,1H3/b10-6+,14-11+,20-9-

Standard InChI Key:  XCVMDZSUEMPSHQ-YGLVHGNISA-N

Molfile:  

     RDKit          2D

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    7.1548   -3.1754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4940   -3.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3153   -4.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6340   -2.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4542   -2.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7962   -3.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6222   -3.2514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0689   -2.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7921   -2.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5119   -2.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5099   -1.1900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7820   -0.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0651   -1.1962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2274   -2.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9408   -2.0205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7766    0.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4883    0.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4829    1.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2010    1.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1960    2.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4783    2.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7643    2.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7728    1.6943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3340   -3.0934    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.6563   -2.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3696   -2.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0851   -2.4275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3675   -1.1919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7984   -2.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5140   -2.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 14  2  0
  6  7  1  0
 14 15  1  0
  7  9  1  0
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  8  5  1  0
 16 17  2  0
  1  2  2  0
 17 18  1  0
  5  4  2  0
 18 19  2  0
  8  9  2  0
 19 20  1  0
  4  1  1  0
 20 21  2  0
  9 10  1  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
 23 18  1  0
 10 11  1  0
  1 24  1  0
 15 25  2  0
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 25 26  1  0
  2  3  1  0
 26 27  1  0
 12 13  2  0
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 13  8  1  0
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  3  6  2  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA375808

   ethyl (E,4Z)-4-[8-bromo-2-[(E)-2-phenylethenyl]-[1]benzofuro[3,2-d][1,3]oxazin-4-ylidene]but-2-enoate

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: 464.32

Molecular Weight (Monoisotopic): 463.0419

AlogP: 6.43

#Rotatable Bonds: 5

Polar Surface Area: 61.03

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.17

CX LogP: 6.15

CX LogD: 6.15

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.32

Np Likeness Score: 0.02

References

1. Ando Y, Ando K, Yamaguchi M, Kunitomo J, Koida M, Fukuyama R, Nakamuta H, Yamashita M, Ohta S, Ohishi Y..  (2006)  A novel oxazine ring closure reaction affording (Z)-((E)-2-styrylbenzo[b]furo[3,2-d][1,3]oxazin-4-ylideno)acetaldehydes and their anti-osteoclastic bone resorption activity.,  16  (22): [PMID:16945531] [10.1016/j.bmcl.2006.08.064]

2. Tabuchi Y, Ando Y, Kanemura H, Kawasaki I, Ohishi T, Koida M, Fukuyama R, Nakamuta H, Ohta S, Nishide K, Ohishi Y..  (2009)  Preparation of novel (Z)-4-ylidenebenzo[b]furo[3,2-d][1,3]oxazines and their biological activity.,  17  (11): [PMID:19406645] [10.1016/j.bmc.2009.04.017]

Source

Source(1):

• Scientific Literature