1-{3-[(4-Methyl-1-piperazinyl)carbonyl]benzyl}-1H-naphtho-[2,3-d][1,2,3]triazole-4,9-dione

ID: ALA3628599

Chembl Id: CHEMBL3628599

PubChem CID: 122193596

Max Phase: Preclinical

Molecular Formula: C23H21N5O3

Molecular Weight: 415.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(C(=O)c2cccc(Cn3nnc4c3C(=O)c3ccccc3C4=O)c2)CC1

Standard InChI:  InChI=1S/C23H21N5O3/c1-26-9-11-27(12-10-26)23(31)16-6-4-5-15(13-16)14-28-20-19(24-25-28)21(29)17-7-2-3-8-18(17)22(20)30/h2-8,13H,9-12,14H2,1H3

Standard InChI Key:  XHMWOYOVGULXFN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3628599

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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: 415.45

Molecular Weight (Monoisotopic): 415.1644

AlogP: 1.49

#Rotatable Bonds: 3

Polar Surface Area: 88.40

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.86

CX LogP: 2.14

CX LogD: 2.03

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.50

Np Likeness Score: -1.25

References

1. Wu JS, Lin SY, Liao FY, Hsiao WC, Lee LC, Peng YH, Hsieh CL, Wu MH, Song JS, Yueh A, Chen CH, Yeh SH, Liu CY, Lin SY, Yeh TK, Hsu JT, Shih C, Ueng SH, Hung MS, Wu SY..  (2015)  Identification of Substituted Naphthotriazolediones as Novel Tryptophan 2,3-Dioxygenase (TDO) Inhibitors through Structure-Based Virtual Screening.,  58  (19): [PMID:26348881] [10.1021/acs.jmedchem.5b00921]

2. Huang R, Jing X, Huang X, Pan Y, Fang Y, Liang G, Liao Z, Wang H, Chen Z, Zhang Y..  (2020)  Bifunctional Naphthoquinone Aromatic Amide-Oxime Derivatives Exert Combined Immunotherapeutic and Antitumor Effects through Simultaneous Targeting of Indoleamine-2,3-dioxygenase and Signal Transducer and Activator of Transcription 3.,  63  (4): [PMID:31999451] [10.1021/acs.jmedchem.9b01386]

3. Pan S,Zhou Y,Wang Q,Wang Y,Tian C,Wang T,Huang L,Nan J,Li L,Yang S.  (2020)  Discovery and structure-activity relationship studies of 1-aryl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as potent dual inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1) and trytophan 2,3-dioxygenase (TDO).,  207  [PMID:32871341] [10.1016/j.ejmech.2020.112703]

Source

Source(1):

• Scientific Literature