(E)-6-Fluoro-3-[2-(1H-tetrazol-5-yl)vinyl]-1H-indole

ID: ALA1812545

PubChem CID: 135743630

Product Number: L611561, Order Now?

Max Phase: Preclinical

Molecular Formula: C11H8FN5

Molecular Weight: 229.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Fc1ccc2c(/C=C/c3nnn[nH]3)c[nH]c2c1

Standard InChI:  InChI=1S/C11H8FN5/c12-8-2-3-9-7(6-13-10(9)5-8)1-4-11-14-16-17-15-11/h1-6,13H,(H,14,15,16,17)/b4-1+

Standard InChI Key:  JDBSZVDIUIRSDG-DAFODLJHSA-N

Molfile:  

     RDKit          2D

 17 19  0  0  0  0  0  0  0  0999 V2000
   -3.9681  -26.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9693  -26.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2544  -27.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2562  -25.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5409  -26.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5406  -26.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7501  -27.1340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2618  -26.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7506  -25.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4959  -25.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6890  -24.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4343  -24.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3521  -23.7909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3518  -22.9659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4329  -22.7112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9177  -23.3788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6841  -27.2893    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  4  1  1  0
  9 10  1  0
  5  6  1  0
 10 11  2  0
 11 12  1  0
 15 16  1  0
  2  3  1  0
 13 14  1  0
  3  6  2  0
  1  2  2  0
  5  4  2  0
 12 13  1  0
 14 15  2  0
 16 12  2  0
  6  7  1  0
  2 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1812545

   LM10

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: 229.22

Molecular Weight (Monoisotopic): 229.0764

AlogP: 1.99

#Rotatable Bonds: 2

Polar Surface Area: 70.25

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.41

CX Basic pKa: ┄

CX LogP: 2.04

CX LogD: 0.44

Aromatic Rings: 3

Heavy Atoms: 17

QED Weighted: 0.71

Np Likeness Score: -1.31

References

1. 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]

2. Röhrig UF, Majjigapu SR, Grosdidier A, Bron S, Stroobant V, Pilotte L, Colau D, Vogel P, Van den Eynde BJ, Zoete V, Michielin O..  (2012)  Rational design of 4-aryl-1,2,3-triazoles for indoleamine 2,3-dioxygenase 1 inhibition.,  55  (11): [PMID:22616902] [10.1021/jm300260v]

3. 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]

4. 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]

5. Yang L, Chen Y, He J, Njoya EM, Chen J, Liu S, Xie C, Huang W, Wang F, Wang Z, Li Y, Qian S..  (2019)  4,6-Substituted-1H-Indazoles as potent IDO1/TDO dual inhibitors.,  27  (6): [PMID:30773421] [10.1016/j.bmc.2019.02.014]

6. Zhang S, Qi F, Fang X, Yang D, Hu H, Huang Q, Kuang C, Yang Q..  (2018)  Tryptophan 2,3-dioxygenase inhibitory activities of tryptanthrin derivatives.,  160  [PMID:30321802] [10.1016/j.ejmech.2018.10.017]

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. Huo C, Luo Z, Ning X, Kang X, Yan Q, Guo Y, Li G, Wang Z, Li Y, Qian S..  (2022)  4,6-Disubstituted-1H-Indazole-4-Amine derivatives with immune-chemotherapy effect and in vivo antitumor activity.,  241  [PMID:35952399] [10.1016/j.ejmech.2022.114625]

Source

Source(2):

• Scientific Literature
• CO-ADD antimicrobial screening data