ID: ALA423172

Max Phase: Preclinical

Molecular Formula: C6H6N6O2S

Molecular Weight: 226.22

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  Cn1c([N+](=O)[O-])cnc1-c1nnc(N)s1

Standard InChI:  InChI=1S/C6H6N6O2S/c1-11-3(12(13)14)2-8-4(11)5-9-10-6(7)15-5/h2H,1H3,(H2,7,10)

Standard InChI Key:  VDZZTXBMKRQEPO-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: 226.22

Molecular Weight (Monoisotopic): 226.0273

AlogP: 0.43

#Rotatable Bonds: 2

Polar Surface Area: 112.76

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 0.43

CX LogP: 0.14

CX LogD: 0.14

Aromatic Rings: 2

Heavy Atoms: 15

QED Weighted: 0.59

Np Likeness Score: -1.86

References

1. Chauvière G, Bouteille B, Enanga B, de Albuquerque C, Croft SL, Dumas M, Périé J..  (2003)  Synthesis and biological activity of nitro heterocycles analogous to megazol, a trypanocidal lead.,  46  (3): [PMID:12540242] [10.1021/jm021030a]

2. Carvalho SA, da Silva EF, Santa-Rita RM, de Castro SL, Fraga CA..  (2004)  Synthesis and antitrypanosomal profile of new functionalized 1,3,4-thiadiazole-2-arylhydrazone derivatives, designed as non-mutagenic megazol analogues.,  14  (24): [PMID:15546709] [10.1016/j.bmcl.2004.10.007]

3. Baliani A, Bueno GJ, Stewart ML, Yardley V, Brun R, Barrett MP, Gilbert IH..  (2005)  Design and synthesis of a series of melamine-based nitroheterocycles with activity against Trypanosomatid parasites.,  48  (17): [PMID:16107157] [10.1021/jm050177+]

4. Carvalho SA, Lopes FA, Salomão K, Romeiro NC, Wardell SM, de Castro SL, da Silva EF, Fraga CA..  (2008)  Studies toward the structural optimization of new brazilizone-related trypanocidal 1,3,4-thiadiazole-2-arylhydrazone derivatives.,  16  (1): [PMID:17904851] [10.1016/j.bmc.2007.09.027]

5. Cavalli A, Bolognesi ML..  (2009)  Neglected tropical diseases: multi-target-directed ligands in the search for novel lead candidates against Trypanosoma and Leishmania.,  52  (23): [PMID:19606868] [10.1021/jm9004835]

6. Salomão K, de Souza EM, Carvalho SA, da Silva EF, Fraga CA, Barbosa HS, de Castro SL..  (2010)  In vitro and in vivo activities of 1,3,4-thiadiazole-2-arylhydrazone derivatives of megazol against Trypanosoma cruzi.,  54  (5): [PMID:20231395] [10.1128/aac.01241-09]

7. PubChem BioAssay data set, 

8. Trunz BB, Jędrysiak R, Tweats D, Brun R, Kaiser M, Suwiński J, Torreele E..  (2011)  1-Aryl-4-nitro-1H-imidazoles, a new promising series for the treatment of human African trypanosomiasis.,  46  (5): [PMID:21353728] [10.1016/j.ejmech.2011.01.071]

9. Zhang J, Ba Y, Wang S, Yang H, Hou X, Xu Z..  (2019)  Nitroimidazole-containing compounds and their antibacterial and antitubercular activities.,  179  [PMID:31260891] [10.1016/j.ejmech.2019.06.068]

10. Fernando da Silva Santos-Júnior P, Rocha Silva L, José Quintans-Júnior L, Ferreira da Silva-Júnior E..  (2022)  Nitro compounds against trypanosomatidae parasites: Heroes or villains?,  75  [PMID:36030001] [10.1016/j.bmcl.2022.128930]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays