ID: ALA53153

Max Phase: Preclinical

Molecular Formula: C18H22N4O6S

Molecular Weight: 422.46

Molecule Type: Small molecule

Representations

Synonyms (1): sulfamidas3
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCCN(CCC)c1c([N+](=O)[O-])cc(S(=O)(=O)Nc2ccccc2)cc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C18H22N4O6S/c1-3-10-20(11-4-2)18-16(21(23)24)12-15(13-17(18)22(25)26)29(27,28)19-14-8-6-5-7-9-14/h5-9,12-13,19H,3-4,10-11H2,1-2H3

Standard InChI Key:  RMNVGONASFTVGC-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: 422.46

Molecular Weight (Monoisotopic): 422.1260

AlogP: 3.93

#Rotatable Bonds: 10

Polar Surface Area: 135.69

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.53

CX Basic pKa:

CX LogP: 4.21

CX LogD: 4.00

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: -1.43

References

1. Bhattacharya G, Herman J, Delfín D, Salem MM, Barszcz T, Mollet M, Riccio G, Brun R, Werbovetz KA..  (2004)  Synthesis and antitubulin activity of N1- and N4-substituted 3,5-dinitro sulfanilamides against African trypanosomes and Leishmania.,  47  (7): [PMID:15027874] [10.1021/jm0304461]

2. Bhattacharya G, Salem MM, Werbovetz KA..  (2002)  Antileishmanial dinitroaniline sulfonamides with activity against parasite tubulin.,  12  (17): [PMID:12161141] [10.1016/s0960-894x(02)00465-1]

3. 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]

4. Endeshaw MM, Li C, de Leon J, Yao N, Latibeaudiere K, Premalatha K, Morrissette N, Werbovetz KA..  (2010)  Synthesis and evaluation of oryzalin analogs against Toxoplasma gondii.,  20  (17): [PMID:20675138] [10.1016/j.bmcl.2010.07.003]

5. Ma C, Tran J, Gu F, Ochoa R, Li C, Sept D, Werbovetz K, Morrissette N..  (2010)  Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin.,  54  (4): [PMID:20145086] [10.1128/aac.01150-09]

6. Goodarzi M, da Cunha EF, Freitas MP, Ramalho TC..  (2010)  QSAR and docking studies of novel antileishmanial diaryl sulfides and sulfonamides.,  45  (11): [PMID:20728249] [10.1016/j.ejmech.2010.07.060]

Source

Source(1):

• Scientific Literature