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Search for "apoptosis" in Full Text gives 107 result(s) in Beilstein Journal of Organic Chemistry.
An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals
- Marcus Baumann,
- Ian R. Baxendale,
- Steven V. Ley and
- Nikzad Nikbin
Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57
- has also been approved for familial adenomatous polyposis demonstrating its ability to induce apoptosis in certain cancer cell lines [70]. As this activity is not shared with all COX-2 inhibitors, it is believed that the structural features such as the polar sulfonamide group, the lipophilic tolyl
- moiety and the trifluoromethylated pyrazole core with its negative electrostatic potential play a key role in apoptosis induction. Consequently, the anti-inflammatory and apoptosis inducing properties of celecoxib are assumed to result via different modes of action. In a recent study [71], celecoxib has
Graphical Abstract
Figure 1: Structures of atorvastatin and other commercial statins.
Figure 2: Structure of compactin.
Scheme 1: Synthesis of pentasubstituted pyrroles.
Scheme 2: [3 + 2] Cycloaddition to prepare 5-isopropylpyrroles.
Scheme 3: Regiospecific [3 + 2] cycloaddition to prepare the pyrrole scaffold.
Scheme 4: Formation of the pyrrole core of atorvastatin via [3 + 2] cycloaddition.
Scheme 5: Formation of pyrrole 33 via the Paal–Knorr reaction.
Scheme 6: Convergent synthesis towards atorvastatin.
Figure 3: Binding pocket of sunitinib in the TRK KIT.
Scheme 7: Synthesis of sunitinib.
Scheme 8: Alternative synthesis of sunitinib.
Scheme 9: Key steps in the syntheses of sumatriptan and zolmitriptan.
Scheme 10: Introduction of the N,N-dimethylaminoethyl side chain.
Scheme 11: Japp–Klingemann reaction in the synthesis of sumatriptan.
Scheme 12: Synthesis of the intermediate sulfonyl chlorides 62 and 63.
Scheme 13: Alternative introduction of the sulfonamide.
Scheme 14: Negishi-type coupling to benzylic sulfonamides.
Scheme 15: Heck reaction used to introduce the sulfonamide side chain of naratriptan.
Scheme 16: Synthesis of the oxazolinone appendage of zolmitriptan.
Scheme 17: Grandberg indole synthesis used in the preparation of rizatriptan.
Scheme 18: Improved synthesis of rizatriptan.
Scheme 19: Larock-type synthesis of rizatriptan.
Scheme 20: Synthesis of eletriptan.
Scheme 21: Heck coupling for the indole system in eletriptan.
Scheme 22: Attempted Fischer indole synthesis of elatriptan.
Scheme 23: Successful Fischer indole synthesis for eletriptan.
Scheme 24: Mechanistic rationale for the Bischler–Möhlau reaction.
Scheme 25: Bischler-type indole synthesis used in the fluvastatin sodium synthesis.
Scheme 26: Palladium-mediated synthesis of ondansetron.
Scheme 27: Fischer indole synthesis of ondansetron.
Scheme 28: Optimised Pictet–Spengler reaction towards tadalafil.
Figure 4: Structures of carvedilol 136 and propranolol 137.
Scheme 29: Synthesis of the carbazole core of carvedilol.
Scheme 30: Alternative syntheses of 4-hydroxy-9H-carbazole.
Scheme 31: Convergent synthesis of etodolac.
Scheme 32: Alternative synthesis of etodolac.
Figure 5: Structures of imidazole-containing drugs.
Scheme 33: Synthesis of functionalised imidazoles towards losartan.
Scheme 34: Direct synthesis of the chlorinated imidazole in losartan.
Scheme 35: Synthesis of trisubstituted imidazoles.
Scheme 36: Preparation of the imidazole ring in olmesartan.
Scheme 37: Synthesis of ondansetron.
Scheme 38: Alternative route to ondansetron and its analogues.
Scheme 39: Proton pump inhibitors and synthesis of esomeprazole.
Scheme 40: Synthesis of benzimidazole core pantoprazole.
Figure 6: Structure of rabeprazole 194.
Scheme 41: Synthesis of candesartan.
Scheme 42: Alternative access to the candesartan key intermediate 216.
Scheme 43: .Medicinal chemistry route to telmisartan.
Scheme 44: Improved synthesis of telmisartan.
Scheme 45: Synthesis of zolpidem.
Scheme 46: Copper-catalysed 3-component coupling towards zolpidem.
Figure 7: Structure of celecoxib.
Scheme 47: Preparation of celecoxib.
Scheme 48: Alternative synthesis of celecoxib.
Scheme 49: Regioselective access to celecoxib.
Scheme 50: Synthesis of pazopanib.
Scheme 51: Syntheses of anastrozole, rizatriptan and letrozole.
Scheme 52: Regioselective synthesis of anastrozole.
Scheme 53: Triazine-mediated triazole formation towards anastrozole.
Scheme 54: Alternative routes to 1,2,4-triazoles.
Scheme 55: Initial synthetic route to sitagliptin.
Figure 8: Binding of sitagliptin within DPP-IV.
Scheme 56: The process route to sitagliptin key intermediate 280.
Scheme 57: Synthesis of maraviroc.
Scheme 58: Synthesis of alprazolam.
Scheme 59: The use of N-nitrosoamidine derivatives in the preparation of fused benzodiazepines.
Figure 9: Structures of itraconazole, ravuconazole and voriconazole.
Scheme 60: Synthesis of itraconazole.
Scheme 61: Synthesis of rufinamide.
Scheme 62: Representative tetrazole formation in valsartan.
Figure 10: Structure of tetrazole containing olmesartan, candesartan and irbesartan.
Scheme 63: Early stage introduction of the tetrazole in losartan.
Scheme 64: Synthesis of cilostazol.
Figure 11: Structure of cefdinir.
Scheme 65: Semi-synthesis of cefdinir.
Scheme 66: Thiazole syntheses towards ritonavir.
Scheme 67: Synthesis towards pramipexole.
Scheme 68: Alternative route to pramipexole.
Scheme 69: Synthesis of famotidine.
Scheme 70: Efficient synthesis of the hyperuricemic febuxostat.
Scheme 71: Synthesis of ziprasidone.
Figure 12: Structure of mometasone.
Scheme 72: Industrial access to 2-furoic acid present in mometasone.
Scheme 73: Synthesis of ranitidine from furfuryl alcohol.
Scheme 74: Synthesis of nitrofurantoin.
Scheme 75: Synthesis of benzofuran.
Scheme 76: Synthesis of amiodarone.
Scheme 77: Synthesis of raloxifene.
Scheme 78: Alternative access to the benzo[b]thiophene core of raloxifene.
Scheme 79: Gewald reaction in the synthesis of olanzapine.
Scheme 80: Alternative synthesis of olanzapine.
Figure 13: Access to simple thiophene-containing drugs.
Scheme 81: Synthesis of clopidogrel.
Scheme 82: Pictet–Spengler reaction in the preparation of tetrahydrothieno[3,2-c]pyridine (422).
Scheme 83: Alternative synthesis of key intermediate 422.
Figure 14: Co-crystal structures of timolol (left) and carazolol (right) in the β-adrenergic receptor.
Scheme 84: Synthesis of timolol.
Scheme 85: Synthesis of tizanidine 440.
Scheme 86: Synthesis of leflunomide.
Scheme 87: Synthesis of sulfamethoxazole.
Scheme 88: Synthesis of risperidone.
Figure 15: Relative abundance of selected transformations.
Figure 16: The abundance of heterocycles within top 200 drugs (5-membered rings).
Synthesis and binding studies of two new macrocyclic receptors for the stereoselective recognition of dipeptides
- Ana Maria Castilla,
- M. Morgan Conn and
- Pablo Ballester
Beilstein J. Org. Chem. 2010, 6, No. 5, doi:10.3762/bjoc.6.5
- of protein–protein interactions is gaining interest as they are known to play a critical role in important biological processes such as the normal function of cellular/organelle structure, immune response, enzyme inhibitors, signal transduction, and apoptosis. Rational protein surface recognition
Graphical Abstract
Figure 1: Schematic representation of the design of a host–guest complex based on antiparallel β-sheet geomet...
Figure 2: Molecular structures of the two designed receptors 1 and 2 having different relative orientations o...
Figure 3: CAChe minimized structures for the “endo” complexes formed between receptors 1 (a) and 2 (b) and th...
Scheme 1: Synthesis of tetraprotected bis(alanyl)benzophenones 3 from L-phenylalanine 7.
Scheme 2: Deprotection reactions of bis(alanyl)benzophenone units 3.
Scheme 3: Synthesis of the linear tetrapeptides 15 and 17 as mixtures of diastereoisomers.
Figure 4: a) Molecular structures of the two major diastereoisomers of the cyclic receptors obtained from the...
Figure 5: Reverse-phase HPLC chromatograms of the purified fraction obtained from macrocyclization reactions ...
Figure 6: Variable-temperature 1H NMR experiments of 1 in chloroform-d solution. The proton signals that appe...
Figure 7: Small fraction of the columnar arrangement observed in solid-state packing of receptor 1. Two adjac...
Figure 8: Molecular structures of the guests used in the binding experiments.
Figure 9: Selected region of the variable-concentration 1H NMR spectra acquired using chloroform-d solutions ...
Figure 10: a) Selected region of a series 1H NMR spectra acquired during titration of receptor 2 with n-C6H13-...
Figure 11: CAChe minimized structures for two possible binding geometries, a) exo and b) endo complexes formed...
Studies on polynuclear furoquinones. Part 1: Synthesis of tri- and tetra- cyclic furoquinones simulating BCD/ABCD ring system of furoquinone diterpenoids
- Faruk H. Shaik and
- Gandhi K. Kar
Beilstein J. Org. Chem. 2009, 5, No. 47, doi:10.3762/bjoc.5.47
- ], antioxidant and anti-inflammatory agent [12][13][14] as well as induces apoptosis in human leukemia cell lines [15][16]. It is believed that broad spectrum of activities of Dan Shen are mainly associated with the presence of tetra cyclic furoquinone diterpenoids like Tanshinone I [17][18], Tanshinone IIA and
Graphical Abstract
Figure 1: Some biologically active tetra cyclic furoquinone derivatives (isolated from Dan Shen) and syntheti...
Figure 2: Key strategies for development of C-ring with quinone functionality.
Figure 3: Retro synthesis of tetra cyclic furoquinone 13.
Scheme 1: Reagents and conditions: i) DDQ (1.5 equiv), dry benzene, reflux, argon atmosphere, 37 h, 83%. ii) ...
Figure 4: Assignment of chemical shifts (1H NMR and 13C NMR) of compound 13.
Scheme 2: Reagents and conditions: i) furan-2-boronic acid (1.2 equiv), Et3N, DMF, Pd(PPh3)4 (2 mol %), 110 °...
A short stereoselective synthesis of (+)-(6R,2′S)-cryptocaryalactone via ring- closing metathesis
- Palakodety Radha Krishna,
- Krishnarao Lopinti and
- K. L. N. Reddy
Beilstein J. Org. Chem. 2009, 5, No. 14, doi:10.3762/bjoc.5.14
- ], they inhibit HIV protease [8][9], induce apoptosis [10][11][12][13][14][15], and have even proved to be antileukemic [16]. At least some of these pharmacological effects may be related to the presence of the conjugated double bond, which acts as a Michael acceptor [17][18][19][20][21][22][23]. One of
Graphical Abstract
Figure 1: Some natural products containing styryl lactones.
Figure 2: Retrosynthetic approach.
Scheme 1: Synthesis of chiral propargyl secondary hydroxyl group.
Scheme 2: Determination of the stereochemistry of the 1,3-anti diols.
Scheme 3: Synthesis of cryptocaryalactone by RCM.
Recent progress on the total synthesis of acetogenins from Annonaceae
- Nianguang Li,
- Zhihao Shi,
- Yuping Tang,
- Jianwei Chen and
- Xiang Li
Beilstein J. Org. Chem. 2008, 4, No. 48, doi:10.3762/bjoc.4.48
- ]. Inhibition by these mechanisms results in adenosine triphosphate (ATP) deprivation, which leads to apoptosis of the highly energy demanding tumor cells [11]. The acetogenins are now considered as the most potent (effective in nanomolar concentrations) known inhibitors of the mitochondrial complex I [9][12
Graphical Abstract
Scheme 1: Total synthesis of longifolicin by Marshall’s group.
Scheme 2: Total synthesis of corossoline by Tanaka’s group.
Scheme 3: Total synthesis of corossoline by Wu’s group.
Scheme 4: Total synthesis of pseudo-annonacin A by Hanessian’s group.
Scheme 5: Total synthesis of tonkinecin by Wu’s group.
Scheme 6: Total synthesis of gigantetrocin A by Shi’s group.
Scheme 7: Total synthesis of annonacin by Wu’s group.
Scheme 8: Total synthesis of solamin by Kitahara’s group.
Scheme 9: Total synthesis of solamin by Mioskowski’s group.
Scheme 10: Total synthesis of cis-solamin by Makabe’s group.
Scheme 11: Total synthesis of cis-solamin by Brown’s group.
Scheme 12: The formal synthesis of (+)-cis-solamin by Donohoe’s group.
Scheme 13: Total synthesis of cis-solamin by Stark’s group.
Scheme 14: Total synthesis of mosin B by Tanaka’s group.
Scheme 15: Total synthesis of longicin by Hanessian’s group.
Scheme 16: Total synthesis of murisolin and 16,19-cis-murisolin by Tanaka’s group.
Scheme 17: Synthesis of a stereoisomer library of (+)-murisolin by Curran’s group.
Scheme 18: Total synthesis of murisolin by Makabe’s group.
Scheme 19: Total synthesis of reticulatain-1 by Makabe’s group.
Scheme 20: Total synthesis of muricatetrocin C by Ley’s group.
Scheme 21: Total synthesis of (4R,12S,15S,16S,19R,20R,34S)-muricatetrocin (146) and (4R,12R,15S,16S,19R,20R,34S...
Scheme 22: Total synthesis of parviflorin by Hoye’s group.
Scheme 23: Total synthesis of parviflorin by Trost’s group.
Scheme 24: Total synthesis of trilobacin by Sinha’s group.
Scheme 25: Total synthesis of 15-epi-annonin I 181b by Scharf’s group.
Scheme 26: Total synthesis of squamocin A and squamocin D by Scharf’s group.
Scheme 27: Total synthesis of asiminocin by Marshall’s group.
Scheme 28: Total synthesis of asiminecin by Marshall’s group.
Scheme 29: Total synthesis of (+)-(30S)-bullanin by Marshall’s group.
Scheme 30: Total synthesis of uvaricin by the group of Sinha and Keinan.
Scheme 31: Formal synthesis of uvaricin by Burke’s group.
Scheme 32: Total synthesis of trilobin by Marshall’s group.
Scheme 33: Total synthesis of trilobin by the group of Sinha and Keinan.
Scheme 34: Total synthesis of asimilobin by the group of Wang and Shi.
Scheme 35: Total synthesis of squamotacin by the group of Sinha and Keinan.
Scheme 36: Total synthesis of asimicin by Marshall’s group.
Scheme 37: Total synthesis of asimicin by the group of Sinha and Keinan.
Scheme 38: Total synthesis of asimicin by Roush’s group.
Scheme 39: Total synthesis of asimicin by Marshall’s group.
Scheme 40: Total synthesis of 10-hydroxyasimicin by Ley’s group.
Scheme 41: Total synthesis of asimin by Marshall’s group.
Scheme 42: Total synthesis of bullatacin by the group of Sinha and Keinan.
Scheme 43: Total synthesis of bullatacin by Roush’s group.
Scheme 44: Total synthesis of bullatacin by Pagenkopf’s group.
Scheme 45: Total synthesis of rollidecins C and D by the group of Sinha and Keinan.
Scheme 46: Total synthesis of 30(S)-hydroxybullatacin by Marshall’s group.
Scheme 47: Total synthesis of uvarigrandin A and 5(R)-uvarigrandin A by Marshall’s group.
Scheme 48: Total synthesis of membranacin by Brown’s group.
Scheme 49: Total synthesis of membranacin by Lee’s group.
Scheme 50: Total synthesis of rolliniastatin 1 and rollimembrin by Lee’s group.
Scheme 51: Total synthesis of longimicin D by the group of Maezaki and Tanaka.
Scheme 52: Total synthesis of the structure proposed for mucoxin by Borhan’s group.
Scheme 53: Modular synthesis of adjacent bis-THF annonaceous acetogenins by Marshall’s group.
Scheme 54: Total synthesis of 4-deoxygigantecin by Tanaka’s group.
Scheme 55: Total synthesis of squamostatins D by Marshall’s group.
Scheme 56: Total synthesis of gigantecin by Crimmins’s group.
Scheme 57: Total synthesis of gigantecin by Hoye’s group.
Scheme 58: Total synthesis of cis-sylvaticin by Donohoe’s group.
Scheme 59: Total synthesis of 17(S),18(S)-goniocin by Sinha’s group.
Scheme 60: Total synthesis of goniocin and cyclogoniodenin T by the group of Sinha and Keinan.
Scheme 61: Total synthesis of jimenezin by Takahashi’s group.
Scheme 62: Total synthesis of jimenezin by Lee’s group.
Scheme 63: Total synthesis of jimenezin by Hoffmann’s group.
Scheme 64: Total synthesis of muconin by Jacobsen’s group.
Scheme 65: Total synthesis of (+)-muconin by Kitahara’s group.
Scheme 66: Total synthesis of muconin by Takahashi’s group.
Scheme 67: Total synthesis of muconin by the group of Yoshimitsu and Nagaoka.
Scheme 68: Total synthesis of mucocin by the group of Sinha and Keinan.
Scheme 69: Total synthesis of mucocin by Takahashi’s group.
Scheme 70: Total synthesis of (−)-mucocin by Koert’s group.
Scheme 71: Total synthesis of mucocin by the group of Takahashi and Nakata.
Scheme 72: Total synthesis of mucocin by Evans’s group.
Scheme 73: Total synthesis of mucocin by Mootoo’s group.
Scheme 74: Total synthesis of (−)-mucocin by Crimmins’s group.
Scheme 75: Total synthesis of pyranicin by the group of Takahashi and Nakata.
Scheme 76: Total synthesis of pyranicin by Rein’s group.
Scheme 77: Total synthesis of proposed pyragonicin by the group of Takahashi and Nakata.
Scheme 78: Total synthesis of pyragonicin by Rein’s group.
Scheme 79: Total synthesis of pyragonicin by Takahashi’s group.
Scheme 80: Total synthesis of squamostanal A by Figadère’s group.
Scheme 81: Total synthesis of diepomuricanin by Tanaka’s group.
Scheme 82: Total synthesis of (−)-muricatacin [(R,R)-373a] and its enantiomer (+)-muricatacin [(S,S)-373b] by ...
Scheme 83: Total synthesis of epi-muricatacin (+)-(S,R)-373c and (−)-(R,S)-373d by Scharf’s group.
Scheme 84: Total synthesis of (−)-muricatacin 373a and 5-epi-(−)-muricatacin 373d by Uang’s group.
Scheme 85: Total synthesis of four stereoisomers of muricatacin by Yoon’s group.
Scheme 86: Total synthesis of (+)-muricatacin by Figadère’s group.
Scheme 87: Total synthesis of (+)-epi-muricatacin and (−)-muricatacin by Couladouros’s group.
Scheme 88: Total synthesis of muricatacin by Trost’s group.
Scheme 89: Total synthesis of (−)-(4R,5R)-muricatacin by Heck and Mioskowski’s group.
Scheme 90: Total synthesis of muricatacin (−)-373a by the group of Carda and Marco.
Scheme 91: Total synthesis of (−)- and (+)-muricatacin by Popsavin’s group.
Scheme 92: Total synthesis of (−)-muricatacin by the group of Bernard and Piras.
Scheme 93: Total synthesis of (−)-muricatacin by the group of Yoshimitsu and Nagaoka.
Scheme 94: Total synthesis of (−)-muricatacin by Quinn’s group.
Scheme 95: Total synthesis of montecristin by Brückner’s group.
Scheme 96: Total synthesis of (−)-acaterin by the group of Franck and Figadère.
Scheme 97: Total synthesis of (−)-acaterin by Singh’s group.
Scheme 98: Total synthesis of (−)-acaterin by Kumar’s group.
Scheme 99: Total synthesis of rollicosin by Quinn’s group.
Scheme 100: Total synthesis of Rollicosin by Makabe’s group.
Scheme 101: Total synthesis of squamostolide by Makabe’s group.
Scheme 102: Total synthesis of tonkinelin by Makabe’s group.
Stereoselective synthesis of (2S,3S,4Z)-4-fluoro- 1,3-dihydroxy- 2-(octadecanoylamino)octadec- 4-ene, [(Z)-4-fluoroceramide], and its phase behavior at the air/water interface
- Gergana S. Nikolova and
- Günter Haufe
Beilstein J. Org. Chem. 2008, 4, No. 12, doi:10.3762/bjoc.4.12
- in sphingolipid metabolism, sphingosine and its N-octadecanoyl-derivative, ceramide, exhibit a variety of biological functions. These compounds play a crucial role in many essential biological processes such as cell growth, cell differentiation, cell recognition and apoptosis. More specifically
- such as cell growth, cell differentiation, cell recognition and apoptosis [3][4][5][6][7][8][9]. Moreover, sphingosine is known as an inhibitor of protein kinase C [10][11]. The dynamic balance between ceramide, sphingosine and sphingosine-1-phosphate seems to be decisive for cell growth or apoptosis
- [12][13]. The specific initiation of apoptosis by suitable derivatives of these signal molecules is discussed as a new method for treatment of numerous diseases [1][14][15], and of cancer in particular [16][17][18]. A few years ago Herdewijn et al. showed that fluorinated ceramide and dihydroceramide
Graphical Abstract
Figure 1: Natural sphingosines 1a, 2a and synthesized fluorinated analogues 1b, 2b.
Scheme 1: Synthesis of 4-fluorosphingosine (2b); Reagents: i ClTi(OEt)3/Et3N, CH2Cl2, 13 h, 0 °C; ii 15% aq c...
Scheme 2: Mechanism of the aldol reaction.
Figure 2: Favorable conformations of the tert-butyl amino acid ester 7.
Figure 3: π–A Isotherms of ceramide (2a) and 4-fluoroceramide (2b) at 20 °C (80 cm2/min compression velocity)....
Figure 4: Cycles of compression and expansion for ceramide (2a) and 4-fluoroceramide (2b).
Colchitaxel, a coupled compound made from microtubule inhibitors colchicine and paclitaxel
- Karunananda Bombuwala,
- Thomas Kinstle,
- Vladimir Popik,
- Sonal O. Uppal,
- James B. Olesen,
- Jose Viña and
- Carol A. Heckman
Beilstein J. Org. Chem. 2006, 2, No. 13, doi:10.1186/1860-5397-2-13
- when two microtubule-polymerizing agents were used, synergistic inhibition of microtubule dynamicity could be observed [46]. Paclitaxel and discodermolide also synergistically affected G2-M arrest, proliferation, and apoptosis [46]. Some workers speculate that such synergy might arise from the
- that cells enter apoptosis shortly after paclitaxel exposure, suggesting that they are directed into a cell death pathway before entering the mitotic phase of the cell cycle [52][53]. Conversely, certain cells treated at high concentrations could pass through mitosis but still avoid apoptosis. This was
Graphical Abstract
Scheme 1: Reagents and conditions for synthesis of N-glutaryl-deacetylcolchicine. The reagents used at each s...
Scheme 2: Reagents and conditions for protection of paclitaxel and coupling to N-glutaryl-deacetylcolchicine ...
Figure 1: Microtubule arrangement as visualized by immunofluorescence localization of β-tubulin. Cells were t...
Figure 2: Projections of a VRO showing + ends localized by antibody against EB1 in a control cell. Cell was t...
Figure 3: Projections of a VRO showing + ends localized by antibody against EB1 in colchitaxel-treated cell. ...
Figure 4: Microtubule arrangement as visualized by immunofluorescence localization of β-tubulin. Cells were t...
