ABT-770 - CAS 220614-50-6
Catalog number: 220614-50-6
Category: Inhibitor
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C22H22F3N3O6
Molecular Weight:
481.42
COA:
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Targets:
MMP
Description:
ABT-770 is a selective and orally bioavailable MMP inhibitor.
Purity:
>98%
Appearance:
Solid powder
Synonyms:
N-[(2S)-1-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-3-[4-[4-(trifluoromethoxy)phenyl]phenoxy]propan-2-yl]-N-hydroxyformamide; UNII-I8NWP25THF; CHEMBL40143; ABT-770
MSDS:
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InChIKey:
IIHFBHZWJNGWRC-INIZCTEOSA-N
InChI:
1S/C22H22F3N3O6/c1-21(2)19(30)27(20(31)26-21)11-16(28(32)13-29)12-33-17-7-3-14(4-8-17)15-5-9-18(10-6-15)34-22(23,24)25/h3-10,13,16,32H,11-12H2,1-2H3,(H,26,31)/t16-/m0/s1
Canonical SMILES:
CC1(C(=O)N(C(=O)N1)CC(COC2=CC=C(C=C2)C3=CC=C(C=C3)OC(F)(F)F)N(C=O)O)C
1.The evolution of the matrix metalloproteinase inhibitor drug discovery program at abbott laboratories.
Wada CK Curr Top Med Chem. 2004;4(12):1255-67.
Matrix metalloproteinases (MMPs) have been implicated in several pathologies. At Abbott Laboratories, the matrix metalloproteinases inhibitor drug discovery program has focused on the discovery of a potent, selective, orally bioavailable MMP inhibitor for the treatment of cancer. The program evolved from early succinate-based inhibitors to utilizing in-house technology such as SAR by NMR to develop a novel class of biaryl hydroxamate MMP inhibitors. The metabolic instability of the biaryl hydroxamates led to the discovery of a new class of N-formylhydroxylamine (retrohydroxamate) biaryl ethers, exemplified by ABT-770 (16). Toxicity issues with this pre-clinical candidate led to the discovery of another novel class of retrohydroxamate MMP inhibitors, the phenoxyphenyl sulfones such as ABT-518 (19j). ABT-518 is a potent, orally bioavailable, selective inhibitor of MMP-2 and 9 over MMP-1 that has been evaluated in Phase I clinical trials in cancer patients.
2.Phenoxyphenyl sulfone N-formylhydroxylamines (retrohydroxamates) as potent, selective, orally bioavailable matrix metalloproteinase inhibitors.
Wada CK;Holms JH;Curtin ML;Dai Y;Florjancic AS;Garland RB;Guo Y;Heyman HR;Stacey JR;Steinman DH;Albert DH;Bouska JJ;Elmore IN;Goodfellow CL;Marcotte PA;Tapang P;Morgan DW;Michaelides MR;Davidsen SK J Med Chem. 2002 Jan 3;45(1):219-32.
A novel series of sulfone N-formylhydroxylamines (retrohydroxamates) have been investigated as matrix metalloproteinases (MMP) inhibitors. The substitution of the ether linkage of ABT-770 (5) with a sulfone group 13a led to a substantial increase in activity against MMP-9 but was accompanied by a loss of selectivity for inhibition of MMP-2 and -9 over MMP-1 and diminished oral exposure. Replacement of the biphenyl P1' substituent with a phenoxyphenyl group provided compounds that are highly selective for inhibition of MMP-2 and -9 over MMP-1. Optimization of the substituent adjacent to the retrohydroxamate center in this series led to the clinical candidate ABT-518 (6), a highly potent, selective, orally bioavailable MMP inhibitor that has been shown to significantly inhibit tumor growth in animal cancer models.
3.Discovery and characterization of the potent, selective and orally bioavailable MMP inhibitor ABT-770.
Curtin ML;Florjancic AS;Heyman HR;Michaelides MR;Garland RB;Holms JH;Steinman DH;Dellaria JF;Gong J;Wada CK;Guo Y;Elmore IB;Tapang P;Albert DH;Magoc TJ;Marcotte PA;Bouska JJ;Goodfellow CL;Bauch JL;Marsh KC;Morgan DW;Davidsen SK Bioorg Med Chem Lett. 2001 Jun 18;11(12):1557-60.
Modification of the biphenyl portion of MMP inhibitor 2a gave analogue 2i which is greater than 1000-fold selective against MMP-2 versus MMP-1. The stereospecific synthesis of both enantiomers of 2i was achieved beginning with (S)- or (R)-benzyl glycidyl ether. The (S)-enantiomer, 11 (ABT-770), is orally bioavailable and efficacious in an in vivo model of tumor growth.
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