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Search for "anticancer agent" in Full Text gives 33 result(s) in Beilstein Journal of Organic Chemistry.
The synthesis of active pharmaceutical ingredients (APIs) using continuous flow chemistry
- Marcus Baumann and
- Ian R. Baxendale
Beilstein J. Org. Chem. 2015, 11, 1194–1219, doi:10.3762/bjoc.11.134
- continuous synthesis of the important anticancer agent tamoxifen (132) in 2013 [106]. The synthesis starts with a halogen–lithium exchange reaction between arylbromide 133 and n-BuLi at −50 °C and the subsequent addition of the formed aryllithium species to ketone 134 at the same temperature (Scheme 23
Graphical Abstract
Figure 1: Pharmaceutical structures targeted in early flow syntheses.
Scheme 1: Flow synthesis of 6-hydroxybuspirone (9). Inserted photograph reprinted with permission from [45]. Copy...
Figure 2: Configuration of a baffled reactor tube (left) and its schematic working principle (right).
Scheme 2: McQuade’s flow synthesis of ibuprofen (16).
Scheme 3: Jamison’s flow synthesis of ibuprofen sodium salt (17).
Scheme 4: Flow synthesis of imatinib (23).
Scheme 5: Flow synthesis of the potent 5HT1B antagonist 28.
Scheme 6: Flow synthesis of a selective δ-opioid receptor agonist 33.
Scheme 7: Flow synthesis of a casein kinase I inhibitor library (38).
Scheme 8: Flow synthesis of fluoxetine (46).
Scheme 9: Flow synthesis of artemisinin (55).
Scheme 10: Telescoped flow synthesis of artemisinin (55) and derivatives (62–64).
Scheme 11: Flow approach towards AZD6906 (65).
Scheme 12: Pilot scale flow synthesis of key intermediate 73.
Scheme 13: Semi-flow synthesis of vildagliptine (77).
Scheme 14: Pilot scale asymmetric flow hydrogenation towards 83. Inserted photograph reprinted with permission...
Figure 3: Schematic representation of the ‘tube-in-tube’ reactor.
Scheme 15: Flow synthesis of fanetizole (87) via tube-in-tube system.
Scheme 16: Flow synthesis of diphenhydramine.HCl (92).
Scheme 17: Flow synthesis of rufinamide (95).
Scheme 18: Large scale flow synthesis of rufinamide precursor 102.
Scheme 19: First stage in the flow synthesis of meclinertant (103).
Scheme 20: Completion of the flow synthesis of meclinertant (103).
Scheme 21: Flow synthesis of olanzapine (121) utilising inductive heating techniques.
Scheme 22: Flow synthesis of amitriptyline·HCl (127).
Scheme 23: Flow synthesis of E/Z-tamoxifen (132) using peristaltic pumping modules.
Figure 4: Container sized portable mini factory (photograph credit: INVITE GmbH, Leverkusen Germany).
Scheme 24: Flow synthesis of imidazo[1,2-a]pyridines 136 linked to frontal affinity chromatography (FAC).
Figure 5: Structures of zolpidem (142) and alpidem (143).
Scheme 25: Synthesis and screening loops in the discovery of new Abl kinase inhibitors.
Figure 6: Schotten–Baumann approach towards LY573636.Na (147).
Scheme 26: Pilot scale flow synthesis of LY2886721 (146).
Scheme 27: Continuous flow manufacture of alikiren hemifumarate 152.
Formulation development, stability and anticancer efficacy of core-shell cyclodextrin nanocapsules for oral chemotherapy with camptothecin
- Hale Ünal,
- Naile Öztürk and
- Erem Bilensoy
Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22
- 10.3762/bjoc.11.22 Abstract Background: The aim of this study was to design and evaluate hybrid cyclodextrin (CD) nanocapsules intended for the oral delivery of the anticancer agent camptothecin (CPT) in order to maintain drug stability in the body and to improve its eventual bioavailability. For this
- the molecules against the harsh environment [16]. In cancer therapy, a common problem is drug ineffectiveness because of physicochemical and biopharmaceutical problems of drugs and CPT is cited as a prime example. CPT is a very effective anticancer agent against a wide spectrum of cancers such as
- nanocapsules for the oral delivery of the anticancer agent CPT, which has a limited clinical usage by maintaining its stability and improving its eventual bioavailability. For this reason, amphiphilic CD, 6OCAPRO (heptakis(6-O-hexanoyl)cyclomaltoheptose) was used as core polymer for nanocapsules. These
Graphical Abstract
Figure 1: Scanning electron microphotographs of A) 6OCAPRO nanocapsules and B) CS-6OCAPRO nanocapsules.
Figure 2: In vitro release profiles of CPT from anionic and cationic CD nanocapsules in pH 1.2 PBS A) in 2 ho...
Figure 3: Cell viability of blank 6OCAPRO and CS-6OCAPRO nanocapsules against L929 cells after 48 h incubatio...
Figure 4: Viability of MCF-7 cells cultured with CPT loaded 6OCAPRO and CS-6OCAPRO nanocapsules in comparison...
Figure 5: Apparent permeability coefficient (Paap) of different CPT formulations: CPT in DMSO solution, CPT l...
The chemistry of isoindole natural products
- Klaus Speck and
- Thomas Magauer
Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243
- cellular signaling and their association with cancer, a tremendous effort in the development of selective protein kinase inhibitors was undertaken. This resulted in the discovery of the anticancer agent imatinib (Gleevec, 34) by rational drug design (Figure 4). Midostaurin (35), a semisynthetic derivative
Graphical Abstract
Figure 1: a) Structural features and b) selected examples of non-natural congeners.
Scheme 1: Synthesis of isoindole 18.
Scheme 2: Staining amines with 1,4-diketone 19 (R = H).
Figure 2: Representative members of the indolocarbazole alkaloid family.
Figure 3: Staurosporine (26) bound to the adenosine-binding pocket [19] (from pdb1stc).
Figure 4: Structure of imatinib (34) and midostaurin (35).
Scheme 3: Biosynthesis of staurosporine (26).
Scheme 4: Wood’s synthesis of K-252a via the common intermediate 48.
Scheme 5: Synthesis of 26, 27, 49 and 50 diverging from the common intermediate 48.
Figure 5: Selected members of the cytochalasan alkaloid family.
Scheme 6: Biosynthesis of chaetoglobosin A (57) [56].
Scheme 7: Synthesis of cytochalasin D (70) by Thomas [63].
Scheme 8: Synthesis of L-696,474 (78).
Scheme 9: Synthesis of aldehyde 85 (R = TBDPS).
Scheme 10: Synthesis of (+)-aspergillin PZ (79) by Tanis.
Figure 6: Representative Berberis alkaloids.
Scheme 11: Proposed biosynthetic pathway to chilenine (93).
Scheme 12: Synthesis of magallanesine (97) by Danishefsky [84].
Scheme 13: Kurihara’s synthesis of magallanesine (85).
Scheme 14: Proposed biosynthesis of 113, 117 and 125.
Scheme 15: DNA lesion caused by aristolochic acid I (117) [102].
Scheme 16: Snieckus’ synthesis of piperolactam C (131).
Scheme 17: Synthesis of aristolactam BII (104).
Figure 7: Representative cularine alkaloids.
Scheme 18: Proposed biosynthesis of 136.
Scheme 19: The syntheses of 136 and 137 reported by Castedo and Suau.
Scheme 20: Synthesis of 136 by Couture.
Figure 8: Representative isoindolinone meroterpenoids.
Scheme 21: Postulated biosynthetic pathway for the formation of 156 (adopted from George) [143].
Scheme 22: Synthesis of stachyflin (156) by Katoh [144].
Figure 9: Selected examples of spirodihydrobenzofuranlactams.
Scheme 23: Synthesis of stachybotrylactam I (157).
Scheme 24: Synthesis of pestalachloride A (193) by Schmalz.
Scheme 25: Proposed mechanism for the BF3-catalyzed metal-free carbonyl–olefin metathesis [149].
Scheme 26: Preparation of the isoindoline core of muironolide A (204).
Scheme 27: Proposed biosynthesis of 208.
Scheme 28: Model for the biosynthesis of 215 and 217.
Scheme 29: Synthesis of lactonamycin (215) and lactonamycin Z (217).
Figure 10: Hetisine alkaloids 225–228.
Scheme 30: Biosynthetic proposal for the formation of the hetisine core [167].
Scheme 31: Synthesis of nominine (225).
Cyclodextrin-based nanosponges as drug carriers
- Francesco Trotta,
- Marco Zanetti and
- Roberta Cavalli
Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235
- released at pH 7.4. The anticancer agent paclitaxel is another drug difficult to formulate. Paclitaxel has a very low solubility in water, i.e., less than 0.3 μg/mL. As a consequence, the dosage form available for clinical administration requires the use of other pharmaceutical solvents or emulsifying
Graphical Abstract
Scheme 1: Synthetic routes to cyclodextrin nanosponges. (a) Cyclodextrin carbonate nanosponges. (b) Cyclodext...
Figure 1: Molecular structure of cyclodextrin carbonate nanosponges.
Figure 2: TEM microphotograph of cyclodextrin carbonate nanosponge (magnification 46,000×).
Bioactive selaginellins from Selaginella tamariscina (Beauv.) Spring
- Chao Yang,
- Yutian Shao,
- Kang Li and
- Wujiong Xia
Beilstein J. Org. Chem. 2012, 8, 1884–1889, doi:10.3762/bjoc.8.217
- ]. The anticancer agent cisplatin was used as a positive control. The cytotoxicity data were expressed as IC50 (half inhibition concentration) values. ABTS radical scavenging assay. The assay was performed according to the established protocol [26]. The ABTS•+ radical was generated by mixing 7 mM aqueous
Graphical Abstract
Figure 1: Structures of selaginellins from S. tamariscina.
Figure 2: Key HMBC correlations of compound 1.
Syntheses and applications of furanyl-functionalised 2,2’:6’,2’’-terpyridines
- Jérôme Husson and
- Michael Knorr
Beilstein J. Org. Chem. 2012, 8, 379–389, doi:10.3762/bjoc.8.41
- anticancer agent. Additionally, their cytotoxicity against normal cells was evaluated (Table 3). As can be seen from Table 3, these furanyl-functionalised terpyridines display, in many cases, better cytotoxicity than doxorubicin. Unfortunately, they are also more toxic toward normal cells (RPTEC). Note that
Graphical Abstract
Figure 1: Structure and atomic numbering of 2,2’:6’,2’’-terpyridines.
Scheme 1: Synthesis of furanyl-substituted terpyridines 12–14 by using Kröhnke’s method.
Scheme 2: Synthesis of terpyridines under solvent-free conditions.
Scheme 3: Preparation of 4,4′,4′′-trisubstituted terpyridine containing carboxylate moieties.
Scheme 4: Synthetic pathway for the preparation of a furanyl-functionalised quinquepyridine.
Scheme 5: Utilization of an iminium salt in the preparation of a furanyl-substituted tpy.
Figure 2: Chemical structure of U- and S-shaped isomers.
Scheme 6: Preparation of an asymmetric furanyl-substituted terpyridine.
Scheme 7: Synthesis of tpy by Stille cross-coupling reaction.
Scheme 8: Oxidation of the furan ring of furanyl-substituted terpyridines.
Scheme 9: Direct oxidation of a furan ring attached on Ru(II) tpy complexes.
Figure 3: Example of polyoxometalate frameworks functionalised with tpy ligands and tpy-complex (reprinted wi...
Scheme 10: Synthetic pathway to europium(III) and samarium(III) chelates 56 and 57.
Scheme 11: Synthetic pathway to prepare thiocyanato-functionalised tpys as potential biomolecule-labelling age...
Scheme 12: Synthetic sequence envisioned for biomolecules labelling by click-chemistry.
Figure 4: Structure of pyrrolyl (66), thienyl (67) and bithienyl (68)-substituted complexes analogous to comp...
Molecular recognition of organic ammonium ions in solution using synthetic receptors
- Andreas Späth and
- Burkhard König
Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32
Graphical Abstract
Figure 1: Biologically important amines and quaternary ammonium salts: histamine (1), dopamine (2) and acetyl...
Figure 2: Crown ether 18-crown-6.
Figure 3: Conformations of 18-crown-6 (4) in solvents of different polarity.
Figure 4: Binding topologies of the ammonium ion depending on the crown ring size.
Figure 5: A “pseudorotaxane” structure consisting of 24-crown-8 and a secondary ammonium ion (5); R = Ph.
Figure 6: Typical examples of azacrown ethers, cryptands and related aza macrocycles.
Figure 7: Binding of ammonium to azacrown ethers and cryptands [111-113].
Figure 8: A 19-crown-6-ether with decalino blocking groups (11) and a thiazole-dibenzo-18-crown-6-ether (12).
Figure 9: 1,3-Bis(6-oxopyridazin-1-yl)propane derivatives 13 and 14 by Campayo et al.
Figure 10: Fluorescent azacrown-PET-sensors based on coumarin.
Figure 11: Two different pyridino-cryptands (17 and 18) compared to a pyridino-crown (19); chiral ammonium ion...
Figure 12: Pyridino-18-crown-6 ligand (21), a similar acridino-18-crown-6 ligand (22) and a structurally relat...
Figure 13: Ciral pyridine-azacrown ether receptors 24.
Figure 14: Chiral 15-crown-5 receptors 26 and an analogue 18-crown-6 ligand 27 derived from amino alcohols.
Figure 15: C2-symmetric chiral 18-crown-6 amino alcohol derivatives 28 and related macrocycles.
Figure 16: Macrocycles with diamide-diester groups (30).
Figure 17: C2-symmetric chiral aza-18-crown-6 ethers (31) with phenethylamine residues.
Figure 18: Chiral C-pivot p-methoxy-phenoxy-lariat ethers.
Figure 19: Chiral lariat crown ether 34.
Figure 20: Sucrose-based chiral crown ether receptors 36.
Figure 21: Permethylated fructooligosaccharide 37 showing induced-fit chiral recognition.
Figure 22: Biphenanthryl-18-crown-6 derivative 38.
Figure 23: Chiral lariat crown ethers derived from binol by Fuji et al.
Figure 24: Chiral phenolic crown ether 41 with “aryl chiral barriers” and guest amines.
Figure 25: Chiral bis-crown receptor 43 with a meso-ternaphthalene backbone.
Figure 26: Chromogenic pH-dependent bis-crown chemosensor 44 for diamines.
Figure 27: Triamine guests for binding to receptor 44.
Figure 28: Chiral bis-crown phenolphthalein chemosensors 46.
Figure 29: Crown ether amino acid 47.
Figure 30: Luminescent receptor 48 for bis-alkylammonium guests.
Figure 31: Luminescent CEAA (49a), a bis-CEAA receptor for amino acids (49b) and the structure of lysine bindi...
Figure 32: Luminescent CEAA tripeptide for binding small peptides.
Figure 33: Bis crown ether 51a self assembles co-operatively with C60-ammonium ion 51b.
Figure 34: Triptycene-based macrotricyclic dibenzo-[24]-crown-8 ether host 52 and guests.
Figure 35: Copper imido diacetic acid azacrown receptor 53a and the suggested His-Lys binding motif; a copper ...
Figure 36: Urea (54) and thiourea (55) benzo crown receptor for transport and extraction of amino acids.
Figure 37: Crown pyryliums ion receptors 56 for amino acids.
Figure 38: Ditopic sulfonamide bridged crown ether receptor 57.
Figure 39: Luminescent peptide receptor 58.
Figure 40: Luminescent receptor 59 for the detection of D-glucosamine hydrochloride in water/ethanol and lumin...
Figure 41: Guanidinium azacrown receptor 61 for simple amino acids and ditopic receptor 62 with crown ether an...
Figure 42: Chiral bicyclic guanidinium azacrown receptor 63 and similar receptor 64 for the enantioselective t...
Figure 43: Receptors for zwitterionic species based on luminescent CEAAs.
Figure 44: 1,10-Azacrown ethers with sugar podand arms and the anticancer agent busulfan.
Figure 45: Benzo-18-crown-6 modified β-cyclodextrin 69 and β-cyclodextrin functionalized with diaza-18-crown-6...
Figure 46: Receptors for colorimetric detection of primary and secondary ammonium ions.
Figure 47: Porphyrine-crown-receptors 72.
Figure 48: Porphyrin-crown ether conjugate 73 and fullerene-ammonium ion guest 74.
Figure 49: Calix[4]arene (75a), homooxocalix[4]arene (75b) and resorcin[4]arene (75c) compared (R = H, alkyl c...
Figure 50: Calix[4]arene and ammonium ion guest (R = H, alkyl, OAcyl etc.), possible binding sites; A: co-ordi...
Figure 51: Typical guests for studies with calixarenes and related molecules.
Figure 52: Lower rim modified p-tert-butylcalix[5]arenes 82.
Figure 53: The first example of a water soluble calixarene.
Figure 54: Sulfonated water soluble calix[n]arenes that bind ammonium ions.
Figure 55: Displacement assay for acetylcholine (3) with a sulfonato-calix[6]arene (84b).
Figure 56: Amino acid inclusion in p-sulfonatocalix[4]arene (84a).
Figure 57: Calixarene receptor family 86 with upper and lower rim functionalization.
Figure 58: Calix[6]arenes 87 with one carboxylic acid functionality.
Figure 59: Sulfonated calix[n]arenes with mono-substitution at the lower rim systematically studied on their r...
Figure 60: Cyclotetrachromotropylene host (91) and its binding to lysine (81c).
Figure 61: Calixarenes 92 and 93 with phosphonic acids groups.
Figure 62: Calix[4]arene tetraphosphonic acid (94a) and a double bridged analogue (94b).
Figure 63: Calix[4]arene tetraphosphonic acid ester (92c) for surface recognition experiments.
Figure 64: Calixarene receptors 95 with α-aminophosphonate groups.
Figure 65: A bridged homocalix[3]arene 95 and a distally bridged homocalix[4]crown 96.
Figure 66: Homocalix[3]arene ammonium ion receptor 97a and the Reichardt’s dye (97b) for colorimetric assays.
Figure 67: Chromogenic diazo-bridged calix[4]arene 98.
Figure 68: Calixarene receptor 99 by Huang et al.
Figure 69: Calixarenes 100 reported by Parisi et al.
Figure 70: Guest molecules for inclusion in calixarenes 100: DAP × 2 HCl (101a), APA (101b) and Lys-OMe × 2 HC...
Figure 71: Different N-linked peptido-calixarenes open and with glycol chain bridges.
Figure 72: (S)-1,1′-Bi-2-naphthol calixarene derivative 104 published by Kubo et al.
Figure 73: A chiral ammonium-ion receptor 105 based on the calix[4]arene skeleton.
Figure 74: R-/S-phenylalaninol functionalized calix[6]arenes 106a and 106b.
Figure 75: Capped homocalix[3]arene ammonium ion receptor 107.
Figure 76: Two C3 symmetric capped calix[6]arenes 108 and 109.
Figure 77: Phosphorous-containing rigidified calix[6]arene 110.
Figure 78: Calix[6]azacryptand 111.
Figure 79: Further substituted calix[6]azacryptands 112.
Figure 80: Resorcin[4]arene (75c) and the cavitands (113).
Figure 81: Tetrasulfonatomethylcalix[4]resorcinarene (114).
Figure 82: Resorcin[4]arenes (115a/b) and pyrogallo[4]arenes (115c, 116).
Figure 83: Displacement assay for acetylcholine (3) with tetracyanoresorcin[4]arene (117).
Figure 84: Tetramethoxy resorcinarene mono-crown-5 (118).
Figure 85: Components of a resorcinarene based displacement assay for ammonium ions.
Figure 86: Chiral basket resorcin[4]arenas 121.
Figure 87: Resorcinarenes with deeper cavitand structure (122).
Figure 88: Resorcinarene with partially open deeper cavitand structure (123).
Figure 89: Water-stabilized deep cavitands with partially structure (124, 125).
Figure 90: Charged cavitands 126 for tetralkylammonium ions.
Figure 91: Ditopic calix[4]arene receptor 127 capped with glycol chains.
Figure 92: A calix[5]arene dimer for diammonium salt recognition.
Figure 93: Calixarene parts 92c and 129 for the formation molecular capsules.
Figure 94: Encapsulation of a quaternary ammonium cation by two resorcin[4]arene molecules (NMe4+@[75c]2 × Cl−...
Figure 95: Encapsulation of a quaternary ammonium cation by six resorcin[4]arene molecules (NMe3D+@[130]6 × Cl−...
Figure 96: Structure and schematic of cucurbit[6]uril (CB[6], 131a).
Figure 97: Cyclohexanocucurbit[6]uril (CB′[6], 132) and the guest molecule spermine (133).
Figure 98: α,α,δ,δ-Tetramethylcucurbit[6]uril (134).
Figure 99: Structure of the cucurbituril-phthalhydrazide analogue 135.
Figure 100: Organic cavities for the displacement assay for amine differentiation.
Figure 101: Displacement assay methodology for diammonium- and related guests involving cucurbiturils and some ...
Figure 102: Nor-seco-Cucurbituril (±)-bis-ns-CB[6] (140) and guest molecules.
Figure 103: The cucurbit[6]uril based complexes 141 for chiral discrimination.
Figure 104: Cucurbit[7]uril (131c) and its ferrocene guests (142) opposed.
Figure 105: Cucurbit[7]uril (131c) guest inclusion and representative guests.
Figure 106: Cucurbit[7]uril (131c) binding to succinylcholine (145) and different bis-ammonium and bis-phosphon...
Figure 107: Paraquat-cucurbit[8]uril complex 149.
Figure 108: Gluconuril-based ammonium receptors 150.
Figure 109: Examples of clefts (151a), tweezers (151b, 151c, 151d) and clips (151e).
Figure 110: Kemp’s triacid (152a), on example of Rebek’s receptors (152b) and guests.
Figure 111: Amino acid receptor (154) by Rebek et al.
Figure 112: Hexagonal lattice designed hosts by Bell et al.
Figure 113: Bell’s amidinium receptor (156) and the amidinium ion (157).
Figure 114: Aromatic phosphonic acids.
Figure 115: Xylene phosphonates 159 and 160a/b for recognition of amines and amino alcohols.
Figure 116: Bisphosphonate recognition motif 161 for a colorimetric assay with alizarin complexone (163) for ca...
Figure 117: Bisphosphonate/phosphate clip 164 and bisphosphonate cleft 165.
Figure 118: N-Methylpyrazine 166a, N-methylnicotinamide iodide (166b) and NAD+ (166c).
Figure 119: Bisphosphate cavitands.
Figure 120: Bisphosphonate 167 of Schrader and Finocchiaro.
Figure 121: Tweezer 168 for noradrenaline (80b).
Figure 122: Different tripods and heparin (170).
Figure 123: Squaramide based receptors 172.
Figure 124: Cage like NH4+ receptor 173 of Kim et al.
Figure 125: Ammonium receptors 174 of Chin et al.
Figure 126: 2-Oxazolin-based ammonium receptors 175a–d and 176 by Ahn et al.
Figure 127: Racemic guest molecules 177.
Figure 128: Tripods based on a imidazole containing macrocycle (178) and the guest molecules employed in the st...
Figure 129: Ammonium ion receptor 180.
Figure 130: Tetraoxa[3.3.3.3]paracyclophanes 181 and a cyclophanic tetraester (182).
Figure 131: Peptidic bridged paraquat-cyclophane.
Figure 132: Shape-selective noradrenaline host.
Figure 133: Receptor 185 for binding of noradrenaline on surface layers from Schrader et al.
Figure 134: Tetraphosphonate receptor for binding of noradrenaline.
Figure 135: Tetraphosphonate 187 of Schrader and Finocchiaro.
Figure 136: Zinc-Porphyrin ammonium-ion receptors 188 and 189 of Mizutani et al.
Figure 137: Zinc porphyrin receptor 190.
Figure 138: Zinc porphyrin receptors 191 capable of amino acid binding.
Figure 139: Zinc-porphyrins with amino acid side chains for stereoinduction.
Figure 140: Bis-zinc-bis-porphyrin based on Tröger’s base 193.
Figure 141: BINAP-zinc-prophyrin derivative 194 and it’s guests.
Figure 142: Bisaryl-linked-zinc-porphyrin receptors.
Figure 143: Bis-zinc-porphyrin 199 for diamine recognition and guests.
Figure 144: Bis-zinc-porphyrin crown ether 201.
Figure 145: Bis-zinc-porphyrin 202 for stereodiscrimination (L = large substituent; S = small substituent).
Figure 146: Bis-zinc-porphyrin[3]rotaxane and its copper complex and guests.
Figure 147: Dien-bipyridyl ligand 206 for co-ordination of two metal atoms.
Figure 148: The ligand and corresponding tetradentate co-complex 207 serving as enantioselective receptor for a...
Figure 149: Bis(oxazoline)–copper(II) complex 208 for the recognition of amino acids in aqueous solution.
Figure 150: Zinc-salen-complexes 209 for the recognition tertiary amines.
Figure 151: Bis(oxazoline)–copper(II) 211 for the recognition of amino acids in aqueous solution.
Figure 152: Zn(II)-complex of a C2 terpyridine crown ether.
Figure 153: Displacement assay and receptor for aspartate over glutamate.
Figure 154: Chiral complex 214 for a colorimetric displacement assay for amino acids.
Figure 155: Metal complex receptor 215 with tripeptide side arms.
Figure 156: A sandwich complex 216 and its displaceable dye 217.
Figure 157: Lanthanide complexes 218–220 for amino acid recognition.
Figure 158: Nonactin (221), valinomycin (222) and vancomycin (223).
Figure 159: Monesin (224a) and a chiral analogue for enantiodiscrimination of ammonium guests (224b).
Figure 160: Chiral podands (226) compared to pentaglyme-dimethylether (225) and 18-crown-6 (4).
Figure 161: Lasalocid A (228).
Figure 162: Lasalocid derivatives (230) of Sessler et al.
Figure 163: The Coporphyrin I tetraanion (231).
Figure 164: Linear and cyclic peptides for ammonium ion recognition.
Figure 165: Cyclic and bicyclic depsipeptides for ammonium ion recognition.
Figure 166: α-Cyclodextrin (136a) and novocaine (236).
Figure 167: Helical diol receptor 237 by Reetz and Sostmann.
Figure 168: Ammonium binding spherand by Cram et al. (238a) and the cyclic[6]metaphenylacetylene 238b in compar...
Figure 169: Receptor for peptide backbone and ammonium binding (239).
Figure 170: Anion sensor principle with 3-hydroxy-2-naphthanilide of Jiang et al.
Figure 171: 7-bromo-3-hydroxy-N-(2-hydroxyphenyl)naphthalene 2-carboxamide (241) and its amine binding.
Figure 172: Naturally occurring catechins with affinity to quaternary ammonium ions.
Figure 173: Spiropyran (244) and merocyanine form (244a) of the amino acid receptors of Fuji et al.
Figure 174: Coumarin aldehyde (245) and its iminium species with amino acid bound (245a) by Glass et al.
Figure 175: Coumarin aldehyde appended with boronic acid.
Figure 176: Quinolone aldehyde dimers by Glass et al.
Figure 177: Chromogenic ammonium ion receptors with trifluoroacetophenone recognition motifs.
Figure 178: Chromogenic ammonium ion receptor with trifluoroacetophenone recognition motif bound on different m...
(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties
- José L. Jiménez Blanco,
- Fernando Ortega-Caballero,
- Carmen Ortiz Mellet and
- José M. García Fernández
Beilstein J. Org. Chem. 2010, 6, No. 20, doi:10.3762/bjoc.6.20
- /telomeric RNA complex is favoured over the telomer substrate, and could be of use as an anticancer agent. Conclusion Over the last 10 years considerable efforts have been expended in the synthesis of novel linear and cyclic pseudoamide-linked oligosaccharide mimics. In particular, important advances in
Graphical Abstract
Figure 1: Schematic representation of sugar aminoacids (SAAs) and (pseudo)amide oligosaccharide mimetics.
Figure 2: Natural SAAs structures and natural nucleosidic antibiotics.
Scheme 1: Synthetic route to the target amide-linked sialooligomers. (a) Fmoc-Cl, NaHCO3, H2O, dioxane, 0 °C....
Figure 3: The general structure of glycoamino acids and their corresponding oligomers.
Figure 4: Conformational analysis of the β(1→2)-amide-linked glucooligomer 9.
Figure 5: Short oligomeric chains of C-glycosyl D-arabino THF amino acid oligomers.
Figure 6: (A) Stereoview of the minimized structure of compound 16 (produced by a 500 ps simulation) that mos...
Figure 7: Structures of linear oxetane-β- and δ-SAA homo-oligomers 19–20.
Figure 8: 10-Membered ring H-bonds in compound 21 consistent with NMR and modelling investigations.
Figure 9: General structure of carbopeptoid-oligonucleotide conjugates.
Figure 10: Protected derivatives of 2,6-diamino-2,6-dideoxy-β-D-glucopyranosyl carboxylic acid 22 and 23.
Figure 11: Cyclic homo-oligomers containing glucopyranoid-SAAs.
Scheme 2: Strategy for solid-phase synthesis of cyclic trimers and tetramers containing pyranoid δ-SAAs.
Figure 12: Cyclic tetramers of L-rhamno- and D-gulo-configured oxetane-SAAs.
Figure 13: Aminoglycosidic antibiotics of the glycocinnamoylspermidine family.
Scheme 3: Synthesis of (thio)trehazoline, via triflate, from β-hydroxy(thio)urea.
Figure 14: Approaches to access pseudoamide-type oligosaccharide mimics.
Figure 15: Calystegine B2 analogues 38 and 39 with urea-linked disaccharide structure.
Figure 16: Rotameric equilibrium shift of 40 by formation of a bidentate hydrogen bond.
Figure 17: Nucleotide analogues with thiourea and S-methylisothiouronium linkers.
Scheme 4: Retrosynthetic approach to synthesize thiourea-linked glycooligomers.
Figure 18: Rotameric equilibria for β-(1→6)-thiourea-linked glucodimer 41.
Figure 19: Schematic representation of (a) cyclodextrin (CDs) and (b) cyclotrehalan (CTs) family members.
Scheme 5: Synthesis of guanidine-linked pseudodisaccharides via carbodiimide.
Figure 20: β(1→6)-Guanidine-linked pseudodi- and pseudotrisaccharides 47 and 48.
Scheme 6: Synthesis of N-benzylguanidine-linked CT2 50.
Figure 21: Structure of RNG and DNG.
Figure 22: Preparation of Fmoc-guanidinium derivatives.
Figure 23: Structures of the homo-oligomeric RNG derivatives 51–55.
Figure 24: Phosphoramidite building block 56.
Figure 25: Structures of DNGs 57–65.
Figure 26: Structure of the phosphoramidite building block 66.
