6-Fluoro-3-((E)-2-pyridin-3-yl-vinyl)-1H-indole

ID: ALA355606

Cas Number: 163239-22-3

PubChem CID: 10014426

Product Number: C274720, Order Now?

Max Phase: Preclinical

Molecular Formula: C15H11FN2

Molecular Weight: 238.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Fc1ccc2c(/C=C/c3cccnc3)c[nH]c2c1

Standard InChI:  InChI=1S/C15H11FN2/c16-13-5-6-14-12(10-18-15(14)8-13)4-3-11-2-1-7-17-9-11/h1-10,18H/b4-3+

Standard InChI Key:  YBSDQTBCNYWBMX-ONEGZZNKSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
    6.0667   -5.4667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -4.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5542   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167   -3.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5625   -5.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5625   -3.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4500   -1.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500   -5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3792   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -5.6167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.1917   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8917   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0875   -0.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  5  2  0
  4  2  1  0
  5  1  1  0
  6  3  1  0
  7  2  2  0
  8  4  2  0
  9  6  2  0
 10 15  1  0
 11  7  1  0
 12 11  2  0
 13  9  1  0
 14 11  1  0
 15 13  2  0
 16 18  1  0
 17 13  1  0
 18 17  2  0
  3  4  1  0
  8 12  1  0
 10 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA355606

   680C91

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: 238.26

Molecular Weight (Monoisotopic): 238.0906

AlogP: 3.87

#Rotatable Bonds: 2

Polar Surface Area: 28.68

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.88

CX LogP: 3.34

CX LogD: 3.34

Aromatic Rings: 3

Heavy Atoms: 18

QED Weighted: 0.72

Np Likeness Score: -0.81

References

1. Madge D, Hazelwood R, Iyer R, Jones H, Salter M.  (1996)  Novel tryptophan dioxygenase inhibitors and combined tryptophan dioxygenase/5-HT reuptake inhibitors,  6  (7): [10.1016/0960-894X(96)00124-2]

2. Dolusić E, Larrieu P, Moineaux L, Stroobant V, Pilotte L, Colau D, Pochet L, Van den Eynde B, Masereel B, Wouters J, Frédérick R..  (2011)  Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators.,  54  (15): [PMID:21726069] [10.1021/jm2006782]

3. Moineaux L, Laurent S, Reniers J, Dolušić E, Galleni M, Frère JM, Masereel B, Frédérick R, Wouters J..  (2012)  Synthesis, crystal structures and electronic properties of isomers of chloro-pyridinylvinyl-1H-indoles.,  54  [PMID:22626654] [10.1016/j.ejmech.2012.04.033]

4. Dounay AB, Tuttle JB, Verhoest PR..  (2015)  Challenges and Opportunities in the Discovery of New Therapeutics Targeting the Kynurenine Pathway.,  58  (22): [PMID:26207924] [10.1021/acs.jmedchem.5b00461]

5. Pan L, Zheng Q, Chen Y, Yang R, Yang Y, Li Z, Meng X..  (2018)  Design, synthesis and biological evaluation of novel naphthoquinone derivatives as IDO1 inhibitors.,  157  [PMID:30103191] [10.1016/j.ejmech.2018.08.013]

6. Yang D, Zhang S, Fang X, Guo L, Hu N, Guo Z, Li X, Yang S, He JC, Kuang C, Yang Q..  (2019)  N-Benzyl/Aryl Substituted Tryptanthrin as Dual Inhibitors of Indoleamine 2,3-Dioxygenase and Tryptophan 2,3-Dioxygenase.,  62  (20): [PMID:31580660] [10.1021/acs.jmedchem.9b01079]

7. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of MMV (CH) - Pandemic Response Box,  [10.6019/CHEMBL4513161]

8. Li Y, Zhang S, Wang R, Cui M, Liu W, Yang Q, Kuang C..  (2020)  Synthesis of novel tryptanthrin derivatives as dual inhibitors of indoleamine 2,3-dioxygenase 1 and tryptophan 2,3-dioxygenase.,  30  (11): [PMID:32247733] [10.1016/j.bmcl.2020.127159]

9. Kozlova A, Thabault L, Liberelle M, Klaessens S, Prévost JRC, Mathieu C, Pilotte L, Stroobant V, Van den Eynde B, Frédérick R..  (2021)  Rational Design of Original Fused-Cycle Selective Inhibitors of Tryptophan 2,3-Dioxygenase.,  64  (15.0): [PMID:34338527] [10.1021/acs.jmedchem.1c00323]

10. Capochiani de Iudicibus R, Tomek P, Palmer BD, Tijono SM, Flanagan JU, Ching LM..  (2021)  Parallel discovery of selective and dual inhibitors of tryptophan dioxygenases IDO1 and TDO2 with a newly-modified enzymatic assay.,  39  [PMID:33901770] [10.1016/j.bmc.2021.116160]

11. Zhang Y, Li Y, Chen X, Chen X, Chen C, Wang L, Dong X, Wang G, Gu R, Li F, Han F, Chen D..  (2022)  Discovery of 1-(Hetero)aryl-β-carboline Derivatives as IDO1/TDO Dual Inhibitors with Antidepressant Activity.,  65  (16.0): [PMID:35938398] [10.1021/acs.jmedchem.2c00677]

Source

Source(2):

• Scientific Literature
• CO-ADD antimicrobial screening data