CA2908575C - Macrolides and methods of their preparation and use - Google Patents

Info

Publication number

CA2908575C

CA2908575C CA2908575A CA2908575A CA2908575C CA 2908575 C CA2908575 C CA 2908575C CA 2908575 A CA2908575 A CA 2908575A CA 2908575 A CA2908575 A CA 2908575A CA 2908575 C CA2908575 C CA 2908575C

Authority

CA

Canada

Prior art keywords

optionally substituted

compound

salt

ring system

membered ring

Prior art date

2013-04-04

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 239000003120 macrolide antibiotic agent Substances 0.000 title abstract description 80
• 229940041033 macrolides Drugs 0.000 title abstract description 31
• 238000000034 method Methods 0.000 title abstract description 28
• 238000002360 preparation method Methods 0.000 title description 3
• 208000035473 Communicable disease Diseases 0.000 claims abstract description 16
• 230000004968 inflammatory condition Effects 0.000 claims abstract description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 669
• 229910052739 hydrogen Inorganic materials 0.000 claims description 369
• 239000001257 hydrogen Substances 0.000 claims description 368
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 261
• 125000000623 heterocyclic group Chemical group 0.000 claims description 251
• 125000001072 heteroaryl group Chemical group 0.000 claims description 212
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 201
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 188
• 150000001875 compounds Chemical class 0.000 claims description 183
• -1 amino, substituted amino Chemical group 0.000 claims description 159
• 125000003107 substituted aryl group Chemical group 0.000 claims description 126
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 116
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 112
• 125000000217 alkyl group Chemical group 0.000 claims description 112
• 150000003839 salts Chemical class 0.000 claims description 105
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 105
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 92
• 229910052736 halogen Inorganic materials 0.000 claims description 88
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 83
• 150000002367 halogens Chemical group 0.000 claims description 74
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 71
• 125000003118 aryl group Chemical group 0.000 claims description 70
• 125000000304 alkynyl group Chemical group 0.000 claims description 62
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 60
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 59
• 125000003342 alkenyl group Chemical group 0.000 claims description 57
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 54
• 229910052757 nitrogen Inorganic materials 0.000 claims description 53
• 150000003573 thiols Chemical class 0.000 claims description 48
• 229910052717 sulfur Inorganic materials 0.000 claims description 37
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 33
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 27
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 23
• 125000001188 haloalkyl group Chemical group 0.000 claims description 22
• 229920002554 vinyl polymer Polymers 0.000 claims description 21
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 208000015181 infectious disease Diseases 0.000 claims description 20
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 20
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 18
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 13
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 13
• 238000011282 treatment Methods 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 10
• 125000002947 alkylene group Chemical group 0.000 claims description 9
• 150000001720 carbohydrates Chemical class 0.000 claims description 9
• 125000000466 oxiranyl group Chemical group 0.000 claims description 9
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
• 101100462341 Homo sapiens OSBPL2 gene Proteins 0.000 claims description 7
• 102100025925 Oxysterol-binding protein-related protein 2 Human genes 0.000 claims description 7
• 101100518421 Schizosaccharomyces pombe (strain 972 / ATCC 24843) orc2 gene Proteins 0.000 claims description 7
• 101100261632 Zea mays TSB2 gene Proteins 0.000 claims description 7
• 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
• 101000992396 Homo sapiens Oxysterol-binding protein-related protein 3 Proteins 0.000 claims description 6
• 102100032154 Oxysterol-binding protein-related protein 3 Human genes 0.000 claims description 6
• 125000004450 alkenylene group Chemical group 0.000 claims description 6
• 125000004419 alkynylene group Chemical group 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• 125000004474 heteroalkylene group Chemical group 0.000 claims description 6
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
• 208000035143 Bacterial infection Diseases 0.000 claims description 5
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 5
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
• 229910002651 NO3 Inorganic materials 0.000 claims description 4
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 4
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 4
• CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 claims description 4
• 102200097959 rs1049306 Human genes 0.000 claims description 4
• 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 claims description 4
• 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 3
• LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 claims description 3
• 241000894006 Bacteria Species 0.000 claims description 3
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 3
• 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
• CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 claims description 3
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 3
• VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 claims description 2
• MNWLUFSDGJCUCA-UHFFFAOYSA-N 2-(methylsulfanylmethoxy)butanoic acid Chemical compound CCC(C(O)=O)OCSC MNWLUFSDGJCUCA-UHFFFAOYSA-N 0.000 claims description 2
• UJRMHFPTLFNSTA-UHFFFAOYSA-N 2-chloro-2,2-diphenylacetic acid Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)O)C1=CC=CC=C1 UJRMHFPTLFNSTA-UHFFFAOYSA-N 0.000 claims description 2
• GPVOTFQILZVCFP-UHFFFAOYSA-N 2-trityloxyacetic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCC(=O)O)C1=CC=CC=C1 GPVOTFQILZVCFP-UHFFFAOYSA-N 0.000 claims description 2
• JOOXCMJARBKPKM-UHFFFAOYSA-M 4-oxopentanoate Chemical compound CC(=O)CCC([O-])=O JOOXCMJARBKPKM-UHFFFAOYSA-M 0.000 claims description 2
• 102100031260 Acyl-coenzyme A thioesterase THEM4 Human genes 0.000 claims description 2
• DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 claims description 2
• 101000638510 Homo sapiens Acyl-coenzyme A thioesterase THEM4 Proteins 0.000 claims description 2
• 101150061258 ITSN1 gene Proteins 0.000 claims description 2
• 208000030852 Parasitic disease Diseases 0.000 claims description 2
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
• BZQVVDBQOLRHEP-UHFFFAOYSA-N [dimethoxy(phenyl)methyl] hydrogen carbonate Chemical compound OC(=O)OC(OC)(OC)C1=CC=CC=C1 BZQVVDBQOLRHEP-UHFFFAOYSA-N 0.000 claims description 2
• NGEQMFXZKWZDMN-UHFFFAOYSA-N [methoxy(phenyl)methyl] hydrogen carbonate Chemical compound OC(=O)OC(OC)C1=CC=CC=C1 NGEQMFXZKWZDMN-UHFFFAOYSA-N 0.000 claims description 2
• WHFDFYJBSORWIP-UHFFFAOYSA-N [nitro(phenyl)methyl] hydrogen carbonate Chemical compound OC(=O)OC([N+]([O-])=O)C1=CC=CC=C1 WHFDFYJBSORWIP-UHFFFAOYSA-N 0.000 claims description 2
• 229940022663 acetate Drugs 0.000 claims description 2
• 125000005585 adamantoate group Chemical group 0.000 claims description 2
• 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
• UXXXZMDJQLPQPH-UHFFFAOYSA-N bis(2-methylpropyl) carbonate Chemical compound CC(C)COC(=O)OCC(C)C UXXXZMDJQLPQPH-UHFFFAOYSA-N 0.000 claims description 2
• JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 claims description 2
• FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 claims description 2
• 229940089960 chloroacetate Drugs 0.000 claims description 2
• LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
• PIZLBWGMERQCOC-UHFFFAOYSA-N dibenzyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OCC1=CC=CC=C1 PIZLBWGMERQCOC-UHFFFAOYSA-N 0.000 claims description 2
• LWPIKYIJCHLEIP-UHFFFAOYSA-N dibromomethyl benzoate Chemical compound BrC(Br)OC(=O)C1=CC=CC=C1 LWPIKYIJCHLEIP-UHFFFAOYSA-N 0.000 claims description 2
• 229940120124 dichloroacetate Drugs 0.000 claims description 2
• JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims description 2
• NUTDTHJGSYGQMW-UHFFFAOYSA-N ethoxycarbonyloxy(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(OC(=O)OCC)C1=CC=CC=C1 NUTDTHJGSYGQMW-UHFFFAOYSA-N 0.000 claims description 2
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 2
• 229940058352 levulinate Drugs 0.000 claims description 2
• RMIODHQZRUFFFF-UHFFFAOYSA-M methoxyacetate Chemical compound COCC([O-])=O RMIODHQZRUFFFF-UHFFFAOYSA-M 0.000 claims description 2
• BZCKRPHEZOHHBK-UHFFFAOYSA-N methyl 2-phenoxyacetate Chemical compound COC(=O)COC1=CC=CC=C1 BZCKRPHEZOHHBK-UHFFFAOYSA-N 0.000 claims description 2
• NYEBKUUITGFJAK-UHFFFAOYSA-N methylsulfanylmethanethioic s-acid Chemical compound CSC(O)=S NYEBKUUITGFJAK-UHFFFAOYSA-N 0.000 claims description 2
• FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 claims description 2
• DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 claims description 2
• FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 claims description 2
• NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 claims description 2
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
• 125000005547 pivalate group Chemical group 0.000 claims description 2
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 2
• 229940066528 trichloroacetate Drugs 0.000 claims description 2
• YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 47
• LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims 3
• 206010060976 Bacillus infection Diseases 0.000 claims 1
• 206010061126 Escherichia infection Diseases 0.000 claims 1
• 241000192125 Firmicutes Species 0.000 claims 1
• 206010061190 Haemophilus infection Diseases 0.000 claims 1
• 241000191940 Staphylococcus Species 0.000 claims 1
• 230000001684 chronic effect Effects 0.000 claims 1
• 125000006277 halobenzyl group Chemical group 0.000 claims 1
• 230000002757 inflammatory effect Effects 0.000 claims 1
• 239000000546 pharmaceutical excipient Substances 0.000 claims 1
• 230000002685 pulmonary effect Effects 0.000 claims 1
• 208000011580 syndromic disease Diseases 0.000 claims 1
• 238000005859 coupling reaction Methods 0.000 abstract description 53
• 230000008878 coupling Effects 0.000 abstract description 52
• 238000010168 coupling process Methods 0.000 abstract description 51
• 238000005710 macrocyclization reaction Methods 0.000 abstract description 47
• 230000015572 biosynthetic process Effects 0.000 abstract description 23
• 238000003786 synthesis reaction Methods 0.000 abstract description 14
• 239000000543 intermediate Substances 0.000 abstract description 8
• HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 abstract description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 96
• 125000005842 heteroatom Chemical group 0.000 description 84
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 83
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 71
• 229910052799 carbon Inorganic materials 0.000 description 37
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 35
• 238000007792 addition Methods 0.000 description 34
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
• 125000004404 heteroalkyl group Chemical group 0.000 description 30
• 150000001412 amines Chemical class 0.000 description 29
• 150000002576 ketones Chemical class 0.000 description 29
• 125000001424 substituent group Chemical group 0.000 description 26
• 238000006243 chemical reaction Methods 0.000 description 24
• 229910052760 oxygen Inorganic materials 0.000 description 23
• 239000001301 oxygen Substances 0.000 description 23
• 230000009467 reduction Effects 0.000 description 23
• 238000006722 reduction reaction Methods 0.000 description 23
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 20
• 125000000753 cycloalkyl group Chemical group 0.000 description 20
• 125000005843 halogen group Chemical group 0.000 description 20
• 125000003277 amino group Chemical group 0.000 description 19
• 230000004048 modification Effects 0.000 description 19
• 238000012986 modification Methods 0.000 description 19
• 239000002243 precursor Substances 0.000 description 19
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 18
• 239000011593 sulfur Substances 0.000 description 17
• 239000002585 base Substances 0.000 description 16
• 239000000460 chlorine Substances 0.000 description 16
• 125000001153 fluoro group Chemical group F* 0.000 description 16
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
• 229910019567 Re Re Inorganic materials 0.000 description 15
• 239000003795 chemical substances by application Substances 0.000 description 15
• 230000002829 reductive effect Effects 0.000 description 15
• 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 description 14
• 150000002678 macrocyclic compounds Chemical class 0.000 description 14
• 230000000269 nucleophilic effect Effects 0.000 description 14
• 229920006395 saturated elastomer Polymers 0.000 description 14
• 230000009466 transformation Effects 0.000 description 14
• 125000001309 chloro group Chemical group Cl* 0.000 description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 description 13
• 238000000844 transformation Methods 0.000 description 13
• 150000001299 aldehydes Chemical class 0.000 description 12
• 239000011575 calcium Substances 0.000 description 12
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
• 125000000468 ketone group Chemical group 0.000 description 12
• 150000001408 amides Chemical class 0.000 description 11
• 239000003153 chemical reaction reagent Substances 0.000 description 11
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 11
• 238000006073 displacement reaction Methods 0.000 description 11
• 150000002148 esters Chemical class 0.000 description 11
• 150000002466 imines Chemical class 0.000 description 11
• 125000005647 linker group Chemical group 0.000 description 11
• ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 10
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 10
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
• 150000007970 thio esters Chemical class 0.000 description 10
• 101000854060 Homo sapiens Oxygen-regulated protein 1 Proteins 0.000 description 9
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 9
• 125000001246 bromo group Chemical group Br* 0.000 description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 8
• 125000005915 C6-C14 aryl group Chemical group 0.000 description 8
• 102100035714 Oxygen-regulated protein 1 Human genes 0.000 description 8
• 239000002253 acid Substances 0.000 description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
• 125000006239 protecting group Chemical group 0.000 description 8
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 8
• 150000003254 radicals Chemical class 0.000 description 8
• 238000006268 reductive amination reaction Methods 0.000 description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 7
• 238000006845 Michael addition reaction Methods 0.000 description 7
• 235000014633 carbohydrates Nutrition 0.000 description 7
• 125000004093 cyano group Chemical group *C#N 0.000 description 7
• 238000007306 functionalization reaction Methods 0.000 description 7
• 238000005935 nucleophilic addition reaction Methods 0.000 description 7
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 6
• 229930194542 Keto Natural products 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• 238000007239 Wittig reaction Methods 0.000 description 6
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