ID: ALA343131

Max Phase: Preclinical

Molecular Formula: C13H6Cl2N2O3

Molecular Weight: 309.11

Molecule Type: Small molecule

Representations

Synonyms (1): MDL-860
Synonyms from Alternative Forms(1):

Canonical SMILES:  N#Cc1cc([N+](=O)[O-])ccc1Oc1ccc(Cl)c(Cl)c1

Standard InChI:  InChI=1S/C13H6Cl2N2O3/c14-11-3-2-10(6-12(11)15)20-13-4-1-9(17(18)19)5-8(13)7-16/h1-6H

Standard InChI Key:  QAYKDRUKUZJJSO-UHFFFAOYSA-N

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

Properties

Molecular Weight: 309.11

Molecular Weight (Monoisotopic): 307.9755

AlogP: 4.57

#Rotatable Bonds: 3

Polar Surface Area: 76.16

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 4.48

CX LogD: 4.48

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.61

Np Likeness Score: -1.79

References

1. Markley LD, Tong YC, Dulworth JK, Steward DL, Goralski CT, Johnston H, Wood SG, Vinogradoff AP, Bargar TM..  (1986)  Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.,  29  (3): [PMID:3005578] [10.1021/jm00153a020]

2. Barral K, Courcambeck J, Pèpe G, Balzarini J, Neyts J, De Clercq E, Camplo M..  (2005)  Synthesis and antiviral evaluation of cis-substituted cyclohexenyl and cyclohexanyl nucleosides.,  48  (2): [PMID:15658858] [10.1021/jm0493966]

3. Pürstinger G, De Palma AM, Zimmerhofer G, Huber S, Ladurner S, Neyts J..  (2008)  Synthesis and anti-CVB 3 evaluation of substituted 5-nitro-2-phenoxybenzonitriles.,  18  (18): [PMID:18710805] [10.1016/j.bmcl.2008.07.099]

4. Dobrikov GM, Slavchev I, Nikolova I, Stoyanova A, Nikolova N, Mukova L, Nikolova R, Shivachev B, Galabov AS..  (2017)  Synthesis and anti-enterovirus activity of new analogues of MDL-860.,  27  (19): [PMID:28870395] [10.1016/j.bmcl.2017.08.056]

5. Liu, Rui, Markley, Lowell, Miller, Patricia A., Franzblau, Scott, Shetye, Gauri, Ma, Rui, Savkova, Karin, Mikusova, Katarina, Lee, Bei Shi, Pethe, Kevin, Moraski, Garrett C., Miller, Marvin J..  (2021)  Hydride-induced Meisenheimer complex formation reflects activity of nitro aromatic anti-tuberculosis compounds,  12  (1): [PMID:34046598] [10.1039/d0md00390e]

Source

Source(1):

• Scientific Literature