ID: ALA2088014

Max Phase: Preclinical

Molecular Formula: C14H9ClF3NO2

Molecular Weight: 315.68

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(Nc1ccc(C(F)(F)F)cc1)c1cc(Cl)ccc1O

Standard InChI:  InChI=1S/C14H9ClF3NO2/c15-9-3-6-12(20)11(7-9)13(21)19-10-4-1-8(2-5-10)14(16,17)18/h1-7,20H,(H,19,21)

Standard InChI Key:  QCRAHGZZLAXPCG-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: 315.68

Molecular Weight (Monoisotopic): 315.0274

AlogP: 4.32

#Rotatable Bonds: 2

Polar Surface Area: 49.33

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.39

CX Basic pKa:

CX LogP: 4.24

CX LogD: 3.94

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.87

Np Likeness Score: -1.53

References

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7. Mook RA, Wang J, Ren XR, Chen M, Spasojevic I, Barak LS, Lyerly HK, Chen W..  (2015)  Structure-activity studies of Wnt/β-catenin inhibition in the Niclosamide chemotype: Identification of derivatives with improved drug exposure.,  23  (17): [PMID:26272032] [10.1016/j.bmc.2015.07.001]

8. Baranyai Z, Krátký M, Vinšová J, Szabó N, Senoner Z, Horváti K, Stolaříková J, Dávid S, Bősze S..  (2015)  Combating highly resistant emerging pathogen Mycobacterium abscessus and Mycobacterium tuberculosis with novel salicylanilide esters and carbamates.,  101  [PMID:26210507] [10.1016/j.ejmech.2015.07.001]

9. Paraskevopoulos G, Monteiro S, Vosátka R, Krátký M, Navrátilová L, Trejtnar F, Stolaříková J, Vinšová J..  (2017)  Novel salicylanilides from 4,5-dihalogenated salicylic acids: Synthesis, antimicrobial activity and cytotoxicity.,  25  (4): [PMID:28126437] [10.1016/j.bmc.2017.01.016]

10. Pospisilova S, Michnova H, Kauerova T, Pauk K, Kollar P, Vinsova J, Imramovsky A, Cizek A, Jampilek J..  (2018)  In vitro activity of salicylamide derivatives against vancomycin-resistant enterococci.,  28  (12): [PMID:29773506] [10.1016/j.bmcl.2018.05.011]

11. Chae HD, Cox N, Capolicchio S, Lee JW, Horikoshi N, Kam S, Ng AA, Edwards J, Butler TL, Chan J, Lee Y, Potter G, Capece MC, Liu CW, Wakatsuki S, Smith M, Sakamoto KM..  (2019)  SAR optimization studies on modified salicylamides as a potential treatment for acute myeloid leukemia through inhibition of the CREB pathway.,  29  (16): [PMID:31253529] [10.1016/j.bmcl.2019.06.023]

12.  (2013)  2-hydroxyarylamide derivative or pharmaceutically acceptable salt thereof, preparation method thereof, and pharmaceutical composition for preventing or treating cancer containing same as active ingredient, 

13.  (2014)  2-hydroxyarylamide derivative or pharmaceutically acceptable salt thereof, preparation method thereof, and pharmaceutical composition for preventing or treating cancer containing same as active ingredient, 

14. Tian M, Abdelrahman A, Baqi Y, Fuentes E, Azazna D, Spanier C, Densborn S, Hinz S, Schmid R, Müller CE..  (2020)  Discovery and Structure Relationships of Salicylanilide Derivatives as Potent, Non-acidic P2X1 Receptor Antagonists.,  63  (11): [PMID:32345019] [10.1021/acs.jmedchem.0c00435]

15. Shamim K, Xu M, Hu X, Lee EM, Lu X, Huang R, Shah P, Xu X, Chen CZ, Shen M, Guo H, Chen L, Itkin Z, Eastman RT, Shinn P, Klumpp-Thomas C, Michael S, Simeonov A, Lo DC, Ming GL, Song H, Tang H, Zheng W, Huang W..  (2021)  Application of niclosamide and analogs as small molecule inhibitors of Zika virus and SARS-CoV-2 infection.,  40  [PMID:33689873] [10.1016/j.bmcl.2021.127906]

16. Juang YP, Chou YT, Lin RX, Ma HH, Chao TL, Jan JT, Chang SY, Liang PH..  (2022)  Design, synthesis and biological evaluations of niclosamide analogues against SARS-CoV-2.,  235  [PMID:35344901] [10.1016/j.ejmech.2022.114295]

17. Baranyai Z, Krátký M, Vosátka R, Szabó E, Senoner Z, Dávid S, Stolaříková J, Vinšová J, Bősze S..  (2017)  In vitro biological evaluation of new antimycobacterial salicylanilide-tuftsin conjugates.,  133  [PMID:28384546] [10.1016/j.ejmech.2017.03.047]

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data