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CalFluors: A Universal Motif for Fluorogenic Azide Probes across the Visible Spectrum
Fluorescent bioorthogonal smart probes across the visible spectrum will enable sensitive visualization of metabolically labeled molecules in biological systems. Here we present a unified design, based on the principle of photoinduced electron transfer, to access a panel of highly fluorogenic azide probes that are activated by conversion to the corresponding triazoles via click chemistry. Termed the CalFluors, these probes possess emission maxima that range from green to far red wavelengths, and enable sensitive biomolecule detection under no-wash conditions. We used the CalFluor probes to image various alkyne-labeled biomolecules (glycans, DNA, RNA, and proteins) in cells, developing zebrafish, and mouse brain tissue slices.
Shieh, Peyton,Dien, Vivian T.,Beahm, Brendan J.,Castellano, Joseph M.,Wyss-Coray, Tony,Bertozzi, Carolyn R.
p. 7145 - 7151
(2015)
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NEW COMPOUND HAVING FGFR INHIBITORY ACTIVITY AND PREPARATION AND APPLICATION THEREOF
The present invention relates to a new compound having an FGFR inhibitory activity and preparation and application thereof. In particular, the compound according to the present invention has a structure as shown in formula I, wherein each group and substituent are as defined in the description. Also disclosed in the present invention are a preparation method for the compound and a use thereof in preparation of a drug for treating and/or preventing a tumor-related disease and/or an FGFR-related disease.
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Paragraph 0115; 0116

(2019/05/30)

Discovery of Rogaratinib (BAY 1163877): a pan-FGFR Inhibitor
Rogaratinib (BAY 1163877) is a highly potent and selective small-molecule pan-fibroblast growth factor receptor (FGFR) inhibitor (FGFR1–4) for oral application currently being investigated in phase 1 clinical trials for the treatment of cancer. In this publication, we report its discovery by de novo structure-based design and medicinal chemistry optimization together with its pharmacokinetic profile.
Collin, Marie-Pierre,Lobell, Mario,Hübsch, Walter,Brohm, Dirk,Schirok, Hartmut,Jautelat, Rolf,Lustig, Klemens,B?mer, Ulf,V?hringer, Verena,Héroult, Mélanie,Grünewald, Sylvia,Hess-Stumpp, Holger
supporting information
p. 437 - 445
(2018/02/21)

Direct synthesis of anilines and nitrosobenzenes from phenols
A one-pot synthesis of anilines and nitrosobenzenes from phenols has been developed using an ipso-oxidative aromatic substitution (iSOAr) process. The products are obtained in good yields under mild and metal-free conditions. The leaving group effect on reactions that proceed through mixed quionone monoketals has also been investigated and a predictive model has been established.
St Amant,Frazier,Newmeyer,Fruehauf,Read De Alaniz
p. 5520 - 5524
(2016/07/06)

Synthesis of cell-permeable stapled BH3 peptide-based Mcl-1 inhibitors containing simple aryl and vinylaryl cross-linkers
We report the synthesis of a series of distance-matching aryl and vinylaryl cross-linkers for constructing stapled peptides containing cysteines at i,i+7 positions. Langevin dynamics simulation studies helped to classify these cross-linkers into two categories: the rigid cross-linkers with narrower S-S distance distribution and the flexible cross-linkers with wider S-S distance distribution. The stapled Noxa BH3 peptides with the flexible distance-matching cross-linkers gave the highest degree of helicity as well as the most potent inhibitory activity against Mcl-1. However, the stapled peptides with the highest hydrophobicity showed the most efficient cellular uptake. Together, this work illustrates the divergent nature of binding affinity and cellular uptake, and the vital importance of choosing appropriate cross-linkers in constructing stapled peptides with the drug-like properties.
Muppidi, Avinash,Doi, Kenichiro,Ramil, Carlo P.,Wang, Hong-Gang,Lin, Qing
p. 7740 - 7745
(2014/12/10)

A tandem reduction-oxidation protocol for the conversion of 1-keto-1,2,3,4-tetrahydrocarbazoles to carbazoles via tosylhydrazones through microwave assistance: Efficient synthesis of glycozoline, clausenalene, glycozolicine, and deoxycarbazomycin B and the total synthesis of murrayafoline A
A novel and efficient methodology for the synthesis of carbazoles from 1-keto-1,2,3,4-tetrahydrocarbazoles via the corresponding tosylsulfonhydrazones by a one-pot tandem reduction-oxidation protocol using a combination of NaBH4 and Pd-C on MgSO4·7H2O, a solid support, under microwave is developed. The reaction is successfully extended toward the synthesis of several naturally occurring carbazole alkaloids, namely 3-methylcarbazole, glycozoline, clausenalene, glycozolicine, murrayafoline A, and deoxycarbazomycin B, a carbazole derivative that is known to have a promising antimicrobial activity.
Chakraborty, Suchandra,Chattopadhyay, Gautam,Saha, Chandan
p. 91 - 98
(2013/04/10)

SUBSTITUTED BENZOTHIENYL - PYRROLOTRIAZINES AND USES THEREOF IN THE TREATMENT CANCER
This invention relates to novel substituted 5-(l-benzothiophen-2-yl)pyrrolo[2,l-fJ[l,2,4]triazin-4-amine derivatives having protein tyrosine kinase inhibitory activities, to processes for the preparation of such compounds, to pharmaceutical compositions containing such compounds, and to the use of such compounds or compositions for treating proliferative disorders, in particular cancer and tumor diseases.
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Page/Page column 45

(2013/07/05)

Disubstituted benzothienyl-pyrrolotriazines and uses thereof
This invention relates to novel substituted 5-(1-benzothiophen-2-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine derivatives having protein tyrosine kinase inhibitory activities, to processes for the preparation of such compounds, to pharmaceutical compositions containing such compounds, and to the use of such compounds or compositions for treating proliferative disorders, in particular cancer and tumor diseases.
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Paragraph 0395; 0396; 0397; 0398

(2013/06/28)

SUBSTITUTED BENZOTHIENYL-PYRROLOTRIAZINES AND USES THEREOF
This invention relates to novel substituted 5-(1-benzothiophen-2-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine derivatives having protein tyrosine kinase inhibitory activities, to processes for the preparation of such compounds, to pharmaceutical compositions containing such compounds, and to the use of such compounds or compositions for treating proliferative disorders, in particular cancer and tumor diseases.
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Page/Page column 47

(2013/09/12)

DISUBSTITUTED BENZOTHIENYL-PYRROLOTRIAZINES AND THEIR USE AS FGFR KINASE INHIBITORS
This invention relates to novel substituted 5-(1-benzothiophen-2-yl) pyrrolo[2,1-f][1,2,4]triazin-4-amine derivatives of formula (I) wherein R1 is hydrogen, chloro, methyl or methoxy, R2 is hydrogen or methoxy, with the proviso that at least one of R1 and R2 is other than hydrogen, G1 represents chloro, (C1-C4)-alkyl, (C1-C4)-alkoxycarbonyl, 5-membered aza-heteroaryl, or the group -CH2-OR3, -CH2-NR4R5 or -C(=0)- NR4R6, and G2 represents chloro, cyano, (C1-C4)-alkyl, or the group - CR8AR8B-OH, -CH2-NR9R10, -C(=0)-NR11R12 or -CH2-OR15, having protein tyrosine kinase inhibitory activities, to processes for the preparation of such compounds, to pharmaceutical compositions containing such compounds, and to the use of such compounds or compositions for treating proliferative disorders, in particular cancer and tumor diseases.
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Page/Page column 58

(2013/07/05)

NOVEL ANTIVIRAL COMPOUNDS
The present invention relates to compounds of formula (A) as defined herein having antiviral activity, more specifically HIV (Human Immunodeficiency Virus) replication inhibiting properties. The invention also relates to pharmaceutical compositions comprising an effective amount of such compounds as active ingredients. This invention further relates to the use of such compounds as medicines or in the manufacture of a medicament useful for the treatment of animals suffering from viral infections, in particular HIV infection. This invention further relates to methods for the treatment of viral infections in animals by the administration of a therapeutical amount of such compounds, optionally combined with one or more other drugs having antiviral activity.
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Page/Page column 44

(2013/02/27)

NOVEL VIRAL REPLICATION INHIBITORS
The present invention relates to a series of novel compounds having antiviral activity, more specifically HIV (Human Immunodeficiency Virus) replication inhibiting properties. The invention also relates to methods for the preparation of such compounds, as well as to novel intermediates useful in one or more steps of such syntheses. The invention also relates to pharmaceutical compositions comprising an effective amount of such compounds as active ingredients. This invention further relates to the use of such compounds as medicines or in the manufacture of a medicament useful for the treatment of animals suffering from viral infections, in particular HIV infection. This invention further relates to methods for the treatment of viral infections in animals by the administration of a therapeutical amount of such compounds, optionally combined with one or more other drugs having antiviral activity.
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Page/Page column 134

(2011/02/24)

Efficient and diversity-oriented total synthesis of Riccardin C and application to develop novel macrolactam derivatives
Riccardin C (RC, 1) is a macrocyclic bis(bibenzyl) natural product exhibiting remarkable biological activity as a nuclear liver X receptors (LXRs) ligand and a lipid metabolism mediator. RC is expected to be a lead compound to develop drugs for atherosclerotic diseases, and therefore exploiting diversity-oriented synthesis of RC is a promising approach to drug discovery. In this paper, we report novel total synthesis of RC (7.4% overall yield in 16 steps) by using the intramolecular SNAr reaction as key cyclization reaction. This is the first example of efficient macrocyclization using 3-nitro-4-fluorostilbene as an electrophile. The methodology could be applied to synthesize novel lactam analogs of RC. The diversity-oriented synthesis of RC is versatile method for the synthesis of various types of bis(bibenzyl) natural products and their derivatization.
Iwashita, Masazumi,Fujii, Shinya,Ito, Shigeru,Hirano, Tomoya,Kagechika, Hiroyuki
experimental part
p. 6073 - 6082
(2011/08/22)

Palladium-catalyzed direct arylation-based domino synthesis of annulated N-heterocycles using alkenyl or (hetero)aryl 1,2-dihalides
A palladium-catalyzed reaction sequence consisting of an intermolecular amination and an intramolecular direct arylation enabled highly regioselective syntheses of functionalized indoles or carbazoles and proved to be amenable to the use of inexpensive 1,2dichloroarenes as electrophiles.
Ackermann, Lutz,Althammer, Andreas,Mayer, Peter
scheme or table
p. 3493 - 3503
(2010/02/28)

Acid-free synthesis of carbazoles and carbazolequinones by intramolecular Pd-catalyzed, microwave-assisted oxidative biaryl coupling reactions efficient syntheses of murrayafoline A, 2-methoxy-3-methylcarbazole, and glycozolidine
A mild and. efficient methodology for the synthesis of oxygenated. carbazoles from diarylamines under non-acidic conditions was developed, based on a palladium-catalyzed, microwave-assisted double C-H bond activation process. This new protocol was successfully applied to the synthesis of three naturally occurring carbazoles, namely murrayafoline A, 2-methoxy-3-methylcarbazole, and glycozolidine. The scope of the reaction was also expanded, to include the synthesis of benzo fused carbazolequinones. Wiley-VCH Verlag GmbH & Co. KGaA.
Sridharan, Vellaisamy,Antonia Martin,Carlos Menendez
supporting information; experimental part
p. 4614 - 4621
(2009/12/05)

Synthesis of oxygenated carbazoles by palladium-mediated oxidative double C-H activation of diarylamines assisted by microwave irradiation
Microwave irradiation in the presence of palladium acetate and traces of dimethylformamide allows the fast and efficient cyclodehydrogenation of diphenylamines into carbazoles. The scope of the microwave-assisted reaction is broader than that of the one using conventional conditions in that it allows the preparation of oxygenated carbazoles without apparent loss in yield. The applicability of the method to the preparation of carbazole alkaloids has been demonstrated by the development of a total synthesis of murrayafoline A, which proceeds in 50% overall yield from commercially available materials and is the shortest and most efficient route for the preparation of this alkaloid to date. Georg Thieme Verlag Stuttgart.
Sridharan, Vellaisamy,Martín, Ma. Antonia,Menéndez, J. Carlos
p. 2375 - 2378
(2008/02/09)

BI- OR TETRA-GUANIDINO-BIPHENYL COMPOUNDS AS SMALL MOLECULE CARRIERS
The invention relates to compounds of formula: I, or pharmaceutically acceptable a salts thereof, I wherein X1 X2 and X3 are each independently where Y is an alkylene, alkenylene or alkynylene group, each of which may be optionally substituted with one or more substituents selected from alkyl, halo, CF3, OH, alkoxy, NH2, CN, NO2 and COOH; W is absent or is O, S or NH; Rl, R2, R3 and R4 are each independently selected from H, alkyl, aryl and a protecting group Pl; R7, R8 and R9 are each independently selected from H, alkyl, halo, CF3, OH, alkoxy, NH2, CN, NO2 and COOH; q and r are each independently 1, 2, 3 or 4; q' and r' are each independently 0, 1, 2 or 3, where q + q' and r + r' each equal 4; p is 1, 2, 3, 4 or 5, and p' is 0, 1, 2, 3 or 4, where p + p' is 5; n is 0, 1, 2, 3....6; L is (Z)mNR5R6 where Z is a hydrocarbyl group and m is 0 or 1; where R5 and R6 are each independently H, CO(CH2)jQ1 or C=S(NH)(CH2)kQ2 where j and k are each independently 0, 1, 2, 3, 4 or 5, and Q1 and Q2 are each independently selected from COOH, a chromophore or R5, R6 and the nitrogen to which they are attached together form.
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Page/Page column 36-37

(2008/06/13)

Synthesis of the spirocyclic cyclohexadienone ring system of the schiarisanrins.
[structure: see text] Studies on the synthesis of the spirocyclic cyclohexadienone ring system 2 of the schiarisanrin family of natural products 1 are described and were based on the Lewis acid-promoted C-alkylation of the corresponding phenolic precursor.
Coleman,Guernon,Roland
p. 277 - 280
(2007/10/03)

N-Arylpiperazinyl-N'-propylamino derivatives of heteroaryl amides as functional uroselective α1-adrenoceptor antagonists
Novel arylpiperazines were identified as α1-adrenoceptor (AR) subtype- selective antagonists by functional in vitro screening. 3-[4-(ortho- Substituted phenyl)piperazin-1:yl]propylamines were derivatized with N,N- dimethyl anthranilamides, nicotinamides, as well as carboxamides of quinoline, 1,8-naphthyridine, pyrazolo[3,4-b]pyridine, isoxazolo[3,4- b]pyridine, imidazo[4,5-b]pyridine, and pyrazolo[1,5-a]pyrimidines. Strips of rabbit bladder neck were employed as a predictive assay for antagonism in the human lower tract. Rings of rat aorta were used as a 'negative screen' for the test antagonists. Binding to α1-ARs was relatively sensitive to size and electronic features of the arylpiperazine portion of the antagonists and permissive to these features on the heteroaryl carboxamide side. These structure-affinity findings were exploited to produce nicotinamides (e.g. 13ii and 25x) and pyrazolo[3,4-b]pyridines (e.g. 37f and 37y) ligands with nanomolar affinity at the α1-AR subtype prevalent in the human lower urinary tract (pA2 values: 8.8, 10.7, 9.3, and 9.9, respectively) and displaying 2-3 orders of magnitude selectivity over the α(1D)-AR.
Elworthy, Todd R.,Ford, Anthony P. D. W.,Bantle, Gary W.,Morgans Jr., David J.,Ozer, Rachel S.,Palmer, Wylie S.,Repke, David B.,Romero, Magarita,Sandoval, Leticia,Sjogren, Eric B.,Talamás, Francisco X.,Vazquez, Alfredo,Wu, Helen,Arredondo, Nicolas F.,Blue Jr., David R.,DeSousa, Andrea,Gross, Lisa M.,Kava, M. Shannon,Lesnick, John D.,Vimont, Rachel L.,Williams, Timothy J.,Zhu, Quan-Ming,Pfister, Jürg R.,Clarke, David E.
p. 2674 - 2687
(2007/10/03)

Transition metal-diene complexes in organic synthesis - 16.1 Iron-mediated total synthesis of 1-oxygenated carbazole alkaloids
Using a methodology of consecutive iron-induced C - C and C - N bond formation we describe the total synthesis of murrayafoline A, murrayaquinone A, koenoline, murrayanine, mukoeic acid, and mukonine.
Knoelker, Hans-Joachim,Bauermeister, Michael
p. 11221 - 11236
(2007/10/02)

Mechanism of the Reaction of Carbon and Nitrogen Nucleophiles with the Model Carcinogens O-Pivaloyl-TV-arylhydroxylamines: Competing SN2 Substitution and SN1 Solvolysis
The reaction of N,N-dimethylaniline (4) and aniline (5) with the O-pivaloyl-N-arylhydroxylamines 1a-f) in MeOH exhibits second-order kinetics and generates products of nucleophilic attack on the nitrogen of the hydroxylamine derivative. The characteristics of this reaction are not consistent with a nitrene or SET mechanism, an SN1 reaction with rate-limiting attack of the nucleophile, or nucleophile-assisted ionization. The only mechanism consistent with the available data, including substituent effects (ρ+ ≈ -3.0), cyclic voltammetry results, and product identifications, is an SN2 process. This reaction occurs in competition with an SN1 solvolysis that shows significant substituent dependence (ρ+ = -8.5). The reaction of 1 with 5 generates products of nucleophilic attack by both carbon (8, 9) and nitrogen (10). Competitive attack by carbon apparently occurs because of transition-state stabilization caused by the incipient C-N bond. The successful competition of the 8N2 reactions with SN1 solvolysis for the esters 1a and 1b, which are similar in reactivity to the putative carcinogens 2a-c, indicates that certain adducts isolated from in vivo experiments, including 3, may be formed via SN2 mechanisms.
Helmick, John S.,Martin, Kristy A.,Heinrich, Julie L.,Novak, Michael
p. 3459 - 3466
(2007/10/02)

Iron-mediated Total Synthesis of the Cytotoxic Carbazole Koenoline and Related Alkaloids
The total syntheses of the alkaloids mukonine, murrayanine, and koenoline are described using an iron-mediated arylamine cyclization as the key step.
Knoelker, Hans-Joachim,Bauermeister, Michael
p. 664 - 665
(2007/10/02)

Synthesis of The Gilvocarcin-M Aglycone
The synthesis of the aglycone of the antibiotic Gilvocarcin-M by a sequential Meerwein Diels-Alder route is reported.The D-ring of the aglycone is attached by a halogen atom directed Meerwein arylation reaction and the A-ring is attached by a halogen atom directed Diels-Alder reaction.In the key step the directing chlorine atom is removed by a new thiophenylation reduction sequence.
McKenzie, Thomas C.,Hassen, Wesley,Macdonald, Simon J. F.
p. 5435 - 5436
(2007/10/02)

Synthesis and evaluation of the antiovulatory activity of a variety of melatonin analogues
A series of melatonin analogues was synthesized and examined for ovulation-blocking activity. Deviation from the 5-methoxy group or substitution of the 1 position prevented activity. Activity was not particularly sensitive to minor variations in the N-acyl group nor was it significantly altered by methylation of position 2 or the α-methylene; however, a pronounced enhancement resulted from halogenation of the 6 position.
Flaugh,Crowell,Clemens,Sawyer
p. 63 - 69
(2007/10/04)