WO1998012156B1 - Combinatorial approach for generating novel coordination complexes - Google Patents
Combinatorial approach for generating novel coordination complexesInfo
- Publication number
- WO1998012156B1 WO1998012156B1 PCT/US1997/016740 US9716740W WO9812156B1 WO 1998012156 B1 WO1998012156 B1 WO 1998012156B1 US 9716740 W US9716740 W US 9716740W WO 9812156 B1 WO9812156 B1 WO 9812156B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- groups
- pbm
- bicyclo
- metal
- library
- Prior art date
Links
- 229910052751 metal Inorganic materials 0.000 claims abstract 36
- 239000002184 metal Substances 0.000 claims abstract 36
- 125000004429 atoms Chemical group 0.000 claims abstract 17
- 230000027455 binding Effects 0.000 claims abstract 16
- 150000002500 ions Chemical class 0.000 claims abstract 6
- -1 carboline Chemical compound 0.000 claims 30
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 12
- 150000003568 thioethers Chemical class 0.000 claims 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 8
- ABLZXFCXXLZCGV-UHFFFAOYSA-L CHEBI:8154 Chemical class [O-]P([O-])=O ABLZXFCXXLZCGV-UHFFFAOYSA-L 0.000 claims 6
- 229940093912 Gynecological Sulfonamides Drugs 0.000 claims 6
- VJKDMEHBNCSKBM-UHFFFAOYSA-N NP[O-] Chemical class NP[O-] VJKDMEHBNCSKBM-UHFFFAOYSA-N 0.000 claims 6
- BKIMMITUMNQMOS-UHFFFAOYSA-N Nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims 6
- AQSJGOWTSHOLKH-UHFFFAOYSA-N Phosphite Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims 6
- 125000003368 amide group Chemical group 0.000 claims 6
- 150000001412 amines Chemical class 0.000 claims 6
- 150000001414 amino alcohols Chemical class 0.000 claims 6
- 125000003277 amino group Chemical group 0.000 claims 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 6
- 150000004982 aromatic amines Chemical class 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- 150000001720 carbohydrates Chemical group 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 6
- 125000004185 ester group Chemical group 0.000 claims 6
- 150000002170 ethers Chemical class 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 6
- 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 claims 6
- 150000002576 ketones Chemical class 0.000 claims 6
- AWIJRPNMLHPLNC-UHFFFAOYSA-N methanethioic S-acid Chemical compound SC=O AWIJRPNMLHPLNC-UHFFFAOYSA-N 0.000 claims 6
- 150000002825 nitriles Chemical class 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims 6
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 claims 6
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims 6
- 235000021317 phosphate Nutrition 0.000 claims 6
- 150000008298 phosphoramidates Chemical class 0.000 claims 6
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 6
- 150000003456 sulfonamides Chemical class 0.000 claims 6
- 150000003871 sulfonates Chemical class 0.000 claims 6
- 150000003460 sulfonic acids Chemical class 0.000 claims 6
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 6
- 150000003573 thiols Chemical class 0.000 claims 6
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical class [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims 6
- 229940026752 topical Sulfonamides Drugs 0.000 claims 6
- LGVJRKCQQHOWAU-IUCAKERBSA-N (4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-1H-naphthalen-2-one Chemical compound C1CCC[C@H]2CC(=O)CC[C@@H]21 LGVJRKCQQHOWAU-IUCAKERBSA-N 0.000 claims 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 4
- RAOIDOHSFRTOEL-UHFFFAOYSA-N Tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 4
- 150000001336 alkenes Chemical class 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 4
- 238000006555 catalytic reaction Methods 0.000 claims 4
- 239000002738 chelating agent Substances 0.000 claims 4
- NNBZCPXTIHJBJL-AOOOYVTPSA-N cis-decalin Chemical compound C1CCC[C@H]2CCCC[C@H]21 NNBZCPXTIHJBJL-AOOOYVTPSA-N 0.000 claims 4
- 150000002402 hexoses Chemical class 0.000 claims 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 150000002972 pentoses Chemical class 0.000 claims 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 125000003367 polycyclic group Chemical group 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 230000002194 synthesizing Effects 0.000 claims 4
- 150000003512 tertiary amines Chemical class 0.000 claims 4
- 239000003863 metallic catalyst Substances 0.000 claims 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 3
- 125000002524 organometallic group Chemical group 0.000 claims 3
- 229910052723 transition metal Inorganic materials 0.000 claims 3
- 150000003624 transition metals Chemical class 0.000 claims 3
- LQRRFNCMOSZKEG-QCNOEVLYSA-N (1R,3S,5R,6S)-3-ethyl-5-propan-2-ylbicyclo[4.1.0]heptane Chemical compound CC(C)[C@H]1C[C@@H](CC)C[C@@H]2C[C@@H]21 LQRRFNCMOSZKEG-QCNOEVLYSA-N 0.000 claims 2
- ZPTPRBUZSDEMFW-IDWGSYCQSA-N (2S,3S)-3-ethyl-2-methylbicyclo[2.2.2]octane Chemical compound C1CC2[C@H](CC)[C@@H](C)C1CC2 ZPTPRBUZSDEMFW-IDWGSYCQSA-N 0.000 claims 2
- MMFIVCKQSHNWOM-IUCAKERBSA-N (3aS,7aS)-3a,7a-dibromo-2,3,4,5,6,7-hexahydro-1H-indene Chemical compound C1CCC[C@@]2(Br)[C@@]1(Br)CCC2 MMFIVCKQSHNWOM-IUCAKERBSA-N 0.000 claims 2
- AEBWATHAIVJLTA-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropentalene Chemical compound C1CCC2CCCC21 AEBWATHAIVJLTA-UHFFFAOYSA-N 0.000 claims 2
- DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 claims 2
- LSXZUNNXVYAILL-UHFFFAOYSA-N 1,4-di(propan-2-yl)bicyclo[2.2.2]octane Chemical compound C1CC2(C(C)C)CCC1(C(C)C)CC2 LSXZUNNXVYAILL-UHFFFAOYSA-N 0.000 claims 2
- WCSGCOPRAGHXFK-UHFFFAOYSA-N 1,4-dimethylbicyclo[2.2.0]hexane Chemical compound C1CC2(C)CCC21C WCSGCOPRAGHXFK-UHFFFAOYSA-N 0.000 claims 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 2
- ILFYOWGJBKEMSK-UHFFFAOYSA-N 10H-phenoselenazine Chemical compound C1=CC=C2NC3=CC=CC=C3[Se]C2=C1 ILFYOWGJBKEMSK-UHFFFAOYSA-N 0.000 claims 2
- ZKUOFPDCKZKYBF-UHFFFAOYSA-N 10H-phenoxaphosphinine Chemical compound C1=CC=C2OC3=CC=CC=C3PC2=C1 ZKUOFPDCKZKYBF-UHFFFAOYSA-N 0.000 claims 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 2
- MFJCPDOGFAYSTF-UHFFFAOYSA-N 1H-isochromene Chemical compound C1=CC=C2COC=CC2=C1 MFJCPDOGFAYSTF-UHFFFAOYSA-N 0.000 claims 2
- AAQTWLBJPNLKHT-UHFFFAOYSA-N 1H-perimidine Chemical compound N1C=NC2=CC=CC3=CC=CC1=C32 AAQTWLBJPNLKHT-UHFFFAOYSA-N 0.000 claims 2
- ODMMNALOCMNQJZ-UHFFFAOYSA-N 1H-pyrrolizine Chemical compound C1=CC=C2CC=CN21 ODMMNALOCMNQJZ-UHFFFAOYSA-N 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims 2
- AJMWCFROLSOPQL-UHFFFAOYSA-N 2H-isophosphindole Chemical compound C1=CC=CC2=CPC=C21 AJMWCFROLSOPQL-UHFFFAOYSA-N 0.000 claims 2
- FSNXAYJQMDEIOT-UHFFFAOYSA-N 3-methylbicyclo[2.1.0]pentane Chemical compound CC1CC2CC12 FSNXAYJQMDEIOT-UHFFFAOYSA-N 0.000 claims 2
- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 claims 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N Acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N Anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N Azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 2
- SELUFQBSYXBQEB-UHFFFAOYSA-N C1=CC=C2OC3=CC=CC=C3[AsH]C2=C1 Chemical compound C1=CC=C2OC3=CC=CC=C3[AsH]C2=C1 SELUFQBSYXBQEB-UHFFFAOYSA-N 0.000 claims 2
- WGSAXLDKNVEUON-UHFFFAOYSA-N C1=CC=C2OC3=CC=CC=C3[SbH]C2=C1 Chemical compound C1=CC=C2OC3=CC=CC=C3[SbH]C2=C1 WGSAXLDKNVEUON-UHFFFAOYSA-N 0.000 claims 2
- MSVSJBJSJCKNJD-UHFFFAOYSA-N C1=CC=CC2=C[AsH]C=C21 Chemical compound C1=CC=CC2=C[AsH]C=C21 MSVSJBJSJCKNJD-UHFFFAOYSA-N 0.000 claims 2
- KUQYFTVHQPWHPP-UHFFFAOYSA-N C1=CC=CC2=[As]C3=CC=CC=C3C=C12 Chemical compound C1=CC=CC2=[As]C3=CC=CC=C3C=C12 KUQYFTVHQPWHPP-UHFFFAOYSA-N 0.000 claims 2
- HEZMQKDNJZOBEM-NOFOHJPNSA-N C1CCC[C@@H]2CCCC[C@H]21.C1CCC[C@@H]2CCCC[C@H]21 Chemical compound C1CCC[C@@H]2CCCC[C@H]21.C1CCC[C@@H]2CCCC[C@H]21 HEZMQKDNJZOBEM-NOFOHJPNSA-N 0.000 claims 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N Cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims 2
- TXWRERCHRDBNLG-UHFFFAOYSA-N Cubane Chemical compound C12C3C4C1C1C4C3C12 TXWRERCHRDBNLG-UHFFFAOYSA-N 0.000 claims 2
- ZICQBHNGXDOVJF-UHFFFAOYSA-N Diamantane Chemical compound C1C2C3CC(C4)CC2C2C4C3CC1C2 ZICQBHNGXDOVJF-UHFFFAOYSA-N 0.000 claims 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N Indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims 2
- HOBCFUWDNJPFHB-UHFFFAOYSA-N Indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims 2
- UXGVMFHEKMGWMA-UHFFFAOYSA-N Isobenzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N Isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N Isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N Isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 2
- 241000711937 Marburg marburgvirus Species 0.000 claims 2
- WPHGSKGZRAQSGP-UHFFFAOYSA-N Norcarane Chemical compound C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 claims 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N Phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical compound C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N Phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims 2
- 229950000688 Phenothiazine Drugs 0.000 claims 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N Phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N Phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims 2
- CPNGPNLZQNNVQM-UHFFFAOYSA-N Pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 claims 2
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N Pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N Pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N Quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N Quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 2
- GVIJJXMXTUZIOD-UHFFFAOYSA-N Thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 claims 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N Xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 2
- KQXCHJWEKGZFKJ-UHFFFAOYSA-N [As]1=CC=CC2=CC=CC=C12 Chemical compound [As]1=CC=CC2=CC=CC=C12 KQXCHJWEKGZFKJ-UHFFFAOYSA-N 0.000 claims 2
- BVUSIQTYUVWOSX-UHFFFAOYSA-N arsindole Chemical compound C1=CC=C2[As]C=CC2=C1 BVUSIQTYUVWOSX-UHFFFAOYSA-N 0.000 claims 2
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 claims 2
- JAPMJSVZDUYFKL-UHFFFAOYSA-N bicyclo[3.1.0]hexane Chemical compound C1CCC2CC21 JAPMJSVZDUYFKL-UHFFFAOYSA-N 0.000 claims 2
- AWYMFBJJKFTCFO-UHFFFAOYSA-N bicyclo[3.2.0]heptane Chemical compound C1CCC2CCC21 AWYMFBJJKFTCFO-UHFFFAOYSA-N 0.000 claims 2
- GNTFBMAGLFYMMZ-UHFFFAOYSA-N bicyclo[3.2.2]nonane Chemical compound C1CC2CCC1CCC2 GNTFBMAGLFYMMZ-UHFFFAOYSA-N 0.000 claims 2
- NAVGAEZCCRCJQT-UHFFFAOYSA-N bicyclo[3.3.3]undecane Chemical compound C1CCC2CCCC1CCC2 NAVGAEZCCRCJQT-UHFFFAOYSA-N 0.000 claims 2
- OOSCHYDNHHSIKU-UHFFFAOYSA-N bicyclo[4.3.2]undecane Chemical compound C1CC2CCCC1CCCC2 OOSCHYDNHHSIKU-UHFFFAOYSA-N 0.000 claims 2
- MYQCLBRBMFFFGU-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2OC=C=CC2=C1 MYQCLBRBMFFFGU-UHFFFAOYSA-N 0.000 claims 2
- 150000001913 cyanates Chemical class 0.000 claims 2
- HTFFABIIOAKIBH-UHFFFAOYSA-N diazinane Chemical compound C1CCNNC1 HTFFABIIOAKIBH-UHFFFAOYSA-N 0.000 claims 2
- QXYJCZRRLLQGCR-UHFFFAOYSA-N dioxomolybdenum Chemical compound O=[Mo]=O QXYJCZRRLLQGCR-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N furane Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- TYRUNUXIEAQAMR-UHFFFAOYSA-N furazan Chemical compound C=1=[CH]=NON=1 TYRUNUXIEAQAMR-UHFFFAOYSA-N 0.000 claims 2
- 150000002466 imines Chemical class 0.000 claims 2
- 150000002513 isocyanates Chemical class 0.000 claims 2
- 150000002527 isonitriles Chemical class 0.000 claims 2
- ODZILJDRJCJHKM-UHFFFAOYSA-N isophosphinoline Chemical compound C1=PC=CC2=CC=CC=C21 ODZILJDRJCJHKM-UHFFFAOYSA-N 0.000 claims 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims 2
- 150000002602 lanthanoids Chemical class 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 239000011159 matrix material Substances 0.000 claims 2
- 235000013919 monopotassium glutamate Nutrition 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 229940113083 morpholine Drugs 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 150000005038 phenomercurazines Chemical class 0.000 claims 2
- 150000005037 phenotellurazines Chemical class 0.000 claims 2
- IZEKPBQZEZRUJK-UHFFFAOYSA-N phenoxaselenine Chemical compound C1=CC=C2OC3=CC=CC=C3[Se]C2=C1 IZEKPBQZEZRUJK-UHFFFAOYSA-N 0.000 claims 2
- ALKPUAAMDTXQAK-UHFFFAOYSA-N phenoxatellurine Chemical compound C1=CC=C2OC3=CC=CC=C3[Te]C2=C1 ALKPUAAMDTXQAK-UHFFFAOYSA-N 0.000 claims 2
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 claims 2
- 150000003003 phosphines Chemical class 0.000 claims 2
- SRHXVXDPXODKQP-UHFFFAOYSA-N phosphinoline Chemical compound P1=CC=CC2=CC=CC=C21 SRHXVXDPXODKQP-UHFFFAOYSA-N 0.000 claims 2
- 125000000708 phosphoindolyl group Chemical class P(=O)(=O)C1=C(NC2=CC=CC=C12)* 0.000 claims 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- IESITBBFRHFJKD-UHFFFAOYSA-N selenanthrene Chemical compound C1=CC=C2[Se]C3=CC=CC=C3[Se]C2=C1 IESITBBFRHFJKD-UHFFFAOYSA-N 0.000 claims 2
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 claims 2
- 241000894007 species Species 0.000 claims 2
- 230000000707 stereoselective Effects 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- TULWUZJYDBGXMY-UHFFFAOYSA-N tellurophene Chemical compound [Te]1C=CC=C1 TULWUZJYDBGXMY-UHFFFAOYSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 150000004043 trisaccharides Chemical class 0.000 claims 2
- SAMNWPYLFOORHG-UHFFFAOYSA-N 1,6a-dimethyl-2,3,3a,4,5,6-hexahydro-1H-pentalene Chemical compound C1CCC2(C)C(C)CCC21 SAMNWPYLFOORHG-UHFFFAOYSA-N 0.000 claims 1
- MHUTYVBIXPTFHF-UHFFFAOYSA-N 6,9-dimethylbicyclo[4.2.1]nonane Chemical compound C1CCCC2(C)CCC1C2C MHUTYVBIXPTFHF-UHFFFAOYSA-N 0.000 claims 1
- NGSMAXPULGPQNT-UHFFFAOYSA-N 7,7-dimethylbicyclo[2.2.1]heptane Chemical compound C1CC2CCC1C2(C)C NGSMAXPULGPQNT-UHFFFAOYSA-N 0.000 claims 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N Octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 1
- JSMRMEYFZHIPJV-UHFFFAOYSA-N bicyclo[2.1.1]hexane Chemical compound C1C2CC1CC2 JSMRMEYFZHIPJV-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229910052803 cobalt Inorganic materials 0.000 claims 1
- 238000006352 cycloaddition reaction Methods 0.000 claims 1
- 238000006735 epoxidation reaction Methods 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane Chemical compound CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 claims 1
- 229930006728 pinane Natural products 0.000 claims 1
- 238000007142 ring opening reaction Methods 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 abstract 1
- 125000002091 cationic group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052755 nonmetal Inorganic materials 0.000 abstract 1
Abstract
The present invention provides methods and compositions, i.e. synthetic libraries of binding moities, for identifying compounds which bind to a metal atom or to non-metal ions, e.g., cationic or anionic molecules.
Claims
1. A method for identifying a chelating agent for a metal or ion, comprising
(a) chemically synthesizing a variegated library of potential binding moieties (PBMs) from a variegated assortment of metal binding groups (MBGs) bearing Lewis basic atoms and turn elements, the PBMs of the PBM library having at least one turn element substituted at least twice with MBGs; and
(b) isolating PBMs from the PBM library on the basis of ability to bind to a metal or ion.
2. The method of claim 1 , wherein the turn element is has a reduced number of internal rotational bonds.
3. The method of claim 1 , wherein the turn element is a carbocycle or heterocycle.
4. The method of claim 3. wherein the turn element is selected from the group consisting of a monocyclic ring and a polycyclic ring.
5. The method of claim 3, wherein the turn element is selected from the group consisting of acridarsine. acridine, anthracene . arsindole, arsinoline, azepane, benzene, carbazole, carboline, chromene, cinnoline, furan, furazan, hexahydropyridazine, hexahydropyrimidine, imidazole, indane, indazole, indole, indolizine, isoarsindole, isobenzofuran, isochromene, isoindole, isophosphindole, isophosphinoline, isoquinoline, isorasinoline, isothiazole, isoxazole, morpholine, naphthalene, naphthyridine, oxazole. oxolane, perimidine. phenanthrene. phenanthridine, phenanthroline, phenarsazine, phenazine, phenomercurazine, phenomercurin, phenophosphazine, phenoselenazine, phenotellurazine. phenothiarsine, phenoxantimonin, phenoxaphosphine, phenoxarsine, phenoxaselenin, phenoxatellurin, phenothiazine, phenoxathiin, phenoxazine. phosphanthene. phosphindole, phosphinoline, phthalazine, piperazine, piperazine, piperidine, piperidine, pteridine, purine, pyran, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyrrolidine, pyrrolidine, pyrrolizine, quinazoline. quinoline, quinolizine, quinoxaline. selenanthrene, selenophene. tellurophene. tetrahydrofuran, tetrahydrothiophene. thianthrene. thiazole, thiolane, thiophene and xanthene.
6. The method of claim 3. wherein the turn element is a bicyclo[x.y.z]alkane, where x, y and z are each integers of 1 or greater.
7. The method of claim 6, wherein the bicyclo[x.y.z]alkane, is selected from the group consisting of 2-methylbicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, 1,4- dimethylbicyclo [2.2.0]hexane, bicyclo[2,2,l]heptane (norbornane), 7,7- dimethylbicyclo[2.2.1 ]heptane, endo-2-Isopropyl-7,7-dimethylbicyclo[2.2.1 Jheptane. trans-bicyclo[4.4.0]decan-3-one, bicyclo[2.2.2]octane, 1,4- diisopropylbicyclo[2.2.2]octane, (2S,3S)-2-ethyl-3-methyl-bicyclo[2.2.2]octane, bicyclo[3.1.0]hexane, 2,6,6-Trimethylbicyclo[3.1.1]heptane. bicyclo-[3.2.0]heptane, bicyclo[3.2.2]nonane, bicyclo [3, 3,0] octane, l,2-dimethylbicyclo-[3.3.0]octane, bicyclo[3.3.3]undecane, bicyclo[4.1.0]heptane, (l S,2R,4S,6R)-4-Ethyl-2- isopropylbicyclo[4.1.0]heptane, cis-bicyclo[4.2.1]nonane, 1 ,9-Dimethylbicyclo- [4.2.1]nonane, trans-1 ,6-dibromobicyclo[4,3,0]nonane, l-Methyl-8-propylbicyclo- [4.3.0]nonane, bicyclo[4.3.2]undecane, cis-bicyclo[4.4.0]decane (cis-Decalin), trans- bicyclo[4.4.0]decane (trans-Decalin), and trans-Bicyclo[4.4.0]decan-3-one.
8. The method of claim 3, wherein the turn element is a bridged heterocycle.
9. The method of claim 3, wherein the turn element is a caged polycycle.
10. The method of claim 9, wherein the caged polycycle is selected from the group consisting of adamantane. diamantane, cubane and quadricyclene.
1 1. The method of claim 3, wherein the turn element is a saccharide.
12. The method of claim 1 1 , wherein the saccharide is a mono-, di- or trisaccharide.
13. The method of claim 1 1, wherein the saccharide is a pentose or hexose sugar, or pentose or hexose azasugar.
14. The method of any of claims 1-13, wherein at least one turn element provided in the PBM library is a chiral turn element.
15. The method of claim 14, wherein the PBM library includes at least two stereoisomers of a chiral turn elements.
16. The method of claim 15, wherein the stereoisomers are enantiomeric chiral turn elements.
17. The method of claim 15, wherein the stereoisomers are diastereomeric chiral turn elements.
18. The method of any of claims 1-13, wherein the PBM library is variegated with respect to turn elements incorporated in the individual PBMs.
19. The method of claim 1 , wherein PBM library includes MBGs having one or more Lewis basic atoms.
20. The method of claim 19, wherein the Lewis basic groups atoms are selected from Group 15 and Group 16 atoms.
21. The method of claim 19, wherein the Lewis basic groups atoms are selected from Nitrogen, Oxygen, Phosphorous and Sulfur.
22. The method of claim 19, wherein the MBGs are selected from the group consisting of amines (primary, secondary, and tertiary), aromatic amines, amino groups, amido groups, nitro groups, nitroso groups, amino alcohols, nitriles, isonitriles, cyanates, isocyanates, imino groups, phosphates, phosphonates, phosphites, substituted and unsubsituted phosphines, phosphine oxides, phosphorothioates, phosphoramidates, phosphonamidites, hydroxyls, carbonyls (e.g., carboxyl, ester and formyl groups), aldehydes, ketones, ethers, carbamoyl groups, thiols, sulfides, thiocarbonyls (e.g., thiolcarboxyl, thiolester and thiolformyl groups), thioethers, mercaptans, sulfonic acids, sulfates, sulfonates, sulfonones, sulfonamides, sulfamoyls and sulfinyls.
23. The method of claim 1, wherein the PBM library is immobilized on an insoluble matrix.
24. The method of claim 1 , wherein PBMs are isolated from the PBM library on the basis of ability to bind to a metal.
25. The method of claim 24, wherein the metal is a transition metal.
26. The method of claim 24, wherein the metal is a Lanthanide metal.
27. The method of claim 24, wherein the metal is selected from the group consisting of Co +, Cr3+, Hg2+, Pd +, Pt +, Pd4+, Pt4+, Rh3+, Ir3+, Ru3+, Co +, Ni2+, Cu +, Zn2+, Cd +, Pb2+, Mn2+, Fe3+, Fe2+, Au3+, Au+, Ag+, Cu+, MO2 2+, Ti +, Bi3+, CH3Hg+, Al3+, Ga3+, Ce3+, UO2 2+, and La +.
28. The method of claim 1, wherein the PBM library includes at least 102 different PBM species.
29. A method for identifying a chelating agent for a metal or ion, comprising
(a) chemically synthesizing a variegated library of potential binding moieties (PBMs) represented by the general formula:
wherein
A represents a carbocycle or heterocycle which can be monocyclic or polycyclic, aromatic or non-aromatic;
RI and R2 each represent, independently for each occurrence in a PBM of the PBM library, an MPG including a moiety selected from the group consisting of amines (primary, secondary, and tertiary and aromatic amines), amino groups, amido groups, nitro groups, nitroso groups, amino alcohols, nitriles, imino groups, phosphates, phosphonates, phosphites, (substituted) phosphines, phosphine oxides, phosphorothioates, phosphoramidates, phosphonamidites, hydroxyls, carbonyls (e.g., carboxyl, ester and formyl groups), aldehydes, ketones, ethers, carbamoyl groups, thiols, sulfides, thiocarbonyls (e.g., thiolcarboxyl, thiolester and thiolformyl groups), thioethers, mercaptans, sulfonic acids, sulfates, sulfonates, sulfonones, sulfonamides, sulfamoyls and sulfinyls, or alkyl, alkenyl or alkynyl groups (preferably in the range of Cj-C30) substituted therewith; R3 is absent or represents one or more further MPG substitutions to the ring
A, each occurrence of which independently includes a moiety selected from the group consisting of amines (primary, secondary, and tertiary and aromatic amines), amino groups, amido groups, nitro groups, nitroso groups, amino alcohols, nitriles, imino groups, phosphates, phosphonates, phosphites, (substituted) phosphines, phosphine oxides, phosphorothioates, phosphoramidates, phosphonamidites, hydroxyls, carbonyls (e.g., carboxyl, ester and formyl groups), aldehydes, ketones, ethers, carbamoyl groups, thiols, sulfides, thiocarbonyls (e.g., thiolcarboxyl, thiolester and thiolformyl groups), thioethers, mercaptans, sulfonic acids, sulfates, sulfonates, sulfonones, sulfonamides, sulfamoyls and sulfinyls, or alkyl, alkenyl or alkynyl groups (preferably in the range of C j -C3o) substituted therewith
(b) isolating PBMs from the PBM library on the basis of ability to bind to a metal or ion.
30. A library of potential metal binding ligands comprising at least one turn element represented by the general formula: T-R1(-R2)(-R3), wherein T is a turn element, RI and R2 are, individually, substituents of turn element T each having at least one Lewis basic moiety for binding to a metal atom, and R3 is absent or represents one or more substituents of T each having at least one Lewis basic moiety for binding to a metal atom.
31. A chelating agent identified according to the method of claim 1 or 29.
32. A method for generating an organo-metallic catalyst, comprising
(a) chemically synthesizing a variegated library of potential binding moieties (PBMs) from a variegated assortment of metal binding groups (MBGs) bearing Lewis basic atoms and turn elements, the PBMs of the PBM library having at least one turn element substituted at least twice with MBGs; and
(b) contacting the PBM library, during or after its synthesis, with one or more metals under conditions wherein PBMs able to bind to the metal form PBM-metal complexes
(c) determining the ability of the PBM-metal complexes to catalyze a reaction.
33. The method of claim 32, wherein the turn element has a reduced number of internal rotatable bonds.
34. The method of claim 32, wherein the turn element is a carbocycle or heterocycle.
35. The method of claim 34, wherein the turn element is selected from the group consisting of a monocyclic ring and a polycyclic ring.
36. The method of claim 34, wherein the turn element is selected from the group consisting of acridarsine, acridine. anthracene, arsindole, arsinoline. azepane, benzene, carbazole, carboline, chromene, cinnoline, furan, furazan, hexahydropyridazine, hexahydropyrimidine, imidazole, indane, indazole, indole, indolizine, isoarsindole, isobenzofuran, isochromene, isoindole, isophosphindole, isophosphinoline, isoquinoline, isorasinoline, isothiazole, isoxazole, morpholine, naphthalene, naphthyridine, oxazole, oxolane, perimidine, phenanthrene, phenanthridine, phenanthroline, phenarsazine, phenazine. phenomercurazine, phenomercurin, phenophosphazine, phenoselenazine, phenotellurazine, phenothiarsine, phenoxantimonin, phenoxaphosphine, phenoxarsine, phenoxaselenin, phenoxatellurin, phenothiazine, phenoxathiin, phenoxazine, phosphanthene, phosphindole, phosphinoline, phthalazine, piperazine, piperazine, piperidine, piperidine, pteridine, purine, pyran, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyrrolidine, pyrrolidine, pyrrolizine, quinazoline, quinoline, quinolizine, quinoxaline, selenanthrene, selenophene, tellurophene, tetrahydrofuran, tetrahydrothiophene, thianthrene, thiazole, thiolane, thiophene and xanthene.
37. The method of claim 34, wherein the turn element is a bicyclo[x.y.z]alkane, where x, y and z are each integers of 0 or greater.
38. The method of claim 37, wherein the bicyclo[x.y.z]alkane, is selected from the group consisting of 2-methylbicyclo[2.1.0]pentane, bicyclo[2.1.1 Jhexane, 1 ,4- dimethylbicyclo [2.2.0]hexane, bicyclo[2,2,l]heptane (norbornane), 7,7- dimethylbicyclo[2.2.1 jheptane, endo-2-Isopropyl-7,7- dimethylbicyclo[2.2.1 Jheptane, trans-bicyclo[4.4.0]decan-3-one, bicyclo[2.2.2]octane, 1 ,4-diisopropylbicyclo[2.2.2]octane, (2S,3S)-2-ethyl-3- methyl-bicyclo[2.2.2]octane, bicyclo[3.1.0]hexane, 2,6,6- Trimethylbicyclo[3.1.l]heptane, bicyclo-[3.2.0]heptane, bicyclo[3.2.2]nonane, bicyclo[3,3,0]octane, 1 ,2-dimethylbicyclo- [3.3.0] octane, bicyclo[3.3.3]undecane, bicyclo[4.1.0]heptane, ( 1 S,2R,4S,6R)-4-Ethyl-2-isopropylbicyclo[4.1.0]heptane, cis- bicyclo[4.2.1]nonane, l,9-Dimethylbicyclo-[4.2.1]nonane, trans-1,6- dibromobicyclo[4,3,0]nonane, l-Methyl-8-propylbicyclo-[4.3.0]nonane, bicyclo[4.3.2]undecane, cis-bicyclo[4.4.0]decane (cis-Decalin), trans- bicyclo[4.4.0]decane (trans-Decalin), and trans-Bicyclo[4.4.0]decan-3-one.
39. The method of claim 34, wherein the turn element is a bridged heterocycle.
40. The method of claim 34, wherein the turn element is a caged polycycle.
41. The method of claim 40, wherein the caged polycycle is selected from the group consisting of adamantane, diamantane, cubane and quadricyclene.
42. The method of claim 34, wherein the turn element is a saccharide.
43. The method of claim 42, wherein the saccharide is a mono-, di- or trisaccharide.
44. The method of claim 42, wherein the saccharide is a pentose or hexose sugar, or pentose or hexose azasugar.
45. The method of any of claims 32-44. wherein at least one turn element provided in the PBM library is a chiral turn element.
46. The method of claim 45, wherein the PBM library includes at least two stereoisomers of a chiral turn element.
47. The method of claim 46, wherein the stereoisomers are enantiomeric chiral turn elements.
48. The method of claim 46, wherein the stereoisomers are diastereomeric chiral turn elements.
49. The method of any of claims 32-44, wherein the PBM library is variegated with respect to turn elements incorporated in the individual PBMs.
50. The method of claim 42, wherein the PBM library includes MBGs having one or more Lewis basic atoms.
51. The method of claim 50, wherein the Lewis basic atoms are selected from Group 15 and Group 16 atoms.
52. The method of claim 50, wherein the Lewis basic atoms are selected from Nitrogen, Oxygen, Phosphorous and Sulfur.
53. The method of claim 49, wherein the MBGs are selected from the group consisting of amines (primary, secondary, and tertiary), aromatic amines, amino groups, amido groups, nitro groups, nitroso groups, amino alcohols, nitriles, isonitriles, cyanates, isocyanates, imino groups, phosphates, phosphonates, phosphites, substituted and unsubsituted phosphines, phosphine oxides, phosphorothioates, phosphoramidates, phosphonamidites, hydroxyls, carbonyls (e.g., carboxyl, ester and formyl groups), aldehydes, ketones, ethers, carbamoyl groups, thiols, sulfides, thiocarbonyls (e.g., thiolcarboxyl, thiolester and thiolformyl groups), thioethers, mercaptans, sulfonic acids, sulfates, sulfonates, sulfonones, sulfonamides, sulfamoyls and sulfinyls.
54. The method of claim 32, wherein the PBM library is immobilized on an insoluble matrix.
55. The method of claim 32, wherein the metal is a transition metal.
56. The method of claim 32, wherein the metal is a Lanthanide metal.
57. The method of claim 32, wherein the metal is selected from the group consisting of Co3+, Cr3+, Hg2+, Pd2+, Pt +, Pd4+ Pt4+, Rh3+, Ir3+, Ru3+, Co2+ Ni2+s Cu2+ Zn2+ Cd2+ Pb2+ Mn2+5 Fe3+ Fe2+5 Au3+ Au+ Ag+
Cu+, MoO2 2+, Ti3+, Bi +, CH3Hg+, Al3+, Ga3+ Ce3+, UO2 2+, and La3+.
58. The method of claim 32, wherein the PBM library includes at least 102 different PBM species.
59. The method of claim 32, wherein the PBM-metal complexes include PBMs which chelate the metal.
60. The method of claim 32 or 59, wherien the metal of the PBM-metal complexes has at least 2 free coordination sites.
61. The method of claim 32, wherein the ability of the PBM-metal complexes to catalyze a stereoselective reaction is determined.
62. The method of claim 32 or 61, wherein the efficiency of the PBM-metal complexes to catalyze a reaction is determined.
63. The method of claim 32 or 61, wherein the selectivity of the PBM-metal complexes to catalyze a reaction is determined.
64. The method of claim 32, wherein the PBM library includes at least 100 diversomers represented by the general formula:
wherein
A represents a carbocycle or heterocycle which can be monocyclic or polycyclic, aromatic or non-aromatic;
RI and R2 each represent, independently for each occurrence in a PBM of the PBM library, an MBG including at least one moiety selected from the group consisting of amines (primary, secondary, and tertiary and aromatic amines), amino groups, amido groups, nitro groups, nitroso groups, amino alcohols, nitriles, imino groups, phosphates, phosphonates, phosphites, (substituted) phosphines, phosphine oxides, phosphorothioates, phosphoramidates, phosphonamidites, hydroxyls, carbonyls (e.g., carboxyl, ester and formyl groups), aldehydes, ketones, ethers, carbamoyl groups, thiols, sulfides, thiocarbonyls (e.g., thiolcarboxyl, thiolester and thiolformyl groups), thioethers, mercaptans, sulfonic acids, sulfates, sulfonates, sulfonones, sulfonamides, sulfamoyls and sulfinyls, or alkyl, alkenyl or alkynyl groups (preferably in the range of C1-C30) substituted therewith; R3 is absent or represents one or more further MBG substitutions to the ring A, each occurence of which independently includes a moiety selected from the group consisting of amines
(primary, secondary, and tertiary and aromatic amines), amino groups, amido groups, nitro groups, nitroso groups, amino alcohols, nitriles, imino groups, phosphates, phosphonates, phosphites, (substituted) phosphines, phosphine oxides, phosphorothioates, phosphoramidates, phosphonamidites, hydroxyls, carbonyls (e.g., carboxyl, ester and formyl groups), aldehydes, ketones, ethers, carbamoyl groups, thiols, sulfides, thiocarbonyls (e.g., thiolcarboxyl, thiolester and thiolformyl groups), thioethers, mercaptans, sulfonic acids, sulfates, sulfonates, sulfonones, sulfonamides, sulfamoyls and sulfinyls, or alkyl, alkenyl or alkynyl groups (preferably in the range of C1-C30) substituted therewith
(b) isolating PBMs from the PBM library on the basis of ability to bind to a metal or ion.
65. A library of potential metal binding ligands comprising at least one turn element represented by the general formula: T-R1(-R2)(-R3), wherein T is a turn element, RI and R2 are, individually, substituents of turn element T each having at least one Lewis basic moiety for binding to a metal atom, and R3 is absent or represents one or more substituents of T each having at least one Lewis basic moiety for binding to a metal atom.
66. A library of potential organo-metallic catalysts comprising at least one turn element represented by the general formula: T-R1(-R2)(-R3), wherein T is a turn element, RI and R2 are, individually, substituents of turn element T each having at least one Lewis basic moiety for binding to a metal atom, and R3 is absent or represents one or more substituents of T each having at least one Lewis basic moiety for binding to a metal atom.
67. A chelating agent identified according to the method of any of claims 1-30.
68. An organo-metallic catalysts identified according to the method of any of claims 32-64. -60-
69. The method of claim 24, wherein the metal-PBM complexes are further selected on the basis of their ability to catalyze a metal-catalyzed reaction.
70. The method of claim 25, wherein the metal-PBM complexes are further selected on the basis of their ability to catalyze a transition metal -catalyzed reaction.
71. The method of claim 26, wherein the metal-PBM complexes are further selected on the basis of their ability to catalyze a lanthanide-catalyzed reaction.
72. The method of claim 69-71 , wherein the catalyzed reaction is stereoselective.
73. The method of claim 32, wherein the reaction is a ring-opening, a carbonyl addition, a carbonyl reduction, an olefin addition, an olefin reduction, an imine addition, an imine reduction, a cycloaddition, a sigmatropic rearrangement, an olefin epoxidation, or an olefin aziridination.
74. The method of claim 32, wherein the metal-PBM complexes are identified on the basis of their ability to catalyze a reaction which results in a change in absorbence of light of any wavelength, the evolution of gas, a temperature change, or any combination of these results.
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| US6720186B1 (en) | 1998-04-03 | 2004-04-13 | Symyx Technologies, Inc. | Method of research for creating and testing novel catalysts, reactions and polymers |
| US6576906B1 (en) | 1999-10-08 | 2003-06-10 | Symyx Technologies, Inc. | Method and apparatus for screening combinatorial libraries for semiconducting properties |
| AU767185B2 (en) | 1998-03-23 | 2003-11-06 | President And Fellows Of Harvard College | Synthesis of compounds and libraries of compounds |
| AU4170100A (en) * | 1999-03-01 | 2000-09-21 | Combimatrix Corporation | Combinatorial chelator array |
| AU2844901A (en) * | 1999-12-30 | 2001-07-16 | 7Tm Pharma | A method of identifying ligands of biological target molecules |
| WO2002054077A2 (en) * | 2000-12-29 | 2002-07-11 | 7Tm Pharma A/S | Validating biological molecules as drug targets by metal-ion chelates in animal test models |
| US7504364B2 (en) * | 2002-03-01 | 2009-03-17 | Receptors Llc | Methods of making arrays and artificial receptors |
| US20040214232A1 (en) * | 2002-08-16 | 2004-10-28 | Burke Martin D. | Generation of skeletal diversity within a combinatorial library |
| US20050037429A1 (en) * | 2003-03-28 | 2005-02-17 | Receptors Llc | Artificial receptors including reversibly immobilized building blocks and methods |
| US20060057625A1 (en) * | 2002-09-16 | 2006-03-16 | Carlson Robert E | Scaffold-based artificial receptors and methods |
| US20050037381A1 (en) * | 2002-09-16 | 2005-02-17 | Receptors Llc | Artificial receptors, building blocks, and methods |
| US20050136483A1 (en) * | 2003-09-03 | 2005-06-23 | Receptors Llc | Nanodevices employing combinatorial artificial receptors |
| WO2005003326A2 (en) * | 2003-03-28 | 2005-01-13 | Receptors Llc. | Artificial receptors including reversibly immobilized building blocks and methods |
| US20050037428A1 (en) * | 2002-09-16 | 2005-02-17 | Receptors Llc | Artificial receptors including reversibly immobilized building blocks, the building blocks, and methods |
| US20040137481A1 (en) * | 2002-09-16 | 2004-07-15 | Receptors Llc | Artificial receptor building blocks, components, and kits |
| US20050170385A1 (en) * | 2002-09-16 | 2005-08-04 | Receptors Llc | Artificial receptors including gradients |
| US7469076B2 (en) | 2003-09-03 | 2008-12-23 | Receptors Llc | Sensors employing combinatorial artificial receptors |
| WO2006028930A2 (en) | 2004-09-03 | 2006-03-16 | Receptors Llc | Combinatorial artificial receptors including tether building blocks on scaffolds |
| WO2006029383A2 (en) * | 2004-09-11 | 2006-03-16 | Receptors Llc | Combinatorial artificial receptors including peptide building blocks |
| AU2008299784B9 (en) | 2007-08-02 | 2015-06-18 | Gilead Biologics, Inc. | LOX and LOXL2 inhibitors and uses thereof |
| EP3087054A4 (en) | 2013-12-27 | 2017-10-25 | Novus International Inc. | Ethoxylated surfactants |
| US10584306B2 (en) | 2017-08-11 | 2020-03-10 | Board Of Regents Of The University Of Oklahoma | Surfactant microemulsions |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2081213A1 (en) | 1990-05-08 | 1991-11-09 | Richard A. Lerner | Metal binding proteins |
| US5698391A (en) | 1991-08-23 | 1997-12-16 | Isis Pharmaceuticals, Inc. | Methods for synthetic unrandomization of oligomer fragments |
| US5639603A (en) | 1991-09-18 | 1997-06-17 | Affymax Technologies N.V. | Synthesizing and screening molecular diversity |
| US6107059A (en) * | 1992-04-29 | 2000-08-22 | Affymax Technologies N.V. | Peptide library and screening method |
| US5679548A (en) | 1993-02-02 | 1997-10-21 | The Scripps Research Institute | Methods for producing polypeptide metal binding sites and compositions thereof |
| US5840485A (en) * | 1993-05-27 | 1998-11-24 | Selectide Corporation | Topologically segregated, encoded solid phase libraries |
| US5637684A (en) | 1994-02-23 | 1997-06-10 | Isis Pharmaceuticals, Inc. | Phosphoramidate and phosphorothioamidate oligomeric compounds |
| US6030917A (en) * | 1996-07-23 | 2000-02-29 | Symyx Technologies, Inc. | Combinatorial synthesis and analysis of organometallic compounds and catalysts |
| JPH11514012A (en) | 1996-07-23 | 1999-11-30 | サイミックス・テクノロジーズ | Combinatorial synthesis and analysis of organometallic compounds and catalysts |
-
1997
- 1997-09-19 US US08/933,714 patent/US6489093B1/en not_active Expired - Fee Related
- 1997-09-19 WO PCT/US1997/016740 patent/WO1998012156A1/en active Application Filing
- 1997-09-19 AU AU45851/97A patent/AU4585197A/en not_active Abandoned
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