ID: ALA39581

Max Phase: Preclinical

Molecular Formula: C15H13NO2S

Molecular Weight: 271.34

Molecule Type: Small molecule

Representations

Synonyms (1): 4-Phenoxyphenoxyethyl Thiocyanate
Synonyms from Alternative Forms(1):

Canonical SMILES:  N#CSCCOc1ccc(Oc2ccccc2)cc1

Standard InChI:  InChI=1S/C15H13NO2S/c16-12-19-11-10-17-13-6-8-15(9-7-13)18-14-4-2-1-3-5-14/h1-9H,10-11H2

Standard InChI Key:  YQZHGQYIMXWEHI-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: 271.34

Molecular Weight (Monoisotopic): 271.0667

AlogP: 4.07

#Rotatable Bonds: 6

Polar Surface Area: 42.25

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.78

CX LogD: 3.78

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.59

Np Likeness Score: -0.82

References

1. Cinque GM, Szajnman SH, Zhong L, Docampo R, Schvartzapel AJ, Rodriguez JB, Gros EG..  (1998)  Structure-activity relationship of new growth inhibitors of Trypanosoma cruzi.,  41  (9): [PMID:9554887] [10.1021/jm970860z]

2. Szajnman SH, Yan W, Bailey BN, Docampo R, Elhalem E, Rodriguez JB..  (2000)  Design and synthesis of aryloxyethyl thiocyanate derivatives as potent inhibitors of Trypanosoma cruzi proliferation.,  43  (9): [PMID:10794699] [10.1021/jm9905007]

3. Elhalem E, Bailey BN, Docampo R, Ujváry I, Szajnman SH, Rodriguez JB..  (2002)  Design, synthesis, and biological evaluation of aryloxyethyl thiocyanate derivatives against Trypanosoma cruzi.,  45  (18): [PMID:12190320] [10.1021/jm0201518]

4. Szajnman SH, Bailey BN, Docampo R, Rodriguez JB..  (2001)  Bisphosphonates derived from fatty acids are potent growth inhibitors of Trypanosoma cruzi.,  11  (6): [PMID:11277521] [10.1016/s0960-894x(01)00057-9]

5. Szajnman SH, Ravaschino EL, Docampo R, Rodriguez JB..  (2005)  Synthesis and biological evaluation of 1-amino-1,1-bisphosphonates derived from fatty acids against Trypanosoma cruzi targeting farnesyl pyrophosphate synthase.,  15  (21): [PMID:16143525] [10.1016/j.bmcl.2005.07.060]

6. Ravaschino EL, Docampo R, Rodriguez JB..  (2006)  Design, synthesis, and biological evaluation of phosphinopeptides against Trypanosoma cruzi targeting trypanothione biosynthesis.,  49  (1): [PMID:16392828] [10.1021/jm050922i]

7. Liñares GG, Gismondi S, Codesido NO, Moreno SN, Docampo R, Rodriguez JB..  (2007)  Fluorine-containing aryloxyethyl thiocyanate derivatives are potent inhibitors of Trypanosoma cruzi and Toxoplasma gondii proliferation.,  17  (18): [PMID:17643987] [10.1016/j.bmcl.2007.07.012]

8. Szajnman SH, García Liñares GE, Li ZH, Jiang C, Galizzi M, Bontempi EJ, Ferella M, Moreno SN, Docampo R, Rodriguez JB..  (2008)  Synthesis and biological evaluation of 2-alkylaminoethyl-1,1-bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii targeting farnesyl diphosphate synthase.,  16  (6): [PMID:18096393] [10.1016/j.bmc.2007.12.010]

9. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]

10. Lin FY, Liu YL, Li K, Cao R, Zhu W, Axelson J, Pang R, Oldfield E..  (2012)  Head-to-head prenyl tranferases: anti-infective drug targets.,  55  (9): [PMID:22486710] [10.1021/jm300208p]

11. Elicio PD, Chao MN, Galizzi M, Li C, Szajnman SH, Docampo R, Moreno SN, Rodriguez JB..  (2013)  Design, synthesis and biological evaluation of WC-9 analogs as antiparasitic agents.,  69  [PMID:24090919] [10.1016/j.ejmech.2013.09.009]

12. Chao MN, Storey M, Li C, Rodríguez MG, Di Salvo F, Szajnman SH, Moreno SNJ, Docampo R, Rodriguez JB..  (2017)  Selenium-containing analogues of WC-9 are extremely potent inhibitors of Trypanosoma cruzi proliferation.,  25  (24): [PMID:29107437] [10.1016/j.bmc.2017.10.016]

13. Wu RZ, Zhou HY, Song JF, Xia QH, Hu W, Mou XD, Li X..  (2021)  Chemotherapeutics for Toxoplasma gondii: Molecular Biotargets, Binding Modes, and Structure-Activity Relationship Investigations.,  64  (24.0): [PMID:34894691] [10.1021/acs.jmedchem.1c01569]

Source

Source(1):

• Scientific Literature