ID: ALA268177

Max Phase: Preclinical

Molecular Formula: C6H7IN2O2S

Molecular Weight: 298.11

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1ccc(S(N)(=O)=O)cc1I

Standard InChI:  InChI=1S/C6H7IN2O2S/c7-5-3-4(12(9,10)11)1-2-6(5)8/h1-3H,8H2,(H2,9,10,11)

Standard InChI Key:  HCODCRHNVCTCTR-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: 298.11

Molecular Weight (Monoisotopic): 297.9273

AlogP: 0.52

#Rotatable Bonds: 1

Polar Surface Area: 86.18

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.33

CX Basic pKa: 1.33

CX LogP: 0.68

CX LogD: 0.68

Aromatic Rings: 1

Heavy Atoms: 12

QED Weighted: 0.59

Np Likeness Score: -1.45

References

1. Vullo D, Franchi M, Gallori E, Pastorek J, Scozzafava A, Pastorekova S, Supuran CT..  (2003)  Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides.,  13  (6): [PMID:12643899] [10.1016/s0960-894x(03)00091-x]

2. Scozzafava A, Supuran CT..  (2000)  Carbonic anhydrase inhibitors: synthesis of N-morpholylthiocarbonylsulfenylamino aromatic/heterocyclic sulfonamides and their interaction with isozymes I, II and IV.,  10  (10): [PMID:10843231] [10.1016/s0960-894x(00)00178-5]

3. Scozzafava A, Menabuoni L, Mincione F, Supuran CT..  (2002)  Carbonic anhydrase inhibitors. A general approach for the preparation of water-soluble sulfonamides incorporating polyamino-polycarboxylate tails and of their metal complexes possessing long-lasting, topical intraocular pressure-lowering properties.,  45  (7): [PMID:11906288] [10.1021/jm0108202]

4. Ilies MA, Vullo D, Pastorek J, Scozzafava A, Ilies M, Caproiu MT, Pastorekova S, Supuran CT..  (2003)  Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives.,  46  (11): [PMID:12747790] [10.1021/jm021123s]

5. Scozzafava A, Menabuoni L, Mincione F, Briganti F, Mincione G, Supuran CT..  (1999)  Carbonic anhydrase inhibitors. Synthesis of water-soluble, topically effective, intraocular pressure-lowering aromatic/heterocyclic sulfonamides containing cationic or anionic moieties: is the tail more important than the ring?,  42  (14): [PMID:10411484] [10.1021/jm9900523]

6. Scozzafava A, Briganti F, Ilies MA, Supuran CT..  (2000)  Carbonic anhydrase inhibitors: synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus cytosolic isozymes.,  43  (2): [PMID:10649985] [10.1021/jm990479+]

7. Jaiswal M, Khadikar PV, Scozzafava A, Supuran CT..  (2004)  Carbonic anhydrase inhibitors: the first QSAR study on inhibition of tumor-associated isoenzyme IX with aromatic and heterocyclic sulfonamides.,  14  (12): [PMID:15149691] [10.1016/j.bmcl.2004.03.099]

8. Scozzafava A, Briganti F, Mincione G, Menabuoni L, Mincione F, Supuran CT..  (1999)  Carbonic anhydrase inhibitors: synthesis of water-soluble, aminoacyl/dipeptidyl sulfonamides possessing long-lasting intraocular pressure-lowering properties via the topical route.,  42  (18): [PMID:10479300] [10.1021/jm9901879]

9. Lehtonen JM, Parkkila S, Vullo D, Casini A, Scozzafava A, Supuran CT..  (2004)  Carbonic anhydrase inhibitors. Inhibition of cytosolic isozyme XIII with aromatic and heterocyclic sulfonamides: a novel target for the drug design.,  14  (14): [PMID:15203157] [10.1016/j.bmcl.2004.04.106]

10. Agrawal VK, Khadikar PV..  (2003)  Modelling of carbonic anhydrase inhibitory activity of sulfonamides using molecular negentropy.,  13  (3): [PMID:12565948] [10.1016/s0960-894x(02)00954-x]

11. Scozzafava A, Menabuoni L, Mincione F, Mincione G, Supuran CT..  (2001)  Carbonic anhydrase inhibitors: synthesis of sulfonamides incorporating dtpa tails and of their zinc complexes with powerful topical antiglaucoma properties.,  11  (4): [PMID:11229775] [10.1016/s0960-894x(00)00722-8]

12. Vullo D, Voipio J, Innocenti A, Rivera C, Ranki H, Scozzafava A, Kaila K, Supuran CT..  (2005)  Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides.,  15  (4): [PMID:15686895] [10.1016/j.bmcl.2004.12.052]

13. Nishimori I, Vullo D, Innocenti A, Scozzafava A, Mastrolorenzo A, Supuran CT..  (2005)  Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides.,  15  (17): [PMID:16039848] [10.1016/j.bmcl.2005.06.055]

14. Vullo D, Innocenti A, Nishimori I, Pastorek J, Scozzafava A, Pastoreková S, Supuran CT..  (2005)  Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs?,  15  (4): [PMID:15686894] [10.1016/j.bmcl.2004.12.053]

15. Innocenti A, Firnges MA, Antel J, Wurl M, Scozzafava A, Supuran CT..  (2005)  Carbonic anhydrase inhibitors. Inhibition of the membrane-bound human and bovine isozymes IV with sulfonamides.,  15  (4): [PMID:15686931] [10.1016/j.bmcl.2004.12.009]

16. Innocenti A, Antel J, Wurl M, Scozzafava A, Supuran CT..  (2004)  Carbonic anhydrase inhibitors: inhibition of human cytosolic isozyme II and mitochondrial isozyme V with a series of benzene sulfonamide derivatives.,  14  (22): [PMID:15482952] [10.1016/j.bmcl.2004.07.085]

17. Zimmerman S, Innocenti A, Casini A, Ferry JG, Scozzafava A, Supuran CT..  (2004)  Carbonic anhydrase inhibitors. Inhibition of the prokariotic beta and gamma-class enzymes from Archaea with sulfonamides.,  14  (24): [PMID:15546717] [10.1016/j.bmcl.2004.09.085]

18. Nishimori I, Vullo D, Innocenti A, Scozzafava A, Mastrolorenzo A, Supuran CT..  (2005)  Carbonic anhydrase inhibitors. The mitochondrial isozyme VB as a new target for sulfonamide and sulfamate inhibitors.,  48  (24): [PMID:16302824] [10.1021/jm050483n]

19. Nishimori I, Minakuchi T, Morimoto K, Sano S, Onishi S, Takeuchi H, Vullo D, Scozzafava A, Supuran CT..  (2006)  Carbonic anhydrase inhibitors: DNA cloning and inhibition studies of the alpha-carbonic anhydrase from Helicobacter pylori, a new target for developing sulfonamide and sulfamate gastric drugs.,  49  (6): [PMID:16539401] [10.1021/jm0512600]

20. Agrawal VK, Singh J, Khadikar PV, Supuran CT..  (2006)  QSAR study on topically acting sulfonamides incorporating GABA moieties: a molecular connectivity approach.,  16  (7): [PMID:16458003] [10.1016/j.bmcl.2005.08.071]

21. Nishimori I, Vullo D, Minakuchi T, Morimoto K, Onishi S, Scozzafava A, Supuran CT..  (2006)  Carbonic anhydrase inhibitors: cloning and sulfonamide inhibition studies of a carboxyterminal truncated alpha-carbonic anhydrase from Helicobacter pylori.,  16  (8): [PMID:16459077] [10.1016/j.bmcl.2006.01.044]

22. Nishimori I, Minakuchi T, Onishi S, Vullo D, Scozzafava A, Supuran CT..  (2007)  Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors.,  50  (2): [PMID:17228881] [10.1021/jm0612057]

23. Nishimori I, Minakuchi T, Kohsaki T, Onishi S, Takeuchi H, Vullo D, Scozzafava A, Supuran CT..  (2007)  Carbonic anhydrase inhibitors: the beta-carbonic anhydrase from Helicobacter pylori is a new target for sulfonamide and sulfamate inhibitors.,  17  (13): [PMID:17482815] [10.1016/j.bmcl.2007.04.063]

24. Isik S, Kockar F, Aydin M, Arslan O, Guler OO, Innocenti A, Scozzafava A, Supuran CT..  (2009)  Carbonic anhydrase inhibitors: inhibition of the beta-class enzyme from the yeast Saccharomyces cerevisiae with sulfonamides and sulfamates.,  17  (3): [PMID:19124253] [10.1016/j.bmc.2008.12.035]

25. Hilvo M, Salzano AM, Innocenti A, Kulomaa MS, Scozzafava A, Scaloni A, Parkkila S, Supuran CT..  (2009)  Cloning, expression, post-translational modifications and inhibition studies on the latest mammalian carbonic anhydrase isoform, CA XV.,  52  (3): [PMID:19193158] [10.1021/jm801267c]

26. Minakuchi T, Nishimori I, Vullo D, Scozzafava A, Supuran CT..  (2009)  Molecular cloning, characterization, and inhibition studies of the Rv1284 beta-carbonic anhydrase from Mycobacterium tuberculosis with sulfonamides and a sulfamate.,  52  (8): [PMID:19317447] [10.1021/jm9000488]

27. Nishimori I, Minakuchi T, Vullo D, Scozzafava A, Innocenti A, Supuran CT..  (2009)  Carbonic anhydrase inhibitors. Cloning, characterization, and inhibition studies of a new beta-carbonic anhydrase from Mycobacterium tuberculosis.,  52  (9): [PMID:19338333] [10.1021/jm9003126]

28. Innocenti A, Hall RA, Schlicker C, Scozzafava A, Steegborn C, Mühlschlegel FA, Supuran CT..  (2009)  Carbonic anhydrase inhibitors. Inhibition and homology modeling studies of the fungal beta-carbonic anhydrase from Candida albicans with sulfonamides.,  17  (13): [PMID:19450983] [10.1016/j.bmc.2009.05.002]

29. Bertucci A, Innocenti A, Zoccola D, Scozzafava A, Tambutté S, Supuran CT..  (2009)  Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides.,  17  (14): [PMID:19520577] [10.1016/j.bmc.2009.05.063]

30. Carta F, Maresca A, Covarrubias AS, Mowbray SL, Jones TA, Supuran CT..  (2009)  Carbonic anhydrase inhibitors. Characterization and inhibition studies of the most active beta-carbonic anhydrase from Mycobacterium tuberculosis, Rv3588c.,  19  (23): [PMID:19846301] [10.1016/j.bmcl.2009.10.009]

31. Sethi KK, Verma SM, Prasanthi N, Sahoo SK, Parhi RN, Suresh P..  (2010)  3D-QSAR study of benzene sulfonamide analogs as carbonic anhydrase II inhibitors.,  20  (10): [PMID:20443227] [10.1016/j.bmcl.2010.03.104]

32. Bertucci A, Innocenti A, Scozzafava A, Tambutté S, Zoccola D, Supuran CT..  (2011)  Carbonic anhydrase inhibitors. Inhibition studies with anions and sulfonamides of a new cytosolic enzyme from the scleractinian coral Stylophora pistillata.,  21  (2): [PMID:21208801] [10.1016/j.bmcl.2010.11.124]

33. Hewitson KS, Vullo D, Scozzafava A, Mastrolorenzo A, Supuran CT..  (2012)  Molecular cloning, characterization, and inhibition studies of a β-carbonic anhydrase from Malassezia globosa, a potential antidandruff target.,  55  (7): [PMID:22424239] [10.1021/jm300203r]

34. Del Prete S, Isik S, Vullo D, De Luca V, Carginale V, Scozzafava A, Supuran CT, Capasso C..  (2012)  DNA cloning, characterization, and inhibition studies of an α-carbonic anhydrase from the pathogenic bacterium Vibrio cholerae.,  55  (23): [PMID:23181552] [10.1021/jm301611m]

35. Vullo D, Luca VD, Scozzafava A, Carginale V, Rossi M, Supuran CT, Capasso C..  (2013)  The alpha-carbonic anhydrase from the thermophilic bacterium Sulfurihydrogenibium yellowstonense YO3AOP1 is highly susceptible to inhibition by sulfonamides.,  21  (6): [PMID:22883029] [10.1016/j.bmc.2012.07.024]

36. Vullo D, Leewattanapasuk W, Mühlschlegel FA, Mastrolorenzo A, Capasso C, Supuran CT..  (2013)  Carbonic anhydrase inhibitors: inhibition of the β-class enzyme from the pathogenic yeast Candida glabrata with sulfonamides, sulfamates and sulfamides.,  23  (9): [PMID:23511020] [10.1016/j.bmcl.2013.02.092]

37. Vullo D, Bhatt A, Mahon BP, McKenna R, Supuran CT..  (2016)  Sulfonamide inhibition studies of the α-carbonic anhydrase from the gammaproteobacterium Thiomicrospira crunogena XCL-2, TcruCA.,  26  (2): [PMID:26691758] [10.1016/j.bmcl.2015.11.104]

Source

Source(1):

• Scientific Literature