Ethyl 3-[(2E)-3-(10-methyl-10H-phenothiazin-3-yl)prop-2-enoyl]indolizine-1-carboxylate

ID: ALA3828157

PubChem CID: 127043149

Max Phase: Preclinical

Molecular Formula: C27H22N2O3S

Molecular Weight: 454.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc(C(=O)/C=C/c2ccc3c(c2)Sc2ccccc2N3C)n2ccccc12

Standard InChI:  InChI=1S/C27H22N2O3S/c1-3-32-27(31)19-17-23(29-15-7-6-8-20(19)29)24(30)14-12-18-11-13-22-26(16-18)33-25-10-5-4-9-21(25)28(22)2/h4-17H,3H2,1-2H3/b14-12+

Standard InChI Key:  DEBGEDXBSMFDAS-WYMLVPIESA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   -5.1981    1.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8968    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5978    1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5978   -1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8968   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4967    0.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7980    1.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0967    0.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8001    2.6933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2330   -0.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6740   -1.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2683   -2.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3734   -3.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4603   -2.5629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9686   -5.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2531   -5.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4447    1.3544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4361    0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9128    0.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3875    1.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3961    3.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9058    2.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5002    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978    1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8968    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8968   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978   -1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0037   -2.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3 24  1  0
 23  4  1  0
  4  5  2  0
  5  2  1  0
  1  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  2  0
 10 11  1  0
 11 18  2  0
 17  8  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 23 24  2  0
 23 26  1  0
 24 25  1  0
 25 28  1  0
 27 26  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 26 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3828157

   ---

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: 454.55

Molecular Weight (Monoisotopic): 454.1351

AlogP: 6.24

#Rotatable Bonds: 5

Polar Surface Area: 51.02

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.69

CX LogD: 5.69

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.20

Np Likeness Score: -0.83

References

1. Moise IM, Ghinet A, Belei D, Dubois J, Farce A, Bîcu E..  (2016)  New indolizine-chalcones as potent inhibitors of human farnesyltransferase: Design, synthesis and biological evaluation.,  26  (15): [PMID:27282741] [10.1016/j.bmcl.2016.05.074]

2. Homerin G, Nica AS, Farce A, Dubois J, Ghinet A..  (2020)  Ultrasounds-mediated 10-seconds synthesis of chalcones as potential farnesyltransferase inhibitors.,  30  (11): [PMID:32247731] [10.1016/j.bmcl.2020.127149]

Source

Source(1):

• Scientific Literature