(R)-N-Hydroxy-2-[(4-methoxy-benzenesulfonyl)-pyridin-3-ylmethyl-amino]-3-methyl-butyramide

ID: ALA514138

Chembl Id: CHEMBL514138

Cas Number: 169799-04-6

PubChem CID: 9888897

Max Phase: Preclinical

Molecular Formula: C18H24ClN3O5S

Molecular Weight: 393.47

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: CGS-27023A | MMI270B anhydrous|MMI-270B anhydrous|169799-04-6|CGS-27023A anhydrous|CGS-27023A HCl|CGS 27023A|BS0VY94Q43|161314-70-1 (free base)|CHEMBL514138|Butanamide, N-hydroxy-2-(((4-methoxyphenyl)sulfonyl)(3-pyridinylmethyl)amino)-3-methyl-, hydrochloride (1:1), (2R)-|cgs27023a|(2R)-N-hydroxy-2-[(4-methoxyphenyl)sulfonyl-(pyridin-3-ylmethyl)amino]-3-methylbutanamide hydrochloride|ZVYIZSNCEAHMCF-UNTBIKODSA-N|CGS27023Ahydrochloride|UNII-BS0VY94Q43|CGS 27023A hydrochloride|SCHEMBL3158786|AKOS03Show More

Canonical SMILES:  COc1ccc(S(=O)(=O)N(Cc2cccnc2)[C@@H](C(=O)NO)C(C)C)cc1.Cl

Standard InChI:  InChI=1S/C18H23N3O5S.ClH/c1-13(2)17(18(22)20-23)21(12-14-5-4-10-19-11-14)27(24,25)16-8-6-15(26-3)7-9-16;/h4-11,13,17,23H,12H2,1-3H3,(H,20,22);1H/t17-;/m1./s1

Standard InChI Key:  ZVYIZSNCEAHMCF-UNTBIKODSA-N

Associated Targets(Human)

MMP1 Tchem Matrix metalloproteinase-1 (7046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP9 Tchem Matrix metalloproteinase 9 (6779 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP13 Tchem Matrix metalloproteinase 13 (4133 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADAM17 Tchem ADAM17 (3550 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP3 Tchem Matrix metalloproteinase 3 (3433 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP2 Tchem Matrix metalloproteinase-2 (6627 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BMP1 Tchem Bone morphogenetic protein 1 (1282 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP13 Tchem Matrix metalloproteinase (1 and 13) (154 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP7 Tchem Matrix metalloproteinase 7 (1073 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP8 Tchem Matrix metalloproteinase 8 (1942 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP3 Tchem Matrix metalloproteinase (2 and 3) (56 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP14 Tchem Matrix metalloproteinase 14 (1592 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADAMTS4 Tchem ADAMTS4 (425 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA1 Tclin Carbonic anhydrase I (13240 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA2 Tclin Carbonic anhydrase II (17698 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA9 Tclin Carbonic anhydrase IX (8255 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP16 Tchem Matrix metalloproteinase 16 (81 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADAM10 Tchem ADAM10 (375 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-OV-3 (52876 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-468 (9477 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP25 Tchem Matrix metalloproteinase-25 (11 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP12 Tchem Matrix metalloproteinase 12 (1130 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TF Tbio Serotransferrin (88 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRSS1 Tclin Trypsin (2137 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACE Tclin Angiotensin-converting enzyme (1423 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC2 Tclin Histone deacetylase 2 (3971 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Mmp2 Matrix metalloproteinase-2 (12 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mmp9 Matrix metalloproteinase 9 (44 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bos taurus (956 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mmp12 Matrix metalloproteinase 12 (54 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mmp13 Matrix metalloproteinase 13 (19 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
lef Anthrax lethal factor (7585 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPO2 Tyrosinase (3884 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 393.47Molecular Weight (Monoisotopic): 393.1358AlogP: 1.81#Rotatable Bonds: 8
Polar Surface Area: 108.83Molecular Species: NEUTRALHBA: 6HBD: 2
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 8.71CX Basic pKa: 4.81CX LogP: 1.50CX LogD: 1.48
Aromatic Rings: 2Heavy Atoms: 27QED Weighted: 0.52Np Likeness Score: -1.06

References

1. Pikul S, Dunham KM, Almstead NG, De B, Natchus MG, Taiwo YO, Williams LE, Hynd BA, Hsieh LC, Janusz MJ, Gu F, Mieling GE..  (2001)  Heterocycle-based MMP inhibitors with P2' substituents.,  11  (8): [PMID:11327577] [10.1016/s0960-894x(01)00137-8]
2. Delbecq F, Cordonnier G, Pommery N, Barbry D, Hénichart JP..  (2004)  New heteroarylbenzenesulphonamides as matrix metalloproteinase inhibitors.,  14  (5): [PMID:14980648] [10.1016/j.bmcl.2003.12.076]
3. Hanessian S, Bouzbouz S, Boudon A, Tucker GC, Peyroulan D..  (1999)  Picking the S1, S1' and S2' pockets of matrix metalloproteinases. A niche for potent acyclic sulfonamide inhibitors.,  (12): [PMID:10397503] [10.1016/s0960-894x(99)00259-0]
4. Caldarelli M, Habermann J, Ley SV..  (1999)  Synthesis of an array of potential matrix metalloproteinase inhibitors using a sequence of polymer-supported reagents.,  (14): [PMID:10450979] [10.1016/s0960-894x(99)00311-x]
5. Dankwardt SM, Martin RL, Chan CS, Van Wart HE, Walker KA, Delaet NG, Robinson LA..  (2001)  Amino acid derived sulfonamide hydroxamates as inhibitors of procollagen C-proteinase: solid-phase synthesis of ornithine analogues.,  11  (16): [PMID:11514144] [10.1016/s0960-894x(01)00384-5]
6. Levin JI, Chen J, Du M, Hogan M, Kincaid S, Nelson FC, Venkatesan AM, Wehr T, Zask A, DiJoseph J, Killar LM, Skala S, Sung A, Sharr M, Roth C, Jin G, Cowling R, Mohler KM, Black RA, March CJ, Skotnicki JS..  (2001)  The discovery of anthranilic acid-based MMP inhibitors. Part 2: SAR of the 5-position and P1(1) groups.,  11  (16): [PMID:11514167] [10.1016/s0960-894x(01)00419-x]
7. Reiter LA, Mitchell PG, Martinelli GJ, Lopresti-Morrow LL, Yocum SA, Eskra JD..  (2003)  Phosphinic acid-based MMP-13 inhibitors that spare MMP-1 and MMP-3.,  13  (14): [PMID:12824028] [10.1016/s0960-894x(03)00413-x]
8. Aranapakam V, Grosu GT, Davis JM, Hu B, Ellingboe J, Baker JL, Skotnicki JS, Zask A, DiJoseph JF, Sung A, Sharr MA, Killar LM, Walter T, Jin G, Cowling R..  (2003)  Synthesis and structure-activity relationship of alpha-sulfonylhydroxamic acids as novel, orally active matrix metalloproteinase inhibitors for the treatment of osteoarthritis.,  46  (12): [PMID:12773041] [10.1021/jm0205548]
9. Levin JI, Du MT, DiJoseph JF, Killar LM, Sung A, Walter T, Sharr MA, Roth CE, Moy FJ, Powers R, Jin G, Cowling R, Skotnicki JS..  (2001)  The discovery of anthranilic acid-based MMP inhibitors. Part 1: SAR of the 3-position.,  11  (2): [PMID:11206467] [10.1016/s0960-894x(00)00642-9]
10. Aranapakam V, Davis JM, Grosu GT, Baker J, Ellingboe J, Zask A, Levin JI, Sandanayaka VP, Du M, Skotnicki JS, DiJoseph JF, Sung A, Sharr MA, Killar LM, Walter T, Jin G, Cowling R, Tillett J, Zhao W, McDevitt J, Xu ZB..  (2003)  Synthesis and structure-activity relationship of N-substituted 4-arylsulfonylpiperidine-4-hydroxamic acids as novel, orally active matrix metalloproteinase inhibitors for the treatment of osteoarthritis.,  46  (12): [PMID:12773042] [10.1021/jm0205550]
11. MacPherson LJ, Bayburt EK, Capparelli MP, Carroll BJ, Goldstein R, Justice MR, Zhu L, Hu S, Melton RA, Fryer L, Goldberg RL, Doughty JR, Spirito S, Blancuzzi V, Wilson D, O'Byrne EM, Ganu V, Parker DT..  (1997)  Discovery of CGS 27023A, a non-peptidic, potent, and orally active stromelysin inhibitor that blocks cartilage degradation in rabbits.,  40  (16): [PMID:9258358] [10.1021/jm960871c]
12. Levin JI, DiJoseph JF, Killar LM, Sung A, Walter T, Sharr MA, Roth CE, Skotnicki JS, Albright JD..  (1998)  The synthesis and biological activity of a novel series of diazepine MMP inhibitors.,  (19): [PMID:9873598] [10.1016/s0960-894x(98)00473-9]
13. Scozzafava A, Supuran CT..  (2002)  Protease inhibitors: synthesis of matrix metalloproteinase and bacterial collagenase inhibitors incorporating 5-amino-2-mercapto-1,3,4-thiadiazole zinc binding functions.,  12  (19): [PMID:12217351] [10.1016/s0960-894x(02)00564-4]
14. Becker DP, DeCrescenzo G, Freskos J, Getman DP, Hockerman SL, Li M, Mehta P, Munie GE, Swearingen C..  (2001)  alpha-Alkyl-alpha-amino-beta-sulphone hydroxamates as potent MMP inhibitors that spare MMP-1.,  11  (20): [PMID:11591510] [10.1016/s0960-894x(01)00557-1]
15. Källblad P, Todorov NP, Willems HM, Alberts IL..  (2004)  Receptor flexibility in the in silico screening of reagents in the S1' pocket of human collagenase.,  47  (11): [PMID:15139754] [10.1021/jm031061l]
16. Nelson FC, Delos Santos E, Levin JI, Chen JM, Skotnicki JS, DiJoseph JF, Sharr MA, Sung A, Killar LM, Cowling R, Jin G, Roth CE, Albright JD..  (2002)  Benzodiazepine inhibitors of the MMPs and TACE.,  12  (20): [PMID:12270165] [10.1016/s0960-894x(02)00633-9]
17. Levin JI, Chen JM, Du MT, Nelson FC, Wehr T, DiJoseph JF, Killar LM, Skala S, Sung A, Sharr MA, Roth CE, Jin G, Cowling R, Di L, Sherman M, Xu ZB, March CJ, Mohler KM, Black RA, Skotnicki JS..  (2001)  The discovery of anthranilic acid-based MMP inhibitors. Part 3: incorporation of basic amines.,  11  (22): [PMID:11677139] [10.1016/s0960-894x(01)00601-1]
18. Reiter LA, Robinson RP, McClure KF, Jones CS, Reese MR, Mitchell PG, Otterness IG, Bliven ML, Liras J, Cortina SR, Donahue KM, Eskra JD, Griffiths RJ, Lame ME, Lopez-Anaya A, Martinelli GJ, McGahee SM, Yocum SA, Lopresti-Morrow LL, Tobiassen LM, Vaughn-Bowser ML..  (2004)  Pyran-containing sulfonamide hydroxamic acids: potent MMP inhibitors that spare MMP-1.,  14  (13): [PMID:15177439] [10.1016/j.bmcl.2004.04.083]
19. Leung D, Abbenante G, Fairlie DP..  (2000)  Protease inhibitors: current status and future prospects.,  43  (3): [PMID:10669559] [10.1021/jm990412m]
20. Pikul S, McDow Dunham KL, Almstead NG, De B, Natchus MG, Anastasio MV, McPhail SJ, Snider CE, Taiwo YO, Rydel T, Dunaway CM, Gu F, Mieling GE..  (1998)  Discovery of potent, achiral matrix metalloproteinase inhibitors.,  41  (19): [PMID:9733482] [10.1021/jm980253r]
21. Le Diguarher T, Chollet AM, Bertrand M, Hennig P, Raimbaud E, Sabatini M, Guilbaud N, Pierré A, Tucker GC, Casara P..  (2003)  Stereospecific synthesis of 5-substituted 2-bisarylthiocyclopentane carboxylic acids as specific matrix metalloproteinase inhibitors.,  46  (18): [PMID:12930146] [10.1021/jm0307638]
22. Almstead NG, Bradley RS, Pikul S, De B, Natchus MG, Taiwo YO, Gu F, Williams LE, Hynd BA, Janusz MJ, Dunaway CM, Mieling GE..  (1999)  Design, synthesis, and biological evaluation of potent thiazine- and thiazepine-based matrix metalloproteinase inhibitors.,  42  (22): [PMID:10579818] [10.1021/jm990330y]
23. Jeng AY, Chou M, Parker DT..  (1998)  Sulfonamide-based hydroxamic acids as potent inhibitors of mouse macrophage metalloelastase.,  (8): [PMID:9871508] [10.1016/s0960-894x(98)00142-5]
24. Pikul S, McDow Dunham KL, Almstead NG, De B, Natchus MG, Anastasio MV, McPhail SJ, Snider CE, Taiwo YO, Chen L, Dunaway CM, Gu F, Mieling GE..  (1999)  Design and synthesis of phosphinamide-based hydroxamic acids as inhibitors of matrix metalloproteinases.,  42  (1): [PMID:9888835] [10.1021/jm980142s]
25. Rossello A, Nuti E, Carelli P, Orlandini E, Macchia M, Nencetti S, Zandomeneghi M, Balzano F, Uccello Barretta G, Albini A, Benelli R, Cercignani G, Murphy G, Balsamo A..  (2005)  N-i-Propoxy-N-biphenylsulfonylaminobutylhydroxamic acids as potent and selective inhibitors of MMP-2 and MT1-MMP.,  15  (5): [PMID:15713379] [10.1016/j.bmcl.2005.01.024]
26. Breyholz HJ, Schäfers M, Wagner S, Höltke C, Faust A, Rabeneck H, Levkau B, Schober O, Kopka K..  (2005)  C-5-disubstituted barbiturates as potential molecular probes for noninvasive matrix metalloproteinase imaging.,  48  (9): [PMID:15857146] [10.1021/jm049145x]
27. Xiang JS, Hu Y, Rush TS, Thomason JR, Ipek M, Sum PE, Abrous L, Sabatini JJ, Georgiadis K, Reifenberg E, Majumdar M, Morris EA, Tam S..  (2006)  Synthesis and biological evaluation of biphenylsulfonamide carboxylate aggrecanase-1 inhibitors.,  16  (2): [PMID:16275085] [10.1016/j.bmcl.2005.10.001]
28. Xiang JS, Hu Y, Rush TS, Thomason JR, Ipek M, Sum PE, Abrous L, Sabatini JJ, Georgiadis K, Reifenberg E, Majumdar M, Morris EA, Tam S..  (2006)  Synthesis and biological evaluation of biphenylsulfonamide carboxylate aggrecanase-1 inhibitors.,  16  (2): [PMID:16275085] [10.1016/j.bmcl.2005.10.001]
29. Xiong Y, Wiltsie J, Woods A, Guo J, Pivnichny JV, Tang W, Bansal A, Cummings RT, Cunningham BR, Friedlander AM, Douglas CM, Salowe SP, Zaller DM, Scolnick EM, Schmatz DM, Bartizal K, Hermes JD, MacCoss M, Chapman KT..  (2006)  The discovery of a potent and selective lethal factor inhibitor for adjunct therapy of anthrax infection.,  16  (4): [PMID:16338135] [10.1016/j.bmcl.2005.10.088]
30. Nuti E, Orlandini E, Nencetti S, Rossello A, Innocenti A, Scozzafava A, Supuran CT..  (2007)  Carbonic anhydrase and matrix metalloproteinase inhibitors. Inhibition of human tumor-associated isozymes IX and cytosolic isozyme I and II with sulfonylated hydroxamates.,  15  (6): [PMID:17276072] [10.1016/j.bmc.2007.01.023]
31. Santos MA, Enyedy EA, Nuti E, Rossello A, Krupenko NI, Krupenko SA..  (2007)  Methotrexate gamma-hydroxamate derivatives as potential dual target antitumor drugs.,  15  (3): [PMID:17127067] [10.1016/j.bmc.2006.11.017]
32. Wagner S, Breyholz HJ, Law MP, Faust A, Höltke C, Schröer S, Haufe G, Levkau B, Schober O, Schäfers M, Kopka K..  (2007)  Novel fluorinated derivatives of the broad-spectrum MMP inhibitors N-hydroxy-2(R)-[[(4-methoxyphenyl)sulfonyl](benzyl)- and (3-picolyl)-amino]-3-methyl-butanamide as potential tools for the molecular imaging of activated MMPs with PET.,  50  (23): [PMID:17956082] [10.1021/jm0708533]
33. Marques SM, Nuti E, Rossello A, Supuran CT, Tuccinardi T, Martinelli A, Santos MA..  (2008)  Dual inhibitors of matrix metalloproteinases and carbonic anhydrases: iminodiacetyl-based hydroxamate-benzenesulfonamide conjugates.,  51  (24): [PMID:19053764] [10.1021/jm800964f]
34. Monovich LG, Tommasi RA, Fujimoto RA, Blancuzzi V, Clark K, Cornell WD, Doti R, Doughty J, Fang J, Farley D, Fitt J, Ganu V, Goldberg R, Goldstein R, Lavoie S, Kulathila R, Macchia W, Parker DT, Melton R, O'Byrne E, Pastor G, Pellas T, Quadros E, Reel N, Roland DM, Sakane Y, Singh H, Skiles J, Somers J, Toscano K, Wigg A, Zhou S, Zhu L, Shieh WC, Xue S, McQuire LW..  (2009)  Discovery of potent, selective, and orally active carboxylic acid based inhibitors of matrix metalloproteinase-13.,  52  (11): [PMID:19422229] [10.1021/jm801394m]
35. Wilfong EM, Locklear U, Toone EJ..  (2010)  A single step purification for autolytic zinc proteinases.,  20  (1): [PMID:19942433] [10.1016/j.bmcl.2009.10.114]
36. Nuti E, Casalini F, Avramova SI, Santamaria S, Fabbi M, Ferrini S, Marinelli L, La Pietra V, Limongelli V, Novellino E, Cercignani G, Orlandini E, Nencetti S, Rossello A..  (2010)  Potent arylsulfonamide inhibitors of tumor necrosis factor-alpha converting enzyme able to reduce activated leukocyte cell adhesion molecule shedding in cancer cell models.,  53  (6): [PMID:20180536] [10.1021/jm901868z]
37. Nuti E, Casalini F, Santamaria S, Gabelloni P, Bendinelli S, Da Pozzo E, Costa B, Marinelli L, La Pietra V, Novellino E, Margarida Bernardo M, Fridman R, Da Settimo F, Martini C, Rossello A..  (2011)  Synthesis and biological evaluation in U87MG glioma cells of (ethynylthiophene)sulfonamido-based hydroxamates as matrix metalloproteinase inhibitors.,  46  (7): [PMID:21514700] [10.1016/j.ejmech.2011.03.033]
38. Tommasi RA, Weiler S, McQuire LW, Rogel O, Chambers M, Clark K, Doughty J, Fang J, Ganu V, Grob J, Goldberg R, Goldstein R, Lavoie S, Kulathila R, Macchia W, Melton R, Springer C, Walker M, Zhang J, Zhu L, Shultz M..  (2011)  Potent and selective 2-naphthylsulfonamide substituted hydroxamic acid inhibitors of matrix metalloproteinase-13.,  21  (21): [PMID:21937229] [10.1016/j.bmcl.2011.08.087]
39. Marques SM, Tuccinardi T, Nuti E, Santamaria S, André V, Rossello A, Martinelli A, Santos MA..  (2011)  Novel 1-hydroxypiperazine-2,6-diones as new leads in the inhibition of metalloproteinases.,  54  (24): [PMID:22017477] [10.1021/jm200593b]
40. Hugenberg V, Breyholz HJ, Riemann B, Hermann S, Schober O, Schäfers M, Gangadharmath U, Mocharla V, Kolb H, Walsh J, Zhang W, Kopka K, Wagner S..  (2012)  A new class of highly potent matrix metalloproteinase inhibitors based on triazole-substituted hydroxamates: (radio)synthesis and in vitro and first in vivo evaluation.,  55  (10): [PMID:22540974] [10.1021/jm300199g]
41. Jain P, Saravanan C, Singh SK..  (2013)  Sulphonamides: Deserving class as MMP inhibitors?,  60  [PMID:23287054] [10.1016/j.ejmech.2012.10.016]
42. Day JA, Cohen SM..  (2013)  Investigating the selectivity of metalloenzyme inhibitors.,  56  (20): [PMID:24074025] [10.1021/jm401053m]
43. Behrends M, Wagner S, Kopka K, Schober O, Schäfers M, Kumbhar S, Waller M, Haufe G..  (2015)  New matrix metalloproteinase inhibitors based on γ-fluorinated α-aminocarboxylic and α-aminohydroxamic acids.,  23  (13): [PMID:25921268] [10.1016/j.bmc.2015.03.078]

Source